30 days in Midwest Itinerary

30 days in Midwest Itinerary

Created using Inspirock Midwest vacation planner

Make it your trip
Fly
1
Kansas City
— 3 nights
Drive
2
Branson
— 4 nights
Drive
3
Jefferson City
— 1 night
Drive
4
Saint Louis
— 4 nights
Fly
5
Cincinnati
— 3 nights
Fly
6
Detroit
— 3 nights
Fly
7
Cleveland
— 3 nights
Fly
8
Chicago
— 6 nights
Fly
9
Galena
— 2 nights
Drive

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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.
You'll find plenty of places to visit near Kansas City: Weston (Pirtle Winery & Holladay Distillery). There's still lots to do: brush up on your military savvy at National WWI Museum and Memorial, admire the masterpieces at The Nelson-Atkins Museum of Art, steep yourself in history at Union Station, and brush up on your knowledge of spirits at Tom's Town Distilling Co..

To see where to stay, more things to do, other places to visit, and tourist information, use the Kansas City online travel planner.

Madison to Kansas City is an approximately 3-hour flight. You can also drive; or take a bus. Traveling from Madison in November, things will get somewhat warmer in Kansas City: highs are around 56°F and lows about 38°F. Finish your sightseeing early on the 20th (Sat) so you can drive to Branson.

Things to do in Kansas City

Breweries & Distilleries · Wineries · Historic Sites · Museums

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.
Take a break from Branson with a short trip to NRA National Sporting Arms Museum in Springfield, about 54 minutes away. The adventure continues: find something for the whole family at Silver Dollar City, stroll through National Tiger Sanctuary, take some stellar pictures from College of the Ozarks, and awaken your taste buds at VIP Tours of Branson.

To find other places to visit, where to stay, traveler tips, and tourist information, read Branson trip itinerary app.

You can drive from Kansas City to Branson in 4 hours. Alternatively, you can take a bus; or fly. November in Branson sees daily highs of 58°F and lows of 38°F at night. Finish up your sightseeing early on the 24th (Wed) so you can travel to Jefferson City.

Things to do in Branson

Theme Parks · Parks · Museums · Wineries

Side Trips

Jefferson City

— 1 night
Jefferson City is the capital of the State of Missouri and the fifteenth most populous city in the state. Start off your visit on the 25th (Thu): admire the striking features of America's National Churchill Museum and then steep yourself in history at Missouri State Penitentiary.

To find reviews, maps, photos, and tourist information, read our Jefferson City day trip website.

Getting from Branson to Jefferson City by car takes about 3 hours. In November, plan for daily highs up to 56°F, and evening lows to 35°F. Finish your sightseeing early on the 25th (Thu) so you can travel to Saint Louis.

Things to do in Jefferson City

Historic Sites · Museums

Side Trip

Saint Louis

— 4 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.
Venture out of the city with trips to Great Rivers Scenic Route (in Alton) and Pinckney Bend Distillery (in New Haven). Next up on the itinerary: enjoy breathtaking views from The Gateway Arch, admire the natural beauty at Missouri Botanical Garden, explore the galleries of Campbell House Museum, and indulge in some culinary diversions at a local gastronomic tour.

To see traveler tips, reviews, where to stay, and other tourist information, read Saint Louis trip planning website.

You can drive from Jefferson City to Saint Louis in 2.5 hours. In November, plan for daily highs up to 56°F, and evening lows to 35°F. Finish your sightseeing early on the 29th (Mon) so you can fly to Cincinnati.

Things to do in Saint Louis

Parks · Historic Sites · Museums · Scenic Drive

Side Trips

Cincinnati

— 3 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.
Get out of town with these interesting Cincinnati side-trips: Dayton (Carillon Historical Park & National Museum of the US Air Force). There's still lots to do: learn the secrets of beer at a beer tour and tasting, try your luck at JACK Cincinnati Casino, contemplate in the serene atmosphere at Cathedral Basilica of the Assumption, and stroll through Spring Grove Cemetery & Arboretum.

To find where to stay, traveler tips, and tourist information, you can read our Cincinnati trip itinerary maker site.

Traveling by flight from Saint Louis to Cincinnati takes 3 hours. Alternatively, you can drive; or take a bus. Traveling from Saint Louis to Cincinnati, you'll lose 1 hour due to the time zone difference. In November, daytime highs in Cincinnati are 54°F, while nighttime lows are 33°F. Finish up your sightseeing early on the 2nd (Thu) so you can catch the flight to Detroit.

Things to do in Cincinnati

Historic Sites · Museums · Breweries & Distilleries · Casinos

Side Trip

Detroit

— 3 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.
When in Detroit, make a side trip to see Flint Institute of Arts in Flint, approximately Flint away. There's still lots to do: admire the masterpieces at Detroit Institute of Arts, examine the collection at The Henry Ford, steep yourself in history at The Ford Piquette Avenue Plant, and explore the galleries of Motown Museum.

To find more things to do, photos, traveler tips, and other tourist information, read our Detroit trip builder tool.

Getting from Cincinnati to Detroit by flight takes about 3 hours. Other options: drive; or take a bus. Traveling from Cincinnati in December, expect nights in Detroit to be about the same, around 27°F, while days are little chillier, around 37°F. Cap off your sightseeing on the 5th (Sun) early enough to catch the flight to Cleveland.

Things to do in Detroit

Museums · Historic Sites

Side Trips

Cleveland

— 3 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.
Cleveland is known for museums, casinos, and shopping. Your trip includes some of its best attractions: explore the world behind art at The Cleveland Museum of Art, make a trip to Heinen's Downtown, try your luck at JACK Cleveland Casino, and examine the collection at Rock & Roll Hall of Fame.

Start your trip to Cleveland by creating a personalized itinerary on Inspirock.

Traveling by flight from Detroit to Cleveland takes 2.5 hours. Alternatively, you can drive; or take a bus. In December in Cleveland, expect temperatures between 42°F during the day and 31°F at night. Cap off your sightseeing on the 8th (Wed) early enough to catch the flight to Chicago.

Things to do in Cleveland

Museums · Historic Sites · Casinos · Parks

Side Trip

Chicago

— 6 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, take in the waterfront at Navy Pier, get to know the resident critters at Lincoln Park Zoo, and take a stroll through The Magnificent Mile.

To find ratings, more things to do, where to stay, and tourist information, use the Chicago driving holiday tool.

Fly from Cleveland to Chicago in 3 hours. Alternatively, you can drive; or take a train. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. Traveling from Cleveland in December, you can expect nighttime temperatures to be slightly colder in Chicago, with lows of 26°F. Finish up your sightseeing early on the 14th (Tue) so you can catch the flight to Galena.

Things to do in Chicago

Museums · Childrens Museums · Parks · Zoos & Aquariums

Side Trip

Galena

— 2 nights
Galena is the largest city in and the county seat of Jo Daviess County, Illinois, with a population of 3,429 at the 2010 census. On the 15th (Wed), grab your bike and head to Heritage Trail and then appreciate the history behind Galena Veterans Memorial Park. Here are some ideas for day two: contemplate the long history of Ulysses S. Grant Home, then brush up on your knowledge of spirits at Blaum Bros. Distilling Co., and then get the lay of the land with Walking tours.

Quickly create a custom-made itinerary for Galena using our trip planner.

Getting from Chicago to Galena by flight takes about 2.5 hours. Other options: drive; or take a bus. In December, Galena is little chillier than Chicago - with highs of 31°F and lows of 18°F. Wrap up your sightseeing on the 16th (Thu) early enough to drive back home.

Things to do in Galena

Breweries & Distilleries · Outdoors · Parks · Trails

Side Trip