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$104+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JFK
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Chicago to Newburgh

Keep the following information in mind while searching for Chicago to Newburgh flight deals. Data was last updated September 16, 2025.

Round-trip from

$213
(Kiwi.com)

One-way from

$104
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$187
From Chicago (CHI) to Newburgh
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One-way flight from Chicago (CHI) to Newburgh
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/117:49 pmORD - SWF
1 stop21h 51mMultiple Airlines
Mon 12/1512:27 pmSWF - ORD
1 stop9h 33mMultiple Airlines
Deal found 9/14$213
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:59 pmORD - SWF
1 stop15h 42mMultiple Airlines
Mon 11/1012:01 pmSWF - ORD
1 stop9h 59mMultiple Airlines
Deal found 9/15$214
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:44 pmORD - SWF
1 stop15h 37mMultiple Airlines
Mon 10/611:01 amSWF - ORD
1 stop13h 44mMultiple Airlines
Deal found 9/15$219
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/125:05 amORD - SWF
1 stop28h 06mMultiple Airlines
Sun 10/1911:43 amSWF - ORD
2 stops24h 35mMultiple Airlines
Deal found 9/14$320
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 12/1010:18 amORD - SWF
1 stop23h 45mMultiple Airlines
Thu 12/116:28 pmSWF - ORD
2 stops27h 32mMultiple Airlines
Deal found 9/15$362
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/38:56 pmORD - SWF
2 stops37h 07mMultiple Airlines
Fri 10/1011:41 amSWF - ORD
1 stop24h 09mMultiple Airlines
Deal found 9/13$373
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/16:30 amORD - SWF
1 stop27h 33mMultiple Airlines
Sun 10/511:43 amSWF - ORD
1 stop10h 50mMultiple Airlines
Deal found 9/15$387
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/125:20 amMDW - SWF
1 stop12h 01mMultiple Airlines
Sun 10/1911:43 amSWF - MDW
2 stops21h 48mMultiple Airlines
Deal found 9/14$427
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/47:49 pmORD - SWF
2 stops14h 55mMultiple Airlines
Sun 12/711:43 amSWF - ORD
1 stop10h 40mMultiple Airlines
Deal found 9/14$452
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/257:43 pmORD - SWF
1 stop14h 20mMultiple Airlines
Mon 10/2712:24 pmSWF - ORD
2 stops10h 09mMultiple Airlines
Deal found 9/15$520
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 11/218:41 pmMDW - SWF
2 stops37h 22mMultiple Airlines
Fri 11/287:28 pmSWF - MDW
1 stop15h 04mMultiple Airlines
Deal found 9/16$817

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 September 16, 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 12/11

7:49 pm-6:40 pm

1 stop21h 51m

New Windsor Stewart

Mon 12/15

12:27 pm-9:00 pm

1 stop9h 33m

$213

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/6

5:59 pm-10:41 am

1 stop15h 42m

New Windsor Stewart

Mon 11/10

12:01 pm-9:00 pm

1 stop9h 59m

$214

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/2

6:44 pm-11:21 am

1 stop15h 37m

New Windsor Stewart

Mon 10/6

11:01 am-11:45 pm

1 stop13h 44m

$219

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 10/12

5:05 am-10:11 am

1 stop28h 06m

New Windsor Stewart

Sun 10/19

11:43 am-11:18 am

2 stops24h 35m

$320

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/10

10:18 am-11:03 am

1 stop23h 45m

New Windsor Stewart

Thu 12/11

6:28 pm-9:00 pm

2 stops27h 32m

$362

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 10/1

6:30 am-11:03 am

1 stop27h 33m

New Windsor Stewart

Sun 10/5

11:43 am-9:33 pm

1 stop10h 50m

$387

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sun 10/12

5:20 am-6:21 pm

1 stop12h 01m

New Windsor Stewart

Sun 10/19

11:43 am-8:31 am

2 stops21h 48m

$427

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/4

7:49 pm-11:44 am

2 stops14h 55m

New Windsor Stewart

Sun 12/7

11:43 am-9:23 pm

1 stop10h 40m

$452

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 11/21

8:41 pm-11:03 am

2 stops37h 22m

New Windsor Stewart

Fri 11/28

7:28 pm-9:32 am

1 stop15h 04m

$817

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 10/5

7:43 pm-10:11 am

1 stop13h 28m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 27 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 $236). Flying from Chicago to Newburgh in June is currently the most expensive (average of $313). 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 September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Newburgh as you normally would.

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 16, 2024.

Travelers seeking maximum savings on their Chicago to Newburgh flight should consider departing on Friday afternoons when fares are most often at their lowest. Friday afternoons 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 September 16, 2025.

The most flights from CHI to N3W are scheduled on a Monday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (31 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 (100%), LATAM Airlines (88%) and Royal Air Maroc (86%).

  • What are the cheapest flights from Chicago to Newburgh?

    Looking for the cheapest flight from Chicago to Newburgh? While on average our users pay $723, our data indicates the cheapest price to be $77. The most popular route (Chicago O'Hare Intl - New Windsor Stewart), is priced around $213.

  • 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 $236). Flying from Chicago to Newburgh in June is currently the most expensive (average of $313). 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

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$202FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$60Average$140FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$73Average$233FlexibilityNo cancel feeOn-time62%
DeltaCheapest$105Average$307FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$147Average$312FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$282FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$162Average$289FlexibilityNo cancel feeOn-time63%

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