Things to Do

People who've lived here their whole lives still haven't done it all. This page sorts the city by what you're into, with a short take on each and links to our longer pages. If you want the big-name sights in one place, start with attractions in Chicago. If you're on a budget, free and cheap things to do will fill a weekend by itself.

Architecture

Chicago is where the skyscraper grew up, and the buildings are the main event even if you've never cared about architecture before. The Chicago Architecture Center River Cruise is the best $57 you'll spend here. It's 90 minutes on the river from 112 E. Wacker Dr. with a trained volunteer docent, and it runs from mid-March to late November. The Chicago Architecture Center itself is across the street at 111 E. Wacker. After that, walk the Loop and look up, or go out to Oak Park for the Frank Lloyd Wright Home and Studio, where Wright lived and worked for two decades (see things to see and do in Oak Park). For the view from the top, compare Skydeck and 360 CHICAGO on our attractions page, and for other guided options see sightseeing tours and unusual tours.

The lakefront and the river

Lake Michigan is Chicago's best free attraction. On hot summer days the beaches are packed, and Oak Street Beach is a short walk from the Magnificent Mile. Grant Park and Millennium Park are free and full of free concerts in summer (see free summer events). The Riverwalk runs along the south bank of the river from the lake to Lake Street, with bars and kayak rentals. Navy Pier is worth an hour for the skyline view back from the end, less so for a whole day. For boats, paddling and the rest, see 5 ways to get out on the water, how to plan a summer picnic and the Chicago Air and Water Show, held every August. Lincoln Park Zoo, a few blocks from the lake, is free every day of the year.

Away from the lake, The 606 is a 2.7-mile trail on an old elevated rail line along the border between Bucktown and Wicker Park and on west through Humboldt Park and Logan Square. It's a good way to see the Northwest Side on foot or by bike.

Museums

The Art Institute alone is worth the trip, and the Field Museum, Shedd Aquarium, Adler Planetarium and the Griffin Museum of Science and Industry (the old MSI) aren't far behind. They're also expensive, at $25 to $55 for adults. Our museums in Chicago page has current prices and the free ones, and you can save with free museum days or a discount city pass. When the weather turns, things to do on rainy days has more.

Neighborhoods

Chicago's neighborhoods are where you find out what the city's actually like, and most are an easy L ride from downtown. Neighborhoods to visit using public transportation is the place to start. Then pick from Lincoln Park, Lakeview, Bucktown, Old Town and River North, the Gold Coast, the Magnificent Mile and Streeterville and Little Italy. Pilsen, on the Pink Line, has the free National Museum of Mexican Art and a lot of murals. In summer nearly every neighborhood throws a street festival with food, beer and bands, and most charge little or nothing to get in (see neighborhood festivals).

Sports

Chicago has two baseball teams and people take sides. The Cubs play at Wrigley Field, their home since 1916, and a day game there is a good afternoon even if you don't follow baseball. See Chicago Cubs games, the Chicago Cubs, hotels near Wrigley and where to eat and drink near Wrigley. The White Sox play on the South Side at Rate Field, which opened as Comiskey Park in 1991 and has had a few names since. The Bears play at Soldier Field, and the Bulls and Blackhawks share the United Center on the Near West Side.

The old version of this page sent you to the races at Arlington Park. That's done. Arlington Park held its last races in 2021, and the Chicago Bears bought the site in 2023.

If you'd rather play than watch, see ways to work out in Chicago.

Music

Chicago is a blues town first. Our blues and jazz clubs page covers where to go, and the Green Mill on Broadway in Uptown still has live music on its calendar most nights. In summer, the Grant Park Music Festival puts on ten weeks of free outdoor classical concerts downtown, and the city's Chicago Blues Festival takes over three days in early June. Lollapalooza fills Grant Park for four days every summer, so book a hotel early if your dates overlap. Up in Highland Park, Ravinia runs outdoor concerts from June to September and has been the Chicago Symphony Orchestra's summer home since 1936. Bring a picnic and sit on the lawn.

Theatre and comedy

Chicago's theatre scene is bigger than most people expect, from touring Broadway shows in the Loop to storefront companies in Lakeview. Steppenwolf, the company Gary Sinise co-founded in 1974, is on Halsted Street in Lincoln Park, and The Second City has been doing improv here since 1959. See theatre in Chicago for more.

Food and drink

If food is why you travel, Chicago holds up. Start with the local stuff, which means pizza (deep dish, and the thin tavern-style cut into squares), Chicago-style hot dogs and burgers. For a splurge, see Michelin-starred restaurants. To keep costs down, try cheap eats, dining on a budget and BYOB restaurants. There's also brunch, outdoor dining, vegetarian and vegan, international food and farmers markets, including Green City Market. Our food and drink section has everything else.

For drinks, see nightlife, rooftop bars, unique bars and breweries and brewpubs.

Shopping

The Magnificent Mile (Michigan Avenue north of the river) is the famous stretch, but most of what's there you can buy at home. The independent shops in neighborhoods like Bucktown are more fun. Our shopping page has both.

Events and holidays

Chicago celebrates all year, and some events are worth planning a trip around, like the river turning green for St. Patrick's Day and Christmas downtown. See holidays and events in Chicago for the full list, or go by month, starting with September, October and November.

Trips out of town

If you have an extra day, see easy day and overnight trips from Chicago, things to do in Milwaukee, or start a Route 66 road trip from its first mile in the Loop.

Putting it all together? Try three days in Chicago, planning a family trip or romantic things to do.

Photo by Stuck in Customs