Private charter · KDLL → MDW
Wisconsin Dells to Chicago
158 miles, about 55 min in a Cirrus SR20. One price for the whole airplane.
Price your flight from Wisconsin Dells to Chicago
The trip
Wisconsin Dells to Chicago, door to door faster.
Trade about 3½ hours on the road for about 55 min in the air. Littlebird flies you direct from Baraboo Wisconsin Dells Regional Airport in Wisconsin Dells to Chicago Midway International Airport in Chicago, 158 miles in a Cirrus SR20. You get the whole airplane for one price, with every fee and tax shown before you book.
- Distance
- 158 mi
- Flight
- 55 min
- Driving
- 3½ hours
- Passengers
- Up to 5
Flight time by aircraft
- Cirrus SR20 · up to 3 passengers55 min
- Cirrus Vision Jet · up to 5 passengers30 min
Planned times in the air. Your quote shows exact departure and arrival times.
Departing Wisconsin Dells
Airports in Wisconsin Dells
KDLL
Regional airportBaraboo Wisconsin Dells Regional Airport
Baraboo
- From downtown
- 8 mi
- Longest runway
- 5,010 ft
KC35
Regional airportReedsburg Municipal Airport
Reedsburg
- From downtown
- 13 mi
- Longest runway
- 4,840 ft
KC47
Regional airportPortage Municipal Airport
Portage
- From downtown
- 16 mi
- Longest runway
- 3,775 ft
K63C
Regional airportAdams County Legion Field
Adams
- From downtown
- 22 mi
- Longest runway
- 3,400 ft
K82C
Regional airportMauston New Lisbon Union Airport
New Lisbon
- From downtown
- 23 mi
- Longest runway
- 3,688 ft
Arriving 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
KIGQ
Regional airportLansing Municipal Airport
Chicago
- From downtown
- 25 mi
- Longest runway
- 4,002 ft
K05C
Regional airportGriffith-Merrillville Airport
Griffith
- From downtown
- 28 mi
- Longest runway
- 4,900 ft
When you land
Things to do in Chicago
Chicago is the commercial center of the Midwest, a city where commodity and futures trading, banking, law, consulting, logistics and corporate headquarters share a skyline that helped invent the skyscraper. CME Group’s exchanges, the offices along LaSalle Street, the medical and research campuses of Northwestern and the University of Chicago and a long roster of Fortune 500 companies keep executives moving in and out every day, while the Loop, River North and the Magnificent Mile pull in shoppers, conventioneers and theatergoers year-round.
- 01
Art Institute of Chicago
One of the great encyclopedic museums in the world, with celebrated Impressionist paintings, Grant Wood’s American Gothic, Hopper’s Nighthawks and the light-filled Modern Wing facing Millennium Park.
- 02
Millennium Park
Anish Kapoor’s mirrored Cloud Gate, the Crown Fountain and Frank Gehry’s Jay Pritzker Pavilion, which hosts free summer concerts, make this downtown park the city’s favorite gathering place.
- 03
Chicago Architecture Center River Cruise
Docent-led boat tours glide along the Chicago River past more than a century of landmark towers, explaining how the city rebuilt itself after the Great Fire of 1871.
- 04
Wrigley Field
Home of the Cubs since 1916, the ivy-covered ballpark in Lakeview is surrounded by rooftop seating and neighborhood bars, and stadium tours run on many non-game days.
- 05
Field Museum
On the lakefront Museum Campus, this natural history museum is home to SUE, one of the largest and most complete Tyrannosaurus rex skeletons ever found, along with ancient Egypt and gem halls.
- 06
Lincoln Park Zoo
One of the oldest zoos in North America and free to visit, set among lagoons, gardens and the historic Lincoln Park Conservatory just north of downtown.
Questions
Wisconsin Dells to Chicago flights
How long is a private flight from Wisconsin Dells to Chicago?
About 55 min in a Cirrus SR20, for 158 miles direct. Driving the same trip takes about 3½ hours.
Which airports do flights from Wisconsin Dells to Chicago use?
You can depart from Baraboo Wisconsin Dells Regional Airport (KDLL), Reedsburg Municipal Airport (KC35), or Portage Municipal Airport (KC47) and arrive at Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from Wisconsin Dells to Chicago 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 Wisconsin Dells and Chicago?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Chicago back to Wisconsin Dells are priced the same way.
Return flight
Chicago to Wisconsin Dells
More flights from Wisconsin Dells
More flights to Chicago
Explore Wisconsin Dells private charter and Chicago private charter, airports and things to do. Arriving at Chicago Midway International Airport (MDW).
Wisconsin Dells to Chicago, on your schedule
Choose your departure time and see an instant price for the whole airplane. Bring up to 5 passengers for the same price.
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