11 days in Midwest Itinerary

11 days in Midwest Itinerary

Created using Inspirock Midwest trip planner

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Route & dates

11 days in Midwest Itinerary

Start: Philadelphia
Fly:  4​h
1
Chicago
— 1 night
Fly:  4​h 15​min
2
Branson
— 3 nights
Fly + taxi:  6​h 15​min
3
Custer
— 2 nights
taxi + Fly:  8​h 15​min
4
Mackinaw City
— 2 nights
+2
bus + taxi + Fly:  7​h 15​min
End: Philadelphia

1
night
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 17th (Wed): admire the masterpieces at The Art Institute of Chicago, steep yourself in history at Ernest Hemingway Birthplace, and then appreciate the extensive heritage of Millennium Park. Get ready for a full day of sightseeing on the next day: engage your brain at Museum of Science and Industry, examine the collection at The Field Museum, and then enjoy breathtaking views from Skydeck Chicago - Willis Tower.

For other places to visit, traveler tips, more things to do, and more tourist information, you can read our Chicago journey builder site .

Philadelphia to Chicago is an approximately 4-hour flight. You can also do a combination of train and flight; or drive. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. In July, Chicago is slightly colder than Philadelphia - with highs of 83°F and lows of 67°F. Finish your sightseeing early on the 18th (Thu) to allow enough time to travel to Branson.

Things to do in Chicago

Museums Childrens Museums Parks

Side Trip

Ernest Hemingway Birthplace
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry
Field Museum ©
Field Museum

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.
Laura Ingalls Wilder Historic Home and Museum and Stone Hill Winery are good opportunities to explore the local culture. Step out of the city life by going to Fishing Charters & Tours and National Tiger Sanctuary. When in Branson, make a side trip to see Dogwood Canyon Nature Park in Lampe, approximately 34 minutes away. There's still lots to do: explore the activities along Table Rock Lake, explore the fascinating underground world of Talking Rocks Cavern, and identify plant and animal life at Shepherd of the Hills Fish Hatchery.

To see photos, maps, traveler tips, and more tourist information, refer to the Branson journey maker site .

You can fly from Chicago to Branson in 4.5 hours. Other options are to do a combination of flight and car; or drive. Expect a daytime high around 87°F in July, and nighttime lows around 68°F. Finish up your sightseeing early on the 21st (Sun) so you can travel to Custer.

Things to do in Branson

Wildlife Parks Outdoors

Side Trips

Dogwood Canyon Nature Park, National Tiger Sanctuary, Table Rock Lake, Laura Ingalls Wilder Historic Home and Museum
Highlights from your plan
Dogwood Canyon Nature Park ©
Dogwood Canyon Nature Park
National Tiger Sanctuary ©
National Tiger Sanctuary

2
nights
Custer

Custer ©
Generally considered to be the oldest town established by European Americans in the Black Hills, Custer began as a mining town.
Escape the urban bustle at Wind Cave National Park and Sylvan Lake. Your cultural itinerary includes sights like Adams House and Mount Moriah Cemetery. Venture out of the city with trips to Keystone (Big Thunder Gold Mine & Presidential Trail). There's still lots to do: take a memorable drive along Wildlife Loop Road, explore the wealth of natural beauty at Mount Rushmore National Memorial, explore and take pictures at Needles Highway, and take in the dramatic natural features at Needles Eye Tunnel.

For where to stay, other places to visit, and more tourist information, use the Custer attractions planner .

Traveling by combination of flight and taxi from Branson to Custer takes 6.5 hours. Alternatively, you can do a combination of car, flight, and taxi; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Branson to Custer. Traveling from Branson in July, things will get little chillier in Custer: highs are around 80°F and lows about 53°F. Finish up your sightseeing early on the 24th (Wed) so you can travel to Mackinaw City.

Things to do in Custer

Parks Outdoors Nature

Side Trips

Keystone, Deadwood, Needles Highway, Wind Cave National Park
Highlights from your plan
Mount Rushmore National Memorial ©
Mount Rushmore National Memorial
Wind Cave National Park ©
Wind Cave National Park
Needles Eye Tunnel ©
Needles Eye Tunnel

2
nights
Mackinaw City

Mackinaw City ©
Mackinaw City is a village in Emmet and Cheboygan counties in the U.S. Step off the beaten path and head to Icebreaker Mackinaw Maritime Museum Inc. and Historic Mill Creek Discovery Park. Deepen your sense of the past at sights like McGulpin Point Lighthouse & Historic Site and Old Mackinac Point Lighthouse. Explore Mackinaw City's surroundings by going to Oswald's Bear Ranch (in Newberry) and Tahquamenon Falls State Park (in Paradise). The adventure continues: examine the collection at Museum of Ojibwa Culture and stroll around Colonial Michilimackinac.

For ratings, photos, reviews, and other tourist information, refer to the Mackinaw City trip builder .

You can do a combination of taxi and flight from Custer to Mackinaw City in 8.5 hours. Other options are to do a combination of taxi, flight, and bus; or drive. The time zone difference moving from Mountain Standard Time (MST) to Eastern Standard Time (EST) is 2 hours. Expect a bit cooler weather when traveling from Custer in July: highs in Mackinaw City hover around 73°F, while lows dip to 58°F. Wrap up your sightseeing on the 27th (Sat) to allow time to travel back home.

Things to do in Mackinaw City

Parks Historic Sites Museums

Side Trips

Oswald's Bear Ranch, Museum of Ojibwa Culture, Tahquamenon Falls State Park
Highlights from your plan
Oswald's Bear Ranch ©
Oswald's Bear Ranch
Tahquamenon Falls State Park ©
Tahquamenon Falls State Park
Old Mackinac Point Lighthouse ©
Old Mackinac Point Lighthouse

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