Classic Chicago itineraries

Classic Chicago itineraries

The can’t-miss things to see and do.

Multiple plates of food at Spiaggia restaurant in Chicago
Itineraries
3 great Chicago date ideas

Chicago has something for every kind of date, from cozy bars perfect for a first date to romantic restaurants worthy of milestone anniversaries. Whether it’s…

Cloudgate (The Bean) at night

Explore hotels, flights, deals, and more

Plan your trip

Expedia
Expedia
Expedia
Expedia

Newsletter

Chicago Newsletter

Stay in the know

Sign up

Guide

Official Visitors Guide

Start planning today

Get the guide

Your Favorites

Made with  in Chicago