The first thing we realized when planning our trip to Chicago was how much there was to see. Four days wasn’t going to be nearly enough time to make it to our long list of “must-dos”: The Art Institute, Millennium Park, the Navy Pier, Shedd Aquarium, Lincoln Park Zoo, The Museum of Science and Industry, Willis Tower, the Magnificent Mile.
Upon arrival, though, we discovered the secret to getting around Chicago efficiently: go by bike. Chicago, with it’s insane layers of overpasses, underpasses, bridges and tunnels (not to mention one-way streets) is not an easy city to get around. It’s enormous, of course, and the rivers divide it into multiple slices so that it’s not always easy to figure out how to get from point A to point B.
On a bicycle, though, you have your own private escape routes; a number of bike paths cross the water independently of the traffic. It’s pretty satisfying to whiz along the lakeshore bikepath while watching the stopped traffic honk its way along Lakeshore Drive a few feet away. Also, Chicago is flat. Really flat. Look down from the Skydeck at Willis (formerly Sears) Tower and you can see 50 miles on a clear day, and the horizon is still flat. You can easily get away with a seven-speed cruiser; we rented 21-speed “comfort bikes” but never needed the lower or higher gears.
Visitors can rent bicycles easily and conveniently from Bike and Roll Chicago, which has stands at Millennium Park, Navy Pier, and at several of the lakeside beaches. The bikes come equipped with a pouch on the front for your wallet and camera, a rack on the back for your packages, and a lock so you can park your bike safely wherever you want to stop and stay awhile. The cost is $30 to $40 a day, depending on the type of bike you want, and you can save $5 by reserving online ahead of time. The city of Chicago prides itself on its bike-friendliness, and a map of bike routes is available on the city’s web page.
A network of wide, divided, nicely maintained bike paths makes it easy to get to the museums and other cultural attractions scattered up and down the lakeshore and throughout Grant Park and Lincoln Park. And there’s so much to see along the shore of Lake Michigan that you’ll miss from a speeding car, from volleyball rivalries to muscle men to sandcastle competitions.
Well-signed bike lanes are available throughout the city as well, although Chicago’s notoriously aggressive drivers make it a little hairy to ride on crowded streets or during rush hour. In addition, Chicago has a great public transit system made up of both trains and buses and bikes are allowed on both except during rush hour (7-9 a.m. and 4-6 p.m.) The train-bike combo is the perfect way to check out some of Chicago’s eclectic neighborhoods like Wicker Park/Bucktown, Andersonville, and Logan Square.
Midwestern visitors to Chicago got smart some time ago and started bringing their bikes when they visit the City; you can watch families unloading copious bike gear in outlying park and ride lots around the city. Those of us flying in don’t have that option, of course, but renting by the day is definitely the next best thing to being local.
The best place to stay while cycling Chicago? Hotel 71, which has the personality of a boutique hotel but a convenient central location right on the river just a few blocks from the Bike and Roll rental kiosk on Randolph Street.







Interesting idea! I would never have thought of renting a bike in a large city, but it makes sense
What an excellent post and superb idea for eco-travelers!
What a great and helpful post. I would never have thought of biking through Chicago — but you've made it seem attractive and possible.
I know; I was surprised to see all these people on bikes when we got here – it wasn't my image of Chicago either! Our first day it took us forever to get from one end of town to the other; after that, we switched to bikes and it was much easier!
I am so surprised – and pleased – that it's actually possible to bike through a city like Chicago. Thanks so much for this information!
My husband was thinking about future marathons he wants to run and your post made me decide to encourage him to think about Chicago! It looks like a great city.
So glad you and the girls are having a blast in Chicago, one of my favorite cities to visit.
And yet it had never crossed my mind to traverse this major metropolis on two wheels.
chicago is an easy city to navigate as the streets are a nearly perfect grid.
Anonymous is correct; another plus is that it's easy to find your way around Chicago, and you don't have to keep pulling over to yank out your map. Once you find a few routes you like, you're set!
Great write up. I love tackling cities either on foot or wheel. It's a great way to see everything, eliminate the stress of parking and getting lost (ever present in a car) and also get some exercise.
What a perfect way to visit this city. I love Chicago (my mom grew up there). This article makes me want to go back soon!
I've never been to Chicago, but this sounds like fun! I will have to make it out there someday and make a bike ride part of my trip.
If I can cycle a city instead of driving it I'm all for it. Good for Chicago for making it easy & good for you for letting us know. Thanks for the hotel recommendation too.