5 days in Chicago & Anaheim Itinerary

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

Kick off your visit on the 11th (Mon): explore the world behind art at The Art Institute of Chicago, don't miss a visit to Millennium Park, then admire nature's wide array of creatures at Shedd Aquarium, and finally take in panoramic vistas at Skydeck Chicago - Willis Tower.

For where to stay, traveler tips, reviews, and tourist information, use the Chicago trip builder site.

Use the Route module to find suitable travel options from your home destination to Chicago. In January, daytime highs in Chicago are 32°F, while nighttime lows are 18°F. Wrap up your sightseeing on the 11th (Mon) early enough to travel to Anaheim.

Anaheim's major attractions are its world-famous Disney entertainment complex, sports teams, and convention center.

Get outdoors at Off-Road Tours and The Huntington Desert Garden. You'll find plenty of places to visit near Anaheim: Tahquitz Canyon (in Palm Springs), Salt Oasis (in Rancho Cucamonga) and Dolphin & Whale Watching (in Newport Beach). There's still lots to do: get in on the family fun at Disneyland Park and don't miss a visit to Downtown Disney District.

For where to stay, maps, traveler tips, and other tourist information, refer to the Anaheim day trip app.

Traveling by flight from Chicago to Anaheim takes 9 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll gain 2 hours traveling from Chicago to Anaheim. In January, Anaheim is warmer than Chicago - with highs of 71°F and lows of 48°F. On the 15th (Fri), wrap the sightseeing up by early afternoon so you can travel back home.