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

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

Frequently asked questions

How much does a flight from Dutchess County Airport (POU) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight or cheap return flight from Dutchess County Airport (POU) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Dutchess County Airport (POU) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from POU to ORD is , when there's less demand. Off-peak season is generally when better flight deals are available between these airports.
Which airlines fly direct from Dutchess County Airport (POU) to O'Hare Intl. Airport (ORD)?
There are no direct flights from Poughkeepsie, NY (POU-Dutchess County) to O'Hare Intl. Airport (ORD). However, you can find other airports offering nonstop flights. Board your plane at LaGuardia Airport (LGA) and fly straight to Chicago without a layover.
What is the cheapest airline that flies from Dutchess County Airport (POU) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline flying from POU to ORD, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from Dutchess County Airport (POU) to O'Hare Intl. Airport (ORD)?
You'll need to catch a flight with a layover when traveling from Dutchess County Airport (POU) to O'Hare Intl. Airport (ORD). Direct flights don't operate daily on this route. However, simply filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from POU to ORD?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Dutchess County Airport (POU) to O'Hare Intl. Airport (ORD)?
To touch down at O'Hare Intl. Airport (ORD) on schedule, choose a flight that leaves from Dutchess County Airport (POU) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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.
Is it cheaper to buy a plane ticket from Dutchess County Airport (POU) to O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from POU to ORD just before your journey is typically more expensive. However, if you're flexible with your itinerary, you could land a cheap last-minute fare.
Is it cheaper to book a POU to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a POU to ORD flight and hotel package with Expedia could lead to significant savings. Better yet, managing everything in one place will take the hassle out of travel planning. Just secure your flights and choose from our wide range of stays, then customize your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Dutchess County Airport (POU) to O'Hare Intl. Airport (ORD)?
If you booked your POU to ORD flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more information.

Travel information

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

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Poughkeepsie to Chicago Flights

The cheapest times to fly from Poughkeepsie to Chicago

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 Poughkeepsie to Chicago are during the month of . You can find some of the cheapest flights from Poughkeepsie to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Poughkeepsie to Chicago

Sunday is one of the best days to book for cheap flights from Poughkeepsie to Chicago: 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 Poughkeepsie to Chicago

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 Poughkeepsie to Chicago 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 Poughkeepsie to Chicago 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 Poughkeepsie to Chicago 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.

 

Poughkeepsie to Chicago Flights

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*Available to One Key members.