Best Things to Do in Chicago
Planning your trip to Chicago and wondering where to start among all the towering skyscrapers and famous food spots? You will want clear answers on what is genuinely worth your time. This guide breaks down Chicago's top sights, from the stained glass of Chicago Cultural Center and the public art in Millennium Park to architecture cruises on Chicago River and timeless galleries inside Art Institute of Chicago. Discover how ranked tours and tickets stack up so you can plan the perfect itinerary.
Attraction hubs in this guide
Activities featured in this video
Chapters
- 0:00 Things to do in Chicago
- 0:07 Architecture, Food & Lakefront
- 0:20 Chicago Cultural Center
- 0:32 Original Chicago Architecture Interiors Tour:
- 0:46 Millennium Park
- 0:58 Chicago Favorites Ultimate Food and Walking Tour
- 1:12 Chicago River
- 1:22 Chicago River 90-Minute Architecture Boat Tour
- 1:33 Art Institute of Chicago
- 1:47 Skip-the-line: Art Institute of Chicago Guided
- 1:59 How the Outty Ranking works
- 2:14 Start
- 2:23 Find activities on Outty
Keep exploring Chicago
More attractions
Top ranked experiences
- Chicago Murder Mystery TourFrom $3591.8/100
- Chicago Architecture and True Crime: Halloween EditionFrom $3589.7/100
- Chicago in a Day Walking Tour: Food, History & ArchitectureFrom $10189.6/100
- Chicago Bike & Classic Food Tour: Bikes, Bites & Views - AdultsFrom $8989.6/100
- Chicago's Delicious Downtown Donut Tour with 8 Amazing TastingsFrom $7088.8/100
- Haunted Chicago: Crime, Ghosts, and Capone Walking TourFrom $3588.5/100
Full transcript
Introduction
Welcome to Outty. Let's explore Chicago, United States, and the iconic activities waiting across the Windy City.
About the city
Chicago draws travelers with legendary skyline architecture, deep-dish pizza, deep jazz roots, and sweeping Lake Michigan shores. You can cruise historic waterways, stroll scenic parks, or dive into storied downtown corridors.
Chicago Cultural Center
You'll want to check out the Chicago Cultural Center, which houses the world's largest stained-glass Tiffany dome beneath soaring classical arches. Outty has forty three experiences at the Chicago Cultural Center.
Original Chicago Architecture Interiors Tour: Dazzling Interiors
Among them is the highly ranked Original Chicago Architecture Interiors Tour with Dazzling Interiors. It made the Outty 90+ Club with an Outty Ranking of ninety seven, celebrated for breathtaking lobbies and insider historic details.
Millennium Park
No trip to Chicago is complete without the Millennium Park, where monumental public art and lush green gathering spaces meet downtown energy. Outty has eighty one experiences at the Millennium Park.
Chicago Favorites Ultimate Food and Walking Tour
One standout is the Chicago Ultimate Food and Walking Tour. It made the Outty 90+ Club with an Outty Ranking of ninety two point two, giving you tasty deep dish, hot dogs, and local lore.
Chicago River
An absolute must is visiting the Chicago River walk, where canyon-like skyscrapers flank the bustling Riverwalk promenade. Outty has forty five experiences at Chicago River.
Chicago River 90-Minute Architecture Boat Tour
A top pick is Chicago River 90-Minute Architecture Boat Tour, holding a strong Outty Ranking of eighty nine point one for expert narration and unbeatable skyline perspectives.
Art Institute of Chicago
If you only do one thing in Chicago, make it Art Institute of Chicago, showcasing masterpiece Impressionist galleries and iconic bronze lions. Outty has forty five experiences at Art Institute of Chicago.
Skip-the-line: Art Institute of Chicago Guided Tour
Also in the lineup is the highly ranked Skip-the-line: Art Institute of Chicago Guided Tour, earning an Outty Ranking of eighty eight point five by fast-tracking you straight to world-famous paintings.
How the Outty Ranking works
With five hundred and forty nine ranked Chicago experiences on Outty, the zero to one hundred Outty Ranking analyzes traveler sentiment, demand, pricing value, and booking flexibility, highlighting the top three in our ninety plus club.
How to explore
Start with the city. Explore an attraction. Compare the best experiences. Outty connects the dots so you can book Chicago with complete clarity.
Plan with Outty
Find what's worth doing in Chicago, with Outty.
Outty ranks every experience in Chicago on a 0 to 100 scale built from traveler sentiment, demand, value and flexibility, so you can compare the options inside each attraction instead of scrolling near identical star ratings. How the Outty Ranking works.