Bluebird
Litchfield, Connecticut

Private charter · MDW → OXC

Chicago to Litchfield

754 miles. One price for the whole airplane.

Photo: Joe Mabel (on Flickr as Joe Mabel from Seattle, US) · CC BY-SA 3.0

Price your flight from Chicago to Litchfield

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Litchfield, door to door faster.

Trade about 16 hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Waterbury Oxford Airport in Litchfield, 754 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
754 mi
Flight
—
Driving
16 hours
Passengers
Up to 1
MDWChicagoOXCLitchfield
MDW → OXC754 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 Litchfield

Airports in Litchfield

  • OXC

    Regional airport

    Waterbury Oxford Airport

    Oxford · KOXC

    From downtown
    19 mi
    Longest runway
    5,800 ft

  • BDL

    Major airport

    Bradley International Airport

    Hartford · KBDL

    From downtown
    29 mi
    Longest runway
    9,510 ft

When you land

Things to do in Litchfield

Litchfield is the classic town of Connecticut’s northwest hills, with a broad village green, white Congregational church and elm-lined streets of 18th-century houses. In the years after the Revolution it was home to the Litchfield Law School, the first law school in the country, and today the town and its neighbors, including Washington, Roxbury, Kent and Salisbury, form a region of country estates, horse farms, inns and weekend homes for New Yorkers and Bostonians.

  1. 01

    Litchfield Historic District

    The town green and surrounding streets preserve some of the finest colonial and Federal architecture in New England, including the home of patriot Oliver Wolcott.

  2. 02

    Tapping Reeve House and Litchfield Law School

    The house and one-room schoolhouse where Tapping Reeve trained lawyers who included Aaron Burr and John C. Calhoun are now a museum run by the Litchfield Historical Society.

  3. 03

    White Memorial Conservation Center

    Spanning about 4,000 acres around Bantam Lake, Connecticut’s largest nature preserve offers miles of trails, boardwalks over wetlands and a nature museum.

  4. 04

    Haight-Brown Vineyard

    One of Connecticut’s earliest wineries, set on a hillside just outside town, pours estate wines in a converted barn with views across the vineyard.

  5. 05

    Lake Waramaug State Park

    In nearby Kent and Warren, this park on a lake ringed by wooded hills offers swimming, kayaking and picnicking, and the lake road makes a favorite fall drive.

  6. 06

    Kent Falls State Park

    About 20 miles west, a series of cascades drops some 250 feet through the woods, with a trail climbing alongside the falls and a covered bridge near the bottom.

Explore Litchfield charter

Questions

Chicago to Litchfield flights

How long is a private flight from Chicago to Litchfield?

About a short flight in a private jet, for 754 miles direct. Driving the same trip takes about 16 hours.

Which airports do flights from Chicago to Litchfield use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Waterbury Oxford Airport (OXC) or Bradley International Airport (BDL). Pick whichever is closest to where you're starting and where you're headed.

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

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

Return flight

Litchfield to Chicago

More flights from Chicago

More flights to Litchfield

Explore Chicago private charter and Litchfield private charter, airports and things to do. Arriving at Waterbury Oxford Airport (OXC).

Chicago to Litchfield, 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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