5 days in Midwest Itinerary

5 days in Midwest Itinerary

Created using Inspirock Midwest trip itinerary planner

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Route & dates

5 days in Midwest Itinerary

Start: Cleveland
Fly:  3​h 15​min
1
Chicago
— 1 day
Fly + taxi:  5​h 15​min
2
Custer
— 2 nights
taxi + Fly:  6​h 15​min
3
Branson
— 1 night
Fly:  5​h 30​min
End: Cleveland

1
day
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 8th (Mon): explore the world behind art at The Art Institute of Chicago, then get to know the fascinating history of Millennium Park, and then enjoy breathtaking views from Skydeck Chicago - Willis Tower.

For other places to visit, photos, and other tourist information, read Chicago driving holiday planner .

Cleveland to Chicago is an approximately 3.5-hour flight. You can also do a combination of flight, bus, and subway; or drive. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. In July, plan for daily highs up to 83°F, and evening lows to 67°F. Finish up your sightseeing early on the 8th (Mon) so you can travel to Custer.

Things to do in Chicago

Museums Parks
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower

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.
Start off your visit on the 9th (Tue): cruise along Wildlife Loop Road, explore the striking landscape at Needles Eye Tunnel, and then contemplate the waterfront views at Sylvan Lake. Here are some ideas for day two: explore and take pictures at Mount Rushmore National Memorial, hike along Presidential Trail, and then take a memorable drive along Iron Mountain Road.

Plan my Custer trip by asking Inpirock to come up with tips and suggestions.

You can do a combination of flight and taxi from Chicago to Custer in 5.5 hours. Alternatively, you can drive; or do a combination of train and bus. The time zone difference moving from Central Standard Time to Mountain Standard Time is minus 1 hour. Traveling from Chicago in July, plan for slightly colder nights in Custer, with lows around 53°F. Cap off your sightseeing on the 10th (Wed) early enough to travel to Branson.

Things to do in Custer

Outdoors Parks Nature

Side Trip

Keystone
Highlights from your plan
Needles Eye Tunnel ©
Needles Eye Tunnel
Presidential Trail ©
Presidential Trail
Iron Mountain Road ©
Iron Mountain Road

1
night
Branson

Branson ©
Nestled in Missouri's beautiful Ozark Mountains lies one of the country's most attractive vacation towns for year-round family entertainment.
Start off your visit on the 11th (Thu): look for all kinds of wild species at Shepherd of the Hills Fish Hatchery and then see what you can catch with a fishing tour. Keep things going the next day: contemplate the waterfront views at Table Rock Lake, stroll through Talking Rocks Cavern, and then kick your exploration up a notch at some of the top local zipline courses and adventure parks.

For where to stay, traveler tips, other places to visit, and other tourist information, use the Branson trip website .

Getting from Custer to Branson by combination of taxi and flight takes about 6.5 hours. Other options: do a combination of taxi, flight, and car; or drive. The time zone changes from Mountain Standard Time to Central Standard Time, which is usually a 1 hour difference. Expect a bit warmer temperatures when traveling from Custer in July; daily highs in Branson reach 87°F and lows reach 68°F. Finish up your sightseeing early on the 12th (Fri) so you can travel back home.

Things to do in Branson

Wildlife Outdoors Tours

Side Trip

Table Rock Lake
Highlights from your plan
Shepherd of the Hills Fish Hatchery ©
Fishing Charters & Tours
Zipline

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