22 days in Chicago Itinerary

The Art Institute of Chicago and Garfield Park Conservatory are good opportunities to explore the local culture. Get outdoors at Lakefront Trail and Indiana Dunes State Park. Explore the numerous day-trip ideas around Chicago: South Bend (Studebaker National Museum, Grotto of Our Lady Lourdes, &more), Volo Museum (in Volo) and Milwaukee (Pabst Mansion, Milwaukee Art Museum, &more). Next up on the itinerary: examine the collection at Illinois Railway Museum, admire the majestic nature at Matthiessen State Park, get to know the fascinating history of Riverwalk Lot, and hike along Geneva Lake Shore Path.

For ratings, other places to visit, maps, and tourist information, read our Chicago day trip planner.

If you are flying in from United Kingdom, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In May in Chicago, expect temperatures between 25°C during the day and 13°C at night.