Best of Chicago

Lakefront miles, world-class museums, and mural-covered side streets.

3 daysLocal favorites

Trip length

Best time to visit: May to October

Late spring through early fall is warm and lively along the lakefront, with patios and festivals in full swing. Winters are long and bitterly cold.

Day 1 · Architectural Marvels & Millennium Park

1
Chicago Architecture Foundation Center River Cruise
A must-do for understanding the city's iconic skyline from a unique perspective.
2
Millennium Park
Home to 'The Bean' (Cloud Gate), Crown Fountain, and beautiful gardens.
3
Art Institute of Chicago
One of the oldest and largest art museums in the United States, with a world-renowned collection.
4
Deep dish at Lou Malnati's Pizzeria (River North)
A classic Chicago deep dish experience – try the buttercrust!

1
Shedd Aquarium
Explore aquatic life from around the world in a stunning historic building with fantastic city views.
2
Field Museum
See Sue, the most complete T-Rex skeleton, and explore natural history exhibits.
3
Pilsen Murals
Stroll 18th Street and the surrounding blocks to discover vibrant, historically rich street art.
4
Thalia Hall
Catch a show or grab a drink at this beautifully restored historic Pilsen landmark.

1
Promontory Point
Enjoy unparalleled panoramic views of the Chicago skyline from this hidden lakefront gem.
2
Museum of Science and Industry
Explore interactive exhibits, including a German U-boat and a coal mine simulation.
3
Margie's Candies (Bucktown)
Step back in time for an old-fashioned ice cream sundae or handmade chocolates at this Chicago institution.

Start from this curated plan — Runes copies it into your trips so you can tweak dates, budget, pace, and stops. Personalized to your style soon.