6 Chicago’s Best Outdoor Activities

If you think Chicago is all about deep-dish pizza and windy weather, you’re seriously missing out. Explore the many unforgettable outdoor activities in and around Chicago to make memories with your friends and family.

Gear up with the latest kayaks, stand up paddleboards, and hybrid bikes for sale to create your own outdoor adventures in this exciting Midwestern city.

Chicago's Best Outdoor Activities

1. Walking Tours

Chicago’s many neighborhoods are unique and refreshing, so take some time on your next visit or free weekend to walk the streets. Grab some friends and explore the city on foot or with city bicycles.

Consider signing up for a guided tour to brush up on your history or to hear about all the hidden gems around the city.



2. Chicago River Kayaking

Kayak the Chicago River to see the city from a unique perspective. Rent an affordable kayak in the city and set out on a tour or a solo adventure if you’re confident in your abilities.

Look for a themed kayak tour for a fun-filled paddling experience, or get your fill of the historic architecture from this unique angle.

3. Maggie Daley Park Rock Climbing

After a few hours in Maggie Daley Park, you’ll feel like you scaled a mountain. Enjoy the 40-foot outdoor climbing wall to boulder, lead climb, top rope, and take on other rock climbing experiences.

Maggie Daley Park is the perfect place for beginners and experienced climbers alike, and it’s surprisingly affordable for its size.

4. Lake Michigan Stand Up Paddle Boarding

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While Chicago isn’t on an ocean, Lake Michigan feels like one. This sprawling lake offers all the outdoor activities found on the coast.

Bring your surfboard, stand up paddleboard or other seaside activity, and find a great spot to hit the beach. Wait for a calm day or get a great workout paddling against the wind.

5. Bike The Trails

From the Lakefront Trail to the 606, Chicago is packed with great hiking and cycling trails. Ride through diverse neighborhoods or take a stunning stroll right by the beach.

Check out the 606 by heading to either Walsh Park or North Ridgeway Ave. The entire trail is 2.7 miles, so it’s perfect for a long walk or a leisurely ride.

For a more bike-friendly distance, the Lakefront Trail is a full 18 miles of stunning beach and cityscape scenery. Watch for Navy Pier, the Museum District, and Grant Park on one side and breathtaking views of Lake Michigan on the other.

When you’re ready for a break from these iconic trails, find your nearest green space. Chicago is packed with beautiful green spaces and parks full of amenities, so there’s usually a great place to park and have a picnic while you’re hitting the trails.



6. Prepare For Your Next Outdoor Adventure

Whether you’re a long-time resident of the windy city or preparing for your first visit, prepare for your outdoor adventure with the right gear.

Check out the best city cruiser bikes to hit the streets in comfort. Biking is a great way to explore the city and get to your next outdoor adventure.

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