Private charter · MDW → MKE
Chicago to Milwaukee
81 miles, about 30 min in a Cirrus SR20. One price for the whole airplane.
Price your flight from Chicago to Milwaukee
The trip
Chicago to Milwaukee, door to door faster.
Trade about 2 hours on the road for about 30 min in the air. Littlebird flies you direct from Chicago Midway International Airport in Chicago to General Mitchell International Airport in Milwaukee, 81 miles in a Cirrus SR20. You get the whole airplane for one price, with every fee and tax shown before you book.
- Distance
- 81 mi
- Flight
- 30 min
- Driving
- 2 hours
- Passengers
- Up to 5
Flight time by aircraft
- Cirrus SR20 · up to 3 passengers30 min
- Cirrus Vision Jet · up to 5 passengers15 min
Planned times in the air. Your quote shows exact departure and arrival times.
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
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
Arriving Milwaukee
Airports in Milwaukee
MKE
Major airportGeneral Mitchell International Airport
Milwaukee · KMKE
- From downtown
- 8 mi
- Longest runway
- 9,990 ft
MWC
Regional airportLawrence J Timmerman Airport
Milwaukee · KMWC
- From downtown
- 6 mi
- Longest runway
- 4,107 ft
UES
Regional airportWaukesha County Airport
Waukesha · KUES
- From downtown
- 15 mi
- Longest runway
- 5,849 ft
RAC
Regional airportJohn H Batten Airport
Racine · KRAC
- From downtown
- 21 mi
- Longest runway
- 6,574 ft
ETB
Regional airportWest Bend Municipal Airport
West Bend · KETB
- From downtown
- 27 mi
- Longest runway
- 4,494 ft
K57C
Regional airportEast Troy Municipal Airport
East Troy
- From downtown
- 28 mi
- Longest runway
- 3,900 ft
When you land
Things to do in Milwaukee
Milwaukee built its fortune on manufacturing and beer, and both still shape the city. Harley-Davidson, Northwestern Mutual, Rockwell Automation and a long list of industrial, financial and healthcare companies are headquartered here, and the Molson Coors brewery in the Menomonee Valley carries on the Miller tradition. Downtown has been remade in recent decades with a lakefront art museum, a riverwalk lined with restaurants and Fiserv Forum, home of the Bucks, while the Historic Third Ward has become the city’s gallery, design and dining district.
- 01
Milwaukee Art Museum
Santiago Calatrava’s lakefront pavilion, with a sunscreen that opens and closes like wings, houses a large collection that is especially strong in American decorative arts, folk art and German Expressionism.
- 02
Harley-Davidson Museum
In the Menomonee Valley, this museum traces more than a century of the motorcycle maker’s history, with hundreds of bikes, engines and archives, plus a restaurant and shop on site.
- 03
Milwaukee Public Market
In the Historic Third Ward, this indoor market brings together local vendors selling seafood, cheese, spices, baked goods and prepared food, with seating upstairs.
- 04
Milwaukee RiverWalk
A walkway runs for miles along the Milwaukee River through downtown, the Third Ward and Beerline B, passing restaurants, brewpubs and public art, including the Bronze Fonz.
- 05
American Family Field
The Brewers play under a fan-shaped retractable roof, and the parking lots are famous for pregame tailgating with bratwurst and the Famous Racing Sausages.
- 06
Lake Park and the Lakefront
Frederick Law Olmsted designed Lake Park on the bluffs above Lake Michigan, and paths lead down to beaches, the Oak Leaf Trail and the historic North Point Lighthouse.
Questions
Chicago to Milwaukee flights
How long is a private flight from Chicago to Milwaukee?
About 30 min in a Cirrus SR20, for 81 miles direct. Driving the same trip takes about 2 hours.
Which airports do flights from Chicago to Milwaukee use?
You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at General Mitchell International Airport (MKE), Lawrence J Timmerman Airport (MWC), or Waukesha County Airport (UES). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from Chicago to Milwaukee 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 Milwaukee?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Milwaukee back to Chicago are priced the same way.
Return flight
Milwaukee to Chicago
More flights from Chicago
More flights to Milwaukee
Explore Chicago private charter and Milwaukee private charter, airports and things to do. Arriving at General Mitchell International Airport (MKE).
Chicago to Milwaukee, 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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