Destinations overview -> USA -> Chicago

The Windy City offers some of the best year-round art, food, culture, and activities in the world. Check out Broadway in Chicago to see what's playing at the over 200 theaters when you visit. See one of the great sporting events. Take an architecture cruise on the historic Chicago River. Drive down Lakeshore Drive or bike or walk along Lake Shore Trail to see Grant Park, Millenium Park, Lincoln Park and Soldier Field, or to just watch the thousands of people who visit the shore of Lake Michigan each summer.

Great Trips

Mackinac Island featuring The Grand Hotel
7 nights starting at $2,599.00
from Collette
available 5/3/2018 - 5/10/2018
Dixieland & Rhythms With New Orleans Jazz Fest
10 nights starting at $2,359.00
from Cosmos
available 4/27/2018 - 5/7/2018
Coast to Coast Camping Westbound
22 nights starting at $3,349.00
from G Adventures
available 5/12/2018 - 7/14/2018

Find a Trip

Detailed Search