8 days in Midwest Itinerary

8 days in Midwest Itinerary

Created using Inspirock Midwest holiday planner

Make it your trip
1
Chicago
— 1 day
Drive
2
Branson
— 1 night
Drive
3
Saint Louis
— 2 nights
Drive
4
Cincinnati
— 2 nights
Drive

S M T W T F S
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Chicago

— 1 day

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 21st (Sat): contemplate in the serene atmosphere at Frank Lloyd Wright's Unity Temple, stop by Ernest Hemingway Birthplace, admire the landmark architecture of Frank Lloyd Wright Home and Studio, then explore the world behind art at The Art Institute of Chicago, and finally contemplate in the serene atmosphere at Fourth Presbyterian Church.

To find photos, other places to visit, maps, and tourist information, go to the Chicago trip planner.

Use the Route module to see travel options from your home to Chicago. In November, daytime highs in Chicago are 50°F, while nighttime lows are 35°F. Finish your sightseeing early on the 21st (Sat) to allow enough time to fly to Branson.

Things to do in Chicago

Historic Sites · Museums · Shopping

Side Trip

Branson

— 1 night

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.
Kick off your visit on the 22nd (Sun): tour the pleasant surroundings at National Tiger Sanctuary, buy something for everyone on your list at Branson Landing, and then stop by Dick's Oldtime 5 & 10. On the next day, pause for some serene contemplation at Our Lady of the Lake Catholic Church, then see the interesting displays at Titanic Museum, and then awaken your taste buds at VIP Tours of Branson.

To see maps, other places to visit, and other tourist information, use the Branson road trip site.

Traveling by car from Chicago to Branson takes 9.5 hours. Alternatively, you can fly; or drive; or do a combination of train, bus, and taxi. Expect a bit warmer weather when traveling from Chicago in November: highs in Branson hover around 58°F, while lows dip to 38°F. Wrap up your sightseeing on the 23rd (Mon) early enough to drive to Saint Louis.

Things to do in Branson

Shopping · Tours · Wineries · Parks

Side Trip

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 24th (Tue): take in the architecture and atmosphere at Cathedral Basilica of Saint Louis, then stroll through Audubon Center at Riverlands, and then tour the pleasant surroundings at Riverlands Migratory Bird Sanctuary. On the next day, look for gifts at Herbaria, tour the pleasant surroundings at World Bird Sanctuary, then admire the masterpieces at Saint Louis Art Museum, and finally learn the secrets of beer at a beer tour and tasting.

For ratings, where to stay, maps, and other tourist information, read Saint Louis driving holiday planning tool.

Traveling by car from Branson to Saint Louis takes 4.5 hours. Alternatively, you can do a combination of car and flight; or do a combination of taxi and bus. In November, daily temperatures in Saint Louis can reach 56°F, while at night they dip to 35°F. Cap off your sightseeing on the 25th (Wed) early enough to catch the flight to Cincinnati.

Things to do in Saint Louis

Parks · Wildlife · Historic Sites · Tours

Side Trips

Cincinnati

— 2 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.
Popular historic sites such as Spring Grove Cemetery & Arboretum and Cathedral Basilica of the Assumption are in your itinerary. Get a sense of the local culture at Carillon Historical Park and Dayton National Cemetery. Get out of town with these interesting Cincinnati side-trips: Dayton (Dayton Mall & National Museum of the US Air Force) and Jungle Jim's International Market (in Fairfield). There's still lots to do: learn the secrets of beer at a beer tour and tasting, take in the architecture and atmosphere at Cathedral Basilica of St. Peter in Chains, try to win big at JACK Cincinnati Casino, and visit Mount Adams.

For photos, reviews, other places to visit, and other tourist information, you can read our Cincinnati trip itinerary planning site.

Fly from Saint Louis to Cincinnati in 3 hours. Alternatively, you can drive; or take a bus. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. November in Cincinnati sees daily highs of 54°F and lows of 33°F at night. Finish your sightseeing early on the 28th (Sat) to allow enough time to fly back home.

Things to do in Cincinnati

Historic Sites · Shopping · Neighborhoods · Casinos

Side Trips