With affordable flights from both Edmonton and Calgary, there’s never been a better time for a Windy City weekend. Combine a few new sights and some iconic experiences for the perfect Chi-Town getaway.
Originally built in 1893 as a men-only sports club, the Chicago Athletic Association was reborn in 2015 as a lounge-y boutique hotel. Nestled on Michigan Avenue in the heart of the Loop, the polished property is within walking distance of many top sights: the famous Cloud Gate sculpture (a.k.a. the Bean) is just across the street in Millennium Park. For a cheaper but equally chic stay, check into Lincoln Park’s Hotel Versey. The historic building previously served as the Diversey Arms Hotel, popular with jazz musicians of the 1920s. Today, the eclectic decor, much of it crafted by local artists, is Instagram heaven.
Even if you’re not an art aficionado, the Art Institute of Chicago is a must-see. In a building constructed for the 1893 World’s Columbian Exposition, the gallery houses countless classics, including several of Monet’s Water Lilies, Picasso’s Old Guitarist and the meme-friendly American Gothic by Grant Wood. Ferris Bueller fans will recognize the interiors from director John Hughes’s high school romp.
On warm evenings, walk north along Michigan Avenue toward the Chicago River to the Riverwalk, a waterside trail dotted with pubs and wine bars. If you don’t settle on one of the many outdoor patios, cross the river and walk west to Chicago Cut Steakhouse, a classic carnivore eatery.
MORE TO READ
How AMA Travel helps you find the perfect hotel room
The Adler Planetarium’s Doane Observatory houses a powerful aperture tele-scope capable of viewing celestial objects trillions of kilometres away. On select Friday nights, take your stargazing to new heights with a free peek through the lens. The telescope gathers 5,000 times more light than the human eye, allowing you to spot a universe of stars and planets.
Make your way to the River North neighbourhood by crossing the circa-1930 Wabash Avenue Bridge, one of Chicago’s 43 movable bridges still in operation today. Grab a coffee and a sweet breakfast to go at the Doughnut Vault on North Franklin. Expect a queue: The popular takeout window has achieved cult status, owing to confections like chestnut-glazed and wedding cake doughnuts.
As the birthplace of the modern skyscraper, Chicago has always been an incubator of urban design. Popular with Chicagoans and out-of-towners alike, a boat tour reveals this storied past, one building at a time. There are a few operators to choose from, but the Chicago Architecture Center has the most knowledgeable guides. A 90-minute tour sails past modern marvels like Marina City’s twin corncobs and the neo-Gothic Tribune Tower.
Since 1902, the Cubs have reigned supreme in this sports-obsessed town. Head to legendary Wrigley Field for the first pitch—typically at 1:20 p.m. during weekend home stands. For a true fan experience, score an outfield bleacher seat near the historic park’s hand-operated scoreboard. After the game, wander around Wrigleyville, where the raucous crowd spills out into local bars. Of course, the Cubs aren’t the only game in town: You could catch the subway to see the White Sox, pride of Chicago’s South Side. Guaranteed Rate Field boasts a grass-level bar for a player’s-eye view.
MORE TO READ
A taste of Maui: Hawaiian flavours and craft culture
Spice things up for dinner with a table at Leña Brava, the latest restaurant by hometown culinary hero Rick Bayless. Opened in 2016, the upscale West Loop cantina focuses on open-fire cooking and northern Mexican dishes, such as ceviche and roasted black cod. Wash it down with an agave cocktail or a pint from Cruz Blanca, the adjoining brewery and taquería.
Pull up a seat at The Redhead Piano Bar for an old-school nightcap. The dimly lit lounge exudes elegant charm, with patrons sipping single malts as a house musician tickles the ivories. Submit a request to hear your fave jam—anything from a jazz standard to a Top 40 hit. Celeb pianists and crooners like Billy Joel have made surprise appearances in the past.
Start the day with brunch at Hampton Social in River North. The laid-back Cape Cod-meets-Midwest setting is perfect for nibbling on fresh crab and avocado toast or wild berry French toast. Toast with a glass of the house rosé of the day or a slushy peach-flavoured “frosé”.
Get your retail fix on the Magnificent Mile, the Midwest’s premier shopping district. Running from the river north to Oak Street, this stretch of Michigan Avenue is packed with shops, spas and restaurants. Here you’ll find a mix of luxe department stores (Nordstrom, Neiman Marcus), niche shops like American Girl Place, and top fashion brands, from Marc Jacobs to Uniqlo. Consider adding an extra checked bag to your flight before hopping the train to the airport!
• The aptly named Loop is Chicago’s downtown core, which is encircled by a three-kilometre “loop” of elevated train tracks known as the ‘L’. It’s the best way to get around.
• Both of the city’s international airports—O’Hare and Midway—offer downtown train service. From O’Hare, a ride aboard the ‘L’ costs $5 USD and takes 45 minutes.
• Come summer, festivals are plentiful: Taste of Chicago (July 10–14), Lollapalooza (Aug. 1–4), and the Air and Water Show (Aug. 17 & 18) are annual crowd-pleasers.
• Don’t leave town without ordering a pizza. Opt for a local fave stuffed pie: It’s like deep dish but topped with an extra layer of dough. Giordano’s is your best bet.