7 days in Chicago Itinerary

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.

Visiting Boat Tours & Water Sports and Swallow Cliff Stairs will get you outdoors. Get some cultural insight at The Art Institute of Chicago and Field Museum. Explore Chicago's surroundings by going to Cantigny Park (in Wheaton), Little Red Schoolhouse (in Willow Springs) and Lake Geneva Ziplines & Adventures (in Lake Geneva). And it doesn't end there: steep yourself in history at Ernest Hemingway Birthplace, take in the spiritual surroundings of Frank Lloyd Wright's Unity Temple, take a stroll through The Magnificent Mile, and admire the landmark architecture of Frank Lloyd Wright's Robie House.

To see where to stay, reviews, photos, and tourist information, you can read our Chicago trip itinerary builder site.

Expect a daytime high around 65°F in October, and nighttime lows around 49°F.