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American City Break: Chicago

Though our summer intern, Joe, is from the east coast, his favourite city sits about 4 hours away from where he goes to school in the Midwest: Chicago.

The Windy City has an incredible culmination of world-class food, entertainment, architecture, and sports, making it the perfect spot to take a bike journey. On this ride, you’ll get to see all of the top sites in the city and wrap up with a classic Chicago delicacy.

Chicago Cycle Route Bike Tower


 Quick Facts


Wrigley Field, Cloud Gate


15km (one-way) 


Flat, tarmac cycle paths nearly all the way. 



Anytime except for Chicago's famously brutal winters!

How to get there

Regular flights to Chicago O'Hare airport

Which bike

Get the day 'Explorer Pass' for $15 and drop off and pick up Chicago's Divvy bikes all the way along the route


Pedal-power is definitely the best way to take in the city and to enjoy the beautiful shores of Lake Michigan


The Cycle Route 

Chicago City Bike Route Adventure Cycle Ride

Wrigley Field

The trip starts at Chicago’s iconic Wrigley Field. Whether you’re an avid sports fan or not, it is hard not to appreciate this beautiful stadium. Would definitely recommend catching the Cubs play there if possible, as the field makes it feel like you’re watching a baseball game played in the early 20th century.

Chicago Cubs Wrigley Field Starting Bike Route Point

Navy Pier

After biking for a few miles back into downtown Chicago, the next destination is Navy Pier. On this popular boardwalk, you can find an amusement park, a performing arts center, and several great eating options.

From Navy Pier to Adler’s Planetarium, you’ll ride along the water on the gorgeous Chicago Lakefront. There is a paved way to ride along that is meant for both bikers and pedestrians, all while providing an outstanding view of Lake Michigan.


Adler’s Planetarium

Next up is Adler’s Planetarium, which is an astronomy and astrophysics museum. Take the time to stop in for a little bit to see different scientific shows and exhibits.


Buckingham Fountain

Not far from the planetarium is Buckingham Fountain, which if you time it right, you can see it spray 150 ft. in the air at the top of the hour!


Millennium Park

One of the final stops on this trip is Millennium Park. This project almost two decades ago helped urbanize the area and created one of the most famous tourist attractions in the United States. The park is home to several beautiful pieces of art and landscape, including Crown Fountain, Jay Pritzker Pavilion, Grant Park, and, of course, Cloud Gate (also known as “The Bean”).

Millennium Park Cycle Route Bean Chicago


Now that you’ve finished seeing Chicago and all its beauty, celebrate the end of your trip at Portillo’s, where you can get the best hot dog you have ever had and a chocolate cake shake!

Chicago Portillos Hot Dog Bike Route

And there you have it! An alternative way of seeing the home of the Cubs, Oprah, and deep dish pizza.