A quintessentially American city, Chicago has a reputation for making every type of tourist swoon, whether they’re seeking culture, art or food. While other American cities neighbouring Toronto can feel touristy, Chicago’s identity remains inimitable.

A quick flight from Toronto brings you to a sprawling city that inspires awe with its rich architecture, good food and the best libations in the Midwest. Chicago’s tapestry of neighbourhoods means that no two trips will feel the same, and with the right planning, you can explore good chunks of it on foot.

Where to stay

Grant Park is an ideal area for a first visit, and the nearby Blackstone Hotel mixes grand views of the park and Lake Michigan with a history rooted in Chicago’s legendary past, going back to the days of Al Capone. The hotel is also a leisurely walk away from Chicago’s renowned shopping and eating district, the Magnificent Mile.

Chicago, IL

◆ Population: 2.7 million

◆ Area: 237 square miles

◆ Annual visitors: 40 million

For an up-close and personal look at one of the city’s best food neighbourhoods, the Robey Chicago is a good bet. The hotel recently opened in the Wicker Park area, and it oozes style from its contemporary rooms and its bustling bistro café. And as one of the only skyscrapers in the area, it offers a unique and gorgeous 360-degree view of Chicago.

Where to eat 

Located in the hustle and bustle of the food-rich Wicker Park neighbourhood, Publican Anker is from the same team behind one of Chicago’s most popular and critically acclaimed restaurants: the Publican. This spinoff is a casual snack bar that exudes an ultra-cool vibe from the moment you step into the saloon-like interior. It only recently opened, but Publican Anker has quickly become one of Chicago’s hippest spots for snacks and drinks. The menu is expansive and just plain fun: plates of freshly shucked oysters join forces with roast chicken from the wood-fired grill, spicy wings and blood sausage. The cocktails are some of the best in town, too, as is the well-curated wine list.

After becoming acquainted with Chicago on the street level, it’s time to take things up a few floors. How about 95 floors? Sitting high above the city within the John Hancock Center, the Signature Room’s lounge and cocktail bar present magnificent views of the city with little to no obstruction. It also has a lavish brunch program, so you can enjoy plates of snow crab and caviar from the luxurious buffet to pair with the views. The Signature Room also boasts an extensive international wine list. Reservations are recommended. 

What to do

Like Toronto, Chicago is a rich mosaic of sprawling neighbhourhoods, each with its own personality. And also like Toronto, Chicago’s neighbourhoods can be challenging to navigate if you don’t know where you’re going. We recommend spending a day exploring the city’s corners with local connoisseur Steve Dolinsky. As a food writer and host of the popular Feed podcast, Dolinsky is a vocal proponent of Chicago’s many culinary identities, and he is the best guide with whom to eat your way through the city. He’ll take you from Wicker Park to Chinatown to help you get a full sense of Chicago’s scene. Dolinsky doesn’t advertise his food tours, so to book one, visit his website and shoot him an email. 

Getting There

Porter Airlines is your best bet, offering daily nonstop flights to Chicago from Billy Bishop Airport. flyporter.com

Chicago’s skyline architecture is world-renowned, and the best way to become acquainted with it is via a boat cruise. Yes a boat cruise. Trust us: the Shoreline Sightseeing tour brings you face-to-face with many of Chicago’s fabled design styles, from early modern to Art Deco to more modern aesthetic phases. Starting off from the Navy Pier, the tour gently floats through various branches of the Chicago River. It’s the best introduction to the big-shouldered town. Also, not to worry, there’s a licensed bar on board. Purchase tickets in advance.