Chicago Attractions

The Chicago Architecture Foundation offers a variety of ways to explore the history and architecture of downtown Chicago and some surrounding neighborhoods. CAF’s popular boat tour provides information about more than 50 buildings along the river, while the walking and bus tours are themed to describe certain groups of architecture. Bike and Segway tours are also offered. Tickets range from $15 for some walking tours, to $44 for boat tours.

Explore a few of Chicago’s 77 diverse neighborhoods with Explore Chicago’s neighborhood tours. Tours are on Thursday, Fridays, and Saturdays at 10:00 am, and focus on a different area each time. You might want to learn more about the pubs, historic parks, art in the public transportation systems, or the foods of a certain culture in the area. Tour tickets range from $30- $55. You can also venture to these neighborhoods on a self-led tour: see the Neighborhoods section below for more information.

If the plethora of Chicago’s downtown and neighborhood restaurants delights your taste buds, you may want to go on a tour focusing on food. Chicago Food Planet offers a number of filling 3-hour culture and food-tasting walking tours. Prices range from $45-$60. Bike Chicago offers Bike & Food tours, which allow you to explore the foods that made Chicago famous, or taste the city’s sweets. Prices range from $50-$60, including bike rental.

Chicago Detours, founded by a UChicago Alum, shares stories and places even locals don’t know through guided tours of Chicago architecture, history and culture. Walking tours of interior architecture, historic bars, food history and Chicago neighborhoods are available seven days a week, all year. 

Visit the Chicago Cultural Center to see the world’s largest Tiffany stained-glass dome and ornate mosaics and learn more about Chicago from the Visitor Center. Free public tours are every Wednesday, Friday, and Saturday, at 1:15 pm, but are limited to the first 20 people.

Navy Pier is Chicago’s amusement park. Located between the Loop and the Magnificent Mile, the Pier hosts Cirque du Soliel shows, fireworks, carnival games, and a number of dining and shopping locations.

The Museum of Contemporary Art features a number of eclectic collections at a time, changing every three months or so. MCA also hosts occasional dance and song performances as well. Admission is $12 for adults, $7 for students, and free for IL residents on Tuesdays.

In addition to the comprehensive collection of science and art museums, Chicago is also home to a number of cultural museums. These may focus on the story of the Chicago River, African American history, Mexican history, broadcast communication, and beyond. Visit UofC Chicago Studies or the Chicago tourism website for more.

The community of Chinatown is decorated with traditional red arches and dragons, and a favorite location for all styles of Chinese food, bubble tea, and dim sum. There are a number of pastry shops and supermarkets that offer authentic Chinese products.

Pilsen is the home of the historical Museum of Mexican Art, and is a bustling center for art galleries and authetic Mexican food. The buildings here are vibrantly colored. Irish, German, Polish, and Italian cultures are also found here.

Greektown keeps the Greek heritage alive, with the National Hellenic Museum, an annual Taste of Greece, and well-established Greek restaurants. The area known as Little Italy features a number of Catholic churches, the Hull House Museum, the University of Illinois at Chicago, and the expected Italian restaurants.

Old Town is where the busy heart of Chicago used to be, with ornate upscale townhomes, picturesque landscaping, and a number of boutiques. Second City, along with the Steppenwolf Theatre, find their homes here.

Lincoln Park is right by the lakeshore, with good beaches and tree-lined streets for jogging. There are a number of boutique stores and restaurants here, as well as a number of attractions. The Lincoln Park Zoo, Chicago History Museum, Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and the Alfred Caldwell Lily Pool are all here.

The Wicker Park and Bucktown area is famous for its numerous art galleries, theatres, nightclubs, and coffeehouses. Thrift and gift shopping are favorites here. Restaurants and buildings in the area have German and Eastern European influences.

Lakeview is a neighborhood with a number of diverse cultural stores and cuisines, as well as entertainment groups small and large. It encompasses Boystown, the home of the annual Chicago Pride parade, features many LGBTQ-oriented shops, bars, and restaurants. The Center on Halstead here is one of the premiere LGBTQ community centers in the world.

Andersonville is a good choice for brunch, Middle Eastern bakeries, gastro-pubs, and Swedish restaurants. Its architecture seems to have Greek roots, and the buildings are painted cleanly and colorfully. Andersonville is also home to a vibrant gay and lesbian community.

Rogers Park is a little like Hyde Park in that it is a college town (Loyola University), features some Frank Lloyd Wright architecture, and a number of live theatres. It is also is adjacent to a few nice beaches. There is a plethora of ethnic restaurants here, ranging from Pakistani to Russian.