Work it Out in the Windy City

When you think Chicago and sports, the Cubs and Bears come to mind, but this midwest charm of a town also offers loads of fun sporty adventures right in the city if you’re looking to inject some fitness into your itinerary. —Karen Kwan

stay. The sleek W Chicago Lakeshore has a buzzy atmosphere weekend nights in the lobby, but the spacious rooms in this tower serve up serene views of Lake Michigan and Navy Pier (you’ll have a primo view of the fireworks show held Wednesdays and Saturdays from Memorial Day through to Labor Day). Its prime location has you just a short walk through the underground pedestrian walkway to the Ohio Street Beach for a swim or for a run along the lakeshore path.

see. The architectural cruises in the Chicago River are an essential for every Chicago visitor but for a more informal tour during which you’ll learn about the city’s history while also working up a sweat, book a kayak tour (you can go in a single or double kayak) of the Chicago Riverwalk with Urban Kayaks. Paddle about five kilometres during this 90-minute tour — it’s easy enough for beginner paddlers — as you learn about architectural landmarks and fun pop culture tidbits (including one about Dave Matthews that may make you wanting to clamour out of the river!).

sweat. Rent wheels from Divvy (Chicago’s bike-share program) for a bike tour of Humboldt, Palmer Square and the 606 with the Chicago Architectural Foundation. The highlight of the tour for us is the 606, which is often compared to New York City’s High Line. This 2.7 miles of abandoned rail line is now a green space featuring art and with event space, replete with paths for bikes, runners and pedestrians. For a workout on land, make your way to Maggie Daley Park to the Climbing Wall. While the tourists take selfies at the nearby Cloud Gate, you’ll be getting a rush from climbing the 40-foot tall walls and getting a unique view of Chicago’s stunning skyline.

savour. Burning so many calories with an action-packed itinerary means you’re justified in eating in some indulgent meals. At The Gage, their sticky bun is life-changing and worthy enough for making a stop here for brunch. For a light fresh lunch, head out to check out the Lakeview neighbourhood, and go for a fried green tomato sandwich at Uncommon Ground, named in 2011 as the country’s greenest restaurant (where the water is heated by solar panels and produce is grown on the rooftop garden. Finally, do more than just go for deep dish pizza; book a tour with Pizza City USA to get the 411 on all of the different types of pizza in Chicago (there are 10!) and taste test several while you’re at it. This tour company is helmed by respected award-winning food reporter Steve Dolinsky (you may know him from the podcast The Feed), so you know it’s legit.

stroll. Much of Chicago feels like an art display thanks to the number of murals peppered throughout the streets. Spend an hour or so walking through the Wabash Arts Corridor (it stretches from about Van Buren to Roosevelt) to discover the works in this initiative launched by Columbia College Chicago to revitalize the South Loop. Started in 2013, there are now nearly 40 large-scale pieces, including “Moose Bubblegum Bubble” by Jacob Watts.