9 days in Chicago, Denver & South Dakota Itinerary

9 days in Chicago, Denver & South Dakota Itinerary

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Route & dates

9 days in Chicago, Denver & South Dakota Itinerary

Start: Chicago
1
Chicago
— 1 night
Fly:  4​h 30​min
2
Denver
— 1 night
Fly + taxi:  3​h 45​min
3
Deadwood
— Few hours
Drive:  1​h 30​min
4
Custer
— 5 nights
Drive:  2​h
5
Badlands National Park
— 1 night
taxi + Fly:  5​h 15​min
End: Chicago

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 30th (Sat): don't miss a visit to Buckingham Fountain, admire the masterpieces at The Art Institute of Chicago, then appreciate the history behind Cloud Gate, then appreciate the extensive heritage of Millennium Park, and finally take in panoramic vistas at Skydeck Chicago - Willis Tower.

To see reviews, ratings, and more tourist information, go to the Chicago vacation trip planner.

Use the Route module to see travel options from your home to Chicago. In September, daily temperatures in Chicago can reach 77°F, while at night they dip to 60°F. Cap off your sightseeing on the 1st (Sun) early enough to travel to Denver.

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

1
night
Denver

Denver ©
Aptly nicknamed the "Mile-High City," Denver sits at an altitude of 1,600 m (5,280 ft) above sea level, located right where the Great Plains give way to the Rocky Mountains.
Kick off your visit on the 1st (Sun): stroll the grounds of The Buffalo Bill Museum and Grave and then contemplate the long history of Union Station, Denver, CO.

For ratings, reviews, traveler tips, and tourist information, use the Denver tour planner.

You can fly from Chicago to Denver in 4.5 hours. Alternatively, you can drive; or take a train. Traveling from Chicago to Denver, you'll gain 1 hour due to the time zone difference. Traveling from Chicago in October, Denver is little chillier at night with lows of 40°F. Finish up your sightseeing early on the 2nd (Mon) so you can travel to Deadwood.

Things to do in Denver

Historic Sites Museums

Side Trip

Buffalo Bill Grave and Museum
Highlights from your plan
Denver Union Station ©
Denver Union Station
Buffalo Bill Grave and Museum ©
Buffalo Bill Grave and Museum

few
hours
Deadwood

Deadwood ©
Deadwood is a city in South Dakota, United States, and the county seat of Lawrence County. To find more things to do, where to stay, and other tourist information, read our Deadwood trip generator.

Traveling by combination of flight and taxi from Denver to Deadwood takes 4 hours. Alternatively, you can drive; or do a combination of bus and taxi. Due to the time zone difference, you'll lose 1 hour traveling from Denver to Deadwood. When traveling from Denver in October, plan for a bit cooler days and about the same nights in Deadwood: temperatures range from 56°F by day to 37°F at night. Finish up your sightseeing early on the 2nd (Mon) so you can go by car to Custer.

Things to do in Deadwood

Historic Sites Museums
Highlights from your plan
Mount Moriah Cemetery ©
Mount Moriah Cemetery
Adams House ©
Adams House

5
nights
Custer

Custer ©
Generally considered to be the oldest town established by European Americans in the Black Hills, Custer began as a mining town.
Get in touch with nature at Jewel Cave National Monument and Presidential Trail. Discover out-of-the-way places like Needles Eye Tunnel and Wildlife Loop Road. You'll find plenty of places to visit near Custer: Mammoth Site of Hot Springs (in Hot Springs) and Windcross Conservancy (in Buffalo Gap). The adventure continues: explore the activities along Sylvan Lake, stroll through Mount Rushmore National Memorial, learn about winemaking at Prairie Berry Winery, and admire all the interesting features of Iron Mountain Road.

For reviews, ratings, more things to do, and more tourist information, go to the Custer itinerary maker.

Traveling by car from Deadwood to Custer takes 1.5 hours. The time zone changes from Central Standard Time to Mountain Standard Time, which is usually a -1 hour difference. Traveling from Deadwood in October, you can expect nighttime temperatures to be a bit cooler in Custer, with lows of 32°F. Wrap up your sightseeing on the 7th (Sat) to allow time to drive to Badlands National Park.

Things to do in Custer

Parks Nature Outdoors

Side Trips

Keystone, Windcross Conservancy, Mammoth Site of Hot Springs, Prairie Berry Winery
Highlights from your plan
Iron Mountain Road ©
Iron Mountain Road
Needles Eye Tunnel ©
Needles Eye Tunnel
Presidential Trail ©
Presidential Trail

1
night
Badlands National Park

Badlands National Park ©
Although Badlands National Park's name might not be the most inviting, its landscape of pinnacles, eroded buttes, spires, and an expansive, pristine mixed-grass prairie remain enticing.
On the 7th (Sat), explore the wealth of natural beauty at Minuteman Missile National Historic Site and then take a memorable drive along Loop Road. Keep things going the next day: look for all kinds of wild species at Roberts Prairie Dog Town and then explore the striking landscape at Badlands Wall.

For other places to visit, reviews, traveler tips, and tourist information, read Badlands National Park trip planner.

Getting from Custer to Badlands National Park by car takes about 2 hours. Other options: do a combination of taxi and bus. The time zone changes from Mountain Standard Time to Central Standard Time, which is usually a 1 hour difference. Finish up your sightseeing early on the 8th (Sun) so you can travel back home.

Things to do in Badlands National Park

Parks Nature Wildlife

Side Trip

Minuteman Missile National Historic Site
Highlights from your plan
Badlands Wall ©
Badlands Wall
Loop Road ©
Loop Road

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