Bluebird
Poughkeepsie, New York

Private charter · MDW → POU

Chicago to Poughkeepsie

715 miles. One price for the whole airplane.

Photo: Juliancolton · Public domain

Price your flight from Chicago to Poughkeepsie

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Poughkeepsie, door to door faster.

Trade about 15½ hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Dutchess County Airport in Poughkeepsie, 715 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
715 mi
Flight
—
Driving
15½ hours
Passengers
Up to 1
MDWChicagoPOUPoughkeepsie
MDW → POU715 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 Poughkeepsie

Airports in Poughkeepsie

  • POU

    Commercial airport

    Dutchess County Airport

    Poughkeepsie · KPOU

    From downtown
    6 mi
    Longest runway
    5,001 ft

  • SWF

    Commercial airport

    New York Stewart International Airport

    Newburgh · KSWF

    From downtown
    17 mi
    Longest runway
    11,817 ft

  • MGJ

    Regional airport

    Orange County Airport

    Montgomery · KMGJ

    From downtown
    22 mi
    Longest runway
    5,006 ft

When you land

Things to do in Poughkeepsie

Poughkeepsie is the main city of the mid-Hudson Valley, on the river roughly halfway between New York City and Albany. It is home to Vassar College and Marist College, and IBM, which built large mainframe operations here in the twentieth century, still keeps a presence in the area. Today the region’s economy blends health care, education, technology and a growing hospitality and second-home market as New Yorkers settle in the river towns and farm country of Dutchess and Ulster counties.

  1. 01

    Walkway Over the Hudson

    A former railroad bridge converted into a pedestrian park stretches about 1.3 miles across the river, offering sweeping views up and down the Hudson Valley.

  2. 02

    Home of Franklin D. Roosevelt National Historic Site

    In Hyde Park, Springwood, FDR’s lifelong home, stands beside the first presidential library, and Eleanor Roosevelt’s Val-Kill cottage is nearby.

  3. 03

    The Culinary Institute of America

    The country’s leading culinary college runs student-staffed restaurants on its Hyde Park campus overlooking the river, a fun way to sample the next generation’s cooking.

  4. 04

    Vanderbilt Mansion National Historic Site

    A Gilded Age country house with Beaux-Arts interiors, formal Italian gardens and grounds with long views over the Hudson, just north of Hyde Park.

  5. 05

    Dia Beacon

    Housed in a former Nabisco box-printing factory in Beacon, this museum displays large-scale works by artists such as Richard Serra, Donald Judd and Dan Flavin.

  6. 06

    Rhinebeck

    About 20 miles north, this historic village is known for its restaurants, shops and inns, the Old Rhinebeck Aerodrome and the Dutchess County Fair each August.

Explore Poughkeepsie charter

Questions

Chicago to Poughkeepsie flights

How long is a private flight from Chicago to Poughkeepsie?

About a short flight in a private jet, for 715 miles direct. Driving the same trip takes about 15½ hours.

Which airports do flights from Chicago to Poughkeepsie use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Dutchess County Airport (POU), New York Stewart International Airport (SWF), or Orange County Airport (MGJ). Pick whichever is closest to where you're starting and where you're headed.

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

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

Return flight

Poughkeepsie to Chicago

More flights from Chicago

More flights to Poughkeepsie

Explore Chicago private charter and Poughkeepsie private charter, airports and things to do. Arriving at Dutchess County Airport (POU).

Chicago to Poughkeepsie, 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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