Chicago

Things to do in Chicago

Chicago’s diverse blend of design, art, culture, music, and architecture means you’ll never run out of things to do in Chicago. For a relaxing, loosely structured day, visit Millennium Park to take in views of the Chicago waterfront and admire Cloud Gate, Chicago’s famous reflective bean sculpture. Stimulate your artistic side with a visit to Museum Campus, which houses three museums in one, and showcases the world’s most complete Tyrannosaurus skeleton, among other amazing treasures. One of the most popular things to do in Chicago is to visit the Chicago Blues Festival. Taking place over three days and across five stages, this festival, celebrating Chicago’s foundational role in the blues movement, draws more than half a million fans from around the world to celebrate the scene’s past, present and future. Created in 1984 to honor Muddy Waters, one of the progenitors of the Chicago blues style, the festival has hosted famous performers like BB King, Ray Charles, Bonnie Raitt, and Chuck Berry. (Jazz lovers can take in the Chicago Jazz Festival, too).

More cerebral Chicago activities come courtesy of the Chicago Architecture Foundation, which operates nearly 90 different tours, which you can take by boat, by bus, or on foot, and which cover everything from the city’s ultramodern skyscrapers to the historic downtown district and tours of various neighbourhoods. The foundation also organizes an Appetite for Design series, which merges culinary and architectural appreciation at some of Chicago’s top restaurants.

On a clear, warm day, admire Chicago’s architecture from a unique vantage point: the Chicago River. Wateriders offers guided kayak tours through downtown Chicago for a truly one-of-a-kind sightseeing experience that includes Willis Tower, Wrigley Building, and Merchandise Mart.

Founded by two Polish brothers, Gene’s boasts 40 varieties of artisan smoked meats and naturally cased sausages, prepared in-house, as well as an equally impressive assortment of imported beers and wines, and European candies, condiments, and foodstuffs for picnicking.

Specializing in artisanal cheese, bread, and wine, Pastoral is a neighborhood favorite. Its sandwiches, made with crusty bread from beloved Bennison’s Bakery and stacked with top-quality meats and cheeses, are some of the best in the city.

Although there’s no sign or clearly marked door, a yellow light bulb heralds this Wicker Park cocktail lounge, where crystal chandeliers and cornflower blue velvet curtains enhance the speakeasy vibe.

With its white deli cases, waxed butcher paper, and gingham-patterned walls, you might be tempted to order a corned beef on rye or pastrami, but the setting is actually the backdrop for this customizable T-shirt shop in Bucktown.

Add some color to an afternoon in Chicago with a visit to the Museum of Contemporary Art, one of the largest contemporary art museums in the country.

Instead of visiting the John Hancock Center’s zenith during daylight hours, opt for an evening cocktail in the building’s high-flying lounge. Located on the 96th floor, the dimly lit bar has dazzling 360-degree views of the city.

Established in 1961 by a group of 17 bibliophiles, this community-owned shop is now considered one of the world’s finest academic bookstores and has expanded to two additional locations in Chicago.

Housed in the 1904 Santa Fe Building designed by Daniel Burnham, the Chicago Architecture Foundation’s ArchiCenter features temporary exhibits as well as a permanent display entitled Chicago: You Are Here.

Small plates and martini boîte.

Once a historic movie theater, the two-story venue transformed itself in 1996 as an outlet for up-and-coming jazz, R&B, funk, and hip-hop musicians. If you hanker to hear local blues music, have dinner at the Back Porch and stay for the live 10 p.m. show.