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Cycling Chicago

By Jacqui Snyder

Chicago-at-nightChicago has won many awards for being one of the top cycle-friendly cities in the US, and justifiably so. They have an extensive waterfront trail that runs North and South along the shores of Lake Michigan. At certain places the bike routes head away from the water to provide a more scenic, less traffic-congested route. There are also miles of trails, including old railway lines that meander all over the expansive city. In all, there are over 111 miles (179 km) of dedicated bike lanes covering much of the city. There are also several miles of roads dotted with share-the-road signs (consisting of bike and chevron symbols, or bike symbols and arrows). Bikes are permitted on the transit system at all times except weekdays from 7-9 am and 4-6 pm.


We decided to go during the Blues festival weekend, assuming that would keep us busy, and it did. What we didn’t know prior to booking is that Chicago would win the Stanley Cup the day before we arrived! The City was lit-up with Black Hawk logos on corporate offices and lamp-posts and residents were in full celebration mode.

On Friday we took our bikes to Evanston, where the beautiful Northwestern University campus is. It took some time to get there. We were sidetracked by the Stanley Cup Parade — caught in the masses of screaming fans. I couldn’t help but feel proud for them.

After a little jaunt around the infamous Navy Pier — reminiscent of a ‘50’s waterfront-historical-fair, with tall ships, ferris wheels and food stalls — we made it to our destination and found a lovely little beach where we could swim. The waterfront trail took us along cement docks, grassy parks, sandy beaches, and residential streets of various sizes.

Chicago-Bike-PathChicago has a large population of active people. We passed many athletes training for triathlons and other sports, who take advantage of the accessible waterfront paths. We returned on the same route and went straight to the Petrillo Music Shell to take in some of the Blues festival. The concessions had spiked lemonade that was very refreshing after our long ride, and we picked up a few things to nibble on, which we consumed on a grassy field surrounded by thousands of other spectators and the Chicago skyline.Chicago-Blues-Fest

On Saturday we joined the Chicago Bike Club for a ride through the North side. They were very welcoming, and customized the tour for the Canadian contingent by adding in a little loop through an area where there were buildings designed by Frank Lloyd Wright. The route also meandered through forested trails and near marshlands. It started to pour just as we arrived at the Botanical Gardens.  After a bite to eat and a rest, the rain stopped and we headed off again to continue our route along the North Branch Trial, Sculpture Trail and ended up at Moody’s Pub in Edgewater for a late lunch on an outdoor, treed patio.

Chicago-Blues-BusFor a change of scenery, on our last day we headed South on the lakeshore path. Sunday is the day for marathons, triathlons and charitable events, so the path was quite busy. After this, we stopped at the Jazz Festival again where they were selling enormous messy Turkey drumsticks smothered in sauce, corn on the cob, jambalaya and other interesting foods. Finally, after packing up, we made our last happy hour at our hotel, the trendy Kempinsky Hotel Allegro in the theatre district.


We chose to drive (10 hours from Toronto) so we could have our own bikes. That meant forfeiting 2 days in Chicago. But you can fly Porter from Toronto to Chicago for about $750 depending upon when you go.

For more information on cycling in Chicago, visit the Wikipedia Cycling in Chicago site, where you will also find a PDF map to download.

For more information, feel free to contact me at [email protected]

Jacqui Snyder
ADVENTOURUS Active Vacations
CAN-BIKE Instructor
[email protected]
647-404-9380

Jacqui Snyder is an avid sports-person, trained Chef (George Brown College graduate; trained in Switzerland and England), foodie, people-person and traveler. She is a certified CAN-BIKE instructor and has cycled for as long as she can remember. Jacqui runs ADVENTOURUS Active Vacations, organizing skiing, cycling, and hiking vacations.

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