Chicago is a city that lives and breathes on its waterways. With the shimmering Lake Michigan, the flowing Chicago River, and numerous smaller waterways, it’s an ideal destination for Canoe & Kayak Experiences. Whether you want to paddle past soaring skyscrapers, explore peaceful natural habitats, or combine outdoor fun with city sightseeing, Chicago offers something for every water lover. We especially like the Chicago: Classic Food and Walking Tour with Free Bike/Kayak for its blend of city highlights, local eats, and bonus outdoor activity—it’s a great way to see Chicago’s famous Millennium Park and Riverwalk while enjoying a free kayak rental.
If you prefer a serene, lakeside paddle, the Chicago’s Lake Michigan Downtown Kayak Rental at Ohio Street Beach offers a relaxed, flexible experience with stunning skyline views. For a more urban adventure, the guided Chicago: History and Architecture Guided Kayak Tour provides an up-close look at downtown Chicago’s iconic structures and engineering marvels. Whatever your interest, this list covers the best ways to paddle in Chicago.
1. Chicago: Classic Food and Walking Tour with Free Bike/Kayak
This tour stands out for combining a guided food tour with a free kayak or bike rental, making it a fantastic way to explore Chicago’s highlights actively. For just $80, you’ll spend about 3 hours enjoying Chicago’s famous eats—deep-dish pizza, hot dogs, Italian beef, and desserts—while also visiting landmarks like Millennium Park and the Chicago Riverwalk. The highlight is the FREE 2-hour bike or kayak rental, which you can enjoy within three days of booking, adding a wonderful outdoor element to your city visit.
What makes this tour special is its perfect balance of cultural insight, local flavors, and outdoor fun. The tour is praised for its personable, professional guide who shares stories about Chicago’s history and cuisine. The value is excellent, considering the food, guided commentary, and outdoor rental are all included. It’s ideal for travelers who want to combine city sightseeing with waterside recreation without paying separate rental fees.
Bottom Line: A well-rounded option for food lovers and active explorers who want a taste of Chicago’s best—from its iconic foods to its scenic riverfront.
2. Chicago’s Lake Michigan Downtown Kayak Rental at Ohio Street Beach
Offering a pure lakefront kayaking experience, this rental at Ohio Street Beach is perfect for those who want flexibility and stunning skyline views. For $39.99 per person, you get a 1 to 2-hour rental of a single or tandem kayak, with the option to extend your time. The location is slightly tucked away, but the calm waters of Lake Michigan provide a peaceful escape from the city’s hustle.
This experience is highly rated for its simplicity and scenic rewards. You can paddle at your own pace, enjoying vistas of Chicago’s skyline, Navy Pier, and the shoreline. Beginners can partner with more experienced paddlers using tandem kayaks, and older children (13+) are welcome with adult supervision. Reviewers mention the helpful staff and the surreal, mesmerizing views.
Bottom Line: An excellent choice if you want the freedom to paddle on Lake Michigan with minimal fuss and maximum scenery.
3. Chicago: 2-Hour Downtown Kayak Rental
This rental offers the chance to paddle in the heart of Chicago on the Chicago River itself. For $63, you’ll enjoy a 2-hour rental of a single or tandem kayak, with easy access to the city’s most iconic architecture. The experience begins with a paddling lesson, ensuring even beginners feel comfortable navigating the river.
What sets this apart is the chance to get close to Chicago’s stunning skyline, including views of the Willis Tower and the John Hancock Center. It’s a self-guided experience, perfect for those who want a flexible schedule and a more active outing. Reviewers appreciate the straightforward process and the fun of paddling through downtown’s lively waterway.
Bottom Line: A great option for urban adventurers who want to combine active outdoor fun with sightseeing of Chicago’s architectural wonders.
4. Chicago: History and Architecture Guided Kayak Tour
For around $64, this guided kayak tour takes you through downtown Chicago’s river system with an emphasis on its history and architecture. Led by a knowledgeable guide, you’ll paddle beneath ironwork bridges and alongside towering skyscrapers, learning how the city’s engineering feats shaped its skyline. The tour includes stories about the river’s fascinating reversal flow and notable buildings.
Guests love the personal touch and in-depth storytelling, with a focus on Chicago’s role in shaping modern urban design. The tour lasts about 2 hours and is suitable for most paddlers. It’s ideal for travelers interested in the city’s development, engineering, and landmark architecture.
Bottom Line: An immersive, educational paddle for history buffs and architecture enthusiasts who want a guided experience.
5. Chicago Highlights Walking Tour with Free Bike or Kayak Rental
If you prefer exploring on foot but want outdoor activity included, this walking tour covers Chicago’s must-see sights like Millennium Park, the Art Institute, and the Riverwalk. Priced at $44.99 for about 2 hours, it comes with a bonus free 2-hour bike or kayak rental to extend your day.
This tour is praised for its lively storytelling and renowned location stops, including the Art Institute and Millennium Park. During the tour, you’ll get insider tips, and afterward, you can take advantage of the outdoor rental to bike along the scenic Lakefront Trail or paddle on Lake Michigan. It’s perfect for those who want a deep dive into Chicago’s culture, then enjoy outdoor recreation at their own pace.
Bottom Line: An excellent combo for those who enjoy walking and want the option to add outdoor fun without extra cost.
6. Chicago: 2-Hour Kayak Rental from Bridgeport
This rental offers a peaceful paddle through the calm waters of Bubbly Creek in Bridgeport. For $49 per person, you can enjoy 2 hours exploring this historic waterway, known for its connection to Chicago’s stockyards. You’ll see wildlife such as herons and turtles and experience a different side of the city’s natural environment.
What makes this experience unique is its focus on the quiet, natural habitat away from the busy downtown. Reviewers comment on the tranquility and the opportunity to observe local wildlife. It’s best suited for paddlers seeking a low-key, natural escape rather than city architecture.
Bottom Line: Ideal for nature lovers wanting a peaceful paddle close to Chicago’s industrial past.
$49 per person
7. Chicago Half-Day Walking Food Tour with Free Bike or Kayak Rental
This comprehensive 5-hour walking tour combines Chicago’s top culinary delights with sightseeing. Starting with deep-dish pizza at Lou Malnati’s, and lunch at Billy Goat Tavern, the tour covers iconic spots like Millennium Park and the Chicago Theatre. For just $99, it also includes a bonus 2-hour free bike or kayak rental to extend your day.
Guests rave about the food, the lively guide, and the chance to see major landmarks. The tour provides rich context about Chicago’s history and culture, making it perfect for first-timers or those wanting a full day of activity. After the tour, you can take advantage of the outdoor rental for additional sightseeing.
Bottom Line: An immersive, full-day experience blending food, culture, and outdoor adventure.
$99.00 per person
8. Chicago: Moonlight Paddle Tour on the Chicago River
Paddle at night on this moonlight tour for a different perspective of Chicago. For $58, you glide along the river with the city’s skyline lit by moonlight and city lights. The tour lasts about 1.5 hours and offers a tranquil, less crowded route through downtown.
Reviews mention the surreal feeling of paddling in the quiet night, with views of Willis Tower and Marina City. It’s perfect for couples or anyone wanting a romantic or peaceful evening paddle. No prior experience is needed as orientation is provided.
Bottom Line: A magical way to see Chicago’s skyline in the evening, ideal for date nights or sunset lovers.
9. Chicago: Sunset Kayak Tour on the Chicago River
This sunset tour provides a peaceful paddle during the golden hour. For $58, you’ll enjoy about 1.5 hours exploring the river with views of the Willis Tower and Civic Opera Building as the sun sets. The tour is leisurely paced, perfect for all skill levels, and includes a brief safety orientation.
Reviewers love the changing sky colors and the chance to see the city’s landmarks bathed in sunset light. It offers a relaxed, scenic experience that’s ideal for photography or simply enjoying Chicago’s evening ambiance.
Bottom Line: A calm, scenic paddle that captures the city’s beauty at dusk, perfect for sunset seekers.
10. Chicago: Full Day Food Walking Tour + Free Bike/Kayak Rental
This tour combines Chicago’s top food stops with sightseeing and outdoor activities. Over 5 hours, you get tastes of deep-dish pizza, hot dogs, Italian beef, and more, along with visits to Millennium Park, the Riverwalk, and Michigan Avenue. The $100 price includes a free 2-hour bike or kayak rental, making it easy to extend your exploration.
Guests appreciate the mix of delicious food and cultural insights, with a focus on local favorites. After the tour, you can use the outdoor rental to explore the lakefront or paddle on Lake Michigan. It’s suited for those wanting a full-day experience combining tastes and outdoor fun.
Bottom Line: Perfect for those who want a comprehensive Chicago experience—food, culture, and outdoor activities—all in one day.
11. Chicago: Characters and Con-Guided Kayak Tour
This tour offers a unique look into Chicago’s criminal past, focusing on figures like Leo Koretz and the Leopold and Loeb case. For $63, you paddle through the river system with a guide sharing riveting stories of Chicago’s notorious con men and murderers.
It’s a 2-hour guided adventure, perfect for history buffs or those interested in Chicago’s darker stories. The personalized storytelling makes this tour stand out from standard kayak rentals, adding a layer of intrigue to the city’s architectural landscape.
Bottom Line: An engaging, story-driven kayak tour for those fascinated by Chicago’s criminal side.
$63 per person
12. Chicago: Ghosts and Gangsters Night Kayak Tour
Experience Chicago’s spooky side on this night kayak tour, where stories of mobsters and haunted locations come alive. For $71, you paddle in the dark, passing sites linked to Al Capone and haunted spots, with storytelling that adds a thrill to your paddle.
Reviews note the eerie atmosphere and the excitement of paddling through a city with a dark, storied past. It’s tailored for night owls or those who love ghost stories. The peaceful, less crowded night makes for a memorable adventure.
Bottom Line: An exciting, slightly spooky paddle for those interested in Chicago’s mobster lore and haunted history.
$71 per person
13. Chicago Adventure Pass: Bike, Kayak and Swim
This all-in-one outdoor pass offers a 4-hour bike ride along the Lakefront Trail, 2 hours kayaking on Lake Michigan, and 2 hours swimming at beach spots. Costs $79.99 and is perfect for active travelers wanting multiple outdoor experiences in one package.
The Lakefront Trail ride covers 20 miles, passing major landmarks like Millennium Park and Buckingham Fountain. The kayak and swim options provide a complete outdoor day, with rentals departing from Ohio Street Beach. Reviewers mention the flexibility and fun of combining multiple activities.
Bottom Line: An ideal choice for outdoor enthusiasts seeking variety and full-day adventure with all equipment included.
$79.99 per person
How to Choose Your Chicago Canoe & Kayak Experience
When deciding between these options, consider your budget, time, and interests. For a city-centric experience with food and architecture, the Classic Food and Walking Tour or the Half-Day Food Tour offer rich cultural highlights plus outdoor fun. If a peaceful lakeside paddle is more your style, the Lake Michigan rental provides flexibility and stunning views.
For those interested in a guided, educational tour, the History and Architecture Guided Kayak is perfect, while the Night Tours and Ghosts and Gangsters are better suited for thrill-seekers or those fascinated by Chicago’s darker tales.
Booking early can secure your spot, especially during peak summer months. Think about your fitness level—most tours are accessible to beginners, but guided tours are often the easiest to enjoy without worry.
To sum it up, Chicago’s waterways offer a fantastic variety of paddle experiences. From relaxing lakefront rentals to guided city tours, there’s something to match every interest and schedule. For a lively blend of food, culture, and outdoor activity, the Chicago: Classic Food and Walking Tour with Free Bike/Kayak is hard to beat. For serenity and skyline views, the Lake Michigan rental shines. Whatever you choose, early booking ensures you won’t miss out on these memorable Chicago water adventures.