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$108+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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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 septiembre 16, 2025.

Round-trip from

$228
(Mytrip)

One-way from

$108
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$213
From Newburgh to Chicago (CHI)
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One-way flight from Newburgh to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($17 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 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 septiembre 16, 2025.

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.
vie. 10/312:11 pmSWF - ORD
1 stop11h 37mMultiple Airlines
dom. 10/57:43 pmORD - SWF
1 stop13h 28mMultiple Airlines
Deal found 9/15$228
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.
vie. 10/312:11 pmSWF - ORD
1 stop23h 41mMultiple Airlines
dom. 10/125:05 amORD - SWF
1 stop28h 06mMultiple Airlines
Deal found 9/14$231
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.
lun. 10/2011:01 amSWF - ORD
1 stop13h 44mMultiple Airlines
vie. 10/249:54 pmORD - SWF
2 stops36h 09mMultiple Airlines
Deal found 9/15$289
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.
jue. 10/911:43 amSWF - ORD
1 stop20h 51mMultiple Airlines
dom. 10/125:05 amORD - SWF
1 stop28h 06mMultiple Airlines
Deal found 9/14$291
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.
jue. 10/1611:43 amSWF - ORD
1 stop20h 51mMultiple Airlines
lun. 10/275:05 amORD - SWF
1 stop8h 06mMultiple Airlines
Deal found 9/15$297
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.
jue. 10/27:11 pmSWF - MDW
1 stop18h 33mMultiple Airlines
dom. 10/56:21 amMDW - SWF
1 stop11h 00mMultiple Airlines
Deal found 9/16$328
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/306:16 pmSWF - MDW
2 stops23h 46mAllegiant Air
lun. 11/32:45 pmMDW - SWF
2 stops18h 41mAllegiant Air
Deal found 9/14$404
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.
jue. 10/167:11 pmSWF - RFD
1 stop13h 53mAllegiant Air
lun. 10/278:44 amRFD - SWF
1 stop24h 42mAllegiant Air
Deal found 9/15$417
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.
vie. 10/312:11 pmSWF - MDW
2 stops12h 30mMultiple Airlines
dom. 10/125:20 amMDW - SWF
1 stop12h 01mMultiple Airlines
Deal found 9/14$419
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.
lun. 10/1311:01 amSWF - ORD
1 stop13h 44mMultiple Airlines
vie. 10/179:54 pmORD - SWF
2 stops36h 09mMultiple Airlines
Deal found 9/15$430
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/27:11 pmSWF - MDW
2 stops22h 23mAllegiant Air
lun. 10/612:08 pmMDW - SWF
2 stops21h 18mAllegiant Air
Deal found 9/16$470
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.
vie. 10/1012:24 pmSWF - ORD
2 stops10h 09mMultiple Airlines
sáb. 10/117:43 pmORD - SWF
1 stop14h 20mMultiple Airlines
Deal found 9/15$515

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 septiembre 16, 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

vie. 10/3

12:11 pm-10:52 am

1 stop23h 41m

Chicago O'Hare Intl

dom. 10/12

5:05 am-10:11 am

1 stop28h 06m

$231

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

lun. 10/20

11:01 am-11:45 pm

1 stop13h 44m

Chicago O'Hare Intl

vie. 10/24

9:54 pm-11:03 am

2 stops36h 09m

$289

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

jue. 10/9

11:43 am-7:34 am

1 stop20h 51m

Chicago O'Hare Intl

dom. 10/12

5:05 am-10:11 am

1 stop28h 06m

$291

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

jue. 10/16

11:43 am-7:34 am

1 stop20h 51m

Chicago O'Hare Intl

lun. 10/27

5:05 am-2:11 pm

1 stop8h 06m

$297

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

jue. 10/2

7:11 pm-12:44 pm

1 stop18h 33m

Chicago Midway

dom. 10/5

6:21 am-6:21 pm

1 stop11h 00m

$328

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

jue. 10/30

6:16 pm-5:02 pm

2 stops23h 46m

Chicago Midway

lun. 11/3

2:45 pm-10:26 am

2 stops18h 41m

$404

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

jue. 10/16

7:11 pm-8:04 am

1 stop13h 53m

Chicago Greater Rockford

lun. 10/27

8:44 am-10:26 am

1 stop24h 42m

$417

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

vie. 10/3

12:11 pm-11:41 pm

2 stops12h 30m

Chicago Midway

dom. 10/12

5:20 am-6:21 pm

1 stop12h 01m

$419

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

lun. 10/13

11:01 am-11:45 pm

1 stop13h 44m

Chicago O'Hare Intl

vie. 10/17

9:54 pm-11:03 am

2 stops36h 09m

$430

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

jue. 10/2

7:11 pm-4:34 pm

2 stops22h 23m

Chicago Midway

lun. 10/6

12:08 pm-10:26 am

2 stops21h 18m

$470

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 38 results
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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, August is the cheapest month in which you can book a flight from Newburgh to Chicago (average of $245). Flying from Newburgh to Chicago in March is currently the most expensive (average of $321). 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 septiembre 16, 2025.

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

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. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Newburgh to Chicago

Explore weekly flight availability from Newburgh to Chicago. 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 septiembre 16, 2025.

The most flights from N3W to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 on average).

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 23h 46m. The distance from Newburgh to Chicago is about 704 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 Greater Rockford or New Windsor Stewart - Chicago Midway 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: LATAM Airlines (93%), China Airlines (92%), Republic Airways( 80%).

  • What are the cheapest flights from Newburgh to Chicago?

    The cheapest flight price from Newburgh to Chicago is $64. On average you can expect to pay $411. The most popular route, (New Windsor Stewart - Chicago O'Hare Intl), can usually be booked for $228.

  • 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, August is the cheapest month in which you can book a flight from Newburgh to Chicago (average of $245). Flying from Newburgh to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

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Alternative routes for Newburgh to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$67Average$202FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$245FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$84Average$228FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$96Average$347FlexibilityNo cancel feeOn-time69%
DeltaCheapest$101Average$353FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$147Average$324FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$154Average$263FlexibilityNo cancel feeOn-time63%

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