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$84+ Cheap flights from Chicago (CHI) to Newburgh, NY

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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JFK
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Chicago to Newburgh

Cheapest flights from Chicago to Newburgh
Explore the most affordable flight options available from Chicago to Newburgh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/316:12 amMDW - SWF
2 stops27h 51mMultiple Airlines
Sun 2/112:13 pmSWF - MDW
1 stop8h 39mMultiple Airlines
Deal found 12/16$358
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/3112:09 pmORD - SWF
1 stop21h 54mMultiple Airlines
Sun 1/411:43 amSWF - ORD
2 stops24h 47mMultiple Airlines
Deal found 12/16$548
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/316:12 amMDW - SWF
2 stops27h 51mMultiple Airlines
Sun 1/411:43 amSWF - MDW
1 stop10h 10mMultiple Airlines
Deal found 12/16$614
This Mytrip deal was found by Cheapflights users on 12/16. 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.
Thu 12/2512:09 pmORD - SWF
2 stops21h 58mMultiple Airlines
Mon 12/2911:37 amSWF - ORD
1 stop8h 02mMultiple Airlines
Deal found 12/16$737
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/222:15 pmORD - SWF
2 stops19h 48mMultiple Airlines
Mon 12/2911:37 amSWF - ORD
1 stop24h 37mMultiple Airlines
Deal found 12/15$756
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/288:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Thu 1/111:43 amSWF - ORD
1 stop8h 19mMultiple Airlines
Deal found 12/16$843
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Sat 12/275:08 pmORD - SWF
1 stop15h 51mMultiple Airlines
Sat 1/38:45 pmSWF - ORD
1 stop13h 17mMultiple Airlines
Deal found 12/16$851
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/223:10 pmMDW - SWF
1 stop18h 53mMultiple Airlines
Mon 12/2912:24 pmSWF - MDW
2 stops10h 34mMultiple Airlines
Deal found 12/15$885
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/288:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Tue 12/3011:43 amSWF - ORD
1 stop8h 19mMultiple Airlines
Deal found 12/16$914
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/218:26 pmORD - SWF
2 stops14h 18mMultiple Airlines
Thu 12/2511:43 amSWF - ORD
1 stop8h 19mMultiple Airlines
Deal found 12/16$968
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/189:09 pmORD - SWF
2 stops19h 57mMultiple Airlines
Mon 12/228:25 pmSWF - ORD
1 stop20h 17mMultiple Airlines
Deal found 12/17$975
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/2110:50 pmMDW - SWF
2 stops35h 13mMultiple Airlines
Sun 12/2811:43 amSWF - MDW
1 stop10h 21mMultiple Airlines
Deal found 12/16$1,007

Find flight deals from Chicago to Newburgh

Keep the following information in mind while searching for Chicago to Newburgh flight deals. Data was last updated December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$211
(Kiwi.com)

One-way from

$84
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$232
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
Search Deals
From Chicago (CHI) to Newburgh
Search Deals
One-way flight from Chicago (CHI) to Newburgh
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($13 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 December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Newburgh 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 December 18, 2025.
Use the filters below to find and compare flights from Chicago to Newburgh that are best for you.

Fly from

Chicago

Fly to

Newburgh

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Thu 1/22

12:13 pm-7:41 pm

1 stop8h 28m

$211

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 1/18

8:51 pm-6:43 pm

1 stop20h 52m

New Windsor Stewart

Thu 1/22

12:13 pm-10:35 am

1 stop23h 22m

$237

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 1/16

8:43 pm-11:33 am

2 stops37h 50m

New Windsor Stewart

Fri 1/23

11:09 am-9:03 pm

1 stop10h 54m

$288

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 12/31

6:12 am-11:03 am

2 stops27h 51m

New Windsor Stewart

Sun 2/1

12:13 pm-7:52 pm

1 stop8h 39m

$358

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 3/14

7:41 pm-11:39 am

1 stop14h 58m

New Windsor Stewart

Sun 3/22

10:29 am-6:33 pm

1 stop9h 04m

$403

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 2/8

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Sun 2/15

11:42 am-9:13 pm

1 stop10h 31m

$431

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/1

7:20 am-11:07 am

1 stop26h 47m

New Windsor Stewart

Mon 1/5

11:37 am-12:54 pm

2 stops26h 17m

$515

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 1/4

8:09 pm-11:44 am

2 stops14h 35m

New Windsor Stewart

Thu 1/8

12:13 pm-7:41 pm

1 stop8h 28m

$533

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/31

12:09 pm-11:03 am

1 stop21h 54m

New Windsor Stewart

Sun 1/4

11:43 am-11:30 am

2 stops24h 47m

$548

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 12/31

6:12 am-11:03 am

2 stops27h 51m

New Windsor Stewart

Sun 1/4

11:43 am-8:53 pm

1 stop10h 10m

$614

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 26 results
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Best time to book a flight from Chicago to Newburgh

Have a flexible travel schedule? Discover the best time to fly to Newburgh from Chicago 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 Chicago to Newburgh

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Newburgh (average of $36). Flying from Chicago to Newburgh in July is currently the most expensive (average of $104). 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 CHI to N3W?

Find hourly flight availability from Chicago to Newburgh. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 33% on flights from Chicago to Newburgh by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Newburgh. Price data was last updated on December 13, 2025.

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

Weekly flight availability from Chicago to Newburgh

Explore weekly flight availability from Chicago to Newburgh. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 18, 2025.

The most flights from CHI to N3W are scheduled on a Thursday (42 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

Related info for your journey

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

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

    The top 3 most reliable airlines when flying from Chicago to Newburgh are China Eastern (94%), LATAM Airlines (83%) and Republic Airways (82%).

  • What are the cheapest flights from Chicago to Newburgh?

    Looking for the cheapest flight from Chicago to Newburgh? While on average our users pay $1,020, our data indicates the cheapest price to be $43. The most popular route (Chicago O'Hare Intl - New Windsor Stewart), is priced around $288.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Newburgh 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 Chicago to Newburgh?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Newburgh (average of $36). Flying from Chicago to Newburgh in July is currently the most expensive (average of $104). 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

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 Chicago to Newburgh

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Chicago to Newburgh

Discover the top 7 airlines that operate flights from Chicago to Newburgh. 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$40Average$169FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$42Average$138FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$92Average$232FlexibilityNo cancel feeOn-time62%
DeltaCheapest$103Average$305FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$142Average$280FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$301FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$302FlexibilityNo cancel feeOn-time63%

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