HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$94+ Cheap flights from Newburgh, NY to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Dec 1 — Dec 81
Mon 12/1
Mon 12/8
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Newburgh to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Newburgh to Chicago

Cheapest flights from Newburgh to Chicago
Explore the most affordable flight options available from Newburgh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 1, 2025.

This Mytrip deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2111:12 amSWF - ORD
1 stop13h 01mMultiple Airlines
Sun 11/233:26 pmORD - SWF
1 stop17h 41mMultiple Airlines
Deal found 10/31$226
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2410:57 amSWF - ORD
1 stop23h 20mMultiple Airlines
Tue 11/253:43 pmORD - SWF
1 stop18h 44mMultiple Airlines
Deal found 10/30$249
This Mytrip deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1512:27 pmSWF - ORD
1 stop8h 34mMultiple Airlines
Mon 12/225:00 amORD - SWF
1 stop13h 35mMultiple Airlines
Deal found 10/31$252
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1012:01 pmSWF - ORD
1 stop22h 46mMultiple Airlines
Thu 11/138:26 amORD - SWF
2 stops24h 45mMultiple Airlines
Deal found 10/29$263
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1411:01 amSWF - ORD
1 stop25h 11mMultiple Airlines
Sat 11/155:45 pmORD - SWF
2 stops16h 18mMultiple Airlines
Deal found 10/30$312
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/711:43 amSWF - ORD
2 stops30h 11mMultiple Airlines
Sat 12/1312:09 pmORD - SWF
1 stop21h 54mMultiple Airlines
Deal found 10/31$339
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:24 pmSWF - MDW
2 stops10h 46mMultiple Airlines
Sat 11/1511:36 amMDW - SWF
1 stop22h 27mMultiple Airlines
Deal found 10/30$395
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/177:42 pmSWF - RFD
1 stop14h 54mAllegiant Air
Mon 11/248:02 pmRFD - SWF
1 stop13h 44mAllegiant Air
Deal found 10/30$404
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/166:14 pmSWF - RFD
1 stop14h 56mAllegiant Air
Thu 11/206:28 pmRFD - SWF
1 stop23h 10mAllegiant Air
Deal found 11/1$544
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/319:16 pmSWF - RFD
1 stop22h 15mAllegiant Air
Fri 12/510:38 amRFD - SWF
1 stop7h 02mAllegiant Air
Deal found 10/31$584
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/61:32 pmSWF - MDW
2 stops33h 48mMultiple Airlines
Mon 11/106:06 pmMDW - SWF
1 stop15h 20mMultiple Airlines
Deal found 10/31$630
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:24 pmSWF - MDW
2 stops23h 02mMultiple Airlines
Sun 11/24:46 pmMDW - SWF
1 stop25h 30mMultiple Airlines
Deal found 10/30$656

Cheap flight deals from Newburgh to Chicago

Keep the following information in mind while searching for Newburgh to Chicago flight deals. Data was last updated November 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$226
(Mytrip)

One-way from

$94
(Mytrip)

Popular in

August

Cheapest in

January

Average price

$234
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
Search Deals
From Newburgh to Chicago (CHI)
Search Deals
One-way flight from Newburgh to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Newburgh to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 1, 2025.
Use the filters below to find and compare flights from Newburgh to Chicago that are best for you.

Fly from

Newburgh

Fly to

Chicago

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/21

11:12 am-11:13 pm

1 stop13h 01m

Chicago O'Hare Intl

Sun 11/23

3:26 pm-10:07 am

1 stop17h 41m

$226

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/23

11:09 am-11:42 pm

1 stop13h 33m

Chicago O'Hare Intl

Sun 1/25

5:59 pm-10:19 am

1 stop15h 20m

$231

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 11/24

10:57 am-9:17 am

1 stop23h 20m

Chicago O'Hare Intl

Tue 11/25

3:43 pm-11:27 am

1 stop18h 44m

$249

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 12/15

12:27 pm-8:01 pm

1 stop8h 34m

Chicago O'Hare Intl

Mon 12/22

5:00 am-7:35 pm

1 stop13h 35m

$252

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/14

11:01 am-11:12 am

1 stop25h 11m

Chicago O'Hare Intl

Sat 11/15

5:45 pm-11:03 am

2 stops16h 18m

$312

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 12/7

11:43 am-4:54 pm

2 stops30h 11m

Chicago O'Hare Intl

Sat 12/13

12:09 pm-11:03 am

1 stop21h 54m

$339

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/19

6:56 pm-11:14 am

1 stop17h 18m

Chicago O'Hare Intl

Sun 12/21

9:09 pm-7:35 pm

2 stops21h 26m

$347

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/19

6:56 pm-11:14 am

1 stop17h 18m

Chicago O'Hare Intl

Sun 12/28

1:34 pm-10:47 am

2 stops20h 13m

$370

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Fri 11/14

12:24 pm-10:10 pm

2 stops10h 46m

Chicago Midway

Sat 11/15

11:36 am-11:03 am

1 stop22h 27m

$395

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Mon 11/17

7:42 pm-9:36 am

1 stop14h 54m

Chicago Greater Rockford

Mon 11/24

8:02 pm-10:46 am

1 stop13h 44m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 37 results
1
2
3
4

Best time to book a flight from Newburgh to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Newburgh with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Newburgh to Chicago

What is the cheapest month to book a flight from Newburgh to Chicago?

Currently, November is the cheapest month in which you can book a flight from Newburgh to Chicago (average of $54). Flying from Newburgh to Chicago in July is currently the most expensive (average of $126). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from N3W to CHI?

Find hourly flight availability from Newburgh to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 1, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 37% on flights from Newburgh to Chicago by exploring options for tickets in the evening.

What is the cheapest day to fly from Newburgh to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Newburgh to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Newburgh to Chicago flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

Find useful and relevant information for your journey from Newburgh to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Newburgh to Chicago?

    Departing from Newburgh to Chicago will take you 14h 54m. The distance from Newburgh to Chicago is about 772 mi.

  • What are the most popular routes from Newburgh to Chicago?

    Most travelers choose New Windsor Stewart - Chicago O'Hare Intl, New Windsor Stewart - Chicago Midway or New Windsor Stewart - Chicago Greater Rockford when deciding on the best route from Newburgh to Chicago.

  • What are the most reliable airlines from Newburgh to Chicago?

    Before booking your flight to Chicago from Newburgh, check out the most reliable airlines to get you to your destination on time: Atlas Air (100%), Finnair (100%), Hawaiian Airlines( 95%).

  • What are the cheapest flights from Newburgh to Chicago?

    The cheapest flight price from Newburgh to Chicago is $30. On average you can expect to pay $614. The most popular route, (New Windsor Stewart - Chicago O'Hare Intl), can usually be booked for $226.

  • Can I find deals for flights from Newburgh to Chicago that include hotel bookings?

    Yes. In addition to deals on Newburgh to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Newburgh to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Newburgh to Chicago.

  • Can I find deals for business class flights from Newburgh to Chicago?

    Yes. Cheapflights offers flight deals from Newburgh to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Newburgh to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Newburgh to Chicago (average of $54). Flying from Newburgh to Chicago in July is currently the most expensive (average of $126). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Newburgh to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
John F Kennedy Intl to Midway flights
LaGuardia to Midway flights
Newark to St. Louis flights
LaGuardia to St. Louis flights
John F Kennedy Intl to St. Louis flights
Newark to Midway flights
Syracuse to O'Hare Intl flights
White Plains to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Rochester to O'Hare Intl flights
Albany to O'Hare Intl flights
Rochester to Midway flights
Albany to Midway flights
Syracuse to Midway flights
White Plains to Midway flights
Buffalo to Midway flights
Ithaca to O'Hare Intl flights
LaGuardia to Moline flights
Buffalo to St. Louis flights
Syracuse to St. Louis flights
John F Kennedy Intl to Moline flights
Stewart to O'Hare Intl flights
Newark to Moline flights
Albany to St. Louis flights
White Plains to St. Louis flights
Rochester to St. Louis flights
LaGuardia to Peoria flights
Islip to O'Hare Intl flights
Elmira to St. Louis flights
Newark to Peoria flights
LaGuardia to Decatur flights
Stewart to St. Louis flights
Newark to Champaign flights
John F Kennedy Intl to Champaign flights
Newark to Bloomington flights
Albany to Evansville flights
John F Kennedy Intl to Peoria flights
Ithaca to Midway flights
John F Kennedy Intl to Bloomington flights
LaGuardia to Champaign flights
Plattsburgh to O'Hare Intl flights
Binghamton to O'Hare Intl flights
Elmira to O'Hare Intl flights
Ithaca to St. Louis flights
Binghamton to Midway flights
Stewart to Peoria flights
Syracuse to Moline flights

Top 7 airlines flying from Newburgh to Chicago

Discover the top 7 airlines that operate flights from Newburgh to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$207FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$66Average$198FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$87Average$229FlexibilityNo cancel feeOn-time62%
DeltaCheapest$101Average$367FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$147Average$303FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$329FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$156Average$275FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights