Chicago Bike Tours and Rentals

This post reviews and compares the best bike tours and rental companies and other options in Chicago.  One of the best ways to explore the Windy City is on two wheels!  Whether it’s along the many bike paths or over 200 miles of bike lanes, you will be able to see more of the city faster, while giving your feet a rest.  This post will help you find the best biking option for your time in Chicago.  Whether you are looking for a guided tour, self-guided tour, or just an affordable bike rental, we are confident you will find the right bike option for you to see all that this city has to offer.

Guided Bike Tours

Chicago’s Bike Share Program

Deals and Discounts

Pay-What-You-Like Bike Tours

Bike Rentals

Self-Guided Bike Tour



Free Tours By Foot Bike Tour   Coming Soon!

Free Tours By Foot offers the best pay-what-you-like walking tour in Chicago.  And starting in summer 2017 we will have bike tours as well! Operating on a BYOB (bring your own bike) basis, local guides will safely escort you around the city, while pausing to point out important landmarks along the route.  Most bike tours in the city will cost around $40 per person for two hours.  With bike rentals starting at $10 an hour, or $34 for the full day, this tour option allows for a flexible and affordable way to explore Chicago. Tours will begin at a partner bike shop, providing a smooth transition into a bike tour.


Avoid the traffic, high cab fares, and hectic parking search as you make your way around the city on two wheels. Guided bike tours allow you to see various parts of the city while your expert guides bring you from stop to stop. Learn about the history of the area you are riding through while enjoying the fresh air and exercise. Bobby’s Bike Hike and Bike and Roll are two of the best bike tour companies in Chicago.  These two companies provide multiple bike tours, and have been impressing guest after guest. 


Bobby’s Bike Hike

Bobby’s Bike Hike offers seven different bike tours, showcasing various parts of the city.  The variety of tours cater to different interests, from the gangsters of the 1920s to a food bike tour sampling Chicago’s best food. Read about all of their tour options here, including one designed specifically for kids.  Prices:  Bike tours start at $34.75 for an adult for a 2 hour tour, up to $65.50 for an adult for a 4 hour food tour.  More information and to book.



Bobby’s Bike Hike is one of the top rated tour companies on TripAdvisor.  With a 5 star rating based off of over 2,000 reviews, it easy to see that this tour company has been impressing guests for a while!  Reviews suggest that these tours provide a wonderful way to see some of the best parts of the city, while learning about the history and stories of the area. Knowledgeable and interactive guides add to the positive experience. Even in the rain and colder weather, guests stated that this tour was an enjoyable adventure and informative way to see parts of the city that they would not have made it to otherwise.

Many couples and friends have participated in these tours, and speak highly of the personnel and tour content of this company. Solo travelers commented that this is a great way to meet people. Families have also recommended this tour company, stating that it is perfect for the whole family, as you travel at a leisurely pace while enjoying the stops along the way. Only a couple of negative reviews commented on the bike equipment and the tour route, but many stated that they would join this company for another tour!


Bike and Roll 

Bike and Roll is another top rated bike tour company in Chicago.  Offering three seasonal tours (May-September), this company provides an affordable bike adventure fit for the whole family. Enjoy a leisurely ride along the Lakefront Trail to see some of the top tourist spots and some nature along the route, or appreciate the city illuminated at night by city lights and fireworks. Bike and Roll also provides a Bike and Brewery Tour, escorting guests south of downtown to Laguinta’s Brewery, educating you on the brewery and city history while bikers enjoy sample from popular restaurants along the way.



Prices: vary from $40 for an adult for a 2-3 hour tour, up to $70 for an adult for the 4 hour brewery tour.

Reviews of Bike and Roll Chicago

Bike and Roll has a 4 1/2 star rating on TripAdvisor based off of over 700 reviews.  Guests commented on the humorous guides that always emphasized safety first, allowing for relaxed and entertaining tours.  Comments shared that there were enough stops to rest and learn interesting facts about the area, while still keeping up the energy of the tour. Solo travelers and groups alike commented that these bike tours provided a great way to explore parts of the city that they would not have found on their own. Families also enjoyed their experience, stating that it was an easy ride for the whole family.

While many reviews complimented the staff, a couple of guests had negative experiences, and also found the bike equipment to be sub-par. Overall, many guests had great experiences with different aspects of the company, and would recommend it in Chicago and other cities across the Unites States.  If bikes aren’t your thing but you still want to see the city on two wheels, Bike and Roll’s Segway tours also come very highly recommended!


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Bike rentals are a great option to see the city at your own pace, allowing you flexibility and autonomy.  Bobby’s Bike Hike and Bike and Roll are the top two companies in Chicago for bike rentals.


Bobby’s Bike Hike Bobby's Bike Hike Logo

Many guests have complimented their experience renting bikes through Bobby’s Bike Hike on TripAdvisor.  Comments stated that it was a smooth rental process, and the personalized service made rookie riders very comfortable on the road. Guests appreciated the affordable price and convenient location. The limited negative feedback commented on the quality of the bikes, but most found this to be a great way to give their feet a break while exploring the city.

Prices: vary based on the style of bicycle but their most popular bike (comfort bike)

  • $10 per hour (2 hour minimum)
  • $25 per 4 hours
  • $34 for a full day rental


Bike and Roll 

Bike and Roll

Bike and Roll has four rental locations within the greater Chicago area, two of these locations being downtown by Navy Pier and Millennium Park.  Bike rentals include a helmet, keyed U-lock, handlebar pouch, and a biking map. Bike and Roll offers a variety of bikes, such as road bikes, hybrids, tandem bikes, kids bikes, and 4-person quad bikes if you are feeling adventurous.

Prices: vary based on the style of bicycle but their most popular bike (comfort bike)

  • $13 for 1 hour (2 hour minimum)
  • $39 for 4 hours
  • $45 for a full day rental

Many customers have had positive experiences renting bikes through Bike and Roll. Comments stated that it was a very smooth process to reserve online and then pick up the bike. The check in and out system is efficient and provided an enjoyable riding experience for the whole family.  Customers appreciated seeing Chicago this way, and not being tied down by a strict time limit with the bikes.  Comments also shared that the pick-up location is convent for accessing the Lakefront trail or seeing the sights downtown.  Only a couple of negative comments shared bad costumer service experiences and dissatisfaction with the bikes that they rented.  Overall, guests have enjoyed renting through this company, and many would do so again in the future!

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Divvy Bike

Divvy Bike, Chicago’s bike sharing program, is a convenient option for commuters and tourists alike.  With over 580 Divvy stations around the city, there are many options to hop on and off, and see more of the city as you make your way from destination to destination.  

Here’s how it works:  for $9.95, you will receive a day pass to use any Divvy Bike.  When you buy the pass you will get a 5-digit ride code that will allow you to unlock bikes from any Divvy Station for the next 24 hours.  You have 30 minutes with each bike before returning it to the next station to exchange it for another, or enjoy your final destination. Each station has a map of close by Divvy bike stations.  Be sure to check out the map online to know where to pick up and drop off your bike, or download the app for maps and details about how many bikes are available at each station.

Divvy Bikes has a 3 1/2 star rating on TripAdvisor based off of over 200 reviews.  Guests said that is a wonderful way to see the city on a nice day, and it saves a lot of money on cabs. Not much experience is needed for the bikes, and they are fairly comfortable. Many found this method of transportation to be quicker than driving, as the city has done a great job of creating bike paths and lanes.  Most of the negative feedback of Divvy Bikes is that the 30 minute time limit can be constricting.  

Some people experienced technical difficulties when they tried to get a bike.  A few customers also ran into equipment problems with their bikes, so they recommend testing the brakes and seat security before riding too far away.  During the warmer months, many Divvy stations near the lakefront clear out, so be sure to guard your bike if you are just at the station to renew your time!  Overall, many people have had positive experiences with Divvy bikes, and found it to be a convenient and enjoyable way to make their way around town.


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Free Tours By Foot: Self-Guided Bike Tour

If you want to bike at your own pace but are not sure where to get started, we’ve created a self-guided bike tour.  With 12 stops conveniently located near Divvy bike stations, this is an easy ride for Divvy bikers, bike renters, and people with their own set of wheels. This tour has directions from stop to stop, mostly bringing bikers on a bike path, accompanied with a brief description of each destination. 

Free Tours By Foot  also has many self-guided walking and food tours in various parts of the city. These would be great neighborhoods to bike to, and allow you to explore a new part of the Chicago. Check out our self-guided walking and food tours here.

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Vacations can get expensive, but there are many ways to save money on top tourist attractions in Chicago, including bike deals!

Go Card Chicago Chicago Go Card

The Go Card Chicago allows you rent from Bike and Roll for a discount.  Combine this experience with others in the All-Inclusive, Explorer, or Build Your Own package to save some money!


You can often find deals on bike tours and even Divvy bikes on Groupon.  Be sure to check them out to see how you can save.


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