12 days in Midwest Itinerary

12 days in Midwest Itinerary

Created using Inspirock Midwest trip itinerary planner
Make it your trip
Fly
1
Chicago
— 3 nights
Fly
2
Saint Louis
— 2 nights
Drive
3
Branson
— 2 nights
Fly
4
Keystone
— 2 nights
Drive
5
Badlands National Park
— 2 nights
Fly

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Chicago — 3 nights

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, get up close and personal with brilliant marine life at Shedd Aquarium, get to know the resident critters at Lincoln Park Zoo, and admire the striking features of Skydeck Chicago - Willis Tower.

To see reviews, traveler tips, other places to visit, and more tourist information, read Chicago sightseeing planner.

Madison to Chicago is an approximately 2.5-hour flight. You can also drive; or take a bus. Traveling from Madison in September, you can expect nighttime temperatures to be a bit warmer in Chicago, with lows of 61°F. Finish up your sightseeing early on the 11th (Sun) so you can catch the flight to Saint Louis.
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Parks · Museums · Zoos & Aquariums · Shopping

Saint Louis — 2 nights

Test the local claim that Saint Louis is second only to Washington, D.C. in the number of free activities available by spending your holiday exploring the city's central neighborhoods, famous for their restored century-old red-brick buildings.
Kick off your visit on the 12th (Mon): walk around Forest Park and then take in the architecture and atmosphere at Cathedral Basilica of Saint Louis. Keep things going the next day: admire the natural beauty at Missouri Botanical Garden and then take in panoramic vistas at The Gateway Arch.

For ratings, where to stay, and tourist information, use the Saint Louis day trip planning tool.

You can fly from Chicago to Saint Louis in 3 hours. Other options are to drive; or take a train. Traveling from Chicago in September, you will find days in Saint Louis are a bit warmer (84°F), and nights are about the same (59°F). Finish your sightseeing early on the 13th (Tue) to allow enough time to drive to Branson.
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Parks · Historic Sites

Branson — 2 nights

Nestled in Missouri's beautiful Ozark Mountains lies one of the country's most attractive vacation towns for year-round family entertainment.
On the 14th (Wed), get in on the family fun at Arcade City, then tour the pleasant surroundings at College of the Ozarks, and then get engrossed in the history at Titanic Museum. Get ready for a full day of sightseeing on the next day: indulge your senses at VIP Tours of Branson and then cool off at Silver Dollar City.

To see ratings, maps, and more tourist information, refer to the Branson road trip app.

You can drive from Saint Louis to Branson in 4.5 hours. Other options are to drive; or fly; or do a combination of flight and car. In September, plan for daily highs up to 82°F, and evening lows to 60°F. Finish your sightseeing early on the 15th (Thu) so you can fly to Keystone.
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Tours · Theme Parks · Wineries · Museums

Keystone — 2 nights

Fewer than 400 people call Keystone home year-round, but the population explodes in summer when crowds flock to nearby Mount Rushmore.
On the 16th (Fri), contemplate the waterfront views at Sylvan Lake and then explore the striking landscape at Needles Eye Tunnel. Get ready for a full day of sightseeing on the 17th (Sat): cruise along Iron Mountain Road, then immerse yourself in nature at Custer State Park, and then explore the wealth of natural beauty at Mount Rushmore National Memorial.

To find other places to visit, traveler tips, and other tourist information, read our Keystone online trip planner.

Traveling by flight from Branson to Keystone takes 6.5 hours. Alternatively, you can drive; or do a combination of bus and taxi. The time zone difference moving from Central Standard Time to Mountain Standard Time is minus 1 hour. Prepare for little chillier weather when traveling from Branson in September: high temperatures in Keystone hover around 71°F and lows are around 45°F. Wrap up your sightseeing on the 17th (Sat) to allow time to drive to Badlands National Park.
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Nature · Parks · Scenic Drive · Outdoors
Side Trip

Badlands National Park — 2 nights

Although Badlands National Park's name might not be the most inviting, its landscape of pinnacles, eroded buttes, spires, and an expansive, pristine mixed-grass prairie remain enticing.
Start off your visit on the 18th (Sun): take some stellar pictures from Yellow Mounds Overlook, then cruise along Loop Road, and then take in the dramatic natural features at Badlands Wall. Keep things going the next day: explore the striking landscape at Big Badlands Overlook and then get outside with Hurley Butte Horseback Riding.

For more things to do, other places to visit, ratings, and tourist information, use the Badlands National Park online visit planner.

You can drive from Keystone to Badlands National Park in 1.5 hours. Another option is to do a combination of taxi and bus. Traveling from Keystone in September, you will find days in Badlands National Park are somewhat warmer (81°F), and nights are about the same (49°F). Finish up your sightseeing early on the 19th (Mon) so you can catch the flight back home.
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Nature · Parks · Outdoors · Scenic Drive
Side Trip