16 days in Midwest Itinerary

16 days in Midwest Itinerary

Created using Inspirock Midwest trip itinerary builder

Make it your trip
Fly
1
Cleveland
— 1 day
Fly
2
Saint Louis
— 2 nights
Drive
3
Branson
— 2 nights
Fly
4
Custer
— 4 nights
Drive
5
Badlands National Park
— 2 nights
Fly
6
Chicago
— 4 nights
Fly
7
Dayton
— 1 night
Fly

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Cleveland

— 1 day

Forest City

A culturally diverse city situated on the shores of Lake Erie, Cleveland boasts many places to visit, such as world-class museums, popular amusement parks, and sprawling recreational areas.
On the 24th (Fri), explore the world behind art at The Cleveland Museum of Art and then examine the collection at Rock & Roll Hall of Fame.

To find reviews, ratings, maps, and tourist information, read our Cleveland day trip planning tool.

New York City to Cleveland is an approximately 3.5-hour flight. You can also drive; or take a bus. When traveling from New York City in September, plan for a bit cooler days and about the same nights in Cleveland: temperatures range from 75°F by day to 62°F at night. Wrap up your sightseeing on the 24th (Fri) to allow time to fly to Saint Louis.

Things to do in Cleveland

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Saint Louis

— 2 nights

Gateway to the West

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 25th (Sat): walk around Forest Park and then pause for some serene contemplation at Cathedral Basilica of Saint Louis. Get ready for a full day of sightseeing on the 26th (Sun): admire the natural beauty at Missouri Botanical Garden and then take in panoramic vistas at The Gateway Arch.

For traveler tips, other places to visit, where to stay, and tourist information, refer to the Saint Louis trip itinerary builder site.

Traveling by flight from Cleveland to Saint Louis takes 3 hours. Alternatively, you can drive; or take a bus. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. Expect somewhat warmer weather when traveling from Cleveland in September: highs in Saint Louis hover around 84°F, while lows dip to 59°F. Wrap up your sightseeing on the 26th (Sun) early enough to drive to Branson.

Things to do in Saint Louis

Parks · Historic Sites
Find places to stay Sep 24 — 26:
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Branson

— 2 nights

Live Entertainment Capital of the World

Nestled in Missouri's beautiful Ozark Mountains lies one of the country's most attractive vacation towns for year-round family entertainment.
Start off your visit on the 27th (Mon): get great views at College of the Ozarks, then find something for the whole family at Arcade City, and then cool off at Silver Dollar City. Keep things going the next day: browse the exhibits of Titanic Museum and then indulge your senses at VIP Tours of Branson.

To find photos, traveler tips, other places to visit, and other tourist information, you can read our Branson trip itinerary builder app.

You can drive from Saint Louis to Branson in 4.5 hours. Other options are to do a combination of flight and car; or do a combination of bus and taxi. In September, daytime highs in Branson are 82°F, while nighttime lows are 60°F. Wrap up your sightseeing on the 28th (Tue) to allow time to fly to Custer.

Things to do in Branson

Tours · Theme Parks · Wineries · Parks
Find places to stay Sep 26 — 28:
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Custer

— 4 nights
Generally considered to be the oldest town established by European Americans in the Black Hills, Custer began as a mining town.
Step out of Custer to go to Keystone and see Presidential Trail, which is approximately 30 minutes away. There's lots more to do: explore the striking landscape of Mount Rushmore National Memorial, admire all the interesting features of Needles Highway, admire the majestic nature at Custer State Park, and take in the dramatic natural features at Needles Eye Tunnel.

For traveler tips, ratings, reviews, and tourist information, read our Custer trip planner.

Getting from Branson to Custer by flight takes about 6.5 hours. Other options: drive; or do a combination of bus and taxi. The time zone difference when traveling from Branson to Custer is minus 1 hour. Expect little chillier temperatures when traveling from Branson in September; daily highs in Custer reach 71°F and lows reach 45°F. Finish your sightseeing early on the 2nd (Sat) to allow enough time to drive to Badlands National Park.

Things to do in Custer

Parks · Nature · Outdoors · Scenic Drive

Side Trips

Find places to stay Sep 28 — Oct 2:
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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.
Kick off your visit on the 3rd (Sun): stroll through Yellow Mounds Overlook, then take a memorable drive along Loop Road, and then explore the striking landscape at Badlands Wall. On the next day, take in the dramatic natural features at Big Badlands Overlook and then hike along Door Trail.

For photos, traveler tips, maps, and tourist information, refer to the Badlands National Park holiday planning website.

Drive from Custer to Badlands National Park in 2 hours. Alternatively, you can do a combination of taxi and bus. When traveling from Custer in October, plan for somewhat warmer days and about the same nights in Badlands National Park: temperatures range from 65°F by day to 36°F at night. Wrap up your sightseeing on the 4th (Mon) early enough to fly to Chicago.

Things to do in Badlands National Park

Parks · Nature · Outdoors · Scenic Drive
Find places to stay Oct 2 — 4:
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Chicago

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, nightlife, and parks. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, get curious at Field Museum, get up close and personal with brilliant marine life at Shedd Aquarium, and enjoy breathtaking views from 360 Chicago Observation Deck.

For where to stay, ratings, other places to visit, and tourist information, you can read our Chicago tour itinerary planner.

You can fly from Badlands National Park to Chicago in 4 hours. Other options are to drive; or do a combination of taxi and bus. Traveling from Badlands National Park to Chicago, you'll lose 1 hour due to the time zone difference. Traveling from Badlands National Park in October, you can expect nighttime temperatures to be somewhat warmer in Chicago, with lows of 49°F. Finish your sightseeing early on the 8th (Fri) to allow enough time to fly to Dayton.

Things to do in Chicago

Museums · Childrens Museums · Theme Parks · Parks
Find places to stay Oct 4 — 8:
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Dayton

— 1 night

Gem City

Home of airplane pioneers the Wright brothers, Dayton prides itself on its inventors, including Charles F. Kettering, inventor of the automobile self starter.
Start off your visit on the 9th (Sat): steep yourself in history at Carillon Historical Park, examine the collection at National Museum of the US Air Force, and then sample some tasty brews at a beer tour and tasting.

To see reviews, where to stay, more things to do, and more tourist information, refer to the Dayton trip itinerary maker.

You can fly from Chicago to Dayton in 2.5 hours. Other options are to drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Dayton. In October, daytime highs in Dayton are 67°F, while nighttime lows are 46°F. Cap off your sightseeing on the 9th (Sat) early enough to catch the flight back home.

Things to do in Dayton

Historic Sites · Museums · Breweries & Distilleries · Tours
Find places to stay Oct 8 — 9:
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