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$86+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JFK
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$220
(Kiwi.com)

One-way from

$86
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$209
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
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From Chicago (CHI) to Newburgh
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One-way flight from Chicago (CHI) to Newburgh
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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 3, 2025.

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.
Thu 12/411:44 amORD - SWF
2 stops22h 53mMultiple Airlines
Thu 12/1111:43 amSWF - ORD
1 stop26h 33mMultiple Airlines
Deal found 11/1$220
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.
Sat 12/62:26 pmORD - SWF
1 stop19h 37mMultiple Airlines
Thu 12/1111:43 amSWF - ORD
1 stop26h 33mMultiple Airlines
Deal found 11/1$230
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.
Sat 12/62:26 pmORD - SWF
1 stop19h 37mMultiple Airlines
Mon 12/812:27 pmSWF - ORD
1 stop23h 41mMultiple Airlines
Deal found 11/1$232
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.
Wed 12/38:00 amORD - SWF
2 stops26h 03mMultiple Airlines
Fri 12/512:27 pmSWF - ORD
1 stop8h 34mMultiple Airlines
Deal found 11/1$239
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.
Wed 12/38:00 amORD - SWF
2 stops26h 03mMultiple Airlines
Thu 12/1111:43 amSWF - ORD
1 stop26h 33mMultiple Airlines
Deal found 11/1$242
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.
Wed 12/38:00 amORD - SWF
2 stops26h 03mMultiple Airlines
Mon 12/812:27 pmSWF - ORD
1 stop23h 41mMultiple Airlines
Deal found 11/1$245
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.
Thu 12/44:21 pmORD - SWF
1 stop18h 16mMultiple Airlines
Mon 12/812:27 pmSWF - ORD
1 stop23h 41mMultiple Airlines
Deal found 11/1$246
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/133:26 pmORD - SWF
1 stop17h 45mMultiple Airlines
Mon 11/1712:01 pmSWF - ORD
1 stop13h 26mMultiple Airlines
Deal found 11/1$255
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/96:15 amMDW - SWF
2 stops27h 56mMultiple Airlines
Sun 11/1611:43 amSWF - MDW
1 stop21h 49mMultiple Airlines
Deal found 11/2$470
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 12/146:37 pmMDW - SWF
2 stops16h 07mMultiple Airlines
Thu 12/1811:43 amSWF - MDW
1 stop11h 15mMultiple Airlines
Deal found 10/31$637
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/226:02 pmMDW - SWF
1 stop16h 01mMultiple Airlines
Sat 11/297:02 pmSWF - MDW
2 stops22h 28mMultiple Airlines
Deal found 11/2$943

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 November 3, 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 12/4

11:44 am-11:37 am

2 stops22h 53m

New Windsor Stewart

Thu 12/11

11:43 am-1:16 pm

1 stop26h 33m

$220

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/3

8:00 am-11:03 am

2 stops26h 03m

New Windsor Stewart

Fri 12/5

12:27 pm-8:01 pm

1 stop8h 34m

$239

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/3

8:00 am-11:03 am

2 stops26h 03m

New Windsor Stewart

Thu 12/11

11:43 am-1:16 pm

1 stop26h 33m

$242

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/4

4:21 pm-11:37 am

1 stop18h 16m

New Windsor Stewart

Mon 12/8

12:27 pm-11:08 am

1 stop23h 41m

$246

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/13

3:26 pm-10:11 am

1 stop17h 45m

New Windsor Stewart

Mon 11/17

12:01 pm-12:27 am

1 stop13h 26m

$255

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/3

6:48 am-11:03 am

1 stop27h 15m

New Windsor Stewart

Mon 12/8

12:27 pm-11:08 am

1 stop23h 41m

$256

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 12/6

4:49 pm-11:03 am

2 stops17h 14m

New Windsor Stewart

Thu 12/11

11:43 am-1:16 pm

1 stop26h 33m

$270

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sun 12/14

6:37 pm-11:44 am

2 stops16h 07m

New Windsor Stewart

Thu 12/18

11:43 am-9:58 pm

1 stop11h 15m

$637

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sat 11/22

6:02 pm-11:03 am

1 stop16h 01m

New Windsor Stewart

Sat 11/29

7:02 pm-4:30 pm

2 stops22h 28m

$943

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/22

11:42 am-10:19 am

1 stop21h 37m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

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 $37). 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 November 3, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 32% 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 November 2, 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 November 3, 2025.

The most flights from CHI to N3W are scheduled on a Sunday (48 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 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 Hawaiian Airlines (100%), Kenya Airways (94%) and Etihad Airways (94%).

  • What are the cheapest flights from Chicago to Newburgh?

    Looking for the cheapest flight from Chicago to Newburgh? While on average our users pay $1,039, our data indicates the cheapest price to be $35. The most popular route (Chicago O'Hare Intl - New Windsor Stewart), is priced around $245.

  • 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 $37). 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

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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$42Average$133FlexibilityNo cancel feeOn-time65%
FrontierCheapest$42Average$164FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$92Average$232FlexibilityNo cancel feeOn-time62%
DeltaCheapest$103Average$304FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$146Average$268FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$316FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$293FlexibilityNo cancel feeOn-time63%

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