A visit to Chicago could be spent simply exploring its architecture. Its eclectic buildings range from neo-Gothic to Roman revival. While its architectural heritage lends considerable atmosphere, the city also offers visitors chef-driven restaurants, aquatic recreational opportunities, sporting events and shopping.
Where to stay: On Randolph Street, find some of Chicago’s best eateries and the Soho House Chicago, a 40-room hotel and exclusive members-only club located in a century-old factory. Guests have access to a gym, rooftop pool, theatre and five restaurants, including Mediterranean-inspired House Kitchen.
What to do: On a self-guided culinary tour of Chicago’s food halls, spend an afternoon at Eataly sampling fresh Italian pizza and pastries and then tear into tacos and tortas at Latinicity. At Revival Food Hall, many top restaurants maintain stalls. Try the fried chicken at The Budlong or a bowl of steaming ramen at Furious Spoon.
Where to eat: Make reservations now and snag a table at Grace. Although it’s one of the city’s most expensive restaurants, it’s also one of the best, with three Michelin stars. Choose from a flora or fauna tasting menu to sample inventive dishes such as Bay scallops with white poppy, romaine and nasturtium flowers.
Where to stay: The unique design of the Virgin Hotel Chicago in the landmark Old Dearborn Bank Building lets guests section rooms into dressing and bedroom “chambers.” An app allows guests to order room service and control in-room functions. The hotel features a gym and open-air bar with a view of the Loop neighbourhood.
What to do: Easily accessible recreational activities are available on Lake Michigan and the Chicago River. At North Avenue Beach, rent a paddleboard and paddle in Lake Michigan. Or kayak along the Chicago River on a tour with Urban Kayaks and gaze up at architecture such as the neo-gothic Tribune Tower and Wrigley Building.
Where to eat: Start with a healthy breakfast of quinoa cakes and poached eggs or light and fluffy lemon pancakes at Beatrix. For dinner, Eden serves New American food infused with Mediterranean flavours. Dishes include Portuguese spiced chicken and smoked Tajarin (a pasta from the Piedmont region in Italy).
Where to stay: Check into the former sporting club once frequented by one-time Cubs owner William Wrigley Jr. The newly refurbished, Venetian-gothic Chicago Athletic Association Hotel features a grand marble staircase and mosaic floors. In the vintage game room, guests can play bocce, billiards and shuffleboard.
What to do: You must catch a game at Wrigley Field, the 103-year-old home of the 2016 World Series Champion Chicago Cubs and the country’s second-oldest Major League Baseball stadium. Sign up for a daily behind-the-scenes ballpark tour, and, on non-game days, visit the press box and the Cubs dugout and walk onto the field.
Where to eat: In the Wrigleyville neighbourhood, find sports bars like Murphy’s Bleachers and The Cubby Bear, where you can expect rowdy sports fans, buckets of beer and wings. For a quieter spot to watch the game, go a couple blocks west to Southport Corridor and try some of the city’s best pie at Coalfire Pizza.
Where to stay: Check into The Robey, which opened late last year in a historic office building in the Wicker Park neighbourhood, known for its boutique clothing, art and book shops. Enjoy minimalist rooms with hardwood floors and simple furnishings. The rooftop cocktail lounge features a 180-degree view of the city.
What to do: On beautifully landscaped Michigan Avenue, you’ll find Apple and Nike flagship stores and, on Oak Street, high-end shops such as Prada and Jimmy Choo. Stroll through the boutiques of the Wicker Park and Bucktown neighbourhoods to find vintage clothing at Una Mae’s and artist-designed shoes at Bucketfeet.
Where to eat: Enjoy Mexican dished such as chiles toreados (grilled, salted jalapeño peppers) and a local brew on Big Star’s sunny patio, or sip a creative cocktail and sample oysters at the new Publican Anker. Downtown in the River North neighbourhood, try the mezze and the toasted almond and garlic spread at Éma restaurant.
Getting there: WestJet flies to Chicago six times a week from Toronto.
Five Little India Neighbourhoods to Discover
A wide range of North American cities now have Little India neighbourhoods, filled with authentic restaurants and colourful shops. Here's where to indulge in one of the world's most fascinating cultures in Vancouver, Dublin, Chicago, Regina and New York City.