Bluebird
Killington, Vermont

Private charter · MDW → RUT

Chicago to Killington

761 miles. One price for the whole airplane.

Photo: Royalbroil · CC BY-SA 4.0

Price your flight from Chicago to Killington

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Killington, 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 Rutland - Southern Vermont Regional Airport in Killington, 761 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
761 mi
Flight
—
Driving
16 hours
Passengers
Up to 1
MDWChicagoRUTKillington
MDW → RUT761 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 Killington

Airports in Killington

  • RUT

    Commercial airport

    Rutland - Southern Vermont Regional Airport

    Rutland · KRUT

    From downtown
    11 mi
    Longest runway
    5,304 ft

  • LEB

    Commercial airport

    Lebanon Municipal Airport

    Lebanon · KLEB

    From downtown
    25 mi
    Longest runway
    5,496 ft

  • VSF

    Regional airport

    Hartness State Airport

    North Springfield · KVSF

    From downtown
    25 mi
    Longest runway
    5,501 ft

When you land

Things to do in Killington

Killington is home to the largest ski area in the eastern United States, a resort that sprawls across several peaks of the Green Mountains and is known for one of the longest ski seasons in the East. Nicknamed the Beast of the East, the resort draws skiers from across the Northeast, and its sister resort, Pico Mountain, sits just down the road. The town’s economy is almost entirely built on tourism, second homes and the businesses along the Killington Access Road, where lodges, restaurants and après-ski bars line the way up the mountain.

  1. 01

    Killington Resort

    The largest ski area in the eastern U.S. spans multiple peaks with a gondola and extensive snowmaking, and hosts a World Cup women’s slalom and giant slalom over Thanksgiving weekend.

  2. 02

    Pico Mountain

    Just west of Killington and on the same lift ticket, Pico is a smaller, more traditional ski area with a summit offering views across the Green Mountains.

  3. 03

    Killington Bike Park

    In summer, lifts carry riders to a network of downhill mountain bike trails, one of the largest bike parks in the Northeast.

  4. 04

    Killington Peak

    Vermont’s second-highest peak can be reached by gondola or by hiking the Long Trail and Bucklin Trail, with views of five states and Quebec on clear days.

  5. 05

    Gifford Woods State Park

    Near the Appalachian Trail, the park protects a rare old-growth hardwood forest and offers camping and access to Kent Pond for fishing and paddling.

  6. 06

    Woodstock

    About 20 miles east, Woodstock’s village green, covered bridge and Billings Farm & Museum make it one of Vermont’s most picturesque towns.

Explore Killington charter

Questions

Chicago to Killington flights

How long is a private flight from Chicago to Killington?

About a short flight in a private jet, for 761 miles direct. Driving the same trip takes about 16 hours.

Which airports do flights from Chicago to Killington use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Rutland - Southern Vermont Regional Airport (RUT), Lebanon Municipal Airport (LEB), or Hartness State Airport (VSF). Pick whichever is closest to where you're starting and where you're headed.

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

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

Return flight

Killington to Chicago

More flights from Chicago

More flights to Killington

Explore Chicago private charter and Killington private charter, airports and things to do. Arriving at Rutland - Southern Vermont Regional Airport (RUT).

Chicago to Killington, on your schedule

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

Get an instant price