17 days in Midwest Itinerary

17 days in Midwest Itinerary

Created using Inspirock Midwest trip planner

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Route & dates

17 days in Midwest Itinerary

Start: Rochester
train:  4​h
1
Cleveland
— 1 night
Fly:  3​h 15​min
2
Chicago
— 4 nights
Fly:  3​h 15​min
3
Saint Louis
— 3 nights
Fly + Drive:  3​h 45​min
4
Branson
— 2 nights
Drive:  3​h 45​min
5
Kansas City
— 2 nights
Fly + taxi:  7​h 15​min
6
Badlands National Park
— 1 day
Drive:  1​h 45​min
7
Custer
— 3 nights
taxi + Fly:  6​h 45​min
End: Rochester

1
night
Cleveland

Cleveland ©
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.
Start off your visit on the 30th (Fri): stroll around Cleveland Metroparks and then walk around Rocky River Reservation. On the 31st (Sat), you'll have a packed day of sightseeing: contemplate the long history of James A. Garfield National Historic Site, then admire the masterpieces at The Cleveland Museum of Art, and then see the interesting displays at Rock & Roll Hall of Fame.

To find traveler tips, more things to do, ratings, and more tourist information, you can read our Cleveland trip planner.

Rochester to Cleveland is an approximately 4-hour train ride. You can also drive; or fly. Traveling from Rochester in August, you can expect nighttime temperatures to be somewhat warmer in Cleveland, with lows of 67°F. Cap off your sightseeing on the 31st (Sat) early enough to travel to Chicago.

Things to do in Cleveland

Museums Parks Historic Sites

Side Trip

James A. Garfield National Historic Site
Highlights from your plan
The Cleveland Museum of Art ©
The Cleveland Museum of Art
Rock & Roll Hall of Fame ©
Rock & Roll Hall of Fame
Cleveland Metroparks ©
Cleveland Metroparks

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, historic sites, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, appreciate the extensive heritage of Millennium Park, take in panoramic vistas at Skydeck Chicago - Willis Tower, and shop like a local with The Magnificent Mile.

To find other places to visit, ratings, traveler tips, and other tourist information, read Chicago vacation planner.

Traveling by flight from Cleveland to Chicago takes 3.5 hours. Alternatively, you can do a combination of flight, bus, and subway; or drive. Traveling from Cleveland to Chicago, you'll gain 1 hour due to the time zone difference. In August, daytime highs in Chicago are 83°F, while nighttime lows are 67°F. Finish your sightseeing early on the 4th (Wed) so you can travel to Saint Louis.

Things to do in Chicago

Museums Childrens Museums Parks

Side Trip

Frank Lloyd Wright's Unity Temple
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Wrigley Field ©
Wrigley Field

3
nights
Saint Louis

Saint Louis ©
Test the local claim that Saint Louis is second only to Washington, D.C.
Step out of Saint Louis with an excursion to Pinckney Bend Distillery in New Haven--about 1h 10 min away. Next up on the itinerary: take in panoramic vistas at The Gateway Arch, have some family-friendly fun at Top Notch Axe Throwing St. Louis, examine the collection at City Museum, and look for all kinds of wild species at Sachs Butterfly House.

To find traveler tips, photos, reviews, and tourist information, use the Saint Louis journey planner .

You can fly from Chicago to Saint Louis in 3.5 hours. Other options are to do a combination of train and flight; or drive. Traveling from Chicago in September, you will find days in Saint Louis are somewhat warmer (84°F), and nights are about the same (59°F). Wrap up your sightseeing on the 7th (Sat) early enough to travel to Branson.

Things to do in Saint Louis

Parks Zoos & Aquariums Historic Sites

Side Trips

Sachs Butterfly House, Pinckney Bend Distillery
Highlights from your plan
Cathedral Basilica of Saint Louis ©
Cathedral Basilica of Saint Louis
The Gateway Arch ©
The Gateway Arch
Saint Louis Zoo ©
Saint Louis Zoo

2
nights
Branson

Branson ©
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 8th (Sun): cool off at Silver Dollar City. On your second day here, admire the local landmark of Dancing Water Fountain, contemplate the waterfront views at Table Rock Lake, then see the interesting displays at Titanic Museum, and finally have some family-friendly fun at Escape Code.

To see ratings, reviews, traveler tips, and tourist information, refer to the Branson road trip site .

Do a combination of flight and car from Saint Louis to Branson in 4 hours. Alternatively, you can drive; or take a bus. In September in Branson, expect temperatures between 82°F during the day and 60°F at night. Finish up your sightseeing early on the 9th (Mon) so you can go by car to Kansas City.

Things to do in Branson

Theme Parks Nature Parks

Side Trip

Table Rock Lake
Highlights from your plan
Escape Code ©
Escape Code
Silver Dollar City ©
Silver Dollar City
Titanic Museum ©
Titanic Museum

2
nights
Kansas City

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.
Start off your visit on the 10th (Tue): brush up on your knowledge of spirits at Holladay Distillery, then get engrossed in the history at National WWI Museum and Memorial, and then test your team's savvy at popular escape rooms. Here are some ideas for day two: examine the collection at Bingham Waggoner Estate, have some family-friendly fun at Blade & Timber, then admire the masterpieces at The Nelson-Atkins Museum of Art, and finally get your game on at Blade & Timber.

To see reviews, other places to visit, more things to do, and more tourist information, read our Kansas City day trip planning website .

Traveling by car from Branson to Kansas City takes 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. Finish up your sightseeing early on the 11th (Wed) so you can travel to Badlands National Park.

Things to do in Kansas City

Fun & Games Museums Breweries & Distilleries

Side Trips

Bingham Waggoner Estate, Holladay Distillery, Blade & Timber
Highlights from your plan
Holladay Distillery ©
Holladay Distillery
National WWI Museum and Memorial ©
National WWI Museum and Memorial
Room Escape Games

1
day
Badlands National Park

Badlands National Park ©
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.
On the 12th (Thu), explore the striking landscape at Big Badlands Overlook, then take in the dramatic natural features at Badlands Wall, then cruise along Loop Road, and finally take in the dramatic natural features at Yellow Mounds Overlook.

To find photos, maps, reviews, and other tourist information, you can read our Badlands National Park trip planner .

You can do a combination of flight and taxi from Kansas City to Badlands National Park in 7.5 hours. Other options are to drive; or take a bus. You'll gain 1 hour traveling from Kansas City to Badlands National Park due to the time zone difference. Expect a bit cooler evenings in Badlands National Park when traveling from Kansas City in September, with lows around 49°F. Wrap up your sightseeing on the 12th (Thu) to allow time to drive to Custer.

Things to do in Badlands National Park

Nature Parks Outdoors
Highlights from your plan
Loop Road ©
Loop Road
Badlands Wall ©
Badlands Wall
Big Badlands Overlook ©
Big Badlands Overlook

3
nights
Custer

Custer ©
Generally considered to be the oldest town established by European Americans in the Black Hills, Custer began as a mining town.
Go for a jaunt from Custer to Keystone to see Presidential Trail about 30 minutes away. There's still lots to do: explore the wealth of natural beauty at Mount Rushmore National Memorial, take a memorable drive along Needles Highway, identify plant and animal life at Black Hills National Forest, and admire all the interesting features of Iron Mountain Road.

For reviews and tourist information, refer to the Custer trip planning website .

Traveling by car from Badlands National Park to Custer takes 2 hours. Alternatively, you can do a combination of bus and taxi. When traveling from Badlands National Park in September, plan for little chillier days and about the same nights in Custer: temperatures range from 71°F by day to 45°F at night. On the 15th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Custer

Parks Nature Outdoors

Side Trips

Keystone, Needles Highway
Highlights from your plan
Mount Rushmore National Memorial ©
Mount Rushmore National Memorial
Custer State Park ©
Custer State Park
Needles Eye Tunnel ©
Needles Eye Tunnel

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