Top 5 Things to Do in Chicago

My husband and I visited Chicago for 3 days in July 2018. With its iconic architecture, renowned food scene, and world-class entertainment, Chicago had so much to offer we wished we had spent more time! Here are our favorite things we did on this trip:

1. Millennium Park

Why Visit:

Millennium Park is one of Chicago’s most famous attractions — a lively space for art, music, and events in the heart of downtown. It’s home to the city’s most photographed landmark, Cloud Gate (aka “The Bean”), and it’s a hub where locals and visitors gather year-round.

Highlights:

• The Bean → take pictures with the massive mirrored sculpture by artist Anish Kapoor. Walk underneath to see reflections warp in cool ways from below.
• Crown Fountain → two 50-foot glass towers with digital faces that “spit” water.
• Jay Pritzker Pavilion → an open-air concert venue designed by Frank Gehry with free music and movie nights in summer.

How to visit:

It was quite crowded when we visited around noon, so I recommend going early morning or late afternoon for smaller crowds

2. Chicago Riverwalk

The Chicago Riverwalk is one of the most beautiful urban waterfronts in the U.S and the perfect place to take in the city’s world-famous architecture.

Highlights:

• Architecture Boat Tour → the most iconic way to see Chicago’s skyline and learn about the city’s design history.

How to visit:

We booked the architecture boat tour online in advance from Chicago Architecture Center since tours can sell out in summer.

3. Willis Tower Skydeck

Why Visit:

Formerly known as the Sears Tower, Willis Tower is one of Chicago’s most recognizable landmarks. From the Skydeck on the 103rd floor, you’ll get panoramic views stretching up to four states on a clear day.

Highlights:

• The Ledge → step out onto a glass box that extends 4 feet (1.2 m) outside the building and 1,353 feet (412 m) above the ground!

How to visit:

We bought tickets at the door, but you can also buy tickets online, especially if you’re visiting around sunset when lines are longest.

4. Art Institute of Chicago

Why Visit:

The Art Institute of Chicago is one of the world’s top museums. Its massive collection spans thousands of years, from ancient sculptures to modern icons.

Highlights:

• Masterpieces Everywhere → see Grant Wood’s American Gothic, Georges Seurat’s A Sunday Afternoon on the Island of La Grande Jatte, and Monet’s water lilies.
• Gift Shop → one of the best museum stores, full of unique art-inspired gifts.

How to visit:

We bought Fast Pass admission online in advance since lines can be long.

5. Catch a Show

Why Visit:

Chicago has one of the most vibrant performing arts scenes in the U.S. It’s the birthplace of modern improv and blues, and it also hosts major touring Broadway productions throughout the year.

Highlights:

• The Second City → legendary comedy club that launched stars like Tina Fey, Bill Murray, and Steve Carell.
• Broadway in Chicago → touring Broadway hits at historic venues like the CIBC Theatre and Cadillac Palace.

How to Visit:

We booked a comedy show at The Second City online in advance. For Broadway musicals, check the latest lineup at BroadwayInChicago.com.