Chicago, Illinois

We asked Concierge Kristen Klus of Four Seasons Hotel Chicago to gather the savviest sightseeing suggestions she could find—not just her own but also those of other local connoisseurs, including some she works with every day at the Hotel. Discover the glittering city beside the lake, with its iconic architecture, art, sports, shopping and fine dining.

Restaurant Row

Head to Randolph or Jefferson streets in the Warehouse District, which are lined with some of Chicago’s best restaurants: Blackbird and its sister wine bar, Avec, as well as Sepia and Province. Avec, which also has a lengthy beer list, is known for its selection of artisan cheeses from Spain, Italy, France and Portugal. At Blackbird, you might start with a pistachio gazpacho and finish with a dark chocolate financier. Province offers contemporary American cuisine, and Sepia’s seasonal menu features local ingredients and creative flatbreads.

Architecture Boat Tour

Chicago is the birthplace of modern American architecture. You can see 50 of the city’s most significant buildings on the Chicago Architecture Foundation‘s boat tour on the Chicago River. Every tour is led by a CAF-certified docent. The CAF also conducts walking tours of many neighbourhoods.

Shop Talk

Balani at 10 S. LaSalle in the Loop offers men’s suits, while Optimo, on the South Side, is one of the last traditional men’s hatters. For the women, Maria Pinto and Ikram are boutiques that feature first lady Michelle Obama’s favourite designers. Women can design their own purses and bags at 1154 Lill Studio in Lincoln Park.

Sport Time

Chicago is known for its sports teams, but if we had to pick one, it would be catching a Cubs game at one of America’s greatest ballparks, Wrigley Field. If you’re not a baseball fan, or not here in baseball season, there’s football, basketball, hockey, soccer and lacrosse, and the Chicagoland Speedway in nearby Joliet for NASCAR races.