Bluebird
Middleburg, Virginia

Private charter · MDW → KJYO

Chicago to Middleburg

567 miles. One price for the whole airplane.

Photo: La Citta Vita · CC BY-SA 2.0

Price your flight from Chicago to Middleburg

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Middleburg, door to door faster.

Trade about 12 hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Leesburg Executive Airport in Middleburg, 567 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.

Distance
567 mi
Flight
—
Driving
12 hours
Passengers
Up to 1
MDWChicagoKJYOMiddleburg
MDW → KJYO567 miles direct

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

Arriving Middleburg

Airports in Middleburg

  • KJYO

    Regional airport

    Leesburg Executive Airport

    Leesburg

    From downtown
    12 mi
    Longest runway
    5,500 ft

  • IAD

    Major airport

    Washington Dulles International Airport

    Dulles · KIAD

    From downtown
    15 mi
    Longest runway
    11,500 ft

  • MNZ

    Commercial airport

    Washington Manassas Harry P. Davis Field

    Manassas · KHEF

    From downtown
    21 mi
    Longest runway
    6,200 ft

  • WGO

    Regional airport

    Winchester Regional Airport

    Winchester · KOKV

    From downtown
    25 mi
    Longest runway
    5,498 ft

  • KHWY

    Regional airport

    Warrenton Fauquier Airport

    Midland

    From downtown
    26 mi
    Longest runway
    5,000 ft

When you land

Things to do in Middleburg

Middleburg is the heart of Virginia’s hunt country, a landscape of stone walls, horse farms and historic estates in western Loudoun and Fauquier counties. The town is known for fox hunting, steeplechase racing and equestrian sports, and its stone buildings house inns, boutiques, saddlery shops and restaurants. Many residents and weekenders are connected to Washington, about an hour away, and the area’s economy revolves around horses, agriculture, wineries, hospitality and real estate.

  1. 01

    National Sporting Library & Museum

    In the center of town, this library and museum is devoted to horse and field sports, with sporting art, rare books and rotating exhibitions.

  2. 02

    Salamander Middleburg

    Set on hundreds of acres of rolling countryside, this luxury resort offers an equestrian center, a spa, cooking classes and fine dining.

  3. 03

    Red Fox Inn

    One of the oldest inns in the country, the Red Fox has hosted travelers for centuries and offers a historic tavern dining room on Washington Street.

  4. 04

    Virginia Gold Cup

    Held each May at Great Meadow in The Plains, this steeplechase race is a major social event, with elaborate tailgates and spectators in hats and seersucker.

  5. 05

    Loudoun and Fauquier Wineries

    The surrounding countryside is filled with wineries and tasting rooms, many with views of the Blue Ridge and outdoor spaces ideal for long afternoons.

  6. 06

    Sky Meadows State Park

    In nearby Delaplane, this park offers hiking trails, sweeping pastoral views, a historic farm and access to the Appalachian Trail.

Explore Middleburg charter

Questions

Chicago to Middleburg flights

How long is a private flight from Chicago to Middleburg?

About a short flight in a private jet, for 567 miles direct. Driving the same trip takes about 12 hours.

Which airports do flights from Chicago to Middleburg use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Leesburg Executive Airport (KJYO), Washington Dulles International Airport (IAD), or Washington Manassas Harry P. Davis Field (MNZ). Pick whichever is closest to where you're starting and where you're headed.

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

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

Return flight

Middleburg to Chicago

More flights from Chicago

More flights to Middleburg

Explore Chicago private charter and Middleburg private charter, airports and things to do. Arriving at Leesburg Executive Airport (KJYO).

Chicago to Middleburg, on your schedule

Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.

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