72 Hours In The Windy City: Chicago’s Great Outdoors

Portillo’s hot dogs and Italian beef! An architectural cruise! Deep dish pizza! What are we talking about? The Windy City, of course. Now, while Chicago is most often associated with its stunning architecture and foodie finds, its many neighbourhoods actually offer a ton of outdoor activities that’ll get you sweating—which is plenty convenient as you’ll get to work up an appetite and thirst, for which there is no shortage of refueling options.

Where to stay
The glitzy W Chicago Lakeshore comes alive on Friday and Saturday nights (ie. make time to pregame or have a nightcap in the lobby bar) but thankfully, the spacious rooms above are quiet and feature fantastic views of Lake Michigan and Navy Pier. Plus, you can easily walk through the underground walkway to the Ohio Street Beach; pull on a wetsuit and join the people doing laps in the lake or run lakeside as you take in the superb downtown skyline.

What to see
A top-notch way to learn about Chicago’s history and architecture is the architectural cruise. But short of standing up to take photos, it’s a sedentary undertaking. For something that’ll burn more calories, opt for a kayak tour of the Chicago Riverwalk instead with Urban Kayaks. The 90-minute tour will have your paddling about five kilometres peppered with stops to learn about architectural landmarks like the massive Merchandise Building and the devastating Eastland disaster, the Great Lakes shipwreck that claimed 844 lives.

Where to work out
You’ll spot Divvy, Chicago’s bike-share program, all over the city making it a fun option instead of taking the el train or Uber. While you’ve got two wheels, pedal over to the 606 to ride the 2.7 miles of this park, which is a former abandoned rail line that’s been transformed into a green space with paths shared by cyclists, pedestrians and runners. To learn more about how the city’s developed, use your Divvy for a tour with the Chicago Architectural Foundation; the knowledgeable guides will take you through not only the 606 but also Humboldt and Palmer Square as they school you on the growth and changes each hood has undergone.

Where to drink
Craft brew fans have plenty to choose from in Chicago. There’s Goose Island Beer Company (which now has an outpost in Toronto), Alulu Brewery and Pub (a charming spot to enjoy a quick bite from its eclectic menu, which features everything from poutine—oh Canada!—to fried chicken tikka and a kimchi chicken burger, and Greenstar Brewing, Chicago’s first certified organic brewery. For a change of pace from just sitting around and shooting the shit as you drink, hit up Flight Club Social Darts, which turns the traditional game of darts into a fast-paced, instant-scoring game that hook you immediately.

Where to eat
We hate to break it to you, but deep dish is not what Chicagoans typically eat when it comes to pizza. Get the lowdown on what they do order up (psst, it’s called tavern style) and get schooled on the 10 different types of pie in Chicago with Pizza City USA, a tour created by award-winning food writer Steve Dolinsky, who did months of in-depth pizza research for the tours and his book (hello, dream pizza-eating job!). Nice weather have you desperately seeking a fun patio? Hit up Park & Field, a retro gymnasium-inspired sports bar in Logan Square. Its expansive terrace features loads of seating, bocce ball courts and bonfire pits, and their juicy Berkshire pork chop served with corn and black eyed peas will satisfy all of your carnivorous cravings.

Karen Kwan

Karen Kwan

Karen Kwan is a freelance writer based in Toronto. Her work has appeared in Flare, Elle Canada and ElleCanada.com, Glow, Metro, Huffington Post Canada, Travelife and Travel + Escape. She also runs her blog, HealthandSwellness.com, where she writes about health, beauty, fitness and lifestyle.

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