29 days in Midwest Itinerary

29 days in Midwest Itinerary

Created using Inspirock Midwest trip itinerary maker

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Route & dates

29 days in Midwest Itinerary

Start: Boston
Fly:  4​h
1
Columbus
— 2 nights
Drive:  2​h 30​min
2
Sandusky
— 1 night
Drive:  5​h
3
Chicago
— 5 nights
Drive:  3​h 30​min
4
Wisconsin Dells
— 4 nights
Drive:  4​h 30​min
5
Ontonagon
— 2 nights
+2
Drive + Fly + Drive:  8​h 45​min
6
Custer
— 3 nights
Taxi + Fly:  7​h 15​min
7
Kansas City
— 2 nights
Drive:  3​h 45​min
8
Branson
— 4 nights
Drive + Fly:  3​h 45​min
9
Saint Louis
— 4 nights
Fly:  4​h 45​min
End: Boston

2
nights
Columbus

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.
Get out of town with these interesting Columbus side-trips: Rockbridge (Zipline & Conkles Hollow State Nature Preserve), Columbus Zoo and Aquarium (in Powell) and National Museum of the US Air Force (in Dayton). There's much more to do: test your team's savvy at popular escape rooms, Head underground at Ash Cave, and examine the collection at Wagner-Hagans Auto Museum.

For other places to visit, traveler tips, more things to do, and other tourist information, read our Columbus road trip planner.

Boston to Columbus is an approximately 4-hour flight. You can also drive; or take a bus. In August, plan for daily highs up to 84°F, and evening lows to 64°F. Finish up your sightseeing early on the 3rd (Mon) so you can go by car to Sandusky.

Things to do in Columbus

Parks Tours Museums

Side Trips

Rockbridge, Columbus Zoo and Aquarium, Ash Cave, National Museum of the US Air Force
Find places to stay Aug 1 — 3:
Highlights from your plan
Columbus Zoo and Aquarium ©
Columbus Zoo and Aquarium
Zipline
National Museum of the US Air Force ©

1
night
Sandusky

Sandusky ©
Sandusky positively bustles in the summertime due to its famed amusement park.
Kick off your visit on the 4th (Tue): admire nature's wide array of creatures at African Safari Wildlife Park, then find something for the whole family at Ghostly Manor Thrill Center, and then make a splash at Cedar Point.

To find ratings, more things to do, reviews, and more tourist information, read Sandusky trip planner .

Getting from Columbus to Sandusky by car takes about 2.5 hours. Other options: do a combination of bus and train; or take a bus. In August, daily temperatures in Sandusky can reach 83°F, while at night they dip to 66°F. Finish your sightseeing early on the 4th (Tue) to allow enough time to drive to Chicago.

Things to do in Sandusky

Theme Parks Parks Zoos & Aquariums

Side Trip

African Safari Wildlife Park
Find places to stay Aug 3 — 4:
Highlights from your plan
Cedar Point ©
Cedar Point
Ghostly Manor Thrill Center ©
Ghostly Manor Thrill Center
African Safari Wildlife Park ©
African Safari Wildlife Park

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kids will enjoy Museum of Science and Industry and Lincoln Park Zoo. When in Chicago, make a side trip to see Silver Beach Carousel in Saint Joseph, approximately 1h 40 min away. There's much more to do: admire the masterpieces at The Art Institute of Chicago, take in panoramic vistas at 360 Chicago Observation Deck, test your problem-solving skills at Fox in a Box Chicago, and stroll around Millennium Park.

For traveler tips, reviews, more things to do, and other tourist information, use the Chicago road trip planning site .

Drive from Sandusky to Chicago in 5 hours. Alternatively, you can fly; or take a train. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. In August in Chicago, expect temperatures between 83°F during the day and 67°F at night. Cap off your sightseeing on the 9th (Sun) early enough to go by car to Wisconsin Dells.

Things to do in Chicago

Museums Childrens Museums Parks

Side Trips

Ernest Hemingway Birthplace, Silver Beach Carousel
Find places to stay Aug 4 — 9:
Highlights from your plan
Museum of Science and Industry ©
Museum of Science and Industry
Shedd Aquarium ©
Shedd Aquarium
Lincoln Park Zoo ©
Lincoln Park Zoo

4
nights
Wisconsin Dells

Wisconsin Dells ©
Named after a nearby scenic gorge famous for its steep sandstone formations, Wisconsin Dells features more than 20 water parks, making it one of the most popular vacation areas in this region.
Attractions like Zipline and Shalom Wildlife Zoo make great kid-friendly stops. Venture out of the city with trips to Minnesota Marine Art Museum (in Winona) and Taliesin Preservation: Frank Lloyd Wright Visitor Center (in Spring Green). There's lots more to do: examine the collection at Mr Marvel's Wondertorium, walk around Wisconsin Deer Park, test your problem-solving skills at Elusive Escape Rooms, and get your game on at Dells Zombie Outbreak.

For other places to visit, traveler tips, where to stay, and more tourist information, refer to the Wisconsin Dells journey builder website .

You can drive from Chicago to Wisconsin Dells in 3.5 hours. Alternatively, you can take a train; or do a combination of flight and train. Traveling from Chicago in August, expect slightly colder with lows of 59°F in Wisconsin Dells. Finish your sightseeing early on the 13th (Thu) to allow enough time to travel to Ontonagon.

Things to do in Wisconsin Dells

Theme Parks Parks Zoos & Aquariums

Side Trips

Taliesin Preservation: Frank Lloyd Wright Visitor Center , Minnesota Marine Art Museum, Shalom Wildlife Zoo
Find places to stay Aug 9 — 13:
Highlights from your plan
Noah's Ark Water Park ©
Noah's Ark Water Park
Zipline
Shalom Wildlife Zoo ©
Shalom Wildlife Zoo

2
nights
Ontonagon

Ontonagon ©
Ontonagon is a village in the U.S. Kick off your visit on the 14th (Fri): trek along Little Carp River Trail, then stroll through Porcupine Mountains State Park, and then go deep underground at Adventure Mining Company. Keep things going the next day: explore the wealth of natural beauty at Bond Falls.

For more things to do, reviews, and other tourist information, you can read our Ontonagon visit site .

You can drive from Wisconsin Dells to Ontonagon in 4.5 hours. Another option is to do a combination of car and flight. Due to the time zone difference, you'll lose 1 hour traveling from Wisconsin Dells to Ontonagon. While traveling from Wisconsin Dells, expect slightly colder days and about the same nights in Ontonagon, ranging from highs of 73°F to lows of 55°F. Finish your sightseeing early on the 15th (Sat) to allow enough time to travel to Custer.

Things to do in Ontonagon

Parks Nature Trails

Side Trip

Adventure Mining Company
Find places to stay Aug 13 — 15:
Highlights from your plan
Adventure Mining Company ©
Adventure Mining Company
Bond Falls ©
Bond Falls
Porcupine Mountains State Park ©
Porcupine Mountains State Park

3
nights
Custer

Custer ©
Generally considered to be the oldest town established by European Americans in the Black Hills, Custer began as a mining town.
You'll visit kid-friendly attractions like Rushmore Tramway Adventures and Mammoth Site of Hot Springs. There's much more to do: explore the striking landscape of Mount Rushmore National Memorial, explore and take pictures at Needles Highway, take a memorable drive along Iron Mountain Road, and take your sightseeing to a higher altitude at Black Elk Peak.

To see photos, traveler tips, more things to do, and other tourist information, use the Custer itinerary tool .

Use the Route module to find suitable travel options from Ontonagon to Custer. The time zone difference moving from Eastern Standard Time to Mountain Standard Time is minus 2 hours. Expect a daytime high around 77°F in August, and nighttime lows around 51°F. Finish up your sightseeing early on the 18th (Tue) so you can travel to Kansas City.

Things to do in Custer

Parks Nature Theme Parks

Side Trips

Keystone, South Dakota, Mammoth Site of Hot Springs
Find places to stay Aug 15 — 18:
Highlights from your plan
Mount Rushmore National Memorial ©
Mount Rushmore National Memorial
Rushmore Tramway Adventures ©
Rushmore Tramway Adventures
Mammoth Site of Hot Springs ©
Mammoth Site of Hot Springs

2
nights
Kansas City

Kansas City ©
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.
Kids will appreciate attractions like Deanna Rose Children's Farmstead and Kaleidoscope. Explore Kansas City's surroundings by going to Evel Knievel Museum (in Topeka) and Holladay Distillery (in Weston). The adventure continues: test your problem-solving skills at popular escape rooms, brush up on your military savvy at National WWI Museum and Memorial, contemplate the long history of Bingham Waggoner Estate, and admire the masterpieces at The Nelson-Atkins Museum of Art.

To find maps, traveler tips, ratings, and other tourist information, go to the Kansas City day trip tool .

Traveling by combination of taxi and flight from Custer to Kansas City takes 7.5 hours. Alternatively, you can do a combination of car and flight; or drive. The time zone difference moving from Mountain Standard Time to Central Standard Time is 1 hour. Traveling from Custer in August, things will get a bit warmer in Kansas City: highs are around 87°F and lows about 70°F. Wrap up your sightseeing on the 21st (Fri) to allow time to drive to Branson.

Things to do in Kansas City

Museums Parks Zoos & Aquariums

Side Trips

Independence, Deanna Rose Children's Farmstead, Evel Knievel Museum, Holladay Distillery
Find places to stay Aug 18 — 21:
Highlights from your plan
National WWI Museum and Memorial ©
National WWI Museum and Memorial
Deanna Rose Children's Farmstead ©
Deanna Rose Children's Farmstead
Kaleidoscope ©
Kaleidoscope

4
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.
Attractions like Silver Dollar City and 7D Dark Ride Adventure make great kid-friendly stops. There's still lots to do: have some family-friendly fun at Escape Code, take in the architecture and atmosphere at Our Lady of the Lake Catholic Church, take in nature's colorful creations at College of the Ozarks, and bet on your favorite at The Track Family Fun Parks.

To find more things to do, other places to visit, maps, and other tourist information, use the Branson trip app .

You can drive from Kansas City to Branson in 4 hours. Other options are to take a bus; or fly. Expect a daytime high around 85°F in August, and nighttime lows around 66°F. Wrap up your sightseeing on the 25th (Tue) early enough to travel to Saint Louis.

Things to do in Branson

Theme Parks Parks Fun & Games

Side Trip

Table Rock Lake
Find places to stay Aug 21 — 25:
Highlights from your plan
Escape Code ©
Escape Code
Silver Dollar City ©
Silver Dollar City
The Branson Coaster at The Sawmill ©
The Branson Coaster at The Sawmill

4
nights
Saint Louis

Saint Louis ©
Test the local claim that Saint Louis is second only to Washington, D.C.
Bring the kids along to Saint Louis Zoo and Onondaga Cave. Go for a jaunt from Saint Louis to Belleview to see Elephant Rocks State Park about 1h 35 min away. There's lots more to do: don't miss a visit to The Gateway Arch, have some family-friendly fun at Top Notch Axe Throwing St. Louis, identify plant and animal life at Sachs Butterfly House, and tour the pleasant surroundings at Missouri Botanical Garden.

To see traveler tips, more things to do, photos, and other tourist information, go to the Saint Louis trip maker tool .

You can do a combination of car and flight from Branson to Saint Louis in 4 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 87°F in August, and nighttime lows around 66°F. Cap off your sightseeing on the 29th (Sat) early enough to travel back home.

Things to do in Saint Louis

Parks Zoos & Aquariums Nature

Side Trips

Sachs Butterfly House, Elephant Rocks State Park, Onondaga Cave
Find places to stay Aug 25 — 29:
Highlights from your plan
Saint Louis Zoo ©
Saint Louis Zoo
Elephant Rocks State Park ©
Elephant Rocks State Park
City Museum ©
City Museum

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