21 days in Chicago & Valparaiso Itinerary

On the 4th (Sun), enjoy breathtaking views from Skydeck Chicago - Willis Tower, then admire the masterpieces at The Art Institute of Chicago, then walk around Millennium Park, and finally get up close and personal with brilliant marine life at Shedd Aquarium. Keep things going the next day: engage your brain at Museum of Science and Industry, then get to know the resident critters at Lincoln Park Zoo, and then admire the landmark architecture of Reliance Building.

To see maps, reviews, traveler tips, and other tourist information, go to the Chicago trip planning tool.

The Route module shows you all the different ways you can get to Chicago. In December, daily temperatures in Chicago can reach 38°F, while at night they dip to 26°F. Wrap up your sightseeing on the 6th (Tue) early enough to drive to Valparaiso.

Explore the numerous day-trip ideas around Valparaiso: Michigan City (Lubeznik Center for the Arts, Blue Chip Casino, &more), Crown Point (Lake County Historical Museum & The John Dillinger Museum) and New Buffalo (Salmon Hunter Charters, Four Winds Casino New Buffalo, &more). Spend the 12th (Mon) exploring nature at Indiana Dunes National Park.

To see traveler tips, photos, other places to visit, and more tourist information, go to the Valparaiso vacation planning tool.

You can drive from Chicago to Valparaiso in 1.5 hours. In December, daytime highs in Valparaiso are 37°F, while nighttime lows are 23°F.