6 days in Chicago Itinerary

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

Explore hidden gems such as Chicago Cultural Center and The Loop. Your cultural itinerary includes sights like The Art Institute of Chicago and The Magnificent Mile. Change things up with these side-trips from Chicago: Milwaukee (Pabst Mansion, Historic Third Ward, &more). Next up on the itinerary: walk around Lincoln Park, admire the masterpieces at Richard H. Driehaus Museum, sample the tasty concoctions at Begyle Brewing, and buy something for everyone on your list at Water Tower Place.

For more things to do, ratings, and more tourist information, you can read our Chicago trip itinerary maker app.

In December, plan for daily highs up to 38°F, and evening lows to 26°F.