10 days in Midwest Itinerary

10 days in Midwest Itinerary

Created using Inspirock Midwest trip itinerary maker

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Route & dates

10 days in Midwest Itinerary

Start: New York City
Fly + taxi:  4​h 15​min
1
Dayton
— 1 night
taxi + Fly:  4​h 15​min
2
Empire
— 1 night
Fly:  3​h 30​min
3
Chicago
— 3 nights
Drive:  3​h 30​min
4
Springfield
— 1 night
Drive:  1​h 45​min
5
Saint Louis
— 2 nights
6
Cleveland
— 1 night
Fly + bus:  4​h
End: New York City

1
night
Dayton

Dayton ©
Home of airplane pioneers the Wright brothers, Dayton prides itself on its inventors, including Charles F.
Start off your visit on the 18th (Wed): see the interesting displays at National Museum of the US Air Force. On your second day here, get to know the fascinating history of Aullwood Garden MetroPark, then stroll the grounds of Dayton National Cemetery, then explore the different monuments and memorials at The Calvary Cemetery, and finally steep yourself in history at Carillon Historical Park.

For other places to visit, where to stay, reviews, and other tourist information, read our Dayton travel route builder site .

New York City to Dayton is an approximately 4.5-hour combination of flight and taxi. You can also do a combination of bus, flight, and taxi; or drive. Expect slightly colder evenings in Dayton when traveling from New York City in September, with lows around 57°F. Cap off your sightseeing on the 19th (Thu) early enough to travel to Empire.

Things to do in Dayton

Historic Sites Parks Museums

Side Trip

Aullwood Garden MetroPark
Find places to stay Sep 18 — 19:
Highlights from your plan
National Museum of the US Air Force ©
Carillon Historical Park ©
Carillon Historical Park
Aullwood Garden MetroPark ©
Aullwood Garden MetroPark

1
night
Empire

Empire ©
Empire is a village in Leelanau County in the U.S. Kick off your visit on the 20th (Fri): enjoy the sea views from Point Betsie Lighthouse, then have a few drinks at Lake Ann Brewing Company, and then get to know the fascinating history of Sleeping Bear Dunes National Lakeshore.

To find other places to visit, photos, ratings, and more tourist information, read our Empire journey planner.

You can do a combination of taxi and flight from Dayton to Empire in 4.5 hours. Other options are to drive; or take a bus. Traveling from Dayton in September, expect nights in Empire to be about the same, around 53°F, while days are a bit cooler, around 71°F. Wrap up your sightseeing on the 20th (Fri) early enough to travel to Chicago.

Things to do in Empire

Historic Sites Parks Nature

Side Trips

Lake Ann Brewing Company, Point Betsie Lighthouse
Find places to stay Sep 19 — 20:
Highlights from your plan
Point Betsie Lighthouse ©
Point Betsie Lighthouse
Lake Ann Brewing Company ©
Lake Ann Brewing Company

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Let the collections at The Art Institute of Chicago and Cantigny Park capture your imagination. The Magnificent Mile and Frank Lloyd Wright Home and Studio are good opportunities to explore the local culture. There's still lots to do: steep yourself in history at Ernest Hemingway Birthplace, contemplate in the serene atmosphere at Fourth Presbyterian Church, stroll around Millennium Park, and get curious at Museum of Science and Industry.

To find traveler tips, ratings, more things to do, and tourist information, use the Chicago visit planner.

You can fly from Empire to Chicago in 3.5 hours. Other options are to do a combination of taxi and flight; or drive. Traveling from Empire to Chicago, you'll gain 1 hour due to the time zone difference. Plan for somewhat warmer temperatures traveling from Empire in September, with highs in Chicago at 78°F and lows at 61°F. Wrap up your sightseeing on the 23rd (Mon) to allow time to drive to Springfield.

Things to do in Chicago

Museums Childrens Museums Historic Sites

Side Trips

Oak Park, Cantigny Park, Horseshoe Hammond
Find places to stay Sep 20 — 23:
Highlights from your plan
Ernest Hemingway Birthplace ©
Ernest Hemingway Birthplace
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum

1
night
Springfield

Springfield ©
Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.
Kick off your visit on the 24th (Tue): contemplate the long history of Dana-Thomas House, contemplate the long history of Lincoln Home National Historic Site, then get engrossed in the history at Abraham Lincoln Presidential Library and Museum, and finally admire the natural beauty at Lincoln Memorial Garden.

For reviews, other places to visit, where to stay, and other tourist information, go to the Springfield trip itinerary website .

Getting from Chicago to Springfield by car takes about 3.5 hours. Other options: fly; or do a combination of flight and bus. In September, daily temperatures in Springfield can reach 82°F, while at night they dip to 58°F. Finish your sightseeing early on the 24th (Tue) to allow enough time to drive to Saint Louis.

Things to do in Springfield

Museums Historic Sites Parks
Find places to stay Sep 23 — 24:
Highlights from your plan
Lincoln Home National Historic Site ©
Dana-Thomas House ©
Dana-Thomas House

2
nights
Saint Louis

Saint Louis ©
Test the local claim that Saint Louis is second only to Washington, D.C.
Start off your visit on the 25th (Wed): appreciate the extensive heritage of St. Charles Historic District, then see the interesting displays at City Museum, then take in nature's colorful creations at Missouri Botanical Garden, and finally pause for some serene contemplation at Cathedral Basilica of Saint Louis. Get ready for a full day of sightseeing on the 26th (Thu): take in the spiritual surroundings of Shrine of St. Joseph, then steep yourself in history at Cahokia Mounds State Historic Site, then contemplate the long history of Lewis & Clark State Historic Site, and finally stroll the grounds of Eagle Cliff - Miles Cemetery.

Ask Inspirock to suggest an itinerary and make planning a trip to Saint Louis fast, fun, and easy.

You can drive from Springfield to Saint Louis in 2 hours. Other options are to do a combination of taxi and flight; or do a combination of bus and train. Expect a daytime high around 84°F in September, and nighttime lows around 59°F. Cap off your sightseeing on the 26th (Thu) early enough to travel to Cleveland.

Things to do in Saint Louis

Historic Sites Museums Parks

Side Trips

Eagle Cliff - Miles Cemetery, St. Charles Historic District, Cahokia Mounds State Historic Site, Lewis & Clark State Historic Site
Find places to stay Sep 24 — 26:
Highlights from your plan
Cathedral Basilica of Saint Louis ©
Cathedral Basilica of Saint Louis
City Museum ©
City Museum
Missouri Botanical Garden ©
Missouri Botanical Garden

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.
On the 27th (Fri), browse the eclectic array of goods at West Side Market, see the interesting displays at Rock & Roll Hall of Fame, then admire the masterpieces at The Cleveland Museum of Art, and finally contemplate in the serene atmosphere at Our Lady of Lourdes Shrine.

To find traveler tips, other places to visit, maps, and more tourist information, you can read our Cleveland online sightseeing planner .

Fly from Saint Louis to Cleveland in 3.5 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. When traveling from Saint Louis in September, plan for slightly colder days in Cleveland, with highs around 75°F, while nights are about the same with lows around 62°F. Finish up your sightseeing early on the 27th (Fri) so you can travel back home.

Things to do in Cleveland

Museums Historic Sites Shopping

Side Trip

Our Lady of Lourdes Shrine
Find places to stay Sep 26 — 27:
Highlights from your plan
The Cleveland Museum of Art ©
The Cleveland Museum of Art
Rock & Roll Hall of Fame ©
Rock & Roll Hall of Fame
Our Lady of Lourdes Shrine ©
Our Lady of Lourdes Shrine

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