What to Do in Chicago

Head to the Windy City for a long weekend packed with arts, shopping and plenty of good eats


 

With its charming neighbourhoods, multitude of bike lanes and ever-expanding roster of exceptional restaurants, Chicago is a great spot for a mini-escape. Explore its soaring skyscrapers and world-class museums downtown, then do as the locals do and venture out to neighbourhoods like Wicker Park or Logan Square for friendly vibes and cozy corner pubs.

Day One

Morning Grab an espresso at Intelligentsia on Randolph Street, then stroll through the Chicago Cultural Center right next door to see rotating exhibits as well as the gleaming, literary-themed mosaic lobby and soaring Tiffany dome. Make a beeline straight across Michigan Avenue for one of Chicago’s most-visited attractions, the 24.5-acre, smartly designed Millennium Park. Snap a selfie by the iconic Cloud Gate sculpture (a.k.a. the “Bean”).  

Afternoon Duck into Xoco for an affordable and locally sourced lunch of tortas (Mexican sandwiches). Next, hop aboard the official Chicago Architecture Foundation River Cruise. For 90 minutes, you’ll learn heaps of history while marvelling at the stunning skyscrapers along the Chicago River. 

Evening Take a taxi to the West Loop’s Restaurant Row for Chicago’s hottest dining scene. Start at CH Distillery for a creative vodka cocktail, then walk over to the popular Girl & the Goat (reservation required) for innovative, shared plates. Try the roasted pig face—it tastes better than it sounds. 

Day Two

Morning Enjoy a hearty, yet healthy breakfast at Beatrix in Streeterville. Try the quinoa cakes with poached eggs or the fluffy lemon pancakes. Afterward, take a lakefront bike tour with Bobby’s Bike Hike. You’ll get a fantastic overview of the city on the stunning Lakefront path, which runs for 30 kilometres past beaches, through Lincoln Park, and by some of the city’s grand old mansions in the Gold Coast.

Afternoon You’ve worked up an appetite, so dig into a juicy burger at Au Cheval, then head to the Magnificent Mile for big-name shopping and beautifully landscaped streets. When you’re shopped-out, walk south across the iconic Michigan Avenue Bridge and down the stairs to the newly expanded Riverwalk. Wander along the river under many of Chicago’s movable bridges while enjoying the distinct style of each block.

Evening Head to always-chic Lincoln Park for dinner at Oyster Bah, a trendy spot that specializes in super-fresh seafood and oysters. After your meal, continue to the world-famous Second City, the improv launching pad of many comedians, including Bill Murray and Tina Fey.

Day Three

Morning Enjoy breakfast in the stunning atrium at the 3 Arts Club Cafe inside the newly renovated, 102-year-old Three Arts Club building. Next, spend some time in the renowned Art Institute of Chicago, or, if art isn’t your thing, head to the nearby Shedd Aquarium or Adler Planetarium—both sure bets for family fun.

Afternoon Spend some time in the Wicker Park neighbourhood. Grab a Divvy Bike (Chicago’s bike share) and cycle The 606, Chicago’s newest park created from an abandoned elevated rail track. Afterward, grab a cold beer and some tasty tacos on the sunny patio at Big Star. Wander around Milwaukee Avenue for some cool, indy boutiques and one of Chicago’s oldest and largest used bookstores, Myopic.

Evening If you’re not ready to go back to your hotel, head northwest to Logan Square, another of Chicago’s “it” neighbourhoods. Dine at Osteria Langhe, a hidden gem specializing in cuisine from Italy’s Piedmont region. After dinner, saunter a few blocks west to Scofflaw for some inventive, gin-focused cocktails and toast the end of your mini-escape.

Getting there: WestJet flies to Chicago once a day from Calgary.

WestJet Banner