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

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Newburgh economy flight packages

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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 24 - Feb 26

2 night stay

Chicago (MDW) to Newburgh (SWF)

Southwest Airlines • Roundtrip • Coach
Price was $235, price is now $235 per person
$235
per person
found 1 day ago
Great staff, comfy room

Reviewed on Dec 16, 2025

Wildflower Farms, Auberge Collection
5.0-star property

Wildflower Farms, Auberge Collection

9.4/10 Exceptional! (54 reviews)

Feb 27 - Mar 2

3 night stay

Chicago (ORD) to Newburgh (SWF)

Spirit Airlines • Coach

Newburgh (SWF) to Chicago (ORD)

Frontier Airlines • Coach
Price was $2,671, price is now $2,455 per person
$2,455
per person
found 1 day ago
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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

If you are looking for guaranteed low prices on flights from Chicago to Newburgh, then look no further than Orbitz. Orbitz offers everything you need to plan the perfect trip—from cheap deals and bargain holiday packages to cutting-edge mobile tools.

Your Perfect NewburghVacation Package

Orbitz gives you access to exclusive deals and discounts on flights from Chicago to Newburgh. Mix and match hotels and Chicago to Newburgh flights to create your dream vacation. All your options are displayed at a glance with the Orbitz Matrix Display, which shows your package savings and built-in extras, such as free nights.

Stress free Searches Even on the Move

With free mobile apps for iPhone and Android, you never have to miss out on great prices on flights from Chicago to Newburgh. In a hurry? No worry—just check your flight status using m.orbtiz.com via your mobile browser or to book that exclusive hotel deal.

Don’t Forget the Car Rental

Need a car after your Chicago to Newburgh flights? Not only do you get great rental deals when you book in advance with Orbitz, we can send your flight details to the car rental company, so it knows when your flight from Chicago to Newburgh is delayed.

Low Price Guarantee

With the best deals and easy searching options, Orbitz make it easy and fun to find cheap Chicago to Newburgh flights, a great hotel, or a full vacation package. With Orbitz’s low price guarantee, you always get great discounts on air ticket prices.

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.