Chicago is one of those cities that simply begs to be explored on two wheels. With wide lakefront paths, neighborhood charms, and city skyline views, biking in Chicago offers a flexible, fun, and healthy way to see the city’s best sights. Whether you’re a foodie craving deep-dish pizza and hot dogs or a history buff eager to pedal past Wrigley Field and Millennium Park, there’s a bike tour tailored for you. We especially appreciate tours that combine delicious sampling and sightseeing, like Bikes, Bites, and Brews, which takes you through Chicago neighborhoods with generous tastings of local eats and craft beer. For a more relaxed experience, the Chicago’s Ultimate City Bike Tour offers a scenic loop of parks and monuments perfect for families or first-time visitors.
Chicago’s bike-friendly infrastructure and diverse neighborhoods make it a perfect city for cycling tours. Combining urban exploration with local flavor, these experiences not only show you the city’s top attractions but also give you a taste of its character and history. Whether you prefer a guided ride or a rental to explore at your own pace, this list highlights the best options to help you pedal your way through the Windy City.
Quick Overview
Our list includes guided bike tours that cover Chicago’s most famous neighborhoods, parks, and landmarks, often with food and drink stops. From the Lakefront Neighborhoods to the West Side foodie spots, each tour offers a unique perspective. For those wanting flexibility, full-day bike rentals let you craft your own adventure, while shorter options focus on iconic sights like Millennium Park and Wrigley Field. If you’re planning a family trip, the Chicago Family Food and Bike Tour combines sightseeing with kid-friendly snacks. For a more active experience, the E-Bike Tour uses electric bikes to explore the city effortlessly. Keep reading for detailed descriptions of each top-rated tour.
1. Bikes, Bites, and Brews: Chicago’s Signature Dishes Bike Tour
At number 1, this highly rated tour offers a delicious mix of Chicago’s famous foods, neighborhoods, and history. Over approximately 4.5 hours, you’ll cycle around iconic areas like Wrigleyville, Lincoln Park, and the Gold Coast, sampling deep-dish pizza, Chicago hot dogs, brownies, and craft beer. The tour covers about 13 miles at a moderate pace, making it accessible for most riders. Your guide shares engaging stories about Chicago’s culture and architecture, enhancing the experience beyond just food. The day route takes you through Lincoln Park and Wrigley Field, while the night route explores the Riverwalk, Millennium Park, and Buckingham Fountain, both offering stunning city views.
What makes this tour stand out is its generous tastings, which add up to a full meal, plus beer. Guests love the lively guides and the chance to see multiple neighborhoods in one go. With a perfect rating of 5.0/5 from 634 reviews, it’s clear this tour provides great value and fun. Perfect for foodies and those wanting a city overview with a tasty twist.
Bottom line: If you want Chicago’s best bites with a side of local lore, this tour is a reliable, flavorful choice.
2. Bike Tour of Chicago’s Lakefront Neighborhoods
At number 2, this small-group tour offers an intimate look at the city’s scenic lakefront and historic neighborhoods. For around $60, you’ll pedal along quiet streets, parks, and beaches, with a knowledgeable guide leading the way. Highlights include spots like the Lincoln Park Zoo, North Avenue Beach, and views of Lake Michigan. The route passes notable landmarks like Old Town’s Victorian houses and the Playboy Mansion. Bikes and helmets are provided, making this a stress-free way to explore.
Guests comment on the personalized experience and the opportunity to see offbeat attractions you might miss alone. The tour’s 5-star ratings reflect its balanced mix of sightseeing and relaxed pacing. It’s ideal if you want to cover a lot of ground without the hassle of navigating Chicago’s busy streets solo.
Bottom line: For a well-rounded, scenic journey with just the right mix of history and fun, this tour hits the mark.
3. Chicago’s Ultimate City Bike Tour
Number 3 goes to a comprehensive ride that captures Chicago’s most iconic sites, including the Museum Campus, parks, and monuments. The approximately 3-hour route follows bike paths along the waterfront, looping around Buckingham Fountain, the Field Museum, and the Shedd Aquarium, where you’re encouraged to stop and explore. The breeze and skyline views are highlights, making it perfect for families or first-timers. The tour also provides insights into Chicago’s public art, parks, and architecture.
Guests describe it as a relaxed, safe ride with a “fun, informative experience,” especially noting how it covers Chicago’s most memorable landmarks. The price is modest considering the sightseeing packed into this tour, making it great for those who want an overview without a full day commitment.
Bottom line: Ideal for those seeking a family-friendly, relaxed ride with plenty of photo ops and background stories.
4. Chicago’s West Side Foodie Ride Bike Tour
At number 4, this tour is for food lovers who want more than just sightseeing. Over about four hours, you’ll explore Chicago’s West Side neighborhoods, sampling dishes like Polish pierogis, Mexican tacos, and locally made chocolates. The tour includes stops in Wicker Park, Bucktown, and other vibrant districts, with enough tastings to constitute a hearty lunch. The pace is leisurely, and the small group size (max 14) ensures personal attention. An optional VIP beer package adds to the experience.
Guests appreciate the local flavor and the chance to see Chicago’s diverse culinary scene. The tour also features architecture and city views, adding a cultural layer. The reviews highlight the delicious food and friendly guides, making it a top pick for those wanting an active food crawl.
Bottom line: For a tasty adventure through Chicago’s most characterful neighborhoods, this tour delivers both bites and local stories.
5. Bikes, Bites, and Brews Biking Tour
Number 5 combines Chicago’s famous foods and attractions in a 4.5-hour ride. You’ll visit neighborhoods and attractions like Wrigley Field, while savoring pizza, hot dogs, brownies, and beer. This tour is flexible for day or night, with the daytime route taking you past Wrigley Field, and the evening version illuminating Buckingham Fountain.
Guests praise its balance of food and sightseeing, with many describing it as a fun, filling experience. The price is reasonable considering the variety of eats and sights covered. If you want a combination of culinary treats and Chicago icons, this tour is a solid pick.
Bottom line: Perfect for those seeking a delicious, active overview of Chicago’s major neighborhoods and foods.
6. Chicago: Lakefront Neighborhoods Bike Tour
At number 6, this 3-hour tour offers a guided ride along Chicago’s vibrant lakefront, passing historic neighborhoods and parks. Highlights include the Lincoln Park Zoo, Old Town, and Gold Coast mansions. It’s a great way to learn about local culture while enjoying the scenic views of Lake Michigan. Bikes, helmets, and a relaxed pace make it suitable for most riders.
Reviewers mention how the guide “kept us safe and shared interesting stories about each neighborhood,” emphasizing the tour’s informative and enjoyable nature. It’s excellent for those who want a comprehensive tour of lakeside Chicago without overly strenuous riding.
Bottom line: If you’re after a comprehensive lakefront experience with cultural insights, this ride is a top choice.
7. Chicago Family Food and Bike Tour with Top Attractions
Number 7 offers a family-friendly way to see Chicago’s top sights with plenty of food stops. In about four hours, you’ll explore Millennium Park, the Chicago Riverwalk, and enjoy sampling deep-dish pizza, Italian Beef, hot dogs, and brownies. The bike ride is paced for families, with stops at kid-friendly locations, and the route covers major downtown icons.
Guests love how it combines sightseeing and tasting in a manageable format for kids and adults alike. It’s a good choice if you want to introduce children to Chicago’s flavors and landmarks without too much pedaling.
Bottom line: An excellent pick for families wanting a fun, educational, and tasty tour.
8. Chicago: Classic Food and Walking Tour with Free Bike/Kayak
Number 8 blends walking and water experiences with Chicago’s classic foods. Over three hours, you’ll explore Millennium Park, the Chicago Riverwalk, and sample pizza, hot dogs, and Italian beef. As a bonus, a free 2-hour bike or kayak rental allows you to continue exploring on your own afterward.
The tour’s mix of urban sights and culinary delights, combined with free rentals, offers great value. Reviewers mention “learning about Chicago’s landmarks while tasting the city’s best foods,” highlighting its educational and flavorful approach.
Bottom line: Perfect for those who want a guided introduction plus the flexibility to explore independently afterward.
9. Chicago Full Day Bike Rental
Number 9 is the ultimate self-guided option. For just under $30, you get a full day of bike rental, allowing you to explore Chicago at your own pace. With a lock, helmet, and map included, you can visit places like Navy Pier, Millennium Park, or Wrigley Field whenever suits you. It’s ideal for active travelers who prefer to craft their own experience.
Guests report that it’s a great value for flexible exploration, especially since you can visit attractions like the Lincoln Park Zoo or Shedd Aquarium on your own time. No guided tour can match the freedom of this option.
Bottom line: Best for independent explorers comfortable navigating Chicago on their own.
10. Chicago: Ultimate City Attractions Bike Tour
Number 10 covers the city’s most beautiful skyline and parks in a 3-hour ride. Highlights include Millennium and Grant Parks, the Museum Campus, and Northerly Island. The tour emphasizes scenic views and architectural sights, making it suitable for nature and architecture lovers.
Guests describe it as relaxing and scenic, with good insights about the city’s landmarks. It’s a solid choice if you want to capture Chicago’s essence without strenuous hills or overly long rides.
Bottom line: A scenic, no-fuss introduction to Chicago’s stunning lakefront and green spaces.
11. Chicago: Westside Food Tasting Bike Tour with Guide
At number 11, this 4-hour tour takes you through Chicago’s historic neighborhoods, sampling Polish pierogis, tacos, and more. You’ll ride along the 606 trail and Lakefront, enjoying local stories and architecture along the way. The small group ensures a personal experience, with optional VIP beer upgrades.
Guests mention the delicious food and engaging storytelling, especially appreciating the ethnic and architectural insights. It’s suited for travelers ready to explore beyond tourist spots and taste Chicago’s diversity.
Bottom line: Excellent for those interested in culinary diversity and local history on two wheels.
12. Chicago: Downtown Family Food Tour by Bike with Sightseeing
Number 12 offers a compact route for families to explore downtown Chicago. Over four hours, you’ll cycle past The Bean, Buckingham Fountain, and Millennium Park, stopping for Chicago-style pizza, hot dogs, and more. It’s designed for families wanting a kid-friendly, active way to see the city.
Reviews praise its balance of fun and education, noting how it’s perfect for introducing children to Chicago’s landmarks while sampling iconic foods. It’s especially good if your time is limited but you want a well-rounded experience.
Bottom line: A family-friendly option packed with sightseeing and tastings in a manageable schedule.
13. Chicago Half-Day Bike Rental
Number 13 provides a quick, flexible rental for four hours. Pick your bike type from options like e-bikes, child bikes, or road bikes and explore Chicago independently. With locks, helmets, and a map, you can visit neighborhoods, parks, or the lakefront at your own pace.
Guests find this affordable and convenient, especially for those who want to create their own itinerary. It’s perfect for active travelers who prefer a DIY approach.
Bottom line: Best for independent riders who want to see Chicago on their own terms.
14. Chicago: Full-Day or Half-Day Bike Rental
This flexible rental option allows you to choose between half or full-day of cycling. Helmets, locks, and maps come included, with the freedom to visit Navy Pier, Millennium Park, or Lincoln Park. It’s suited for those who want maximum flexibility and control.
Guests appreciate the value and freedom, noting they can explore on their own without strict schedules. It’s a great way to customize your Chicago experience.
Bottom line: For independent explorers wanting to set their own pace, this rental offers unmatched flexibility.
15. Chicago Highlights Walking Tour with Free Bike or Kayak Rental
Number 15 combines a short walking tour of downtown with a bonus free 2-hour bike or kayak rental. You’ll visit Millennium Park, The Art Institute, and the Chicago Riverwalk, then have the chance to continue exploring independently. This tour is perfect for first-timers or those wanting a quick but rich introduction.
Reviewers note the informative guide and value of the free rental as a bonus. It’s ideal if you want a taste of Chicago’s top sights with added flexibility.
Bottom line: A compact tour that packs sightseeing, education, and free rental into a two-hour walk plus extra exploration.
16. Chicago E-Bike Tour: Lakefront, Lincoln Park & Museum Campus
Rounding out the list, this 3-hour E-bike tour offers an easy, energizing way to cover Chicago’s highlights. Riders praise the knowledgeable guide Mike and the fun of first-time e-biking. The route includes the Milton Olive Park, Soldier Field, and Buckingham Fountain, with plenty of photo ops along the lakefront and parks.
Guests love how the electric bikes make covering more ground effortless, especially in a city with hills and long distances. It’s suited for those who want to see a lot without breaking a sweat.
Bottom line: For a comfortable, guided tour that maximizes sightseeing with minimal effort, this e-bike adventure is a winner.
How to Choose the Right Chicago Bike Tour
When selecting your ideal bike tour, consider your budget, fitness level, and interests. If you want a full foodie experience combined with sightseeing, the Bikes, Bites, and Brews is a standout. For independent exploration, full-day rentals like the Chicago Full Day Bike Rental give you the freedom to craft your own adventure. Families with kids should look at the Chicago Family Food and Bike Tour, which balances fun and education.
Booking early is recommended, especially in peak summer months when Chicago’s outdoor activities fill up fast. For those with limited time, shorter tours like the Chicago’s Ultimate City Bike Tour or the Chicago Highlights Walking Tour offer quick but comprehensive glimpses of the city.
Final Recommendations
If you’re a food lover wanting to combine biking with Chicago’s signature bites, the Bikes, Bites, and Brews should top your list. For families or first-time visitors eager for a scenic, relaxed ride, the Chicago’s Ultimate City Bike Tour provides a well-rounded experience. Budget travelers and independent explorers will find the full-day or half-day bike rentals ideal for flexible, self-guided adventures.
Whatever your style, Chicago’s bike tours open a window onto one of America’s most dynamic cities—so don’t forget to book ahead and enjoy pedaling through the Windy City.