29 days in Midwest Itinerary

29 days in Midwest Itinerary

Created using Inspirock Midwest trip itinerary builder

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Route & dates

29 days in Midwest Itinerary

Start: Toronto
Fly:  5​h 45​min
1
Keystone
— 1 night
Fly:  6​h 15​min
2
Empire
— 3 nights
Fly:  3​h 30​min
3
Chicago
— 5 nights
train:  1​h 30​min
4
South Bend
— 1 night
Fly:  5​h
5
Branson
— 3 nights
Drive:  3​h 45​min
6
Independence
— 4 nights
Drive:  4​h
7
Saint Louis
— 5 nights
Fly:  3​h 30​min
8
Columbus
— 5 nights
Fly:  4​h 15​min
End: Toronto

1
night
Keystone

Keystone ©
Fewer than 400 people call Keystone home year-round, but the population explodes in summer when crowds flock to nearby Mount Rushmore.
On the 14th (Mon), explore the wealth of natural beauty at Mount Rushmore National Memorial. Keep things going the next day: contemplate the waterfront views at Sylvan Lake and then delve into the lush surroundings at Black Hills National Forest.

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

Toronto, Canada to Keystone is an approximately 6-hour flight. You can also do a combination of bus and flight; or drive. The time zone difference moving from Eastern Standard Time (EST) to Mountain Standard Time (MST) is minus 2 hours. Traveling from Toronto in October, Keystone is slightly colder at night with lows of 1°C. Finish your sightseeing early on the 15th (Tue) to allow enough time to travel to Empire.

Things to do in Keystone

Parks Nature Wildlife

Side Trip

Custer
Highlights from your plan
Mount Rushmore National Memorial ©
Mount Rushmore National Memorial
Black Hills National Forest ©
Black Hills National Forest
Sylvan Lake ©
Sylvan Lake

3
nights
Empire

Empire ©
Empire is a village in Leelanau County in the U.S. Do some cultural sightseeing at Sleeping Bear Dunes National Lakeshore and Point Betsie Lighthouse. Fayette Historic State Park and Seul Choix Point Lighthouse will appeal to history buffs. Venture out of the city with trips to Fishtown (in Leland) and Historical Village Fayette Park (in Garden). The adventure continues: tour the pleasant surroundings at Empire Bluff Trail and take a memorable drive along Pierce Stocking Scenic Drive.

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

Fly from Keystone to Empire in 6.5 hours. Alternatively, you can do a combination of flight, ferry, and car; or drive. The time zone difference moving from Mountain Standard Time (MST) to Eastern Standard Time (EST) is 2 hours. Traveling from Keystone in October, plan for somewhat warmer nights in Empire, with lows around 7°C. Finish your sightseeing early on the 19th (Sat) to allow enough time to travel to Chicago.

Things to do in Empire

Historic Sites Parks Outdoors

Side Trips

Garden, Point Betsie Lighthouse, Seul Choix Point Lighthouse, Fishtown
Highlights from your plan
Fayette Historic State Park ©
Fayette Historic State Park
Historical Village Fayette Park ©
Historical Village Fayette Park

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get some historical perspective at Ernest Hemingway Birthplace and Fourth Presbyterian Church. Satisfy your inner culture vulture at The Art Institute of Chicago and Frank Lloyd Wright's Robie House. Explore Chicago's surroundings by going to Baha'i House of Worship (in Wilmette), Basilica of St. Josaphat (in Milwaukee) and Cantigny Park (in Wheaton). There's lots more to do: contemplate the long history of Frank Lloyd Wright Home and Studio, admire the landmark architecture of Marquette Building, appreciate the extensive heritage of Chicago Riverwalk, and appreciate the history behind Cloud Gate.

To find reviews, traveler tips, more things to do, and more tourist information, refer to the Chicago trip planner .

Fly from Empire to Chicago in 3.5 hours. Alternatively, you can do a combination of taxi and flight; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Empire to Chicago. Traveling from Empire in October, things will get a bit warmer in Chicago: highs are around 21°C and lows about 11°C. Finish up your sightseeing early on the 24th (Thu) so you can catch the train to South Bend.

Things to do in Chicago

Historic Sites Museums Childrens Museums

Side Trips

Oak Park, Cantigny Park, Baha'i House of Worship, Basilica of St. Josaphat
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Ernest Hemingway Birthplace ©
Ernest Hemingway Birthplace
Field Museum ©
Field Museum

1
night
South Bend

South Bend ©
South Bend is a city in and the county seat of St. Kick off your visit on the 25th (Fri): make a trip to Grotto of Our Lady Lourdes, then take in the architecture and atmosphere at Basilica of the Sacred Heart, then admire the striking features of Havilah Beardsley House, and finally identify plant and animal life at Elkhart Environmental Center.

To find where to stay, photos, more things to do, and more tourist information, refer to the South Bend driving holiday tool .

Traveling by train from Chicago to South Bend takes 1.5 hours. Alternatively, you can drive; or take a bus. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. In October, daytime highs in South Bend are 20°C, while nighttime lows are 8°C. Wrap up your sightseeing on the 25th (Fri) to allow time to travel to Branson.

Things to do in South Bend

Wildlife Parks Historic Sites

Side Trip

Elkhart
Highlights from your plan
Basilica of the Sacred Heart ©
Basilica of the Sacred Heart
Grotto of Our Lady Lourdes ©
Grotto of Our Lady Lourdes
Elkhart Environmental Center ©
Elkhart Environmental Center

3
nights
Branson

Branson ©
Nestled in Missouri's beautiful Ozark Mountains lies one of the country's most attractive vacation towns for year-round family entertainment.
Our Lady of the Lake Catholic Church and Gay Perdita Sinclair Station Route 66 Memorabalia are good opportunities to explore the local culture. Popular historic sites such as Bonniebrook Park and Laura Ingalls Wilder Historic Home and Museum are in your itinerary. Get out of town with these interesting Branson side-trips: James River Church (in Springfield), Wilson's Creek National Battlefield (in Republic) and Mansfield Cemetery (in Mansfield). There's more to do: contemplate in the serene atmosphere at Wilderness Chapel.

To see ratings, photos, traveler tips, and other tourist information, go to the Branson tour itinerary planning site .

Traveling by flight from South Bend to Branson takes 5 hours. Alternatively, you can do a combination of train and flight; or drive. The time zone difference when traveling from South Bend to Branson is minus 1 hour. When traveling from South Bend in October, plan for a bit warmer days in Branson, with highs around 25°C, while nights are about the same with lows around 11°C. Cap off your sightseeing on the 28th (Mon) early enough to go by car to Independence.

Things to do in Branson

Historic Sites Wildlife Parks

Side Trips

Mansfield, James River Church, Gay Perdita Sinclair Station Route 66 Memorabalia, Wilson's Creek National Battlefield
Highlights from your plan

4
nights
Independence

Independence ©
Independence is the fifth-largest city in the state of Missouri. Visit Bingham Waggoner Estate and Jesse James Birthplace Museum for their historical value. Get a sense of the local culture at Squirrel Cage Jail and Court House. Change things up with these side-trips from Independence: Watkins Mill State Park (in Lawson), Bothwell Lodge State Historic Site (in Sedalia) and Battle of Lexington State Historic Site (in Lexington). The adventure continues: steep yourself in history at Fort Osage National Historic Landmark, get engrossed in the history at Jesse James Bank Museum, and take in the architecture and atmosphere at The Stone Church.

To find other places to visit, ratings, where to stay, and tourist information, go to the Independence trip builder tool .

You can drive from Branson to Independence in 4 hours. Another option is to take a bus. In October, daytime highs in Independence are 25°C, while nighttime lows are 12°C. Finish your sightseeing early on the 1st (Fri) to allow enough time to drive to Saint Louis.

Things to do in Independence

Historic Sites Parks Nature

Side Trips

Lexington, Fort Osage National Historic Landmark, Bothwell Lodge State Historic Site, Watkins Mill State Park, Jesse James Bank Museum
Highlights from your plan
Bingham Waggoner Estate ©
Bingham Waggoner Estate
Squirrel Cage Jail ©
Squirrel Cage Jail
Jesse James Birthplace Museum ©
Jesse James Birthplace Museum

5
nights
Saint Louis

Saint Louis ©
Test the local claim that Saint Louis is second only to Washington, D.C.
Get some cultural insight at Cathedral Basilica of Saint Louis and Dana-Thomas House. Get outdoors at Bollinger Mill State Historic Site and Lincoln Memorial Garden. Explore Saint Louis' surroundings by going to Eversgerd’s Civil War Fort (in Germantown), Sugar Creek Covered Bridge (in Glenarm) and Lincoln Home National Historic Site (in Springfield). Next up on the itinerary: admire the natural beauty at Missouri Botanical Garden, stroll the grounds of Eagle Cliff - Miles Cemetery, contemplate in the serene atmosphere at St. Francis Xavier Church, and get to know the fascinating history of St. Charles Historic District.

To find where to stay, maps, other places to visit, and more tourist information, read our Saint Louis online route planner .

Traveling by car from Independence to Saint Louis takes 4 hours. Alternatively, you can take a train; or take a bus. In November, daytime highs in Saint Louis are 15°C, while nighttime lows are 1°C. Finish up your sightseeing early on the 6th (Wed) so you can travel to Columbus.

Things to do in Saint Louis

Historic Sites Parks Nature

Side Trips

Springfield, Marquand Historic Park, Eagle Cliff - Miles Cemetery, Bollinger Mill State Historic Site, Sugar Creek Covered Bridge
Highlights from your plan
Cathedral Basilica of Saint Louis ©
Cathedral Basilica of Saint Louis
Dana-Thomas House ©
Dana-Thomas House
Lincoln Home National Historic Site ©

5
nights
Columbus

More than just one of the nation's top business centers, Columbus is a mixture of many different parts of America, situated at the spot where the so-called "Bible Belt" meets the varied cultures of the Great Plains and Appalachia.
Escape the urban bustle at Zipline and Conkles Hollow State Nature Preserve. Carillon Historical Park and Greek Orthodox Cathedral are good opportunities to explore the local culture. Get out of town with these interesting Columbus side-trips: Greene County Historical Society Museum (in Xenia), Dayton (National Museum of the US Air Force & Dayton National Cemetery) and Great Circle Earthworks (in Heath). There's still lots to do: take in the architecture and atmosphere at Basilica and National Shrine of Our Lady of Consolation, see the interesting displays at Warther Museum, contemplate the long history of J. E. Reeves Victorian Home & Carriage House Museum, and Head underground at Old Man's Cave.

To find reviews, traveler tips, photos, and more tourist information, read our Columbus online trip planner .

Getting from Saint Louis to Columbus by flight takes about 3.5 hours. Other options: drive; or take a bus. You'll lose 1 hour traveling from Saint Louis to Columbus due to the time zone difference. November in Columbus sees daily highs of 13°C and lows of 1°C at night. Finish your sightseeing early on the 11th (Mon) so you can travel back home.

Things to do in Columbus

Historic Sites Museums Parks

Side Trips

Dayton, Dover, Rockbridge, Greene County Historical Society Museum, Great Circle Earthworks
Highlights from your plan
Zipline
National Museum of the US Air Force ©
Warther Museum ©
Warther Museum

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