72 Hours In Chicago: Get The Most Out Of A Quick Getaway To The Windy City

By Karen Kwan

Chicago is an easy destination for many of us in North America to get to (and thousands will descend upon the Midwest city this July for NASCAR, which is taking place in Chicago for the first time since 2019, not to mention the annual music festival Lollapalooza, which takes over Grant Park in August). Nicknamed the Windy City thanks to a historical rivalry with Cincinnati, which saw the city as a boastful (although, yes, the city can indeed be breezy thanks to being on the shores of Lake Michigan), with Chicago’s stunning architecture, cultural offerings and stellar food scene, the city certainly warrants showing off everything it has to offer.

Whether you’re discovering the city for the first time or back for another visit, Chicago delivers tenfold on sights and attractions you can’t get anywhere else. Although it’s the third largest city in the U.S., with its friendly locals, lively neighbourhoods and being a very walkable city (although hopping on the CTA makes it easy to get around), this big city has a welcoming appeal that charms everyone. Make the most out of your stay by zeroing in on these signature Chicago spots.


Have some laughs at Second City
Tina Fey, Stephen Colbert, John Candy, Dan Akroyd–the comedic talent that’s come out of Second City is unparallelled. With such an impressive group of alumni, you can rest assured that attending a show at the oldest ongoing improv theatre group in Chicago is going to be full of laughs (and you’ll want to pay extra special attention to all of the performers because they may just become household names soon). Take your visit to Chicago to the next level by attending the show The Best of Second City: Chicago Style, which features songs and sketches about the city’s staples (think deep dish pizza and the Cubs).

See a show at Chicago Magic Lounge
You may have heard of a Chicago-style hot dog but did you know there’s Chicago-style magic? Close-up magic (think quick magic tricks, typically done with a coin or cards, performed at your table in a restaurant or bar setting) is the city’s trademark and you’re sure to be spooked by the tricks you’ll get to experience at Chicago Magic Lounge. This 21+-venue holds shows nightly and before the stage show, experience close-up magic at your cabaret table while sipping on signature cocktails with magically themed names (try the Abracadabra, a mix of tequila, lime juice, maraschino liqueur, simple syrup and creme de violet liqueur) and small bites such as fried chicken sliders and roasted olives.

ABOVE: Get a behind-the-scenes look at the legendary home of the Chicago Cubs by going on a tour of Wrigley Field

Tour Wrigley Field
Even if you’re not a baseball fan, touring this iconic stadium will give you a fascinating deep dive into its history–from stories about one infamous season ticket holder, Al Capone, and how it earned its moniker “the friendly confines” to signature elements that have been around since being established, along with the scoop behind more recent additions, such as the Wrigley rooftop seats on the top of the residential apartments across the street.

ABOVE: Visit Chicago’s highest point, the Skydeck on the 103rd floor of the Willis Tower (formerly known as the Sears Tower)

Check out the view from Skydeck Chicago
Regardless of if you’ve been to Skydeck Chicago at Willis Tower before, it’s worth a visit: the 360-views never get old and there’s the new Skydeck Experience, where you’ll learn fun facts about Chicago’s history via interactive experiences, including photo opps with some classic Chicago foods, such as oversized installations of a Chicago hot dog and deep dish pizza. When you make it to the 103rd floor, don’t miss stepping out on The Ledge, the glass balcony with such a crystal clear floor that it can make even the bravest of us a bit leery of stepping out onto it.


Explore the city on two wheels
When you’ve got limited time to explore the city and also want to fit in some fitness, cover more ground and get your sweat on all at once by joining a bike tour (while also working up an appetite for your next meal). Bobby’s Bike Hike offers a few different tours, which may bring you to the city’s major attractions or to the different lakefront neighbourhoods all while learning about Chicago’s history.

ABOVE: The pedestrian-friendly Chicago Riverwalk stretches 1.25 miles

Join a running tour
Skip the hotel treadmill and make your run do double-duty as a workout and sightseeing tour. Join a run lead by a local with City Running Tours–their Ripped From the Headlines tour will give you insight on on several tragic moments from Chicago’s history, including the Eastland disaster and the 1972 commuter train crash.


Mexican with a twist
When you’ve already had your deep dish pizza and Italian beef sandwich on your trip, head to Tzuco for dinner. Tacos are always a good idea, but this Mexican restaurant from chef Carlos Gaytan elevates the cuisine with beautiful, flavourful plates of food; choose from chorizo and PEI mussels in a saffron beurre blanc and a hearty, fall-off-the-bone cochinita pibil served with black bean puree, habanero salsa, pickled red onions and warm tortillas.

A classic breakfast
Sweet breakfast lovers will not want to miss the signature 11 City French Toast at Eleven City Diner. This classic diner serves up a pile of fresh-baked challah french toast, topped with strawberries, bananas and toasted coconut, all with a generous drizzle of maple syrup, naturally. It’s that ideal sugar fix you’re craving to fuel you for a day of exploring the city.


Have a beer at Goose Island Brewery
Pop into award-winning Goose Island Brewery for a tour and to enjoy a pint at this local brewery darling. Now with three locations and acquired 12 years ago by Anheuser-Busch, Goose Island continues to grow and be a pioneer in the industry (they introduce bourbon-aged beer process in 1992).

Starbucks anyone?
Why add a Starbucks to your Chicago itinerary? This isn’t your average ’bucks. The five-story Starbucks Reserve Roastery on Michigan Ave. is the largest Starbucks in the world clocking in at more than 35,000 square feet. Here you’ll find on-site roasting, a rooftop deck, alcoholic beverages including the much-buzzed about Oleato Golden Foam Espresso Martini and Chicago bevvies only available at this location, such as the Roastery Boilermaker (made with cold brew, malort, whiskey, bitters, club soda and grapefruit juice). So you’re not drinking on an empty stomach, this Reserve location also serves up an array of pastries, pizzas and sandwiches, all made in house, by Italian bakery Princi. Book a tour or spend some time on each floor–you’ll find photo opps including art installations, an eye-catching food carousel, coffee card designs and the only spiral escalator in the Midwest.


ABOVE: The luxurious Godfrey Hotel in Chicago

Kick back at the Godfrey Chicago
Centrally located in the River North neighbourhood, the spacious, contemporary rooms at The Godfrey Chicago make it easy to feel right at home. Enjoy a quiet escape here (so you can be sure to get the restful sleep you need) while being within walking distance to the major sights including Cloud Gate, the Art Institute of Chicago and the Magnificent Mile. Plus, with a fantastic rooftop bar, I/O Rooftop Lounge, grabbing an afternoon cocktail or evening night cap is just an elevator ride away.

Tags: Chicago, travel, Travel Essentials, Travel Guide, travel tips

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