Chicago, Illinois

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

Photo: TheWxResearcher · CC BY-SA 4.0

Price a private flight from Chicago

Trip type
1

Times are local to each departure airport.

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 airport

    Chicago Midway International Airport

    Chicago · KMDW

    From downtown
    9 mi
    Longest runway
    6,522 ft
  • ORD

    Major airport

    Chicago O'Hare International Airport

    Chicago · KORD

    From downtown
    16 mi
    Longest runway
    13,000 ft
  • PWK

    Commercial airport

    Chicago Executive Airport

    Chicago/Prospect Heights/Wheeling · KPWK

    From downtown
    21 mi
    Longest runway
    5,001 ft
  • GYY

    Commercial airport

    Gary/Chicago International Airport

    Gary · KGYY

    From downtown
    21 mi
    Longest runway
    8,859 ft
  • KIGQ

    Regional airport

    Lansing Municipal Airport

    Chicago

    From downtown
    25 mi
    Longest runway
    4,002 ft
  • K05C

    Regional airport

    Griffith-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.

  1. 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.

  2. 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.

  3. 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.

  4. 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.

  5. 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.

  6. 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

Every route from Chicago

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