Things to do in Chicago, IL

Get Your Bearings in Chicago

By Jamie Bartosch
Chicago Expert

See & Do

Things to See

There is always SO MUCH to see and do in Chicago, it will be a struggle for visitors to decide between the world-class museums, the miles (and malls-full) of shopping, the Broadway theater shows (or the famous Second City comedy) and the creative guided tours led on foot, bikes, boats and segways. Even if you just chill along the postcard-pretty Lake Michigan shore, or stroll through Millenium Park, you'll be awed by Chicago's beauty and charm.


Criss-crossing the city. Traffic and parking searches will eat up your time and money. Better to pick a neighborhood and explore it.

Hot Tips:

Seeing a lot of museums and sites? Get a Chicago City Pass to save money on admissions.

Where to Stay

Chicago is in the midst of a hotel construction boom, which is good news for visitors because it means increased hotel room quality and quantity. The newest hotels target the luxury traveler, but Chicago still has plenty of budget-friendly and mid-priced options. Whether you prefer a big downtown hotel, a small boutique hotel or a rental property, there's no shortage of comfortable and welcoming places to stay.


Chicago tacks a lot of add-on taxes to hotel bills, so budget accordingly.


Paying the daily parking fee at your hotel. Ditch your car, and take cabs or public transportation. Chicago's traffic is bad and parking is expensive.

What to Eat

Everyone knows Chicago is famous for its deep-dish pizza, hot dogs and Italian beef sandwiches. And with good reason. But to focus only on those foods would deny you the chance to dine at Chicago's world-class restaurants, led by some of the nation's top chefs, or to sample the city's global smorgasbord of authentic, ethnic restaurants. Chicago loves its meat, and many steakhouses are institutions. A few even still have that Rat Pack vibe to them. Fun specialty food shops also dot the city, selling everything from Chicago mix (caramel-cheese) popcorn to gourmet coffee.

Hot Tips:

Ethnic restaurants are often a better value than downtown restuarants.

Be Sure to Sample:

Deep-dish pizza. Cliche, yes, but the quintessential Chicago experience.

Places to Party

During Chicago summers, the hottest spots in town are the swanky, open-air rooftop bars and the large outdoor music venues. But when the weather's not so nice, it's the dance and live music clubs that dominate the city's nightlife. Above all, Chicago is a sports town, which is why visitors are drawn to its rowdy sports bars and friendly neighborhood taverns for game-watching.

Take It or Leave It:

The Park at Rosemont, near O'Hare Airport, is a new open-air mall filled with bars and other entertainment. But the sheer size and national-chain vibe is a little overwhelming.

Hot Tips:

Chicago's smaller clubs and bars are just as fun as the big ones.

Where to Shop

Whether you prefer shopping at Tory Burch or Target, every imaginable store exists in Chicago. Chicago's most popular shopping area is "The Magnificent Mile" - block after block of well-known stores up and down Michigan Avenue, anchored by the Water Tower Place mall. But save some room on the credit card for the boutiques in Wicker Park, the trinkets in Chinatown and the expansive suburban malls.


Sales tax is a whopping 9.25 percent.

Best Local Souvenir:

Nothing says Chicago more than a jersey, hat or T-shirt from Chicago's sports teams or stars on the Bears, Bulls, Cubs, White Sox or Blackhawks.



10Best Lists
Airport Guide

Things to do in Chicago

Chicago is known for...

Five of Chicago's most unique features and characteristics.

1. The Arts:

Comedy, theater, art, music, culture - Chicago has all of it in world-class forms. The Second City comedy club spawns some of Hollywood's biggest stars, including Tina Fey and Stephen Colbert. Chicago's theater scene rivals New York City's, with acclaimed actors, dancers and shows. And the city is a hot spot for music, from the massive Lollapalooza festival to intimate jazz and blues shows, plus the Chicago Symphony Orchestra. Many of the art world's masterpieces hang in The Art Institute of Chicago. Or, just down the street is a relatively new art icon, the mirrored sculpture, Cloud Gate (aka "The Bean").

2. Sports:

Chicagoans LOVE their sports teams. Perhaps it's most beloved team is the football team, the Chicago Bears, (or "Da Bears," as they were called in a famous "Saturday Night Live" sketch about the team's fans). But there's also deep love for the Chicago Cubs, the Chicago White Sox, the Chicago Bulls, and the Chicago Blackhawks, who have won three Stanley Cups in recent years. The sports bar hub is around historic Wrigley Field, where the Cubs play, in a north side neighborhood known as "Wrigleyville." There, you'll always find crowds watching sports in the TV screen-covered bars.


3. Neighborhoods:

The city is characterized by an incredible diversity of cultures and lifestyles. Each neighborhood has an identity, a contradiction in nightlife, attractions, dining and ambiance. Officially, more than 180 neighborhoods are distinguished, from historic college areas to gentrified hotspots. Up-and-coming areas like Humboldt Park and Pilsen neighborhoods brim with Latino culture, while the young professionals pile into the West and South Loop neighborhoods. Artsy types and hipsters mix in Bucktown, Ukranian Village and Wicker Park, while the frat boy crowd parties in Wrigleyville. The well-to-do appreciate the designer boutiques and gourmet dining in the Gold Coast and Streeterville.

4. Politics:

Chicago is proud to be home to President Barack Obama, but residents are less proud of their local government. Illinois is synonymous with political corruption - two recent governors have ended up in jail - and the city's reputation isn't much better. Former Mayor Richard J. Daley, a Democrat, had such power over the city in the mid 1960s and 70s that he and his supporters became known as the "Democratic machine," able to elect whomever they wanted. While more transparent now, the city remains a Democratic stronghold. The current mayor, Rahm Emanuel, is Obama's former Chief of Staff.

5. Architecture:

Chicago's world-famous skyline reflects powerhouse names in architecture like Ludwig Mies van de Rohe and Skidmore, Owings and Merrill. Architecture itself is the city's biggest attraction. The tour business thrives on showcasing these award-winning designs. You can walk, kayak, sail and even helicopter past the sites. Structural creativity reaches more than just eye-catching views. The stunning architecture in Millennium Park (especially the concert area at Jay Pritzker Pavilion), as well as the winding ribbon design of nearby Maggie Daley Park, bring gorgeous design and iconic images to the lakefront.