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.

The first upscale women's clothing store in Lakeview, Krista K was established in 2002 and quickly became a go-to shop for fashion-forward Chicagoans.

Three feet wide at its narrowest, The Matchbox claims to be “Chicago’s most intimate bar,” and it may also be its tiniest.

CB2

The younger, trendier sister store to Crate & Barrel, CB2 was founded in Old Town in 2000 and is now an ever-growing American and Canadian chain.

Some claim this spot has the best fashion selection in the Central time zone and others accuse it of having passed its hipster use-by date.

Cocktail culture meets small plates at The Drawing Room at Le Passage in the Gold Coast neighborhood. This culinary cocktail lounge’s natural backdrop (zebrawood walls, green plants, white curtains) and limited seating for just 60 patrons evoke a tony intimacy.

This elegant cocktail lounge, located on the ground floor of Chicago's Peninsula hotel, is a popular after-work hangout for locals and travelers in-the-know. Wood-paneled walls and a roaring fireplace pair nicely with the mix of jazz and funk music to create a low-key atmosphere.

Billed as Chicago’s oldest used bookstore, O’Gara & Wilson has been a preferred spot for South Side booklovers since it first opened back in 1882.

This Bucktown wine shop was founded by passionate co-owners Sean Krainik and Nathan Adams in 1998. Crafted from reclaimed, 100-year-old barn wood, Red & White’s spacious interior showcases a carefully selected variety of wine, beer, and spirits from across the globe.

Founded in 1959 by Alan Arkin and several cohorts, this comedic theater company has been the training ground for the likes of John Belushi, Mike Myers, Gilda Radner, Bill Murray, Steve Carell, Stephen Colbert, Amy Sedaris, and many others.

Inside this Andersonville shop, designed with whitewashed floors and coffered ceilings, owner Terry Ledford showcases hand-selected, refinished vintage furniture dating from the early 1900’s on up.

The Motel Bar gives patrons the comforts and cocktails of a hotel lobby bar minus the hotel.

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.