5 Days trip in Chicago, Illinois, United States
Chicago is a vibrant metropolis known for its stunning architecture, world-class museums, and delicious deep-dish pizza.
Itinerary
Kayak
Kiwi
Trip.com- 1Chicago
The Art Institute of Chicago
Visit one of the oldest and largest art museums in the United States, featuring a collection of over 300,000 works of art from around the world.
- 3Chicago
The Signature Room at the 95th
Dine at one of the best restaurants in Chicago with panoramic views of the city from the 95th floor of the John Hancock Center.
- 4Chicago
Green Mill Cocktail Lounge
Listen to live jazz music and enjoy classic cocktails at this historic Chicago bar that was once frequented by famous gangsters.
- 5Chicago
St. Clair Hotel
Check into the newly renovated St. Clair Hotel located in the trendy River North neighborhood.
- 6Chicago
Millennium Park
Take a morning stroll through the famous Millennium Park, home to Cloud Gate (aka The Bean) and many other fascinating sculptures and public art installations.
- 7Chicago
Chicago Riverwalk
Explore the Chicago Riverwalk, a pedestrian waterfront featuring stunning views of the city skyline, architecture, and plenty of shops and restaurants.
- 8Chicago
Chicago Architecture Center
Learn about the rich architectural history of Chicago with exhibits, tours, and workshops at the Chicago Architecture Center.
- 9Chicago
Lou Malnati's Pizzeria
Indulge in deep-dish pizza at one of Chicago's most famous pizzerias, Lou Malnati's.
- 10Chicago
Second City
Laugh the night away at Second City, a comedy club and theater that has launched the careers of many famous comedians.
- 11Chicago
Lincoln Park Zoo
Visit the free Lincoln Park Zoo, home to over 200 species of animals from around the world.
- 12Chicago
Oak Street Beach
Spend the afternoon lounging on Oak Street Beach, one of the most popular beaches in Chicago with stunning views of Lake Michigan and the city skyline.
- 13Chicago
The Purple Pig
Experience Mediterranean-inspired small plates and wine at The Purple Pig, a popular Chicago restaurant located on the Magnificent Mile.
- 14Chicago
Kingston Mines
Listen to live blues music at the iconic Kingston Mines, one of the oldest and most famous blues clubs in Chicago.
- 15
- 16Chicago
Museum of Science and Industry
Explore the Museum of Science and Industry, one of the largest science museums in the world, with hands-on exhibits, interactive displays, and live demonstrations.
- 17Chicago
Wrigley Field
Visit the famous Wrigley Field, home to the Chicago Cubs baseball team since 1916, and take a guided tour of the stadium.
- 18Chicago
Girl & the Goat
Experience unique and flavorful dishes at Girl & the Goat, a popular Chicago restaurant known for its creative twists on classic dishes.
- 19Chicago
The Second City Improv
Enjoy an evening of improv comedy at The Second City, one of the premier comedy clubs in the country.
- 20
- 21Chicago
Chicago Botanic Garden
Experience the natural beauty of the Chicago Botanic Garden, a 385-acre living museum featuring 27 display gardens and four natural habitats.
- 22Chicago
Maggie Daley Park
Get your adrenaline pumping with the various outdoor activities at Maggie Daley Park, including rock climbing, mini golf, and a skating ribbon.
- 23Chicago
Spiaggia
Indulge in contemporary Italian cuisine at Spiaggia, one of the top fine dining restaurants in Chicago.
- 24Chicago
The Whiskey Room
Sip on rare and unique whiskeys at The Whiskey Room, a cozy bar located in the Loop.
- 25