5 days in Midwest Itinerary

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

Start off your visit on the 17th (Mon): wander the streets of The Magnificent Mile, then admire the masterpieces at The Art Institute of Chicago, and then get to know the fascinating history of Millennium Park.

For other places to visit, traveler tips, ratings, and tourist information, you can read our Chicago trip planner.

Use the Route module to find suitable travel options from your home destination to Chicago. In September in Chicago, expect temperatures between 78°F during the day and 61°F at night. Finish up your sightseeing early on the 17th (Mon) so you can go by car to Wisconsin Dells.

Named after a nearby scenic gorge famous for its steep sandstone formations, Wisconsin Dells features more than 20 water parks, making it one of the most popular vacation areas in this region.

Start off your visit on the 18th (Tue): look for all kinds of wild species at International Crane Foundation, immerse yourself in nature at Devil's Lake State Park, and then whizz through the canopy at some of the top local zipline courses and adventure parks.

For traveler tips, where to stay, maps, and tourist information, refer to the Wisconsin Dells day trip site .

Drive from Chicago to Wisconsin Dells in 3.5 hours. Alternatively, you can take a train; or do a combination of flight and train. Traveling from Chicago in September, plan for slightly colder nights in Wisconsin Dells, with lows around 53°F. Finish your sightseeing early on the 18th (Tue) to allow enough time to travel to Rapid City.

South Dakota's second-largest city, Rapid City has for many years served as a gateway to the West.

On the 19th (Wed), wander the streets of Downtown Rapid City, then explore the activities along Sylvan Lake, and then explore the striking landscape at Needles Eye Tunnel. On the 20th (Thu), you'll have a packed day of sightseeing: stroll through Presidential Trail, then admire all the interesting features of Iron Mountain Road, and then learn about winemaking at Prairie Berry Winery.

To find other places to visit, reviews, more things to do, and other tourist information, go to the Rapid City road trip website .

Do a combination of train, bus, and flight from Wisconsin Dells to Rapid City in 8 hours. Alternatively, you can do a combination of train and flight; or drive. The time zone difference moving from Central Standard Time (CST) to Mountain Standard Time (MST) is minus 1 hour. September in Rapid City sees daily highs of 75°F and lows of 53°F at night. Wrap up your sightseeing on the 20th (Thu) early enough to travel to Branson.

Nestled in Missouri's beautiful Ozark Mountains lies one of the country's most attractive vacation towns for year-round family entertainment.

Kick off your visit on the 21st (Fri): look for all kinds of wild species at National Tiger Sanctuary, look for all kinds of wild species at Shepherd of the Hills Fish Hatchery, and then take a memorable tour with Tours.

For more things to do, ratings, and other tourist information, go to the Branson day trip planning website .

You can do a combination of flight and bus from Rapid City to Branson in 7 hours. Other options are to do a combination of flight and car; or drive. The time zone difference moving from Mountain Standard Time (MST) to Central Standard Time (CST) is 1 hour. Expect a bit warmer temperatures when traveling from Rapid City in September; daily highs in Branson reach 82°F and lows reach 60°F. Finish up your sightseeing early on the 21st (Fri) so you can travel back home.