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Chicago Bike Adventures

Chicago, United States

Check local COVID-19 restrictions before booking

Experience hosted by Steve

4 hours
Includes equipment
Up to 4 people
Hosted in English

What you'll do

We'll meet at my bike loaner HQ in the heart of Chicago's Ukrainian Village where we'll discuss the day's ride and get comfortable riding together. Then, I will lead you on a 4 hour custom bike ride through several Chicago neighborhoods. We'll ride under the historic "L" train, visit several of the city's neighborhoods (historically diverse and modernly hip), get a taste of Chicago's craft beer scene (if requested) and see Chicago's wide range of architectural styles and oddities, 1920s gangster related sites, great skyscraper views, movie locations, cluster of early 1900s movable bridges, and street art. No tour will be the same as it will be adjusted according to your responses to the pre-ride questionnaire.

** I have a small number of older model loaner bikes available for people who do not have one their own. If you prefer to rent newer bikes I can offer some suggestions.**

***As a general rule, unless the next day forecast is for all day thunderstorms, we wait until the morning of to make the final call to cancel. I don't normally cancel the ride if just a shower or two are forecasted. Sometimes we have coordinated with all riders to move the time up or back an hour to avoid bad weather. If a downpour does come during a ride we can wait it out over a snack or a brief look inside a place.***

****Private groups large than 4 contact me directly. We can set it up.****
Other things to note
I highly recommend having a good breakfast before the ride. We can stop anytime for food/drink but it is best to start topped off.
We'll meet at my bike loaner HQ in the heart of Chicago's Ukrainian Village where we'll discuss the day's ride and get comfortable riding together. Then, I will lead you on a 4 hour custom bike ride through several Chicago neighborhoods. We'll ride under the historic "L" train, visit several of the city's neighborhoods (historically diverse and modernly hip), get a taste of Chicago's craft beer scene (if requested) and see Chicago's wide range…

Steve's commitment to safety

This host has committed to Airbnb’s COVID-19-related safety and cleaning guidelines – including adhering to social distancing guidelines, practising good hygiene, and ensuring that all participants wear a mask.
Learn more

What's included

  • Equipment
    Helmet, Bottle of water
From £68
/ person
Sat, 23 Jan
10:00 - 14:00
£68 per person
£68 per person
Sun, 24 Jan
10:00 - 14:00
£68 per person
£68 per person
Mon, 25 Jan
10:00 - 14:00
£68 per person
£68 per person

Meet your host, Steve

Host on Airbnb since 2018
  • 124 Reviews
  • Identity verified
Through cycling I combine so many of the things I love: history, geography, architecture, public art, beer, friends, and the wind in my ever decreasing hair.

A little more about me:
-Transplanted Oklahoman in Chicago for 15 years.
-History/French BA from the University of Oklahoma.
-Former Chicago Public Schools Teacher/Librarian.
-Worked in France, South Korea, and Japan and traveled in 30+ other countries.
-A year around cyclist who enjoys a city ride, a day through a forest preserve, and longer touring (Chicago-Mississippi River, Cleveland-Cincinnati, 7 days in the Kathmandu Valley).
Through cycling I combine so many of the things I love: history, geography, architecture, public art, beer, friends, and the wind in my ever decreasing hair.

A little more about me:
-Transplanted Oklahoman in Chicago for 15 years.
-History/French BA from the University of Oklahoma.
-Former Chicago Public Schools Teacher/Librarian.
-Worked in France, South Korea, and Japan and traveled in 30+ other countries.
-A year around cyclist who enjoys a city ride, a day…
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Where you'll be

We will ride through several distinct neighborhoods that are not always included on Chicago tours. We'll start on the west side in Chicago's Ukrainian Village near the popular Wicker Park/Bucktown neighborhoods. From there we'll ride through the former "Polish Downtown", trendy Fulton market, traditionally Mexican-American Pilsen, Irish Bridgeport, historically African American near South side, Chinatown and ending back in Wicker Park.

Rated 4.94 out of 5 from 124 reviews.

Jen
November 2020
My boyfriend and I came to visit Chicago for a couple of days and thought it would be best to have a native Chicago dweller give us an introductory tour of the city. Steve was an excellent tour guide and took us to neighborhoods that we never would have explored otherwise. He sent us a Google survey before the tour, and tailored it to what we indicated we were interested in. In our particular case, we were interested to see the street art around the city, and he showed us some really amazing murals and was able to talk about the pieces and the artists in depth. You can tell he is really passionate about it! The tour ended up just being the 3 of us (Steve, my boyfriend, and me) and it was great because we got a really personalized tour and we were able to do it at our own pace. I'd highly recommend doing this if you're going to Chicago!
My boyfriend and I came to visit Chicago for a couple of days and thought it would be best to have a native Chicago dweller give us an introductory tour of the city. Steve was an e…
Lauren
October 2020
Steve was a excellent host! It was a beautiful late October fall, the sun was out for most of the ride but Chicago neighborhoods that we saw were on full display! I felt very safe riding bikes around town with my group. It didn’t seem rushed at all. My bike tour was uniquely made for my boyfriend and I. We saw greenery, notorious Chicago and wonderful art murals. During the ride we got hungry and Steve took us to a great local place. On the trip my boyfriend mentioned we have to go back on this tour to see more and I couldn’t agree more. When I was biking through the neighborhoods I felt like it was a true local experience! I would recommend this trip experience for everyone visiting.
Steve was a excellent host! It was a beautiful late October fall, the sun was out for most of the ride but Chicago neighborhoods that we saw were on full display! I felt very safe…
Kate
October 2020
Steve is a cycling encyclopedia. My wife and I did this tour on our first full day visiting Chicago, and we are so glad we did! The personalized tour highlighted all kinds of things we were already interested in but couldn’t have learned anywhere else. If we ever come back, this is the kind of activity we could book again and have a completely different (and still fascinating and engaging!) tour.
Steve is a cycling encyclopedia. My wife and I did this tour on our first full day visiting Chicago, and we are so glad we did! The personalized tour highlighted all kinds of thing…
Emily
October 2020
The bike tour with Steve was great! He went above and beyond by sending out a pre-ride survey gauging our interest in specific topics and tailored the tour to what we really wanted to see. Could not have asked for a better experience. Wonderfully safe way to explore Chicago during times of social distancing.
The bike tour with Steve was great! He went above and beyond by sending out a pre-ride survey gauging our interest in specific topics and tailored the tour to what we really wanted…
Maria
October 2020
Steve was great. The tour was very complete, he took us to all the cool neighborhoods of Chicago. We saw lots of street art, architecture, and many more things. I have been living in Chicago for 5 years, and still managed to see a lot of new things. Had a lot of fun. Thanks Steve!
Steve was great. The tour was very complete, he took us to all the cool neighborhoods of Chicago. We saw lots of street art, architecture, and many more things. I have been living…
Tony
October 2020
If you are looking for a great way to experience the City and get a unique perspective this is for you! Steve is a great guide a will tailor the ride to your skill level.

Choose from available dates

30 available
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Things to know

Cancellation policy

Any experience can be cancelled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Guest requirements

Up to 4 guests ages 18 and up can attend.

What to bring

Weather appropriate comfortable clothing

Snacks