52 days in Midwest Itinerary

52 days in Midwest Itinerary

Created using Inspirock Midwest tour planner

Make it your trip
Fly
1
Chicago
— 7 nights
Fly
2
Branson
— 4 nights
Drive
3
Kansas City
— 5 nights
Fly
4
Saint Louis
— 5 nights
Drive
5
Springfield
— 4 nights
Drive
6
Winona
— 4 nights
Drive
7
Ontonagon
— 2 nights
Drive
8
Duluth
— 5 nights
Fly
9
Detroit
— 4 nights
Fly
10
Cleveland
— 5 nights
Drive
11
Rockbridge
— 1 night
Drive
12
Cincinnati
— 5 nights
Fly

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Chicago

— 7 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, enjoy breathtaking views from 360 Chicago Observation Deck, admire the landmark architecture of Skydeck Chicago - Willis Tower, and wander the streets of The Magnificent Mile.

For photos, more things to do, traveler tips, and other tourist information, read our Chicago road trip planning website.

Sao Paulo, Brazil to Chicago is an approximately 13.5-hour flight. The time zone changes from Brasilia Standard Time to Central Standard Time, which is usually a -3 hour difference. Expect little chillier temperatures when traveling from Sao Paulo in October; daily highs in Chicago reach 21°C and lows reach 11°C. Finish your sightseeing early on the 14th (Thu) so you can fly to Branson.

Things to do in Chicago

Museums · Parks · Childrens Museums · Historic Sites

Side Trips

Branson

— 4 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 trip includes some of its best attractions: cool off at Silver Dollar City, pause for some serene contemplation at Our Lady of the Lake Catholic Church, see the top attractions with VIP Tours of Branson, and tour the pleasant surroundings at College of the Ozarks.

To see ratings, reviews, maps, and tourist information, go to the Branson journey planning website.

Traveling by flight from Chicago to Branson takes 3 hours. Alternatively, you can drive; or do a combination of train, bus, and taxi. When traveling from Chicago in October, plan for somewhat warmer days in Branson, with highs around 25°C, while nights are about the same with lows around 11°C. Finish your sightseeing early on the 18th (Mon) to allow enough time to drive to Kansas City.

Things to do in Branson

Theme Parks · Parks · Museums · Tours

Side Trips

Kansas City

— 5 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.
You'll find plenty of places to visit near Kansas City: Weston (Pirtle Winery & Holladay Distillery). There's much more to do: explore the world behind art at The Nelson-Atkins Museum of Art, contemplate the long history of Bingham Waggoner Mansion & Estate, brush up on your military savvy at National WWI Museum and Memorial, and learn insider's secrets on Barley Bus Tours.

To see ratings, photos, and tourist information, go to the Kansas City route planner.

Traveling by car from Branson to Kansas City takes 4 hours. Alternatively, you can take a bus; or fly. In October, daily temperatures in Kansas City can reach 25°C, while at night they dip to 12°C. Finish up your sightseeing early on the 23rd (Sat) so you can catch the flight to Saint Louis.

Things to do in Kansas City

Museums · Wineries · Breweries & Distilleries · Historic Sites

Side Trips

Saint Louis

— 5 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.
Get out of town with these interesting Saint Louis side-trips: The National Churchill Museum (in Fulton) and New Haven (Pinckney Bend Distillery & Astral Glass Studio and Gallery). There's still lots to do: take in panoramic vistas at The Gateway Arch, get a sense of history and politics at Old Courthouse, take in the architecture and atmosphere at Cathedral Basilica of Saint Louis, and get to know the resident critters at Saint Louis Zoo.

To see ratings, reviews, where to stay, and other tourist information, go to the Saint Louis online day trip planner.

Getting from Kansas City to Saint Louis by flight takes about 2.5 hours. Other options: drive; or take a bus. Expect a daytime high around 26°C in October, and nighttime lows around 11°C. Wrap up your sightseeing on the 28th (Thu) early enough to drive to Springfield.

Things to do in Saint Louis

Museums · Parks · Historic Sites · Zoos & Aquariums

Side Trips

Springfield

— 4 nights

Flower City

Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.
Explore Springfield's surroundings by going to Christ Apple Orchard (in Elmwood) and Grand View Drive (in Peoria). There's lots more to do: get advice or help at Abraham Lincoln Presidential Library and Museum, don't miss a visit to Rees Memorial Carillon, contemplate the long history of Dana-Thomas House, and relax in the rural setting at Apple Barn.

To see maps, reviews, more things to do, and more tourist information, you can read our Springfield driving holiday planner.

You can drive from Saint Louis to Springfield in 2 hours. Other options are to fly; or do a combination of train and bus. In October, daily temperatures in Springfield can reach 24°C, while at night they dip to 9°C. Finish up your sightseeing early on the 1st (Mon) so you can travel to Winona.

Things to do in Springfield

Historic Sites · Museums · Scenic Drive · Outdoors

Side Trips

Winona

— 4 nights
Winona is a city in and the county seat of Winona County, in the state of Minnesota. Get out of town with these interesting Winona side-trips: Alma (Wings Over Alma Nature & Art Center & Buena Vista Park), National Eagle Center (in Wabasha) and Leinie Lodge (in Chippewa Falls). There's lots more to do: admire the masterpieces at Minnesota Marine Art Museum, take a memorable drive along Old Hwy 61, take in the spiritual surroundings of Franciscan Sisters of Perpetual Adoration Motherhouse, and admire all the interesting features of Garvin Heights City Park.

To find where to stay and other tourist information, read our Winona sightseeing planner.

Traveling by car from Springfield to Winona takes 6.5 hours. Alternatively, you can do a combination of flight and car. When traveling from Springfield in November, plan for a bit cooler days and about the same nights in Winona: temperatures range from 7°C by day to -1°C at night. Finish up your sightseeing early on the 5th (Fri) so you can travel to Ontonagon.

Things to do in Winona

Parks · Scenic Drive · Outdoors · Wildlife

Side Trips

Ontonagon

— 2 nights
On the 6th (Sat), take in the dramatic scenery at Bond Falls and then discover the riches below the earth's surface at Adventure Mining Company. On the next day, contemplate the waterfront views at Presque Isle River and then delve into the lush surroundings at Porcupine Mountains State Park.

For reviews, where to stay, maps, and more tourist information, read our Ontonagon trip itinerary maker website.

You can drive from Winona to Ontonagon in 5.5 hours. Alternatively, you can do a combination of car and flight. You'll lose 1 hour traveling from Winona to Ontonagon due to the time zone difference. When traveling from Winona in November, plan for slightly colder days in Ontonagon, with highs around 4°C, while nights are about the same with lows around -3°C. Cap off your sightseeing on the 7th (Sun) early enough to travel to Duluth.

Things to do in Ontonagon

Nature · Parks · Trails · Outdoors

Side Trip

Duluth

— 5 nights

Zenith City of the Unsalted Seas

Situated on the westernmost point of the Lake Superior, Duluth represents a booming port city.
Venture out of the city with trips to Two Harbors (Superior Hiking Trail & Gooseberry Falls State Park), Copper Falls State Park (in Mellen) and Soudan Underground Mine (in Soudan). There's still lots to do: view the masterpieces at Lake Superior Art Glass, take in the views from Aerial Lift Bridge, get engrossed in the history at Lake Superior Railroad Museum, and stroll around Canal Park.

For maps, traveler tips, and more tourist information, read our Duluth tour planner.

Traveling by car from Ontonagon to Duluth takes 3.5 hours. Traveling from Ontonagon to Duluth, you'll gain 1 hour due to the time zone difference. Expect a daytime high around 5°C in November, and nighttime lows around -2°C. Wrap up your sightseeing on the 12th (Fri) to allow time to fly to Detroit.

Things to do in Duluth

Parks · Nature · Outdoors · Museums

Side Trips

Detroit

— 4 nights

The Motor City

Founded in 1701 by a French explorer and adventurer, Detroit exerted a profound impact on the world for most of the 20th century.
Venture out of the city with trips to Erwin's Orchard (in South Lyon), Oak Openings Preserve Metropark (in Toledo) and Bennett's Orchard (in Ottawa Lake). There's still lots to do: examine the collection at The Henry Ford, contemplate the long history of Motown Museum, explore the galleries of The Ford Piquette Avenue Plant, and admire the masterpieces at Detroit Institute of Arts.

To find more things to do, where to stay, maps, and more tourist information, use the Detroit trip itinerary maker tool.

Traveling by flight from Duluth to Detroit takes 5 hours. Alternatively, you can drive; or do a combination of bus and train. Traveling from Duluth to Detroit, you'll lose 1 hour due to the time zone difference. In November, Detroit is a bit warmer than Duluth - with highs of 10°C and lows of 1°C. Finish your sightseeing early on the 16th (Tue) so you can fly to Cleveland.

Things to do in Detroit

Museums · Historic Sites · Parks · Wildlife

Side Trips

Cleveland

— 5 nights

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.
Change things up with these side-trips from Cleveland: Cedar Point (in Sandusky), F.A. Seiberling Nature Realm (in Akron) and The Farm at Walnut Creek (in Sugarcreek). The adventure continues: see the interesting displays at Rock & Roll Hall of Fame, walk around Rocky River Reservation, explore the world behind art at The Cleveland Museum of Art, and browse the exhibits of A Christmas Story House.

For photos, other places to visit, ratings, and other tourist information, use the Cleveland sightseeing planning site.

Traveling by flight from Detroit to Cleveland takes 2.5 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 13°C in November, and nighttime lows around 4°C. Finish your sightseeing early on the 21st (Sun) to allow enough time to drive to Rockbridge.

Things to do in Cleveland

Museums · Parks · Fun & Games · Theme Parks

Side Trips

Rockbridge

— 1 night
Rockbridge is an unincorporated community in eastern Good Hope Township, Hocking County, Ohio, United States. Start off your visit on the 22nd (Mon): head outdoors with Outdoor Activities and then stroll through Conkles Hollow State Nature Preserve.

To see ratings, traveler tips, reviews, and more tourist information, refer to the Rockbridge driving holiday planner.

You can drive from Cleveland to Rockbridge in 3.5 hours. Other options are to do a combination of bus and taxi; or fly. Traveling from Cleveland in November, you can expect nighttime temperatures to be slightly colder in Rockbridge, with lows of 0°C. Finish your sightseeing early on the 22nd (Mon) so you can drive to Cincinnati.

Things to do in Rockbridge

Parks · Tours · Adventure · Wildlife

Cincinnati

— 5 nights

The Queen of the West

Situated on the north bank of the Ohio River, Cincinnati distinguished itself as the only U.S. city that left a favorable impression on one of its most famous 19th-century visitors, English author Charles Dickens.
You'll find plenty of places to visit near Cincinnati: Dayton (Carillon Historical Park & National Museum of the US Air Force) and The Miller House and Garden (in Columbus). Next up on the itinerary: sample some tasty brews at a beer tour and tasting, explore the different monuments and memorials at Spring Grove Cemetery & Arboretum, snap pictures at Roebling Suspension Bridge, and take in nature's colorful creations at Cincinnati Zoo & Botanical Garden.

For traveler tips, maps, ratings, and tourist information, refer to the Cincinnati trip site.

Traveling by car from Rockbridge to Cincinnati takes 2.5 hours. Alternatively, you can do a combination of taxi and bus. In November, daytime highs in Cincinnati are 14°C, while nighttime lows are 0°C. Finish your sightseeing early on the 27th (Sat) to allow enough time to fly back home.

Things to do in Cincinnati

Parks · Historic Sites · Tours · Zoos & Aquariums

Side Trips