Cheap Flights from Chicago (ORD) to Poughkeepsie (POU)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Poughkeepsie, NY (POU-Dutchess County)

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Dutchess County Airport (POU) cost?
Secure a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Dutchess County Airport (POU) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Dutchess County Airport (POU)?
is the most affordable month to fly from ORD to POU. Avoiding peak travel times is often the key to better flight prices.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Dutchess County Airport (POU)?
To find the cheapest airline that'll fly you from ORD to POU, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from O'Hare Intl. Airport (ORD) to Dutchess County Airport (POU)?
Direct flights from O'Hare Intl. Airport (ORD) to Dutchess County Airport (POU) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to POU?
Generally you'll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* But this can change based on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Dutchess County Airport (POU)?
To touch down at Dutchess County Airport (POU) without delays, opt for a flight that leaves from O'Hare Intl. Airport (ORD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Wappingers Falls from O'Hare Intl. Airport (ORD)?
You can arrive at LaGuardia Airport (LGA) or Westchester County Airport (HPN) when traveling to Wappingers Falls on a direct flight from O'Hare Intl. Airport (ORD).
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Dutchess County Airport (POU) last-minute?
Last-minute fares from ORD to POU are typically more expensive. To secure the lowest prices, start looking for flights as soon as possible. That being said, if you can play around with your travel dates, you may score a cheap ticket right before your trip.
Is it cheaper to book an ORD to POU flight and hotel package?
You'll typically save money by booking an ORD to POU flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After selecting your ideal accommodations and flights, consider adding extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Dutchess County Airport (POU)?
Typically, it's possible to cancel or reschedule your ORD to POU flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Dutchess County
Distance
721 mi

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Chicago to Poughkeepsie Flights

The cheapest times to fly from Chicago to Poughkeepsie

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Poughkeepsie are during the month of . You can find some of the cheapest flights from Chicago to Poughkeepsie with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Poughkeepsie

Sunday is one of the best days to book for cheap flights from Chicago to Poughkeepsie: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Poughkeepsie

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Poughkeepsie in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Poughkeepsie flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Poughkeepsie airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Poughkeepsie Flights

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*Available to One Key members.