Private charter · Chicago, IL
Private charter to & from Chicago
Fly private to Chicago for lakefront architecture, world-class museums, serious dining and the business capital of the Midwest
- MDW
- ORD
- PWK
- GYY
- KIGQ
- K05C
Price a private flight from Chicago
Fly private in Chicago
Chicago, without the hub.
- 6
- Airports
- 5
- Passengers
- 49
- Direct routes
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.
O’Hare and Midway are two of the busiest airports in the country, and getting to either one can mean an hour or more on the Kennedy or the Stevenson. Flying private lets you use a quieter field such as Chicago Executive in Wheeling, close to the North Shore suburbs, and fly direct to the places Chicagoans actually go for the weekend: Lake Geneva, Door County, Galena or the beach towns of southwest Michigan. Visitors come for the Art Institute, deep-dish and tavern-style pizza, blues and jazz clubs, Wrigley Field and a lakefront park system that runs for miles along Lake Michigan.
Airports
Charter to and from Chicago airports
Fly into whichever airport puts you closest to where you're going. Littlebird flies to and from these airports in and around Chicago, and the price is for the whole airplane, however many seats you fill.
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
Top attractions
Things to do in Chicago
When to go. Late May through early October is Chicago at its best, when beaches, rooftop bars and lakefront trails come alive. June brings the Chicago Blues Festival, Lollapalooza takes over Grant Park in summer, the Air and Water Show fills the lakefront in August and the Chicago Marathon runs in October. Winters are cold and windy, though the holiday season, with the Christkindlmarket and decorated State Street windows, has its own appeal.
- 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.
Popular routes
Private flights from Chicago

Chicago Milwaukee
82 mi · about 30 min

Chicago Indianapolis
165 mi · about 55 min

Chicago St. Louis
263 mi · about 1 hr 30 min

Chicago Louisville
269 mi · about 1 hr 35 min

Chicago Des Moines
310 mi · about 1 hr 50 min

Chicago Madison
122 mi · about 40 min

Chicago Fort Wayne
140 mi · about 50 min

Chicago Springfield
178 mi · about 1 hr

Chicago Cedar Rapids
208 mi · about 1 hr 10 min
Chicago Lexington
313 mi · about 1 hr 50 min

Chicago Kansas City
413 mi · about 2 hr 25 min
Chicago Champaign
126 mi · about 45 min
Flights to Chicago
- Des Moines310 mi · about 1 hr 50 min
- Cedar Rapids208 mi · about 1 hr 10 min
- Iowa City200 mi · about 1 hr 10 min
- Okoboji395 mi · about 2 hr 15 min
- Sioux City450 mi · about 2 hr 35 min
- Ames308 mi · about 1 hr 45 min
- Springfield178 mi · about 1 hr
- Champaign126 mi · about 45 min
- Peoria131 mi · about 45 min
- Bloomington120 mi · about 40 min
- Galena148 mi · about 50 min
- Rockford78 mi · about 25 min
Every route from Chicago
- Milwaukee82 mi · about 30 min
- Indianapolis165 mi · about 55 min
- St. Louis263 mi · about 1 hr 30 min
- Louisville269 mi · about 1 hr 35 min
- Des Moines310 mi · about 1 hr 50 min
- Madison122 mi · about 40 min
- Fort Wayne140 mi · about 50 min
- Springfield178 mi · about 1 hr
- Cedar Rapids208 mi · about 1 hr 10 min
- Lexington313 mi · about 1 hr 50 min
- Kansas City413 mi · about 2 hr 25 min
- Champaign126 mi · about 45 min
- Iowa City200 mi · about 1 hr 10 min
- Door County219 mi · about 1 hr 15 min
- Bowling Green344 mi · about 2 hr
- Branson473 mi · about 2 hr 45 min
- Peoria131 mi · about 45 min
- Evansville270 mi · about 1 hr 35 min
- Bardstown304 mi · about 1 hr 45 min
- Lake of the Ozarks367 mi · about 2 hr 5 min
- Okoboji395 mi · about 2 hr 15 min
- Bloomington120 mi · about 40 min
- Green Bay183 mi · about 1 hr 5 min
- Bloomington196 mi · about 1 hr 10 min
- Frankfort293 mi · about 1 hr 40 min
- Springfield442 mi · about 2 hr 35 min
- Sioux City450 mi · about 2 hr 35 min
- West Lafayette106 mi · about 35 min
- Kohler128 mi · about 45 min
- Galena148 mi · about 50 min
- Ames308 mi · about 1 hr 45 min
- Columbia320 mi · about 1 hr 50 min
- Paducah337 mi · about 1 hr 55 min
- Rockford78 mi · about 25 min
- Columbus205 mi · about 1 hr 10 min
- Owensboro286 mi · about 1 hr 40 min
- Minocqua294 mi · about 1 hr 40 min
- Jefferson City332 mi · about 1 hr 55 min
- Moline150 mi · about 50 min
- Wisconsin Dells163 mi · about 55 min
- French Lick237 mi · about 1 hr 20 min
- Cape Girardeau332 mi · about 1 hr 55 min
- Somerset368 mi · about 2 hr 10 min
- Appleton169 mi · about 1 hr
- Carbondale300 mi · about 1 hr 45 min
- Joplin494 mi · about 2 hr 50 min
- La Crosse226 mi · about 1 hr 20 min
- Quincy237 mi · about 1 hr 25 min
- St. Joseph404 mi · about 2 hr 20 min
Questions
Flying private in Chicago
Which airports can I charter a private flight to or from in Chicago?
Littlebird flies in and out of Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), Chicago Executive Airport (PWK), Gary/Chicago International Airport (GYY), Lansing Municipal Airport (KIGQ), and Griffith-Merrillville Airport (K05C). Choose the one closest to where you're going; smaller regional airports usually mean a shorter walk from the car to the airplane.
How do I book a private charter from Chicago?
Enter your departure airport, destination, date and number of passengers above. You'll see an instant price for the whole airplane, with taxes and fees included, and you can book online in a few minutes.
How many passengers can fly on a charter from Chicago?
Up to 5 passengers, depending on the aircraft. You pay one price for the whole airplane, not per seat, so traveling together lowers the cost per person.
What are popular private flights from Chicago?
Popular trips include Milwaukee (about 30 min), Indianapolis (about 55 min), St. Louis (about 1 hr 30 min), and Louisville (about 1 hr 35 min). Every route is priced instantly online.
Is private charter in Chicago, IL safe?
Littlebird flights are operated under FAA Part 135 by Jetvia, in Cirrus aircraft that each carry a parachute for the entire airframe (CAPS).
More destinations in Illinois
Your next trip from Chicago starts here
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