22 days in Midwest Itinerary

22 days in Midwest Itinerary

Created using Inspirock Midwest route maker

Make it your trip
Fly
1
Dayton
— 1 day
Drive
2
Toledo
— 2 nights
Drive
3
Cleveland
— 1 night
Fly
4
Chicago
— 5 nights
Fly
5
Badlands National Park
— 2 nights
Drive
6
Custer
— 2 nights
Fly
7
Kansas City
— 3 nights
Drive
8
Branson
— 3 nights
Drive
9
Saint Louis
— 3 nights
Fly

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Dayton

— 1 day

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 10th (Mon): contemplate the long history of Carillon Historical Park, see the interesting displays at National Museum of the US Air Force, and then admire the natural beauty at Wegerzyn Gardens MetroPark.

To see where to stay, photos, more things to do, and other tourist information, read our Dayton attractions tool.

Orlando to Dayton is an approximately 4-hour flight. You can also drive; or take a bus. Expect slightly colder temperatures when traveling from Orlando in May; daily highs in Dayton reach 74°F and lows reach 53°F. Finish your sightseeing early on the 10th (Mon) so you can drive to Toledo.

Things to do in Dayton

Museums · Historic Sites · Parks · Wildlife
Find places to stay May 10 — 11:

Toledo

— 2 nights
Toledo is a city in and the county seat of Lucas County, Ohio, United States. Start off your visit on the 11th (Tue): walk around Oak Openings Preserve Metropark, then stroll through Magee Marsh Wildlife Area, and then tour the pleasant surroundings at Ottawa National Wildlife Refuge. Get ready for a full day of sightseeing on the 12th (Wed): see the interesting displays at National Museum of the Great Lakes, then admire the masterpieces at Toledo Museum of Art, and then savor the flavors at The HandleBar Toledo.

For photos, other places to visit, where to stay, and other tourist information, read our Toledo road trip planning app.

Getting from Dayton to Toledo by car takes about 3 hours. Other options: fly; or take a bus. Expect a daytime high around 72°F in May, and nighttime lows around 52°F. Finish up your sightseeing early on the 12th (Wed) so you can go by car to Cleveland.

Things to do in Toledo

Parks · Wildlife · Museums · Breweries & Distilleries

Side Trip

Find places to stay May 10 — 12:

Cleveland

— 1 night

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 13th (Thu), admire the masterpieces at The Cleveland Museum of Art, examine the collection at Rock & Roll Hall of Fame, and then try your luck at JACK Cleveland Casino.

To see photos, more things to do, ratings, and more tourist information, use the Cleveland vacation builder app.

You can drive from Toledo to Cleveland in 2 hours. Alternatively, you can take a bus; or take a train. In May, daytime highs in Cleveland are 69°F, while nighttime lows are 54°F. Wrap up your sightseeing on the 13th (Thu) to allow time to fly to Chicago.

Things to do in Cleveland

Museums · Casinos · Fun & Games
Find places to stay May 12 — 13:

Chicago

— 5 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, parks, and nightlife. Your plan includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, enjoy breathtaking views from Skydeck Chicago - Willis Tower, take in the waterfront at Navy Pier, and wander the streets of The Magnificent Mile.

To see reviews, traveler tips, photos, and more tourist information, go to the Chicago holiday website.

You can fly from Cleveland to Chicago in 3 hours. Other options are to drive; or take a train. You'll gain 1 hour traveling from Cleveland to Chicago due to the time zone difference. May in Chicago sees daily highs of 71°F and lows of 52°F at night. Wrap up your sightseeing on the 18th (Tue) to allow time to fly to Badlands National Park.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums
Find places to stay May 13 — 18:

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 19th (Wed): explore the striking landscape at Badlands Wall, explore and take pictures at Loop Road, get great views at Yellow Mounds Overlook, take in the dramatic natural features at Bigfoot Pass Overlook, then explore the striking landscape at Big Badlands Overlook, and finally explore the striking landscape at White River Valley Overlook. Here are some ideas for day two: explore the striking landscape of Badlands National Park.

To find ratings, more things to do, photos, and tourist information, you can read our Badlands National Park tour itinerary website.

Getting from Chicago to Badlands National Park by flight takes about 4 hours. Other options: drive; or do a combination of bus and taxi. You'll gain 1 hour traveling from Chicago to Badlands National Park due to the time zone difference. Traveling from Chicago in May, Badlands National Park is a bit cooler at night with lows of 42°F. Cap off your sightseeing on the 20th (Thu) early enough to go by car to Custer.

Things to do in Badlands National Park

Parks · Nature · Scenic Drive · Outdoors

Side Trip

Find places to stay May 18 — 20:

Custer

— 2 nights
Generally considered to be the oldest town established by European Americans in the Black Hills, Custer began as a mining town.
On the 21st (Fri), cruise along Iron Mountain Road, explore the wealth of natural beauty at Mount Rushmore National Memorial, then immerse yourself in nature at Custer State Park, and finally trek along Cathedral Spires Hiking Trail. Keep things going the next day: explore the activities along Sylvan Lake and then take in the dramatic natural features at Needles Eye Tunnel.

For photos, maps, more things to do, and more tourist information, read Custer trip itinerary planning site.

You can drive from Badlands National Park to Custer in 2 hours. Another option is to do a combination of taxi and bus. Plan for a bit cooler temperatures traveling from Badlands National Park in May, with highs in Custer at 59°F and lows at 37°F. Wrap up your sightseeing by early afternoon on the 22nd (Sat) to allow time for the flight to Kansas City.

Things to do in Custer

Parks · Nature · Outdoors · Scenic Drive

Side Trip

Find places to stay May 20 — 22:

Kansas City

— 3 nights

City of Fountains

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.
Take a break from Kansas City with a short trip to Evel Knievel Museum in Topeka, about 1h 5 min away. And it doesn't end there: brush up on your military savvy at National WWI Museum and Memorial, explore the world behind art at The Nelson-Atkins Museum of Art, steep yourself in history at Bingham Waggoner Mansion & Estate, and explore the landscape on two wheels at Little Blue Trace Trail.

For photos, reviews, ratings, and other tourist information, read Kansas City road trip site.

Traveling by flight from Custer to Kansas City takes 5.5 hours. Alternatively, you can drive; or do a combination of taxi and bus. Traveling from Custer to Kansas City, you'll lose 1 hour due to the time zone difference. Prepare for somewhat warmer weather when traveling from Custer in May: high temperatures in Kansas City hover around 76°F and lows are around 57°F. Finish up your sightseeing early on the 25th (Tue) so you can go by car to Branson.

Things to do in Kansas City

Museums · Wineries · Breweries & Distilleries · Tours

Side Trips

Find places to stay May 22 — 25:

Branson

— 3 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.
Branson is known for nightlife, theme parks, and museums. Your plan includes some of its best attractions: cool off at Silver Dollar City, gain interesting insight with VIP Tours of Branson, take an in-depth tour of Titanic Museum, and take in the architecture and atmosphere at Our Lady of the Lake Catholic Church.

For reviews, other places to visit, ratings, and tourist information, use the Branson road trip app.

Getting from Kansas City to Branson by car takes about 4 hours. Other options: take a bus; or fly. In May, daytime highs in Branson are 75°F, while nighttime lows are 55°F. Wrap up your sightseeing on the 28th (Fri) early enough to drive to Saint Louis.

Things to do in Branson

Theme Parks · Parks · Wineries · Tours

Side Trip

Find places to stay May 25 — 28:

Saint Louis

— 3 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.
Saint Louis is known for museums, parks, and zoos & aquariums. Your plan includes some of its best attractions: enjoy breathtaking views from The Gateway Arch, see the interesting displays at Cardinals Hall of Fame and Museum, relax in the rural setting at Grant’s Farm, and take in the architecture and atmosphere at Cathedral Basilica of Saint Louis.

To find maps, where to stay, and tourist information, refer to the Saint Louis online trip itinerary planner.

You can drive from Branson to Saint Louis in 4.5 hours. Alternatively, you can do a combination of car and flight; or do a combination of taxi and bus. May in Saint Louis sees daily highs of 77°F and lows of 57°F at night. Finish your sightseeing early on the 31st (Mon) to allow enough time to fly back home.

Things to do in Saint Louis

Parks · Museums · Zoos & Aquariums · Historic Sites
Find places to stay May 28 — 31: