14 days in Midwest Itinerary

14 days in Midwest Itinerary

Created using Inspirock Midwest trip itinerary planner

Make it your trip
Drive to Newark Liberty International Airport, Fly to Chicago Midway International Airport
1
Chicago
— 4 nights
Fly
2
Saint Louis
— 3 nights
Drive
3
Branson
— 3 nights
Drive
4
Kansas City
— 2 nights
+2
Drive to Kansas City International Airport, Fly to Newark Liberty International Airport, Drive to Wilkes-Barre

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Chicago

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get some historical perspective at Frank Lloyd Wright's Unity Temple and Frank Lloyd Wright Home and Studio. Get outdoors at Boat Tours & Water Sports and Little Red Schoolhouse. Step out of Chicago to go to Highland Park and see Prairie Wolf Slough, which is approximately 42 minutes away. And it doesn't end there: admire the masterpieces at The Art Institute of Chicago, contemplate the long history of Ernest Hemingway Birthplace, engage your brain at Museum of Science and Industry, and ponder the design of Buckingham Fountain.

Plan trip to Chicago with our itinerary maker to find out where to go and what to do.

Wilkes-Barre to Chicago is an approximately 7-hour combination of car and flight. You can also drive. Traveling from Wilkes-Barre to Chicago, you'll gain 1 hour due to the time zone difference. May in Chicago sees daily highs of 71°F and lows of 52°F at night. Finish your sightseeing early on the 5th (Wed) to allow enough time to travel to Saint Louis.

Things to do in Chicago

Parks · Outdoors · Trails · Wildlife

Side Trips

Saint Louis

— 3 nights

Gateway to the West

Test the local claim that Saint Louis is second only to Washington, D.C.
Get outdoors at Powder Valley Conservation Nature Center and World Bird Sanctuary. You'll find plenty of places to visit near Saint Louis: Bluff View Trail (in Wildwood) and Riverlands Migratory Bird Sanctuary (in West Alton). The adventure continues: take in the architecture and atmosphere at Cathedral Basilica of Saint Louis, identify plant and animal life at The Sophia M. Sachs Butterfly House, relax in the rural setting at Grant’s Farm, and stroll around Forest Park.

To find other places to visit, where to stay, and tourist information, go to the Saint Louis trip tool.

Getting from Chicago to Saint Louis by flight takes about 3.5 hours. Other options: drive; or take a train. Traveling from Chicago in May, expect nights in Saint Louis to be about the same, around 57°F, while days are somewhat warmer, around 77°F. Finish up your sightseeing early on the 8th (Sat) so you can go by car to Branson.

Things to do in Saint Louis

Parks · Wildlife · Historic Sites · Trails

Side Trips

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.
Get outdoors at Table Rock Lake and Turpentine Creek Wildlife Refuge. Venture out of the city with trips to Eureka Springs (Thorncrown Chapel & Hippie Biker Chick). There's much more to do: see what you can catch with a fishing tour, whizz through the canopy at some of the top local zipline courses and adventure parks, hike along Table Rock Lakeshore Trail, and identify plant and animal life at Shepherd of the Hills Fish Hatchery.

For maps, ratings, more things to do, and other tourist information, you can read our Branson trip builder tool.

You can drive from Saint Louis to Branson in 4.5 hours. Other options are to do a combination of flight and car; or do a combination of bus and taxi. In May, daily temperatures in Branson can reach 75°F, while at night they dip to 55°F. Finish your sightseeing early on the 11th (Tue) to allow enough time to drive to Kansas City.

Things to do in Branson

Parks · Wildlife · Outdoors · Tours

Side Trips

Kansas City

— 2 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.
On the 12th (Wed), take an in-depth tour of Harry S. Truman Library and Museum, take an in-depth tour of National WWI Museum and Memorial, then steep yourself in history at Union Station, and finally see the interesting displays at Museum of Illusions. Get ready for a full day of sightseeing on the 13th (Thu): contemplate the long history of Bingham Waggoner Mansion & Estate, then look for all kinds of wild species at Burr Oak Woods Conservation Area, then explore the landscape on two wheels at Little Blue Trace Trail, and finally explore the world behind art at The Nelson-Atkins Museum of Art.

To see maps, traveler tips, and more tourist information, read Kansas City day trip planner.

Traveling by car from Branson to Kansas City takes 4 hours. Alternatively, you can take a bus; or fly. In May, daytime highs in Kansas City are 76°F, while nighttime lows are 57°F. Finish your sightseeing early on the 13th (Thu) so you can travel back home.

Things to do in Kansas City

Museums · Parks · Historic Sites · Wildlife

Side Trips