North AmericaFuture itinerary

Travel Plans for Chicago

A city getaway filled with iconic architecture, fascinating museums, neighborhood walks, and plenty of food stops along the way.

SPlanned by Shirley4-day itinerary · September - October and April - May
Travel view of ChicagoPhoto by Christopher Alvarenga on Unsplash
TRIP IDEAS

Chicago

4 days

A city getaway filled with iconic architecture, fascinating museums, neighborhood walks, and plenty of food stops along the way.

ActivitiesThings I want to see and do

Pokemon Fossil Museum at Field Museum

Pokemon Fossil Museum opens May 22, 2026 all the way to April 11, 2027.

Chicago Architecture Boat Tour

Coworker had recommended to do it in the evening saying it's one of the most beautiful skyline.

Millennium Park

The Bean lol the most touristy thing to do but I do want to see it in person.

Art Institute of Chicago

It's also one of the oldest art museum so definitely need to check it out. They have pieces from Monet and van Gogh.

Indiana Dunes National Park

Only 1 hour away from downtown Chicago is the Indiana Dunes National Park. You can take the South Shore Line or rent a car from Turo to the park.

Food placesRestaurants, cafés, and treats on my list

McDonald's Global Menu Restaurant

The only McDonald's in the US with menu items from across the world. My friends and I've been wanting to go to Chicago for years just to try it.