21 days in Chicago & Valparaiso Itinerary

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

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.

Valparaiso is a city and the county seat of Porter County, Indiana, United States. 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. And it doesn't end there: see the interesting displays at Seiberling Mansion, get engrossed in the history at Wabash County Historical Museum, admire the masterpieces at Haan Museum of Indiana Art, and test your team's savvy at popular escape rooms.

For ratings, maps, where to stay, and other tourist information, you can read our Valparaiso trip planner.

You can drive from Chicago to Valparaiso in 1.5 hours. December in Valparaiso sees daily highs of 37°F and lows of 23°F at night.