8 days in Midwest Itinerary

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

Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, meet the residents at Lincoln Park Zoo, enjoy breathtaking views from Skydeck Chicago - Willis Tower, and get a new perspective on nature at Field Museum.

For where to stay, maps, reviews, and tourist information, read Chicago trip itinerary planner.

Green Bay to Chicago is an approximately 2.5-hour flight. You can also drive; or do a combination of bus and train. Prepare for a bit warmer weather when traveling from Green Bay in December: high temperatures in Chicago hover around 38°F and lows are around 26°F. Finish your sightseeing early on the 17th (Sat) to allow enough time to fly to Branson.

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

Explore hidden gems such as Runaway Mountain Coaster and Shepherd of the Hills Fish Hatchery. And it doesn't end there: ponder the design of Dancing Water Fountain, stop by Dick's Oldtime 5 & 10, whizz through the canopy at some of the top local zipline courses and adventure parks, and make a splash at Silver Dollar City.

For more things to do, photos, other places to visit, and other tourist information, you can read our Branson vacation app.

Traveling by flight from Chicago to Branson takes 3 hours. Alternatively, you can drive; or do a combination of train, bus, and taxi. When traveling from Chicago in December, plan for somewhat warmer days in Branson, with highs around 48°F, while nights are about the same with lows around 31°F. Wrap up your sightseeing on the 20th (Tue) early enough to drive to Kansas City.

The largest municipality in Missouri, Kansas City has an impressive array of world-class museums, shopping areas, and great places to eat, all of which attract tourism to the area.

On the 21st (Wed), examine the collection at Harry S. Truman Presidential Library & Museum, explore the engaging exhibits at Kaleidoscope, then contemplate the long history of Union Station, and finally test your problem-solving skills at popular escape rooms.

For reviews, maps, where to stay, and more tourist information, read Kansas City day trip website.

Traveling by car from Branson to Kansas City takes 4 hours. Alternatively, you can take a bus; or fly. In December, plan for daily highs up to 44°F, and evening lows to 28°F. Finish your sightseeing early on the 21st (Wed) to allow enough time to fly to Duluth.

Situated on the westernmost point of the Lake Superior, Duluth represents a booming port city.

Start off your visit on the 22nd (Thu): take an in-depth tour of Glensheen - The Historic Congdon Estate, walk around Canal Park, and then test your problem-solving skills at popular escape rooms.

For traveler tips, other places to visit, maps, and tourist information, read Duluth trip planner.

Fly from Kansas City to Duluth in 5 hours. Alternatively, you can drive; or take a bus. Traveling from Kansas City in December, things will get a bit cooler in Duluth: highs are around 26°F and lows about 15°F. Finish your sightseeing early on the 22nd (Thu) so you can fly back home.