Cheap flight deals from Chicago (CHI) to Newburgh (NYC)

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Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0-star property

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

8.4/10 Very Good! (1,002 reviews)

Feb 12 - Feb 17

5 night stay

Chicago (ORD) to Newburgh (SWF)

Spirit Airlines • Roundtrip • Coach
Price was $330, price is now $330 per person
$330
per person
found 1 day ago
Great staff, comfy room

Reviewed on Dec 16, 2025

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More About Flying To Newburgh from Chicago

Route Information for Flights from Chicago to Newburgh

Origin Airport IATA Code
CHI
Destination Airport IATA Code
NYC
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Newburgh

Whether you want to book cheap flights from Chicago to Newburgh or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Chicago to Newburgh flights.

Make the Most of Your Vacation

Not only does Orbitz have cheap deals for Chicago to Newburgh flights, we can also help you plan your vacation in advance. Why wait in lengthy lines for tickets to shows, amusement parks, and other attractions when you could be making the most of your holiday? Add activities to your flight booking for fewer hassles once you arrive in Newburgh.

Planning on the Go

Book your flights from Chicago to Newburgh wherever you are with the Orbitz app for Android and iPhone. Or simply use m.orbitz.com on your mobile browser to search and book the Chicago to Newburgh flights that you want. And if you’re running late, you check your flight status and baggage claim information on your mobile device too too.

Craft Your Perfect Vacation

Orbitz takes the stress out of vacation planning with great deals on flights from Chicago to Newburgh, hotels, car rentals, cruises, and more. Mix and match results for your perfect trip, or book a complete vacation package.

Keep Informed With Orbitz

With Orbitz’s free alerts service, you will stay informed of flight or services disruptions to your Chicago to Newburgh flights. The alerts can be sent straight to your mobile phone or email.

Frequently asked questions

Are there non-stop flights from Chicago to Newburgh?
There are two carriers that operate direct flights from ORD to Westchester County Airport (HPN). Book your seat now with United Airlines or American Airlines.
What is the shortest flight from Chicago to Newburgh?
It can zip by in as little as 2 hours and 49 minutes. If you strongly believe your vacation hours should be spent 'vacationing' instead of flying, you'll enjoy the flight from Chicago to Newburgh.
What airlines fly from Chicago to Newburgh most frequently?
Consider booking a ticket with United Airlines (UA), which frequently services this route. This airline offers 60 flights every month between O'Hare Intl. Airport (ORD) and White Plains, NY (HPN-Westchester County). Alternatively, secure your favorite window (or aisle) seat with American Airlines (AA). You'll have 34 monthly flights between Chicago and Newburgh to select from with this airline.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.