Bluebird
Walla Walla, Washington

Private charter · MDW → ALW

Chicago to Walla Walla

1,538 miles. One price for the whole airplane.

Photo: Squarestate7 · CC BY-SA 3.0

Price your flight from Chicago to Walla Walla

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Walla Walla, door to door faster.

Trade about 32½ hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Walla Walla Regional Airport in Walla Walla, 1,538 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
1,538 mi
Flight
—
Driving
32½ hours
Passengers
Up to 1
MDWChicagoALWWalla Walla
MDW → ALW1,538 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 Walla Walla

Airports in Walla Walla

  • ALW

    Commercial airport

    Walla Walla Regional Airport

    Walla Walla · KALW

    From downtown
    2 mi
    Longest runway
    6,527 ft

When you land

Things to do in Walla Walla

Walla Walla is a small agricultural city in the southeast corner of Washington that has become one of the country’s most celebrated wine regions. More than a hundred wineries and tasting rooms are spread across the Walla Walla Valley, which crosses into Oregon, from downtown storefronts to former World War II buildings at the airport and estate vineyards in the surrounding hills. Wheat, the famous Walla Walla sweet onion, Whitman College, a regional medical center and the state penitentiary round out an economy with deep roots in farming and education.

  1. 01

    Downtown tasting rooms

    Dozens of winery tasting rooms fill the historic storefronts of Main Street and its side streets, alongside restaurants, cafés and shops, all within an easy walk.

  2. 02

    Airport District wineries

    Small wineries operate out of converted World War II–era Army Air Forces buildings beside Walla Walla Regional Airport, an unusual and convenient place to taste.

  3. 03

    Whitman Mission National Historic Site

    West of town, this site marks the 1836 mission of Marcus and Narcissa Whitman and the conflict with the Cayuse people, told through trails and exhibits.

  4. 04

    Fort Walla Walla Museum

    A pioneer village of historic buildings and galleries of horse-drawn equipment and regional artifacts tells the story of settlement in the Walla Walla Valley.

  5. 05

    Pioneer Park

    Laid out with help from the Olmsted Brothers firm, this shady historic park includes an aviary, a bandstand and graceful old trees near downtown.

  6. 06

    The Rocks District of Milton-Freewater

    Just south across the Oregon line, this distinctive appellation of cobblestone-covered vineyards produces some of the valley’s most sought-after Syrah.

Explore Walla Walla charter

Questions

Chicago to Walla Walla flights

How long is a private flight from Chicago to Walla Walla?

About a short flight in a private jet, for 1,538 miles direct. Driving the same trip takes about 32½ hours.

Which airports do flights from Chicago to Walla Walla use?

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

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

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

Return flight

Walla Walla to Chicago

More flights from Chicago

More flights to Walla Walla

Explore Chicago private charter and Walla Walla private charter, airports and things to do. Arriving at Walla Walla Regional Airport (ALW).

Chicago to Walla Walla, 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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