Private charter · MDW → DIK
Chicago to Dickinson
819 miles. One price for the whole airplane.
Photo: Andrew Filer from Seattle (ex-Minneapolis) · CC BY-SA 2.0
Price your flight from Chicago to Dickinson
The trip
Chicago to Dickinson, door to door faster.
Trade about 17½ hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Dickinson Theodore Roosevelt Regional Airport in Dickinson, 819 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.
- Distance
- 819 mi
- Flight
- —
- Driving
- 17½ hours
- Passengers
- Up to 1
Departing Chicago
Airports in Chicago
MDW
Major airportChicago Midway International Airport
Chicago · KMDW
- From downtown
- 9 mi
- Longest runway
- 6,522 ft
ORD
Major airportChicago O'Hare International Airport
Chicago · KORD
- From downtown
- 16 mi
- Longest runway
- 13,000 ft
PWK
Commercial airportChicago Executive Airport
Chicago/Prospect Heights/Wheeling · KPWK
- From downtown
- 21 mi
- Longest runway
- 5,001 ft
GYY
Commercial airportGary/Chicago International Airport
Gary · KGYY
- From downtown
- 21 mi
- Longest runway
- 8,859 ft
Arriving Dickinson
Airports in Dickinson
DIK
Commercial airportDickinson Theodore Roosevelt Regional Airport
Dickinson · KDIK
- From downtown
- 6 mi
- Longest runway
- 7,301 ft
When you land
Things to do in Dickinson
Dickinson is the main city of southwestern North Dakota, a regional center for energy, agriculture and healthcare at the southern edge of the Bakken oil field. Oil and gas service companies, ranchers, grain and livestock operations and Dickinson State University shape the local economy, and the city serves a large rural region that stretches to the Montana and South Dakota lines. Its Ukrainian, German and Norwegian heritage shows up in local churches and festivals.
- 01
Theodore Roosevelt National Park
The South Unit near Medora protects colorful Badlands where bison, wild horses and prairie dogs roam, with a scenic drive and Roosevelt’s Maltese Cross Cabin.
- 02
Medora Musical
An outdoor summer show at the Burning Hills Amphitheatre in Medora celebrates Theodore Roosevelt and the Old West with music and comedy against a Badlands backdrop.
- 03
Dickinson Museum Center
The Badlands Dinosaur Museum displays fossils and full skeletons from the region, along with pioneer and ranching history exhibits on the same campus.
- 04
Painted Canyon Overlook
Along I-94 east of Medora, this overlook offers sweeping views across the Badlands, with picnic areas and a trail that drops into the canyon.
- 05
Maah Daah Hey Trail
This long-distance single-track trail winds through the Badlands and grasslands, popular with mountain bikers, hikers and horseback riders.
- 06
Enchanted Highway
Southeast of Dickinson, a road from I-94 to Regent is lined with giant scrap-metal sculptures, including a flock of geese and a towering family.
Questions
Chicago to Dickinson flights
How long is a private flight from Chicago to Dickinson?
About a short flight in a private jet, for 819 miles direct. Driving the same trip takes about 17½ hours.
Which airports do flights from Chicago to Dickinson use?
You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Dickinson Theodore Roosevelt Regional Airport (DIK). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from Chicago to Dickinson cost?
The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.
Can I book a round trip between Chicago and Dickinson?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Dickinson back to Chicago are priced the same way.
Return flight
Dickinson to Chicago
More flights from Chicago
More flights to Dickinson
Explore Chicago private charter and Dickinson private charter, airports and things to do. Arriving at Dickinson Theodore Roosevelt Regional Airport (DIK).
Chicago to Dickinson, on your schedule
Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.
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