Your Ultimate Guide to Chicago: Things to Do, Places to Eat, and Where to Stay

Icon Share


Advisor - Alyssa Sharp
Curated By

Alyssa Sharp

  • Chicago

  • Arts & Culture

  • Food & Wine

  • City Travel

  • History

  • Architecture

  • Foodie

  • Entertainment

The Chicago skyline is a breathtaking architectural marvel, defined by iconic skyscrapers.
Curator’s statement

Chicago is a vibrant and exciting city with something to offer everyone. Whether you're interested in history, art, architecture, food, or sports, you're sure to find something to love in Chicago.

The Fora Difference

Book with Alyssa to access exclusive perks and experiences on your trip.

[object Object]
Killer perks

Free upgrades, spa credits and more—we got you

[object Object]
Personalized recs

Customized travel planning for your style

[object Object]
Insider knowledge

Expert advice from people who’ve actually been there

Where to stay in Chicago

Unlock perks by contacting Alyssa to book your trip.

Things to do in Chicago

With the Chicago Boat Tour, you'll see over 40 of the city's famous buildings and hear the city's history.

My favorite three activities are:

Visit the Art Institute of Chicago, one of the world's leading art museums.

Art Institute of Chicago. It is one of my favorite art museums in the world with a collection that spans centuries and the globe. You can find everything from ancient Egyptian artifacts to modern masterpieces, including works by Monet, Picasso, and Van Gogh. The museum also has a number of special exhibitions throughout the year, so there's always something new to see.

Take a boat tour of the Chicago Architecture Center to learn about the city's iconic skyline.

Chicago Architecture Center boat tour

The tour takes you past some of Chicago's most famous buildings, including the Willis Tower, the John Hancock Center, and the Wrigley Building. You'll also learn about the history of Chicago architecture and how the city's unique skyline came to be. I recommend trying to get on the first tour of the day for less crowds and better chance to get great photos

Visit Millennium Park and see the iconic Cloud Gate sculpture, also known as "The Bean."

Millennium Park, Chicago

Cloud Gate is a giant reflective bean that visitors can walk under and around. It's one of the most popular photo spots in Chicago. In addition to Cloud Gate, Millennium Park also features the Lurie Garden, the Jay Pritzker Pavilion, and the BP Bridge. The Lurie Garden is a beautiful public garden with a variety of plants and flowers. The Jay Pritzker Pavilion is a free outdoor concert venue that hosts a variety of performances throughout the year. The BP Bridge is a pedestrian bridge that connects Millennium Park to Maggie Daley Park.

Millennium Park is a great place to spend a day exploring and enjoying the outdoors. It's also a great place to people-watch and take in the sights and sounds of the city.

More things to do to:

Catch a show at Second City, the legendary comedy club that launched the careers of Tina Fey, Steve Carell, and many others.

Field Museum, Chicago

Visit the Field Museum, one of the world's largest natural history museums.

Museum of Science and Industry, Chicago

Visit the Museum of Science and Industry, one of the world's largest and most popular science museums.

Lincoln Park Zoo, Chicago

Visit the Lincoln Park Zoo, one of the country's oldest and largest zoos.

Grant Park, Chicago

Take a walk through Grant Park, one of the city's largest and most popular parks.

See a game at Wrigley Field, home of the Chicago Cubs, or Soldier Field, home of the Chicago Bears.

Chicago Riverwalk

Take a walk along the Chicago Riverwalk, a scenic walkway that winds along the Chicago River.

Magnificent Mile, Chicago

Visit the Magnificent Mile, a world-famous shopping district.

Places to eat & drink in Chicago

Deep-dish pizza is Chicago's style like this one from Giordano's.

Chicago is known for its deep-dish pizza, so be sure to try a slice while you're in town. Some of the most popular deep-dish pizzerias include Lou Malnati's, Giordano's, and Gino's East.

Chicago is also home to a number of Michelin-starred restaurants, such as Alinea, Topolobampo, and The Purple Pig.

If you're looking for something more casual, there are plenty of great options as well, such as Portillo's, The Billy Goat Tavern, and Garrett Popcorn Shops.

Need to Know

Looking for more travel inspiration? Check out my guide, Tour of Prague, Budapest & Vienna.

Advisor - Alyssa Sharp

Travel Advisor

Alyssa Sharp

Get in touch with Alyssa

Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can normally expect a response from Alyssa within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).

This guide is part of our ongoing series on travel to Chicago.