Owensboro, Kentucky

Private charter · MDW → OWB

Chicago to Owensboro

281 miles, about 1 hr 40 min in a Cirrus SR20. One price for the whole airplane.

Photo: Smallbones · Public domain

Price your flight from Chicago to Owensboro

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Owensboro, door to door faster.

Trade about 6 hours on the road for about 1 hr 40 min in the air. Littlebird flies you direct from Chicago Midway International Airport in Chicago to Owensboro Daviess County Airport in Owensboro, 281 miles in a Cirrus SR20. You get the whole airplane for one price, with every fee and tax shown before you book.

Distance
281 mi
Flight
1 hr 40 min
Driving
6 hours
Passengers
Up to 5
MDWChicagoOWBOwensboro
MDW → OWB281 miles direct

Flight time by aircraft

  • Cirrus SR20 · up to 3 passengers1 hr 40 min
  • Cirrus Vision Jet · up to 5 passengers50 min

Planned times in the air. Your quote shows exact departure and arrival times.

Departing Chicago

Airports in Chicago

  • 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

Arriving Owensboro

Airports in Owensboro

  • OWB

    Commercial airport

    Owensboro Daviess County Airport

    Owensboro · KOWB

    From downtown
    3 mi
    Longest runway
    8,000 ft

  • EVV

    Commercial airport

    Evansville Regional Airport

    Evansville · KEVV

    From downtown
    30 mi
    Longest runway
    8,021 ft

  • KJQD

    Regional airport

    Ohio County Airport

    Hartford

    From downtown
    25 mi
    Longest runway
    5,003 ft

  • KTEL

    Regional airport

    Perry County Municipal Airport

    Tell City

    From downtown
    29 mi
    Longest runway
    4,400 ft

  • KKY8

    Regional airport

    Hancock County-Ron Lewis Field

    Lewisport

    From downtown
    20 mi
    Longest runway
    5,002 ft

When you land

Things to do in Owensboro

Owensboro is Kentucky’s fourth-largest city, a river town on the Ohio that grew on tobacco, distilling and manufacturing. Today its economy includes healthcare led by Owensboro Health, food production, manufacturing, energy, financial services and a revived distilling scene. Two small colleges, Kentucky Wesleyan and Brescia, add to the community, and a riverfront redevelopment brought a convention center, a park and hotels to the downtown waterfront. The city is also known as the barbecue capital of Kentucky for its distinctive smoked mutton and burgoo.

  1. 01

    Bluegrass Music Hall of Fame & Museum

    This downtown museum celebrates bluegrass music’s history and artists, with interactive exhibits, a theater for live performances and the home of the ROMP festival.

  2. 02

    Smothers Park

    Owensboro’s riverfront park includes a large playground, fountains and walking paths, with views of the Ohio River and the Blue Bridge.

  3. 03

    Moonlite Bar-B-Q Inn

    A local landmark since the 1960s, Moonlite serves Owensboro’s signature barbecued mutton, burgoo and Southern sides on a large buffet.

  4. 04

    Western Kentucky Botanical Garden

    The garden’s grounds include roses, daylilies, a Japanese garden, butterfly gardens and seasonal displays, with plant sales, concerts and other events throughout the warmer months.

  5. 05

    Owensboro Museum of Fine Art

    The museum’s collections include American, European and Kentucky art, with a historic mansion and a notable collection of stained glass.

  6. 06

    Green River Distilling Co.

    This revived distillery on the site of a historic Owensboro plant offers tours of its bourbon production and aging warehouses.

Explore Owensboro charter

Questions

Chicago to Owensboro flights

How long is a private flight from Chicago to Owensboro?

About 1 hr 40 min in a Cirrus SR20, for 281 miles direct. Driving the same trip takes about 6 hours.

Which airports do flights from Chicago to Owensboro use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Owensboro Daviess County Airport (OWB), Evansville Regional Airport (EVV), or Ohio County Airport (KJQD). Pick whichever is closest to where you're starting and where you're headed.

How much does a private charter from Chicago to Owensboro 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 Owensboro?

Yes. Choose round trip when you search, and pick your return date and time. Flights from Owensboro back to Chicago are priced the same way.

Return flight

Owensboro to Chicago

More flights from Chicago

More flights to Owensboro

Explore Chicago private charter and Owensboro private charter, airports and things to do. Arriving at Owensboro Daviess County Airport (OWB).

Chicago to Owensboro, on your schedule

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