Photo: File:Chicago River ferry.jpg: John Picken derivative work: Georgfotoart, CC BY 2.0

United States

Chicago

The best architecture in America, a lakefront you can cycle for miles, and food worth planning around.

Best over 3 days£££ cost levelWalkability 4/5

Build my Chicago trip

Good for

Architecture
Food
Museums
Music

When to go

Usually at its best in May, June, September, October.

How we plan it

We pull real places from open map data for Chicago, rank them against what you’ve told us you enjoy, then order the day so the route makes sense and everything is actually open when you’d arrive. Change any of it afterwards and the rest adapts around what you keep.

Place data © OpenStreetMap contributors. Prices and opening times change, so it is worth checking official sources before you travel.