Things to do in Chicago, IL

Get Your Bearings in Chicago

By Jamie Bartosch
Chicago Expert

Stay
Eat
See & Do
Party
Shop

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.

Caution:

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

Avoid:

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.

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.

Avoid:

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.

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.

Caution:

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.

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Things to do in Chicago


Chicago is known for...

Five of Chicago's most unique features and characteristics.

1. Wind:

There's nothing satirical about the nickname "Windy City." I've practically seen small dogs take flight. The weather has this habit of changing dramatically as it pleases. Catch the El at South Loop's underground Roosevelt platform during a flurry storm only to find yourself stepping off into a foot of snow at Sheridan. At the onrush of impulsive weather, what better to do than race to the window? Witness the dark outline of neighbors as they push aside curtains to do the same. Many an umbrella have been defeated by nefarious gale-force winds. However fierce, winter's below-zero wind chill doesn't soften the determined Chicagoan spirit.

2. Sports:

Chicago is a born and raised sports town. Watch a Cubs fan turn green defending his team. If you aren't for the Cubs you root for the Sox. Regardless of team loyalty, locals agree that Wrigleyville is sports bar central. French doors open to pour an overflowing house of fans onto the blocks of N Clark. Team flags proudly grace the Michigan Avenue Bridge during playoff seasons. Pass by the Art Institute on game day Saturdays to see life-size lion sculptures sporting blue and orange Bears helmets.

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. The West Loop smells like chocolate. Simply walk south of Wacker Drive and let the wind carry the factory's rich scent. The handful of blocks bordering Ukrainian Village have, in recent years, become the epicenter of up-and-coming urban real estate. Constant renovation of old-style apartment buildings has branded the area "East Village."

4. Politics:

Dirty politics in the Windy City is certainly not unheard of. Like clockwork, during Midterm Elections the scandalous flyers emerge. Dozens of papers scatter the street proclaiming Mr. Candidate an erroneous misanthrope. Pass by a light-post demanding to know "WHO IS THIS GUY?" in bold red. Election slander at it's finest. Chicago is home to bare-knuckle political campaigns. Eliminating party rivals? No problem. Later on down the road, return for a favor. We've seen the evidence in print. Former Governor this... former Senator that... Chicago has its fair share of ex-politicians behind bars. It's an old fashioned city, self-interested for good reason.

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 fly through the sites. Structural creativity reaches more than just eye-catching views. Stationed in the West Loop is a dog park with amenities that rival amusement parks. Fido plays amongst artificial canine grass and oversized dog bowls with continuously streaming water. Upon entrance cool off in a cloud of mist courtesy of the stainless steal gateway.