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Deep dish pizza, baseball games, and stunning architecture…all things that typically come to mind when people think of Chicago. As the third largest city in the United States, brutal winters and a budding food scene mean there are tons of things to do indoors here. What is perhaps more surprising is the abundance of Chicago outdoor activities to try.

With the Chicago River, Lake Michigan, and tons of green spaces at the city’s disposal, Chicago is a fantastic and totally underrated city for outdoor enthusiasts. Here are 10 of the most unique and fun outdoor activities in Chicago.


Want to explore the outdoors in Chicago? Check out our Chicago adventure guides:


Chicago Outdoor Activities: Best Things to Do in Chicago, Illinois

1. Go kayaking on the Chicago River

There’s really no better way to explore Chicago than from the water, and the Chicago River is a great place to start. While you can take the iconic architecture tour or a riverboat city tour, one of our favorite ways to see the city is by kayak.

Renting a kayak in Chicago is a stress-free way to see the city at your leisure. Take in sights like the iconic bridges, the architecture, and the Chicago Riverwalk while enjoying a day on the water.

Kayak rentals in Chicago typically start at $20 per person per hour, and you can rent at several places along the river. Read our Chicago kayaking guide to learn more about the best places to rent a kayak and explore in the city.

If you’d prefer a guided excursion, there are lots of awesome and unique kayaking tours in Chicago. Here are a few of our favorites:

  • Chicago River Kayaking Tour – This classic 2.5-hour kayaking tour of the city, led by a local guide, will take you past historic sights and architectural marvels.
  • Ghosts & Gangsters Kayaking Tour – For a spooky paddling adventure, there’s no tour more unique or active than the Chicago Ghosts & Gangsters Kayaking Tour. Learn about the city’s haunted past while paddling down the historic Chicago River in the dark.

2. Take a free walking tour

Chicago locals take great pride in the fact that their city is such a walkable one, and it’s true! Between the many lines of the “L” train and good old-fashioned walking, you can basically get anywhere in the city without a car.

One of our favorite ways to explore Chicago is simply by walking everywhere. You can explore the various neighborhoods of Chicago on your own, grabbing a famous Chicago deep dish slice or hot dog along the way.

However, if you want to get a deeper glimpse into Chicago, we’d strongly recommend taking one of the city’s free walking tours. If you don’t know how these work, you basically don’t have to pay for your tour, just tip the guide what you thought the tour was worth at the end! Chicago’s free walking tours run every day during the warmer months of the year and cover topics like architecture, ghosts and legends, and the mafia history of the city.

Chicago locals (us included) love these tours as much as tourists do – it’s a great way to learn about the city whether you live here or not!

3. Explore Lake Michigan on a stand up paddle board

There are tons of ways to get out on Lake Michigan, but one of the best and most cost-effective is on a stand up paddle board. Paddle boarding is becoming an increasingly popular activity in Chicago, as the lake water is refreshingly cool in the summer and it’s a fun, active adventure you can have without leaving the city.

While there are lots of places along Lake Michigan that you can rent a stand up paddle board, two of the most popular are at Monroe Harbor (south of Navy Pier) and North Avenue Beach (east of Lincoln Park). Urban Kayaks and Chicago SUP have rental locations at these piers, respectively. Usually, you can simply walk up to either company and rent a paddle board on the spot.

We’ll be the first to admit that on especially windy days, paddle boarding on Lake Michigan isn’t always a walk in the park. However, it can be a wonderful way to get a workout while enjoying Chicago’s outdoors and catching some of the most epic views of Navy Pier and the Chicago skyline.

The Lakefront Trail is one of the most popular Chicago running trails.

4. Run along the Lakefront Trail

For those who want to get some miles under their belts, there’s no better place to go running in Chicago than on the Lakefront Trail. This 18-mile stretch of walking, running, and biking trail runs parallel to the shores of Lake Michigan, meaning you’ll have a great view of the water and the city’s many beaches for the duration of your run. You can also catch great views of Navy Pier, Grant Park, the Museum District, and the city skyline from the Lakefront Trail.

In our opinion, the best time to go for a jog on the Lakefront Trail is in the early morning, before it gets too hot and crowded with people. The trail doesn’t have a ton of shade or tree cover, so it can definitely get hot during the height of the midday sun. There are water fountains along the trail as well as a few snack shacks in case you’re craving a bite to eat or a cold drink.

If you’re planning to do a lot of running in Chicago, there are tons of great running spots you can check out. You can read our complete guide to running in Chicago below:

Photo Credit: Phil Roeder (Flickr CC)

5. Go rock climbing outdoors at Maggie Daley Park

Rock climbing outdoors might seem like a luxury reserved for rural areas and national parks, but there’s actually an opportunity to do it right in the heart of Chicago. Located in Chicago’s Loop, Maggie Daley Park boasts a 40-foot outdoor climbing wall, which has a total of 19,000 square feet of climbing space.

At Maggie Daley Park, there’s bouldering, top roping, and lead climbing for budding climbers, from beginners to intermediate enthusiasts. There are crash pads in the bouldering area and employees on staff to ensure a safe and fun environment. You can also hire a private belayer if you’re new to climbing or came without a belay partner.

For $30, you will get admission, a short lesson on belaying, and all of the necessary rental equipment – shoes, ropes, belay devices, helmets, and chalk. Also, Chicago residents get 20% off climbing admission (so you locals should definitely get on it!).

Photo Credit: Daniel Lobo

6. Take a hike on the 606

One of the most unique Chicago trails is the 606, an elevated urban trail that runs over former railroad tracks. Today, it’s a paved hiking, running, and biking trail that winds through green spaces, charming neighborhoods, and historic areas of Chicago. The 606 is a great place for an urban hike in Chicago, while experiencing some of the city’s iconic neighborhoods along the way.

The entire 606 trail spans 2.7 miles, beginning at Walsh Park and ending at North Ridgeway Ave. If you don’t want to hike the whole thing, there are multiple access points along the trail where you can enter and exit at your leisure. Because it’s paved and mostly flat, it’s one of the best hikes in Chicago and the surrounding areas for all levels of hikers.

To extend your adventure, you can get off at Humboldt Park, which is a peaceful recreation area located in the neighborhood of Wicker Park. Tackle the 2-mile loop trail or simply wander around and enjoy the escape from the bustle of the Loop and downtown Chicago.

For more information on hikes in and around the Chicago area, don’t forget to check out our complete Chicago hiking guide:

7. Rent a Divvy bike and explore on two wheels

Biking is one of the most underrated Chicago outdoor activities – it’s one of the best ways to see both the city’s amazing green spaces as well as its varied neighborhoods. Chicago locals love to bike, and you’ll usually see throngs of bikers on popular trails like the Lakefront Trail and the 606.

To rent a city bike, you can simply go up to any Divvy kiosk (the baby blue bikes) and use your credit card and rent a bike for the day ($15 gets you unlimited rides for 24 hours), then return the bike to any Divvy kiosk when you’re done.

Some of the best trails in the city to bike along include the Lakefront Trail, the 606, and the North Shore Channel Trail. For those who prefer a guided excursion, there are a few really incredible bike tours available to book in Chicago:

If you’d like to get out of the city, there are tons of other nature preserves and mountain biking trails you can enjoy. You’ll need your own bike to leave the city, but it’s well worth it to experience some of the best nature areas in the Midwest.

Lincoln Park is the perfect place to go running in Chicago.

8. Enjoy a walk in Lincoln Park

Lincoln Park is one of the most popular neighborhoods in Chicago, and in the middle of it lies a large, green park area that houses many walking trails, a lake, and the Chicago Zoo. The Lincoln Park Trail winds through the park’s wooded areas provide an easy, leisurely, family-friendly recreational area to go for a walk in the city.

Within the park, you’ll find 1200 acres of green spaces and recreation areas to enjoy. Next to the trails, you’ll see gorgeous Victorian architecture, the Lincoln Park Conservatory, and the zoo. Nearby, the Lincoln Park pathways lead to the North Avenue Beach stretch of the Lakefront Trail, perfect for an extra-long urban hike if you’re wanting to extend your adventure.

9. Enjoy winter activities like skiing and ice skating

Chicago winters might make the bravest souls shudder, but if you’re a skiing or snowboarding enthusiast, there are some pretty awesome places to hit the slopes nearby. You might be surprised to learn that there are actually some slopes and hills to ski down in the middle of the Midwest Prairie, and many of them cater to skiers and snowboarders of all levels.

The bottom line? You can find snowboard and ski resorts as close as 30 minutes from downtown Chicago, and they’re absolutely amazing places to get outdoors during the cold winter months.

Additionally, Chicago is home to an outdoor skating rink in the winter in Millennium Park, where you can actually lace up your skates and speed across the ice…in the middle of the city. It’s a pretty awesome perk of visiting Chicago in the winter, and it’s well worth braving the cold for!

The Chicago Marathon is one of the city’s largest road races. Photo Credit: Marco Verch (Flickr CC)

10. Run in an iconic Chicago road race

As with most big cities, there are tons of wonderful road races you can participate in that show off the best the city has to offer. The races will take you through the iconic sights and neighborhoods of Chicago, and will give you a new perspective on the Windy City. Here are a few of the coolest and quirkiest races you can enjoy in Chicago:

  • Shamrock Shuffle (March) – A St. Patrick’s Day themed 8K run that goes through all of Chicago’s most iconic landmarks.
  • Chicago Half-Marathon (September) – Chicago’s iconic half marathon (13.1 miles) usually takes place in late September and hits all of the city’s best spots.
  • Chicago Marathon (October) – This is Chicago’s iconic marathon (26.2 miles) route and one of the most popular events in the country!
  • Hot Chocolate 5K/15K (October/November) – The best kinds of races end with hot chocolate! This race commemorates the start of the Chicago winter with a run through the brisk air and plenty of warm hot chocolate at the finish line.

Additional Resources


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Chicago might seem like an unlikely place for climbers, but there are actually tons of cool outdoor activities and spots to climb in and around the city. There are stunning places to go climbing at Chicago rock climbing gyms and outdoors at state parks and nature preserves. Whether you’re rock climbing in Chicago for the first time or are a seasoned outdoor climber, you can find a Chicago rock climbing spot that suits your skill levels and preferences.

To help you learn more about places to go climbing in Chicago, we put together this list of 10 of the best spots for climbers in the Windy City.

Rock Climbing Gyms in Chicago

1. First Ascent

  • Locations: Avondale, Uptown, Humboldt Park, Block 37 (Loop)
  • Day Pass: $19 ($15 with student ID)
  • Equipment Rental: $10

First Ascent has the most locations in the Chicagoland area. There’s likely one close to wherever location you are at. Although most of their gyms are bouldering only, you can get your lead or top rope fix at their Avondale location.

One of the highlights of this gym is that your membership enrolls you in a loyalty points system. Earn points with each visit to the gym, by joining one of their fitness classes, or when you refer a friend. Points are redeemable for free guest passes, gear rentals, discount on fitness classes, or pay for a month’s membership with your points!

2. Vertical Endeavors

  • Location: 246 Windy Point Drive
  • Day Pass: $18
  • Equipment Rental: $12

Located further out in the suburbs of Glendale, IL, Vertical Endeavors boasts one of the largest climbing facilities in the country. This Minnesota based company already has several climbing gyms around the Twin Cities area, but its Glendale location is its first location in the Chicago area.

The gym has both top rope routes and lead climbing routes. If you don’t have a climbing partner for the day, the gym also has 3 bouldering walls and 30 auto-belays, making this a great choice for solo climbers.

3. Brooklyn Boulders

  • Location: 100 South Morgan Street
  • Day Pass: $25
  • Equipment Rental: $11

Brooklyn Boulders prides itself on being both a climbing gym and a community hang-out spot. In addition to climbing walls, Brooklyn Boulders also features pop-up events, art showcases, and group exercise class. What truly sets this gym apart, however, is its collaborative working space with free wi-fi. This gym is the perfect spot for freelancers and remote workers to be productive and get their daily exercise in.

In terms of climbing space, the facility offers bouldering, top rope, lead climbing, and several auto-belays. The gym offers a “beginner to badass” package for new members, which includes a one month membership, free classes, gear rental, and a waived activation fee.

4. Chicago Athletic Club

  • Location: 1723 Benson Ave (Evanston), 3212 N. Broadway (Lakeview)
  • Day Pass: $35
  • Equipment Rental: Unlisted

The Chicago Athletic Club is a network of gyms throughout the Chicagoland area. Two of their locations, Evanston Athletic Club and Lakeview Athletic Club have indoor climbing walls. Their Lincoln park location has an outdoor wall, but it is currently undergoing renovations as of September 2019. A monthly membership is $65-$110 monthly depending on what services and classes you add, but it will get you more cross-training equipment compared to a climbing only gym.

The Athletic Clubs have walls up to 65 feet tall, making them the owners of one of the tallest climbing walls in the city. Routes range in difficulty from 5.7 – 5.13. Lead, top rope, and bouldering is available.

Photo Credit: Phil Roeder (Flickr CC)

5. Maggie Daley Park

  • Location: 337 E Randolph Service Street
  • Day Pass: $15
  • Equipment Rental: $15

Looking to get outside and climb without leaving the city? Head over to Maggie Daley Park in the Loop to climb a 40 feet outdoor wall. The climbing wall is run by the nearby Lakeshore Sport & Fitness gym. The wall has 19,000 square feet of climbing surface area and can hold up to 100 climbers at a time. Chicago residents get 20% off all prices with proof of residency.

6. Steelworkers Park

  • Location: East 87th at Lake Michigan
  • Price: Free
  • Equipment Rental: No rental equipment available

A recent addition to Chicago’s climbing scene, the climbing wall at Steelworker’s park opened in 2018 as the South Side’s fist climbing wall. The wall itself is a dozen climbing routes bolted onto the outside of the old South Works steel manufacturing plant. The installation of the wall was part of a larger city-wide project to expand its open spaces and park spaces. The city plans to host open climb days in the summertime and install auto-belay devices. For now, experienced lead climbers and boulderers can send these routes any time the park is open.

The wall is 40 feet tall, and features routes ranging in difficulty from 5.2 to 5.7. A couple of the routes feature 90 degree overhangs and 45 degree pitches.

Outdoor Rock Climbing Near Chicago

Photo Credit: Wisconsin Department of Natural Resources (Flickr CC)

7. Devil’s Lake State Park

  • Location: Baraboo, Wisconsin
  • Distance from Chicago: 180 miles
  • Difficulty: 5.5 to 5.12 (mostly moderates)
  • Gear Needed? Yes, slings for anchors needed

A 3 hour drive from downtown Chicago, Devil’s Lake is a beautiful respite from the urban jungle that is the Windy City. Three towering rock cliffs over a hundred feet in height make up over 1600 different listed routes. These rocks also hold quite a bit of climbing history. Many legendary climbers have left their handprints on the walls of Devil’s Lake. It’s said that the first 5.12 was sent here by Pete Cleveland.

There are no bolts on the wall, so all climbing is traditional. Most of the rock here is quartz. There are plenty of bouldering areas on the wall. Routes range in difficulty from 5.5 to 5.12a.

8. Jackson Falls

  • Location: Shawnee National Forest, Illinois
  • Distance from Chicago: 350 miles
  • Difficulty: 5.6 to 5.13c
  • Gear Needed? Rope

For a weekend long climbing trip, head over to Jackson Falls in the Shawnee National Forest. This park in southern Illinois features the most climbing routes of any other place in the state. It’s also the best location for sport climbers as the rocks have many bolted routes.

Most of the rock is rough sandstone, offering great grips. Walls range in height between 30 to 70 feet, and routes are appropriate for all skill levels (5.6 to 5.13c).

Photo Credit: Joshua Mayer (Flickr CC)

9. Governor Dodge State Park

  • Location: Dodgeville, Wisconsin
  • Distance from Chicago: 190 miles
  • Difficulty: Beginner to moderate
  • Gear Needed? Crash pads

Also located about 3 hours from Chicago, Governor Dodge State Park features smaller crowds and a few bolted routes. The rock here is varied, but most walls will be sandstone. Because of this, the walls are less suited for climbing and the park isn’t necessarily a favorite by the climbing community. Bouldering tends to be the more popular activity at Governor Dodge.

There is a great variety of bouldering routes for all skill levels, ranging from V0 to V9. In the wintertime, head up to Stephens Falls or Cox Hollow for some ice climbing.

10. Holy Boulders

  • Location: Shawnee National Forest, Illinois
  • Distance from Chicago: 350 miles
  • Difficulty: All levels
  • Gear Needed? Crash pads

Holy Boulders is located just an hour and a half West from Jackson Falls. An aptly named park, Holy Boulders is the bouldering Mecca of the state. There are over 200 named problems ranging from V0 to V13. There are also two traditional routes up 30 feet of wall.

This is a new location that was first discovered in 2004, so new routes are named and sent every year. The site was purchased in 2012 by the Illinois Climbers Association and Access Fund, in order to protect the land and open up the park to more climbers.

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With tons of green spaces and picturesque waterways, Chicago is a fantastic city for runners. Running in Chicago is a great way to explore the city, especially during the warmer months of the year. You can run around the Windy City for miles and miles, passing near the Chicago River, trailing along Lake Michigan, or jogging through one of the many parks in the city.

Not sure which trail to hit next? Here’s a list of 12 of the best places to go running in Chicago and the surrounding areas, including paved trails, parks, and nature preserves.

Top Places to Go Running in Chicago

The Lakefront Trail is one of the most popular Chicago running trails.

1. Lakefront Trail

  • Location: Lake Michigan
  • Route Length: Up to 18 miles
  • Trail Type: Paved

The Lakefront Trail is arguably Chicago’s most popular running route. Located on the shores of Lake Michigan, the Lakefront Trail is composed on 18 miles of paved trails that are shared with runners, dog walkers, and bikers. On evenings and weekends, the Lakefront Trail is usually packed with people, making it an especially great place to go if you’re running alone or enjoy being around the masses.

Along the Lakefront Trail, there are tons of sandy beach hangout areas, cute waterfront restaurants and bars, and graffiti-lined underpasses. You’ll also have the opportunity to pass by the iconic Navy Pier, Monroe Harbor, North Avenue Beach, and the Museum District.

The best time to enjoy the Lakefront Trail is at sunrise, when the sun hangs low over the water and you can catch the coolest, crispest summer air in Chicago. It’s also considerably less crowded during this time of day.

The Chicago Riverwalk is a fun place to go running in Chicago!

2. The Riverwalk

  • Location: The Loop
  • Route Length: 3.4 miles
  • Trail Type: Paved

Chicago’s Riverwalk may very well be the heart of the city. Located along the Chicago River, this buzzing boardwalk is full of people at practically all times of day, and is home to many of the city’s coolest views. It’s also a fabulous place to go running in Chicago, as you’ll catch views of some of the city’s most unique architecture.

A run on the 3.4-mile trail on the Riverwalk is best done in the mornings, when the boardwalk isn’t so full of bar-hoppers and large groups. At this time of day, you’ll get more uninterrupted running time and spend less energy dodging other people.

While on the trail, you can see views of the river, the city’s unique buildings, and watch people kayaking along the Chicago River or passing by on boat tours.

3. Grant Park & Millennium Park

  • Location: The Loop
  • Route Length: 3-5 miles
  • Trail Type: Paved

When you close your eyes and think of Chicago, Grant Park probably comes to mind. Home to giant green spaces, Lollapalooza, and the famed Cloud Gate, it’s one of the most epic places to go running in Chicago. And, with various trails winding through the park, there are options to create a route of up to 5 miles in the area.

The reason why we love Grant Park for running is because it’s a great way to see many Chicago icons from a unique perspective. While running, you can soak in several of the city’s best sights – think Navy Pier, the skyline, and the Museum District – all while getting your morning miles in.

4. Magnificent Mile

  • Location: The Loop
  • Route Length: 1-2 miles
  • Trail Type: Urban/paved

The Magnificent Mile is Chicago’s “5th Avenue,” filled with some of the city’s best hotels, shops, and entertainment options. During certain times of day, it can also be an excellent place for running in Chicago, giving you access to the downtown environment during your morning run.

As with many of our recommendations, the Magnificent Mile is best for running in the early morning, before the rush hour crowds begin to flow through the streets. Another thing to keep in mind about this area is that there are several intersections with stop lights, meaning you won’t have many opportunities to run uninterrupted unless you veer off into Millennium Park or the Lakefront Trail.

Photo Credit: David Hilowitz (Flickr CC)

5. Milwaukee Avenue

  • Location: North Side
  • Route Length: Varies
  • Trail Type: Urban/paved

For those craving a longer urban run, Milwaukee Avenue is one of the coolest Chicago running spots. Yes, you’ll have to deal with the minor annoyance of stoplights and sidewalks, but in exchange, you’ll have the opportunity to pass through some of Chicago’s most interesting neighborhoods and explore a completely different side of the city.

A run down Milwaukee Avenue will take you past Wicker Park, one of Chicago’s coolest residential areas, past the Flatiron Arts Building, and past lots of street art and local shops and cafes.

Photo Credit: Luiz Gadelha Jr. (Flickr CC)

6. Hyde Park

  • Location: Hyde Park
  • Route Length: 5-7 miles
  • Trail Type: Paved

Among the more unconventional Chicago running routes on our list takes you into south Chicago’s historic neighborhood of Hyde Park. Home to the University of Chicago, you’ll find Gothic architecture, tree-lined streets, and lots of historic townhomes as you run through the area.

A 5-mile run in Hyde Park will take you through the University of Chicago, Jackson Park, Promontory Point, and Washington Park, as well as past historic homes and Gothic-style buildings. It’s a fantastic contrast to the tall, shiny buildings and busy, crowded streets of the Downtown/Loop area of Chicago!

Lincoln Park is the perfect place to go running in Chicago.
Lincoln Park is a lovely place to go running in the evenings.

7. Lincoln Park

  • Location: Lincoln Park
  • Route Length: Up to 5.5 miles
  • Trail Type: Gravel

Lincoln Park is one of the most beloved residential areas of Chicago, and in the middle of it lies a large, green park area that houses a picturesque lake and many trails that are perfect for running. The Lincoln Park Trail winds through the park’s wooded areas and us a wonderful, shady place for a run.

Within the park, you’ll find over 5 miles of runner-friendly trails. Along your run, you can admire the gorgeous Victorian architecture in the neighborhood, and you can pass by the zoo or the Lincoln Park Conservatory. Nearby, the Lincoln Park trails lead right to the North Avenue Beach stretch of the Lakefront Trail, perfect for extending your run and enjoying the cool, breezy lake air.

8. North Shore Channel Trail

  • Location: North Chicago
  • Route Length: 6.7 miles
  • Trail Type: Paved

Located in the northern part of the city, the North Shore Channel Trail is a refreshing change from the Lakefront Trail for a long run in the city. The trail runs parallel to a quiet waterway called the North Shore Channel, and is lined with green spaces. Dotted with trees and bushes, it’s especially beautiful in the fall when the leaves begin to change colors.

Starting at Ronan Park, the North Shore Channel Trail is a quieter running route that spans almost exactly a half-marathon distance both ways. It’s great for distance training or simply running in a different scene.

9. The 606

  • Location: Bloomingdale
  • Route Length: 2.7 miles
  • Trail Type: Paved

Another one of the most unique Chicago trails is the 606, an elevated trail that runs over former railroad tracks. Today, it’s been repurposed into an urban hiking, running, and biking trail. A run on the 606 will take you through green spaces, charming neighborhoods, and historic areas of Chicago.

The entire 606 trail spans 2.7 miles, beginning at Walsh Park and ending at North Ridgeway Ave. Additionally, there are multiple access points along the route where you can enter and exit at your leisure. Because it’s paved and mostly flat, it’s one of the best and most exciting places to go running in Chicago.

10. Humboldt Park

  • Location: NW Chicago
  • Route Length: 2+ miles
  • Trail Type: Gravel

Humboldt Park is located in Wicker Park, one of Chicago’s most fun and quirky neighborhoods. It’s a beautiful, green park area that has several trails for runners, hikers, and bikers. In our opinion, a run here is best paired with brunch or a coffee in one of Wicker Park’s local cafes.

You can access Humboldt Park from the 606 trail for an extended run, or to explore even more of this lovely area of the city. There’s a loop trail around the park that’s short and sweet for a ~2 mile run around the area.

Photo Credit: Sajith T S (Flickr CC)

11. Busse Woods

  • Location: NW Chicago
  • Route Length: 8-mile loop
  • Trail Type: Paved

With over 3,000 acres of woodlands, there’s no shortage of trails to run at Busse Woods. This forest and marsh area is home to lots of local wildlife and picturesque wooded areas, including an elk pasture. At under an hour from the city center, Busse Woods is a great area for running while immersing yourself in nature.

The most popular trail for runners and bikers is Busse Woods’ main 8-mile trail loop, which will take you around a large part of the park. With paved trails, you can enjoy road running while also enjoying the nature and wildlife viewing opportunities around you.

Running in Chicago: Additional Resources


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As a city that’s surrounded by waterways, Chicago is a fantastic city to explore from the water. Hitting the Chicago River or Lake Michigan is one urban adventure that’s worth doing, whether you’re a local or a visitor. Stand up paddle boarding in Chicago is a wonderful way to experience the city from a new perspective, and get some fresh air in the process!

In this guide, we’ve compiled a list of 8 wonderful Chicago stand up paddle boarding spots to help you plan your adventure!

Best Places to Go Stand Up Paddle Boarding in Chicago

1. The Chicago Riverwalk

Chicago’s most popular and famous area is The Loop, which is the downtown area of the city. It’s home to tons of tourist attractions, hotels, restaurants, and more. With walking access to museums, Millennium Park and Navy Pier, it’s easy to understand why this is one of the most popular areas of the city.

The Loop is home to a vibrant Riverwalk that runs parallel to the Chicago River. Here, there are restaurants, sitting areas, and small parks open to the public. Whether you’re a new to stand up paddle boarding in Chicago or area a seasoned paddler, the river is a perfect place to start. The currents and wind aren’t nearly as bad as out on the lake, making this Chicago paddle boarding experience among the most manageable on our list.

Where to Rent a Stand Up Paddle Board on The Riverwalk: Urban Kayak is a popular kayak and paddle board rental company that’s located in the heart of The Riverwalk.

  • Address: 435 E. Chicago Riverwalk, Chicago, IL 60611

2. Monroe Harbor

Located just south on Navy Pier, Monroe Harbor is another iconic spot to go stand up paddle boarding in Chicago. It’s the perfect place to hit the water with the Chicago skyline behind you. From the lake, you can soak in many of Chicago’s most famous sights. Bordering Millennium Park, Grant Park, and the Museum Campus, Monroe Harbor one of the most iconic and picturesque places to go paddle boarding in Chicago.

Monroe Harbor borders Lake Michigan, meaning you’ll primarily be paddling out on the waves of the lake. This can be extra challenging in windy weather or in times of rough water, so be sure to check conditions before you head out on a paddle board.

Where to Rent a Stand Up Paddle Board in Monroe Harbor: Like in the Riverwalk, Urban Kayak also has a stand up paddle board rental location at Monroe Harbor.

  • Address: 110 N Lake Shore Dr, Chicago, IL 60601
Photo Credit: Harshil Shah (Flickr CC)

3. North Avenue Beach

In the summer, North Avenue Beach is among the most popular beaches in Chicago, with over 22,000 square feet of sandy areas to hang out in and explore. It’s a local favorite because it’s located closer to a lot of the more residential areas of the city. It also has tons of small vendors and restaurants where you can buy snacks and refreshments.

Because it’s so busy and vivacious, North Avenue Beach is also one of the most fun and lively places to go paddle boarding on Lake Michigan. As mentioned before, the lake can provide a more challenging experience than paddle boarding on the river because it’s wide open and often has some wind and currents to paddle against.

Where to Rent a Stand Up Paddle Board at North Avenue Beach: On the shores of North Avenue Beach, Chicago SUP offers stand up paddle board rentals, lessons, and guided tours for all levels.

  • Address: 1603 N Lake Shore Dr, Chicago, IL 60611

4. Goose Island

Between the neighborhoods of Wicker Park and Old Town, the Chicago River splits into two branches before reconvening near River North. The resulting “island” is called Goose Island, and its name was made famous by the iconic Chicago beer brand with the same name. Historically, the area was home to a lot of industrial and manufacturing plants, but recently it’s starting to take on a bit more of a green persona.

Stand up paddle boarding in the Goose Island area offers a different experience from the downtown areas because it’s a quieter, more local-oriented area of town. Additionally, this area is the future home of the “Wild Mile,” a floating conservation area that’s still in development by the city of Chicago.

Where to Rent a Stand Up Paddle Board in Goose Island: Kayak Chicago’s Magnolia Street location has you covered for all things paddle boarding.

  • Address: 1501 N Magnolia Ave, Chicago, IL 60642
Photo Credit: John Picken Photo (Flickr CC)

5. Montrose Beach

Montrose Beach is one of the most beloved local beaches in Chicago. Known for its “Mondog” dog-friendly beach and more local crowds, Montrose Beach is a perfect little getaway from the main stretches of Chicago.

You can, of course, enjoy the beach from the banks, but another fun way to explore is from the water! Kayaking in the Montrose Beach area is a fun way to enjoy the water and scope out adorable dogs in the process.

Where to Rent a Stand Up Paddle Board in Montrose Beach: Kayak Chicago has a rental location that has stand up paddle board rentals in Montrose Beach.

  • Address: W Montrose Harbor Dr, Chicago, IL 60640 (located on the south end of the beach)

Map of Chicago Stand Up Paddle Boarding Spots

Here’s a helpful map of the different places to go paddle boarding in Chicago that we’ve mentioned above:

Best Places to Go Stand Up Paddle Boarding Near Chicago

Photo Credit: CheepShot (Flickr CC)

6. Independence Grove

Located just under an hour outside of Chicago, Independence Grove is a recreational area that offers fantastic opportunities to get on the water. Instead of bustling sidewalks, trains, and skyscrapers, you’ll find beautiful green spaces and some peace and quiet here.

Independence Grove boasts a large, clean lake where you can rent kayaks, paddle boards, or boats. Because it’s located inland, there are fewer currents to paddle against, making it a fantastic area for those new to stand up paddle boarding to get out and learn.

Where to Rent a Stand Up Paddle Board at Independence Grove: The Independence Grove Marina offers kayak and stand up paddle board rentals for day use.

  • Address: 16400 West Buckley Road Libertyville, IL 60048
Indiana Dunes National and State Park is one of the best places to go hiking near Chicago.

7. Indiana Dunes National & State Park

In February 2019, Indiana Dunes was named one of the United States’ newest national parks. Known for its golden sand dunes located next to the expansive blue water of Lake Michigan, Indiana Dunes is one of the most picturesque Chicago day trips, and a perfect place to explore on the water.

At just an hour from Chicago, Indiana Dunes National and State Parks offer so many options for people who love the outdoors. For those wanting to explore from the water, stand up paddle boarding is an easy and affordable option. Note that because Indiana Dunes is located on the lake, paddle boarding may be considerably more challenging than in an inland lake or river, but if you’re up for the challenge, the beautiful views of the park will be an excellent reward.

Where to Rent a Stand Up Paddle Board at Indiana Dunes: Miller’s Marine Center offers paddle board rentals nearest to Indiana Dunes. They have a two-hour rental minimum, but you’ll probably need at least that to paddle to and from the Indiana Dunes Park area.

  • Address: 1330 Crisman Rd, Portage, IN 46368
Photo Credit: gabe popa (Flickr CC)

8. Starved Rock State Park

As one of Illinois’ most popular parks, Starved Rock State Park is a stunning recreation area located just 2 hours from chicago. It’s a National Historic Landmark that outdoor enthusiasts will love, marked by canyon-like rock formations, raging waterfalls, and stunning forests.

Aside from hiking and camping, Starved Rock is also a prime spot for exploring on the water. You can rent a stand up paddle board and paddle around the Illinois River, admiring the variety of plant and animal life that calls this region home.

Where to Rent a Stand Up Paddle Board at Starved Rock: Quest Water Sports offers stand up paddle board rentals at Starved Rock State Park hourly and per day.

  • Address: 1800 N 2871st Rd, Ottawa, IL 61350

Additional Resources


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While many people flock to Chicago to wander through the city, eat deep dish pizza, and paddle the Chicago River, there’s a lot to do here for outdoor adventure travelers, too. One fact people are surprised to hear is that there are a ton of great places to go hiking near Chicago!

Whether you’re hitting one of the urban Chicago hiking trails, or you’re planning on taking a day trip to some hiking trails near Chicago, there are tons of choices for you to explore. Here’s a comprehensive list of the 14 best places for hikes near Chicago.

Know before you go: Chicago locals are lucky to have access to trails that range from leisurely strolls to challenging, technical trails. With that said, it’s important to have the right hiking gear as you get out and explore the wilderness, especially in the colder months of the year. For many of the moderate to challenging hikes on our list, we recommend wearing warm, breathable hiking layers and waterproof hiking boots, and packing a set of collapsible trekking poles in case you need extra support on steep trails.

Looking for the perfect gift for your favorite hiker? Here’s a comprehensive list of our
35 favorite (practical) gifts for hikers, updated for 2020!

Top Places to Go Hiking In Chicago

You might be surprised to learn that there are actually a handful of places to go hiking in Chicago…within the city limits! Here are three of the most unique and popular trails where you can get outdoors without leaving the city.

The Lakefront Trail runs beside the waterfront and along Chicago’s many beaches.

1. Chicago Lakefront Trail

  • Trail Length: 18 miles
  • Location: Lake Michigan (Chicago)
  • Difficulty: Easy

The Lakefront Trail blends the best of Chicago’s urban areas with outdoor adventure, and it’s more or less flat, perfect for any level of hiker. Basically, it’s a paved trail that’s shared with runners, dog walkers, and bikers, so it’s less of your normal hike and more of a place to go for a nice, leisurely walk on a sunny day. However, a hike on the Lakefront Trail is one of the easiest ways to enjoy the outdoors without leaving Chicago’s downtown area.

In total, the Lakefront Trail is 18 whole miles, so you’ll never run out of places to explore while hiking in Chicago. Along it, there are tons of beach hangout areas, cute waterfront restaurants and bars, graffiti-lined underpasses, and plenty of people watching. You’ll also pass by the iconic Navy Pier, Monroe Harbor, the Museum District, and of course, the city skyline itself.

The best time to enjoy the Lakefront Trail is at sunrise, when the sun hangs low over the water and you can catch the coolest, crispest summer air in Chicago.

You can run, hike, or bike on the 606! Photo Credit: Daniel Lobo

2. The 606

  • Trail Length: 2.7 miles
  • Location: Humboldt Park (Chicago)
  • Difficulty: Easy

Another one of the most unique Chicago hiking trails is the 606, an elevated trail that runs over former railroad tracks. Today, it’s an urban hiking, running, and biking trail that runs through green spaces, charming neighborhoods, and historic areas of Chicago. The 606 is a great place to go hiking in Chicago while exploring some of the neighborhoods outside of downtown.

The entire 606 trail spans 2.7 miles, beginning at Walsh Park and ending at North Ridgeway Ave. If you don’t want to hike the whole thing, there are multiple access points along the trail where you can enter and exit at your leisure. Because it’s paved and mostly flat, it’s one of the best hikes in Chicago and the surrounding areas for all levels of hikers.

3. Lincoln Park Trail

  • Trail Length: 5.5 miles
  • Location: Lincoln Park (Chicago)
  • Difficulty: Easy

Lincoln Park is one of the most beloved residential areas of Chicago, and in the middle of it lies a large, green park area that houses many walking trails, a lake, and the Chicago Zoo. The Lincoln Park Trail winds through the park’s wooded areas provide an easy, leisurely, family-friendly area to go for a day hike in the city.

Within the park, you’ll find 1200 acres of green spaces and recreation areas to enjoy. Along your hike, you can admire the gorgeous Victorian architecture in the neighborhood, and you can stop by the zoo or the Lincoln Park Conservatory. Nearby, the Lincoln Park trails lead to the North Avenue Beach stretch of the Lakefront Trail, perfect for an extra-long urban hike if you’re wanting to extend your adventure.

Top Places to Go Hiking Near Chicago

Once you leave Chicago’s bustling downtown area, you’ll start to find more traditional hiking opportunities along gravel trails, forested areas, and rocky terrain. These incredible spots for hiking near Chicago boast sand dunes, gorgeous waterfalls, stunning rock formations, unique wildlife, and more.

4. Waterfall Glen Forest Preserve

  • Trail Length: 11 miles
  • Location: Willowbrook, IL
  • Distance from Chicago: 25 miles (~1 hour)
  • Difficulty: All Levels

Located about an hour outside of Chicago, Waterfall Glen Forest Preserve is a gem of a park for hikers, bikers, and outdoor lovers. The park features a few picturesque waterfalls, and a rocky bluff overlook at Sawmill Creek. Although it’s not far from Chicago, the park features gravel paths, forested areas, and tons of local wildlife and plant species.

One of the perks of Waterfall Glen Forest Preserve is that it’ a year-round destination. In the summer, visitors can hike, bike, and bird-watch, and in the winter, people use the area for cross-country skiing. With gentle slopes and beautiful sights, it’s one of the most fun and family-friendly areas for hikes near Chicago.

Midewin National Tallgrass Prairie

5. Midewin National Tallgrass Prairie

  • Length: 3.6 miles
  • Location: Will County, IL
  • Distance from Chicago: 50 miles (~1.5 hours)
  • Difficulty: Easy

If it’s prairie life you’re looking for, Midewin National Tallgrass Prairie is the perfect place to go hiking near Chicago. This nationally protected prairie area is a popular place to go biking, hiking, and bison-watching. Yup, you heard that right: Midewin National Tallgrass Prairie is home to a bison herd that you can observe with your own two eyes.

People often forget that the prairie is the landscape of the Midwest, and that it can be beautiful in its own way. While you won’t see ton of topography here, Midewin is home to lots of trails that pass through wildflower fields, grazing pastures, and tons of places for bird watching.

6. Kankakee River State Park

  • Length: 3-12 miles
  • Location: Kankakee County, IL
  • Distance from Chicago: 60 miles (~1.5 hours)
  • Difficulty: All Levels

To admire the fall colors and enjoy the crisp, cool weather, there are few better places to go hiking near Chicago than Kankakee River State Park. A historic area that was once home to Native American settlements, this lush, forested river area is equal parts tranquil and full of adventure opportunities.

To explore the park, the best place to start is with the 3-mile Rock Creek Trail. This is one of the most scenic Chicago hiking trails as it twists through rocky canyons, along the flowing river, and past a bubbling waterfall, all with the beautiful forest canopy overhead.

Photo Credit: pedrik (Flickr CC)

7. Fermilab National Accelerator Laboratory Trail

  • Length: Varies, multiple trail variations are possible
  • Location: Batavia, IL
  • Distance from Chicago: 40 miles (~1.5 hours)
  • Difficulty: Easy

In our opinion, the Fermilab National Accelerator Laboratory Trail is one of the strangest options for hikes near Chicago on our list. Where a former particle collider once stood now lies a repurposed hiking, biking, and dog walking recreation area that’s home to nearly 40 miles of trails. After years of renovation, the park is now open as a nature preserve, which provides a home for herds of bison that you may be able to spot during your visit.

There are several different hiking options at Fermilab, depending on how much time you’d like to spend there. If you’re interested in the science behind this area, hike the loop above the decommissioned Tevatron collider to catch a glimpse at it. You can even take a tour after your hike!

Photo Credit: Conal Gallagher Flickr CC

8. Morton Arboretum

  • Length: 0.25-1.5 miles
  • Location: DuPage County, IL
  • Distance from Chicago: 25 miles (~1 hour)
  • Difficulty: Easy

For a peaceful, easy hike through a gorgeous nature area, Morton Arboretum is a great option for hikes near Chicago. As one of the shorter trails on our list, the arboretum is a great place to spend a leisurely afternoon walking around and learning about the protected tree and plant species that grow on the property.

Note that there is a $15 entrance fee for Morton Arboretum that helps to cover the costs of maintaining and caring for the plants.

Photo Credit: Brady Wieland (Flickr CC)

9. Starved Rock State Park

  • Length: 13 miles (trails ranging from 0.3-4.7 miles)
  • Location: LaSalle County, IL
  • Distance from Chicago: 100 miles (~2 hours)
  • Difficulty: All Levels

Perhaps the most popular place to go hiking near Chicago, Starved Rock State Park is a stunning, family-friendly nature area that boasts several miles of forested hiking trails for all levels of hikers. While here, you can see caves, rock formations, canyons, waterfalls, and more as you tackle some of the most famous hikes near Chicago and in Illinois. It does get pretty crowded here in the warmer months of the year, but when you visit, you can easily see why!

Within the park’s grounds, there are over 18 canyons to explore and marvel at. Many of the trails lead through and above these many canyons. Some of the most popular hikes in the park are the Saint Louis Canyon Trail and the LaSalle Canyon Trail. Additionally, the park offers free guided hikes on weekends through late November. We recommend going there in the fall to experience the breathtaking foliage colors.

10. Matthiessen State Park

  • Length: 5 miles
  • Location: LaSalle County, IL
  • Distance from Chicago: 100 miles (~2 hours)
  • Difficulty: All Levels

If it’s more diverse hikes you’re after, Matthiessen State Park is a great Chicago hiking area to start. With caves, canyons, and gorgeous rock formations, this state park is definitely a hidden gem amidst the Midwest prairie. Think of Matthiessen State Park as Starved Rock’s smaller sister – it’s still got beautiful, forested rock canyons but only a fraction of the visitors.

Suitable for all levels of hikers, there are easy hikes along the bluffs and upper areas of the park. For more of a challenge, the more difficult adventures include the Dells Canyon and Bluff Trails, which bring you along steep drop offs and through deep, picturesque canyons. It’s definitely the kind of place you don’t expect to be located just a few hours outside of Chicago!

Photo Credit: Sajith T S (Flickr CC)

11. Ned Brown Forest Preserve

  • Length: 12.9 miles of paved trails
  • Location: Elk Grove Village, IL
  • Distance from Chicago: 20 miles (~45 minutes)
  • Difficulty: All Levels

With over 3,000 acres of woodlands to hike through, there’s no shortage of things to see and do at Ned Brown Forest Preserve. Also known locally as Busse Woods, this forest and marsh area is home to lots of local wildlife and picturesque wooded areas to hike and unwind, including an elk pasture! At under an hour from the city, Ned Brown Forest Preserve is one of the most accessible nature areas from the city.

With a beautiful lake area and lots of wildlife, Busse Woods is also a popular place to go kayaking in the Chicago area. Hiking it by foot gives you the unique advantage of pristine lake views, which are especially beautiful in the fall when the leaves begin to change colors.

12. Glacial Park Conservation Area

  • Length: 8 miles
  • Location: McHenry County, IL
  • Distance from Chicago: 60 miles (~1.5 hours)
  • Difficulty: Easy

If you’re seeking a super photogenic, tranquil hiking trails near Chicago, Glacial Park Conservation Area in McHenry County is a perfect option. With nearly 500 acres of nature preserve, it’s a lovely place to experience local protected species without straying too far from Chicago. It’s also a popular spot for birders in the area, as it’s a common place for migratory wetland birds to pass through.

Most of the 8 miles of trails here consist of open prairie, passing through marshy wetlands and grassy areas. You can spot local wildflowers, birds, and turtles in the area, and visit the visitor’s center to learn more about the species that inhabit the preserve.

One of the most beloved places to go hiking near Chicago - Devil's Lake State Park.
Devil’s Doorway, one of the many trails near Devil’s Lake. Photo Credit: Tom Gill (Flickr CC – also used as feature image)

13. Devil’s Lake State Park

  • Length: Up to 13.7 miles
  • Location: Sauk County, WI
  • Distance from Chicago: 190 miles (~3.5 hours)
  • Difficulty: Moderate to Difficult

For hikers looking for natural beauty paired with challenging trails, Devil’s Lake is one of the few places near Chicago that offers both. While it’s admittedly not that close to the city (~3.5 hours, depending on traffic), we’ve chosen to include it on here because Devil’s Lake is truly a spectacular place to go hiking near Chicago.

As part of the Ice Age National Scientific Reserve, Devil’s Lake is full of striking rock formations that were carved by glaciers during the Ice Age. While it’s popular for outdoor rock climbing near Chicago, it’s also a fantastic place for hiking. One of the most popular trails is the challenging 13.7-mile Ice Age Trail, but there are several trail options of various lengths and difficulties for intrepid hikers.

Note that there is a $16 entrance fee to help protect and maintain the park.

Indiana Dunes National and State Park is one of the best places to go hiking near Chicago.

14. Indiana Dunes National and State Parks

  • Length: 0.5-6.8 miles (21 trails in total)
  • Location: Chesterton, IN
  • Distance from Chicago: 50 miles (~1 hour)
  • Difficulty: All Levels

As one of the newest official national parks, Indiana Dunes is nothing to sneeze at. While this lakefront state and national park area is known for its golden sand dunes and gorgeous location next to Lake Michigan, there are lots of great hikes to enjoy here, too!

The park contains a variety of terrain, from wetlands to savannas, and, of course, the sandy beach. During the warmer months of the year, you’ll find tons of beachgoers here enjoying the sand and sun.

For hikers, there are 21 trails total – 7 in the state park and 14 in the national park. Some of the most popular trails include the West Beach Trail (in the national park) and Trail 10 (in the state park).

Additional Resources


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