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$96+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JFK
Apr 24 — May 11
Fri 4/24
Fri 5/1
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 March 25, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/24. 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 4/227:15 pm
ORD
-
SWF
1 stop14h 40m
Multiple Airlines
Thu 4/3011:45 am
SWF
-
ORD
1 stop10h 32m
Multiple Airlines
Deal found 3/24$207
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 4/297:15 pm
ORD
-
SWF
1 stop14h 40m
Multiple Airlines
Sun 5/311:45 am
SWF
-
ORD
1 stop22h 46m
Multiple Airlines
Deal found 3/24$222
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 5/133:55 pm
ORD
-
SWF
1 stop16h 03m
Multiple Airlines
Thu 5/1411:45 am
SWF
-
ORD
1 stop12h 14m
Multiple Airlines
Deal found 3/23$256
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 5/95:30 pm
ORD
-
SWF
1 stop14h 28m
Multiple Airlines
Sun 5/1711:45 am
SWF
-
ORD
1 stop12h 14m
Multiple Airlines
Deal found 3/20$268
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 5/165:30 pm
ORD
-
SWF
1 stop14h 28m
Multiple Airlines
Sun 5/1711:45 am
SWF
-
ORD
1 stop12h 14m
Multiple Airlines
Deal found 3/23$308
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 5/305:30 pm
ORD
-
SWF
1 stop14h 28m
Multiple Airlines
Mon 6/19:41 am
SWF
-
ORD
1 stop14h 32m
Multiple Airlines
Deal found 3/24$311
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 4/233:08 pm
ORD
-
SWF
2 stops19h 23m
Multiple Airlines
Thu 4/3011:45 am
SWF
-
ORD
1 stop10h 32m
Multiple Airlines
Deal found 3/24$329
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 7/17:19 pm
ORD
-
SWF
1 stop13h 19m
Multiple Airlines
Wed 7/157:46 pm
SWF
-
ORD
2 stops29h 56m
Multiple Airlines
Deal found 3/23$340
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 4/232:05 pm
ORD
-
SWF
2 stops20h 26m
Multiple Airlines
Sun 4/2611:45 am
SWF
-
ORD
1 stop13h 10m
Multiple Airlines
Deal found 3/24$344
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 4/181:27 pm
ORD
-
SWF
1 stop20h 28m
Multiple Airlines
Thu 4/2311:45 am
SWF
-
ORD
1 stop10h 32m
Multiple Airlines
Deal found 3/23$381
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/199:04 am
MDW
-
SWF
2 stops25h 27m
Multiple Airlines
Sun 4/2611:48 am
SWF
-
MDW
1 stop21h 16m
Multiple Airlines
Deal found 3/20$491
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 3/264:55 pm
MDW
-
SWF
2 stops15h 02m
Multiple Airlines
Sat 3/2811:28 am
SWF
-
MDW
1 stop11h 17m
Multiple Airlines
Deal found 3/22$692

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 March 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Kiwi.com)

One-way from

$96
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$256
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. 3% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 25, 2026.
Use the filters below to find and compare flights from Chicago to Newburgh that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 5/13

3:55 pm-8:58 am

1 stop16h 03m

New Windsor Stewart

Thu 5/14

11:45 am-10:59 pm

1 stop12h 14m

$256
Quickest round-trip

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 5/16

5:30 pm-8:58 am

1 stop14h 28m

New Windsor Stewart

Sun 5/17

11:45 am-10:59 pm

1 stop12h 14m

$308

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 5/30

5:30 pm-8:58 am

1 stop14h 28m

New Windsor Stewart

Mon 6/1

9:41 am-11:13 pm

1 stop14h 32m

$311

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 4/23

2:05 pm-11:31 am

2 stops20h 26m

New Windsor Stewart

Sun 4/26

11:45 am-11:55 pm

1 stop13h 10m

$344

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 4/18

1:27 pm-10:55 am

1 stop20h 28m

New Windsor Stewart

Thu 4/23

11:45 am-9:17 pm

1 stop10h 32m

$381

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 4/8

6:10 pm-10:55 am

1 stop15h 45m

New Windsor Stewart

Sun 4/12

11:45 am-6:30 pm

2 stops31h 45m

$388

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 4/5

4:21 pm-11:31 am

2 stops18h 10m

New Windsor Stewart

Thu 4/9

11:45 am-5:15 pm

1 stop30h 30m

$406

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 6/11

5:30 pm-8:49 am

1 stop14h 19m

New Windsor Stewart

Sun 6/14

8:04 pm-5:10 pm

1 stop22h 06m

$407

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 5/21

5:30 pm-8:51 am

1 stop14h 21m

New Windsor Stewart

Sun 5/24

8:10 pm-5:10 pm

1 stop22h 00m

$410

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 4/19

10:31 am-11:31 am

2 stops24h 00m

New Windsor Stewart

Sun 4/26

11:45 am-9:36 am

1 stop22h 51m

$456

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

Showing 1-10 of 30 resultsSorted by cheapest first
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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 $34). Flying from Chicago to Newburgh in July is currently the most expensive (average of $102). 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 March 25, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 37% 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 March 23, 2026.

Travelers seeking maximum savings on their Chicago to Newburgh flight should consider departing on Monday 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 March 25, 2026.

The most flights from CHI to N3W are scheduled on a Tuesday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 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 Royal Jordanian (75%), Singapore Airlines (71%) and Kenya Airways (67%).

  • What are the cheapest flights from Chicago to Newburgh?

    Looking for the cheapest flight from Chicago to Newburgh? While on average our users pay $1,095, our data indicates the cheapest price to be $78. The most popular route (Chicago O'Hare Intl - New Windsor Stewart), is priced around $207.

  • 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 $34). Flying from Chicago to Newburgh in July is currently the most expensive (average of $102). 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.

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 March 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$146FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$40Average$134FlexibilityNo cancel feeOn-time65%
DeltaCheapest$84Average$263FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$85Average$202FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$138Average$281FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$148Average$313FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$163Average$309FlexibilityNo cancel feeOn-time63%

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