Things to do in Chicago, IL

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Get Your Bearings in Chicago

Chicago Expert

By Jacky Runice
Chicago Expert

See & Do
Stay
Eat
Party
Shop

Things to See

If it seems as though there's a limitless list of appealing things to see and do in Chicago, your perceptions are razor sharp. It's a struggle for locals to take in everything they hope to so visitors have the wonderful dilemma of choosing between world-class museums, miles of shopping, poking around the neighborhoods, catching a Broadway show or the famous Second City comedy theater and 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 Millennium Park, you'll be awed by Chicago's breathtaking beauty and Midwestern charm.

Hot Tips: Seeing a lot of attractions? Get a Chicago City Pass to save money on admissions.

Take It or Leave It: Navy Pier is fun for families but adults can skip it unless you're boarding a sightseeing vessel on the dock.

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

Caution: Although Divvy bikes are convenient, maneuvering in between cars and buses is dicey unless you're experienced.

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Where to Stay

It seems as though a new hotel is opening every few months in the city and, in fact, Chicago's Central Business District boasts 132 hotels  with more than 43,000 rooms. This is good news for visitors in terms of quantity and quality of features. Some new properties target luxury travelers and others aim at young adult visitors with almost dorm room features and communal public spaces. There are plenty of budget-friendly and mid-priced options. Choose a spacious downtown hotel, a smaller boutique property or some of the newer hotels offering inventive amenities like robot delivery to your room and DJ's at night. 

Take It or Leave It: Online auction sites may offer lower rates but you could end up in inconvenient location.

Hot Tips: Hop online and check out hotel packages which can include parking, breakfast and museum tickets.

Avoid: Paying a daily parking fee at your hotel which is absurdly pricey. Ditch the car, and take cabs, Uber or public transportation. Chicago's traffic is horrid and parking is expensive.

Caution: There can be add-on taxes and fees to hotel bills, so budget accordingly.

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What to Eat

Don't be shy about sampling deep-dish pizza, hot dogs, a burger at Billy Goat's and Italian beef sandwiches, Chicago's gifts to the casual culinary world. But do some homework about your favorite cuisines and you'll hit upon incredible options  led by the nation's top chefs with Michelin stars. Sure, have a steak (there are at least 30 steakhouses downtown) but take the opportunity to dive into steamy bowls of ramen, platters of house made charcuterie and local cheeses, Honey Butter Fried Chicken, fusion tacos and a burgeoning vegan and vegetarian world of eating. Get to a food hall to try everything. 

Be Sure to Sample: Tavern style pizza, too. It's thin crust, square cut and completely satisfying.

Hot Tips: You can get the same view from atop the Hancock building in the Signature Room's bar without spending beaucoup bucks in the restaurant.

Caution: You may not get ketchup on your hot dog unless you're still in elementary school.

Take It or Leave It: Taste of Chicago: it's crowded, sweaty and not the best culinary rendition of what the city offers.

Avoid: Limiting your dining to downtown. A preponderance of the hottest eateries are in the neighborhoods.

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Places to Party

During Chicago summers, open-air rooftop bars are proliferating. They stay open deep into autumn offering outdoor heaters and hot drinks and bites. When it's cold, dance and live music clubs will entertain in grand fashion. Get to one of the blues bars or jazz clubs, too, and if you're on a budget, know that Millennium Park presents free outdoor concerts in the summer. Chicago is a fanatical sports town, which is why visitors are drawn to rowdy sports bars and friendly neighborhood taverns for game-watching. 

Hot Tips: Neighborhood clubs and bars offer real characters, lots of fun and lower prices.

Take It or Leave It: The Park at Rosemont, near O'Hare Airport, is an open-air mall filled with bars and other entertainment but it's primarily links in national chains.

Avoid: River North nightlife on weekends which can be densely populated by over-served suburbanites.

Caution: Just recall your mom's advice about drinking in clubs and bars when you were in college. It still applies.

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Where to Shop

Whether you prefer shopping at Tory Burch or Target, it's here. Chicago's most popular area is "The Magnificent Mile" - block after block of well-known stores up and down Michigan Avenue, anchored by the Water Tower Place and a couple other indoor malls like the Shops at NorthBridge. But, that means crowds, especially on weekends. Save some space on the credit card for the boutiques in Wicker Park, independently owned shops in Andersonville, vintage in Pilsen and trinkets in Ukrainian Village. 

Best Local Souvenir: A one-of-kind thingy from a museum shop or a Cubs or White Sox item.

Hot Tips: If Mag Mile shopping is your focus, look into special shopping packages at area hotels.

Avoid: The Mag Mile on summer weekends unless groups walking as a monolith don't bother you.

Caution: That bill is correct, sir, Sales tax is a whopping 10.25 percent.

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Things to do in Chicago
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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.