The 6 Best Canoe & Kayak Experiences in Chicago
Chicago’s lakefront and urban waterways make it a prime spot for paddle sports. The city’s iconic architecture, world-class parks, and sprawling Lake Michigan views set the scene for memorable kayaking and canoeing outings. Whether you’re after a guided cultural tour, a leisurely paddle on the lake, or an active day exploring both land and water, Chicago offers options for all levels and interests. Notably, many tours include free bike or kayak rentals, allowing you to extend your adventure beyond the initial experience.
What makes Chicago especially attractive for paddle sports is its combination of scenic natural beauty with lively city sights. You can float past Millennium Park’s Cloud Gate, paddle along the Chicago River, or enjoy the tranquility of Lake Michigan while soaking up skyline views. With options ranging from quick rentals to full-day guided tours, there’s a paddle adventure to match your schedule and curiosity.
Quick Overview
Our list features guided food tours combined with kayak or bike rentals, such as the Chicago: Classic Food Walking Tour with Bike or Kayak Rental, which blends Chicago’s famous eats with urban exploration. For those looking for a more independent experience, the Chicago’s Lake Michigan Downtown Kayak Rental at Ohio Street Beach offers a flexible, scenic paddle in the heart of the city’s most picturesque waterfront. And if you want a comprehensive day combining multiple outdoor activities, the Chicago Adventure Pass: Bike, Kayak and Swim provides a multi-sport outdoor day. Below, we explore each option in detail to help you decide which suits your style best.
1. Chicago: Classic Food Walking Tour with Bike or Kayak Rental
Starting with an engaging twist on Chicago sightseeing, this tour combines tasting local foods with urban exploration. For around $80, you’ll join a guided walk through iconic areas like Millennium Park and the Riverwalk, sampling Chicago-style deep-dish pizza, hot dogs, Italian Beef sandwiches, and the city’s famous brownies. But what we love about this tour is the FREE 2-hour bike or kayak rental, valid within 3 days of booking, which adds a flexible outdoor dimension.
The tour is led by a local, professional guide who shares stories behind Chicago’s culinary scene and landmarks. With a 4.8-star rating from 135 reviews, it’s clear that visitors appreciate the mix of food and city highlights. Reviewers mention the informative guides and delicious samples that truly showcase Chicago’s culinary identity. The tour’s value is enhanced by the rental—offering a chance to revisit sites on your own or explore Lake Michigan’s shoreline afterward.
This experience is ideal for travelers wanting a taste of Chicago’s flavors combined with cultural sights without a long time commitment. It’s perfect for first-time visitors eager to combine eating with outdoor activity. Keep in mind, availability varies, so booking ahead is wise.
Bottom Line: A lively, well-rated tour blending Chicago’s best foods with outdoor rentals, suitable for those who enjoy a flexible, engaging half-day adventure.
2. Chicago’s Lake Michigan Downtown Kayak Rental at Ohio Street Beach
If you’re seeking independent freedom on Lake Michigan, this kayak rental is a top choice. For just $39.99 per person, you get a 1- or 2-hour rental in single or tandem kayaks, perfect for enjoying the city’s skyline at your own pace. The location at Ohio Street Beach is ideal: a short paddle from downtown’s bustling waterfront, with views of Navy Pier and the city’s skyscrapers.
Many reviewers emphasize how straightforward the rental process is—Evan, the staff member, was friendly and helpful, making it easy for first-timers to get started. The calm waters and wide-open views create a surreal experience, especially for those wanting a tranquil break from city streets. The option to extend your rental allows for a relaxed afternoon exploring or simply floating for fun.
Suitable for older children (13+ with adults), this rental is best for independent paddlers comfortable with basic watercraft. If you’re looking to combine scenic views with a flexible schedule, this is a perfect pick.
Bottom Line: An easy, affordable way to paddle Lake Michigan, offering independence with stunning skyline views and a friendly rental process.
3. Chicago: Best of Attractions Walking Tour + Bike/Kayak Rental
At number 3, this guided tour provides a rundown of Chicago’s top sights with a focus on architecture and history. Visiting Millennium Park, exploring the Chicago Theater, and walking along Michigan Avenue, this two-hour tour is led by a local guide who shares context and stories you won’t find in guidebooks.
What makes this tour stand out is the complimentary 2-hour bike or kayak rental, which extends your exploration beyond the walking route. This allows you to revisit Millennium Park, paddle along the Chicago River, or cruise the lakeshore at your leisure. The tour has received perfect scores from recent reviews, with visitors praising the guide’s knowledge and the opportunity to experience Chicago from multiple angles.
This option is well-suited for travelers wanting a balanced mix of guided sightseeing and independent outdoor fun. The inclusion of free rental adds significant value, especially if you want to diversify your time in the city without booking separate activities.
Bottom Line: A perfect combination of cultural sightseeing and outdoor exploration, ideal for visitors wanting a broad taste of Chicago’s highlights.
4. Chicago Highlights Walking Tour with Free Bike or Kayak Rental
Designed for first-timers or anyone eager to cover Chicago’s essentials, this two-hour walking tour takes you from the elegant Palmer House Hilton to Millennium Park and beyond. You’ll see the Art Institute’s famous lions, Cloud Gate, and the bustling Michigan Avenue. The guide, with a knack for storytelling, makes the city’s history and architecture come alive.
What sets this experience apart is the free 2-hour bike or kayak rental offered afterward—an excellent way to continue your exploration without extra costs. Many reviews highlight how this opportunity allows visitors to relax and see the city from different perspectives on their own schedule. The tour’s focus on insider tips makes it especially useful for first-time visitors.
Ideal for travelers who want a compact, informative introduction combined with outdoor activity, this tour balances guided insight with flexible independent adventures. It’s also a good value, given the free rental included in the price.
Bottom Line: An efficient, well-loved tour for those wanting quick immersion into Chicago’s top sights with the option to extend their day on water or bike.
5. Chicago: Full Day Food Walking Tour + Free Bike/Kayak Rental
For those eager to combine a full day of culinary delights with outdoor activities, this tour covers Chicago’s must-eats and attractions over about five hours. Starting with deep-dish pizza, hot dogs, Italian Beef sandwiches, and a brownie, it’s a feast for the senses. The tour also includes stops at Millennium Park, Michigan Avenue, and the Chicago Theatre, all led by a local guide sharing stories and insights.
Adding significant value, this tour’s free 2-hour bike or kayak rental gives you the chance to continue exploring Chicago’s lakefront or revisit favorite spots on your own. Though slightly pricier at $100, reviews suggest it’s a worthwhile splurge for food lovers wanting a comprehensive taste of the city in one day.
Best suited for travelers with a hearty appetite and a full day to spare, this experience offers a balanced mix of guided tasting and independent outdoor fun.
Bottom Line: A delicious, all-encompassing day tour perfect for those eager to savor Chicago’s flavors and scenery without rushing.
6. Chicago Adventure Pass: Bike, Kayak and Swim
This flexible multi-sport outdoor pass is ideal for active travelers who want to get the most out of Chicago’s outdoors in 1 to 3 days. It includes 4 hours of bike rental along the 20-mile Lakefront Trail, which stretches from Evanston to South Shore. Along the way, you’ll pass landmarks like Millennium Park, Buckingham Fountain, and the Museum Campus.
In addition, the pass offers 2 hours of kayaking or paddleboarding at Ohio Street Beach, with skyline views perfect for photos. The option to add a 2-hour swim makes it a full outdoor day. No reviews are available yet, but the itinerary suggests it’s best for those with a good level of fitness and a desire for an active outdoor experience.
This experience is perfect for travelers who want a multi-activity outdoor day, combining cycling, paddling, and swimming—all in the city’s outdoor “front yard.”
Bottom Line: A versatile outdoor pass for active explorers seeking a multi-sport day on Chicago’s lakeshore.
How to Choose the Right Canoe & Kayak Experience
When selecting a paddle experience in Chicago, consider your budget, time availability, and interest in guided versus independent activities. If you prefer a guided cultural and culinary tour, options like the Chicago: Classic Food Walking Tour with Bike or Kayak Rental or the Best of Attractions Walking Tour are excellent choices. For those wanting more independence and flexibility, the Lake Michigan Downtown Kayak Rental provides a simple, scenic paddle.
Active travelers interested in a full outdoor day might prefer the Chicago Adventure Pass, which combines biking, kayaking, and swimming. Meanwhile, if you’re on a tighter schedule or traveling with older children, the quick rentals at Ohio Street Beach are a straightforward option.
Booking early is advisable, especially for popular time slots in summer. Think about whether you want a guided experience with storytelling or prefer to explore at your own pace—both can deliver memorable Chicago water adventures.
Final Thoughts
Chicago’s canoe and kayak experiences range from guided city tours blending food and architecture to independent lakefront paddles offering serenity and skyline views. For a guided, educational outing, the Chicago: Classic Food Walking Tour with Bike or Kayak Rental and the Best of Attractions Walking Tour stand out. If you prefer independent exploration, the Lake Michigan Downtown Kayak Rental is a top choice.
For those looking to maximize outdoor activity in a single day, the Chicago Adventure Pass offers a flexible, energetic experience. Whatever your style, Chicago’s water-based adventures promise unforgettable views and a chance to see the city from a fresh perspective. Be sure to book early, especially during peak summer months, to secure your spot on these popular tours.