29 days in Midwest Itinerary

Explore the numerous day-trip ideas around Detroit: Michigan War Dog Memorial (in South Lyon) and Frankenmuth (St. Lorenz Lutheran Church & Boat Tours & Water Sports). The adventure continues: examine the collection at The Henry Ford, take in the architecture and atmosphere at Sweetest Heart of Mary Roman Catholic Church, take a leisurely stroll along Detroit RiverFront, and contemplate the long history of Motown Museum.

To find more things to do, where to stay, and other tourist information, read Detroit visit planner.

Newark to Detroit is an approximately 3.5-hour flight. You can also drive; or take a bus. When traveling from Newark in September, plan for a bit cooler days in Detroit, with highs around 75°F, while nights are about the same with lows around 58°F. Finish your sightseeing early on the 18th (Mon) so you can fly to Saint Louis.

You'll find plenty of places to visit near Saint Louis: Springfield (Dana-Thomas House & Abraham Lincoln Presidential Library and Museum). The adventure continues: enjoy breathtaking views from The Gateway Arch, stroll around Forest Park, look for all kinds of wild species at The Sophia M. Sachs Butterfly House, and relax in the rural setting at Grant’s Farm.

To find ratings, photos, traveler tips, and other tourist information, use the Saint Louis trip maker tool.

You can fly from Detroit to Saint Louis in 3 hours. Alternatively, you can drive; or take a bus. Traveling from Detroit to Saint Louis, you'll gain 1 hour due to the time zone difference. When traveling from Detroit in September, plan for somewhat warmer days in Saint Louis, with highs around 84°F, while nights are about the same with lows around 59°F. Finish your sightseeing early on the 22nd (Fri) so you can drive to Branson.

Plan for a day of cool, family-friendly fun on the 24th (Sun) at Silver Dollar City. There's much more to do: indulge your senses at VIP Tours of Branson, see what you can catch with a fishing tour, get engrossed in the history at Titanic Museum, and take some stellar pictures from College of the Ozarks.

To find other places to visit and tourist information, refer to the Branson holiday maker app.

You can drive from Saint Louis to Branson in 4.5 hours. Alternatively, you can fly; or do a combination of flight and car. In September, daily temperatures in Branson can reach 82°F, while at night they dip to 60°F. Finish up your sightseeing early on the 26th (Tue) so you can go by car to Kansas City.

Change things up with these side-trips from Kansas City: Evel Knievel Museum (in Topeka) and Holladay Distillery (in Weston). Next up on the itinerary: brush up on your military savvy at National WWI Museum and Memorial, learn about wildlife with up-close encounters at Deanna Rose Children's Farmstead, take an in-depth tour of Arabia Steamboat Museum, and admire the natural beauty at The Ewing and Muriel Kauffman Memorial Garden.

Find out how to plan Kansas City trip without stress by asking Klarna Trips to help create an itinerary.

Drive from Branson to Kansas City in 4 hours. Alternatively, you can take a bus; or fly. In September, daily temperatures in Kansas City can reach 83°F, while at night they dip to 64°F. Wrap up your sightseeing on the 29th (Fri) early enough to fly to Custer.

Custer is known for nature, scenic drive, and trails. Your trip includes some of its best attractions: stroll through Mount Rushmore National Memorial, take a memorable drive along Iron Mountain Road, take a peaceful walk through Black Hills National Forest, and pause for some photo ops at Crazy Horse Memorial.

To see reviews, other places to visit, where to stay, and other tourist information, you can read our Custer trip planner.

Fly from Kansas City to Custer in 5.5 hours. Alternatively, you can drive; or do a combination of bus and taxi. Due to the time zone difference, you'll gain 1 hour traveling from Kansas City to Custer. In September, Custer is a bit cooler than Kansas City - with highs of 71°F and lows of 45°F. Cap off your sightseeing on the 2nd (Mon) early enough to go by car to Badlands National Park.

Go for a jaunt from Badlands National Park to Interior to see Hurley Butte Horseback Riding about 34 minutes away. Spend the 4th (Wed) exploring nature at Badlands National Park. And it doesn't end there: take a memorable drive along Loop Road, explore the striking landscape at Badlands Wall, explore the wealth of natural beauty at Panorama Point Overlook, and get great views at Yellow Mounds Overlook.

For ratings, where to stay, maps, and tourist information, read our Badlands National Park road trip planning tool.

You can drive from Custer to Badlands National Park in 2 hours. Another option is to do a combination of taxi and bus. Expect a bit warmer weather when traveling from Custer in October: highs in Badlands National Park hover around 65°F, while lows dip to 36°F. Cap off your sightseeing on the 5th (Thu) early enough to catch the flight to Chicago.

Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, stroll around Millennium Park, get a new perspective on things with Boat Tours & Water Sports, and wander the streets of The Magnificent Mile.

To find where to stay, traveler tips, more things to do, and more tourist information, read our Chicago trip planner.

Getting from Badlands National Park to Chicago by flight takes about 4 hours. Other options: drive; or do a combination of taxi and bus. The time zone difference moving from Mountain Standard Time to Central Standard Time is 1 hour. Traveling from Badlands National Park in October, Chicago is a bit warmer at night with lows of 49°F. Finish your sightseeing early on the 10th (Tue) so you can fly to Dayton.

On the 11th (Wed), have fun and explore at Carillon Historical Park, then examine the collection at National Museum of the US Air Force, and then sample some tasty brews at a beer tour and tasting.

To find where to stay, other places to visit, reviews, and more tourist information, refer to the Dayton trip builder site.

Traveling by flight from Chicago to Dayton takes 2.5 hours. Alternatively, you can drive; or take a bus. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. In October, daytime highs in Dayton are 67°F, while nighttime lows are 46°F. Cap off your sightseeing on the 11th (Wed) early enough to go by car to Columbus.

On the 12th (Thu), hike along Hemlock Bridge Trail, whizz through the canopy at some of the top local zipline courses and adventure parks, and then learn about winemaking at Rockside Winery and Vineyards. On the 13th (Fri), you'll have a packed day of sightseeing: admire the natural beauty at Inniswood Metro Gardens, test your team's savvy at popular escape rooms, then sample some tasty brews at Pedal Wagon Columbus, and finally see the interesting displays at Wagner-Hagans Auto Museum.

To see more things to do, photos, maps, and more tourist information, use the Columbus day trip site.

You can drive from Dayton to Columbus in 1.5 hours. Alternatively, you can take a bus. In October in Columbus, expect temperatures between 67°F during the day and 47°F at night. Finish your sightseeing early on the 13th (Fri) so you can drive to Cleveland.

Start off your visit on the 14th (Sat): see the interesting displays at Rock & Roll Hall of Fame, then admire the masterpieces at The Cleveland Museum of Art, and then try your luck at JACK Cleveland Casino.

You can plan Cleveland trip in no time by asking Klarna Trips to help create your itinerary.

Drive from Columbus to Cleveland in 2.5 hours. Alternatively, you can drive; or take a bus; or fly. October in Cleveland sees daily highs of 65°F and lows of 51°F at night. Finish up your sightseeing early on the 14th (Sat) so you can catch the flight back home.