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$84+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

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 12/2511:43 amSWF - MDW
1 stop11h 15mMultiple Airlines
Sun 1/42:16 pmMDW - SWF
2 stops20h 28mMultiple Airlines
Deal found 12/17$602
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 12/207:50 pmSWF - MDW
1 stop14h 33mMultiple Airlines
Sun 12/2110:50 pmMDW - SWF
2 stops35h 13mMultiple Airlines
Deal found 12/16$618
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 12/278:45 pmSWF - RFD
1 stop12h 06mAllegiant Air
Tue 12/307:54 pmRFD - SWF
1 stop19h 50mAllegiant Air
Deal found 12/16$642
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.
Sun 12/2111:43 amSWF - RFD
1 stop22h 45mMultiple Airlines
Tue 12/236:50 pmRFD - SWF
1 stop14h 00mMultiple Airlines
Deal found 12/17$666
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.
Mon 12/225:28 pmSWF - MDW
1 stop16h 25mMultiple Airlines
Sat 12/276:12 amMDW - SWF
2 stops51h 35mMultiple Airlines
Deal found 12/17$699
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.
Tue 12/236:28 pmSWF - ORD
2 stops25h 11mMultiple Airlines
Sun 12/288:09 pmORD - SWF
1 stop14h 53mMultiple Airlines
Deal found 12/16$711
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 12/2111:43 amSWF - ORD
1 stop8h 19mMultiple Airlines
Sun 1/48:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Deal found 12/16$732
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.
Mon 12/228:25 pmSWF - ORD
1 stop20h 17mMultiple Airlines
Sat 12/275:08 pmORD - SWF
2 stops40h 39mMultiple Airlines
Deal found 12/17$754
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.
Tue 12/236:28 pmSWF - ORD
2 stops25h 11mMultiple Airlines
Sat 12/275:08 pmORD - SWF
1 stop15h 51mMultiple Airlines
Deal found 12/17$779
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.
Sun 12/216:28 pmSWF - ORD
2 stops31h 02mMultiple Airlines
Sun 12/285:00 amORD - SWF
1 stop28h 47mMultiple Airlines
Deal found 12/17$818
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 12/278:45 pmSWF - RFD
1 stop12h 06mAllegiant Air
Sun 12/287:24 pmRFD - SWF
1 stop13h 06mAllegiant Air
Deal found 12/16$826
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.
Sun 12/2111:43 amSWF - ORD
1 stop8h 19mMultiple Airlines
Fri 12/269:31 pmORD - SWF
2 stops21h 24mMultiple Airlines
Deal found 12/17$853

Find flight deals from Newburgh to Chicago

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

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$407
(Mytrip)

One-way from

$84
(Mytrip)

Popular in

August

Cheapest in

January

Average price

$272
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
Search Deals
From Newburgh to Chicago (CHI)
Search Deals
One-way flight from Newburgh to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($22 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 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 December 18, 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

Thu 4/2

10:29 am-11:41 pm

1 stop14h 12m

Chicago O'Hare Intl

Sat 4/4

5:38 pm-9:39 am

1 stop15h 01m

$407

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 4/2

10:29 am-11:41 pm

1 stop14h 12m

Chicago O'Hare Intl

Mon 4/6

4:00 pm-11:49 am

1 stop18h 49m

$546

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sat 12/27

8:45 pm-7:51 am

1 stop12h 06m

Chicago Greater Rockford

Tue 12/30

7:54 pm-4:44 pm

1 stop19h 50m

$642

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 4/2

8:12 pm-5:27 pm

1 stop22h 15m

Chicago Greater Rockford

Mon 4/6

6:17 pm-11:49 am

1 stop16h 32m

$699

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/2

11:57 am-12:30 am

1 stop13h 33m

Chicago O'Hare Intl

Tue 1/6

5:29 pm-5:59 pm

2 stops47h 30m

$716

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sat 1/3

8:45 pm-7:51 am

1 stop12h 06m

Chicago Greater Rockford

Sun 1/4

7:24 pm-9:30 am

1 stop13h 06m

$783

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/2

11:57 am-6:39 pm

1 stop7h 42m

Chicago O'Hare Intl

Sun 1/4

7:20 am-10:47 am

2 stops26h 27m

$835

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sat 12/27

8:45 pm-7:51 am

1 stop12h 06m

Chicago Greater Rockford

Sun 12/28

7:24 pm-9:30 am

1 stop13h 06m

$855

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sat 12/27

8:45 pm-7:51 am

1 stop12h 06m

Chicago Greater Rockford

Fri 1/2

5:40 pm-10:00 am

1 stop15h 20m

$898

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/23

11:09 am-9:03 pm

1 stop10h 54m

$88

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 34 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, May is the cheapest month in which you can book a flight from Newburgh to Chicago (average of $55). Flying from Newburgh to Chicago in July is currently the most expensive (average of $126). 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 December 18, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 42% on flights from Newburgh to Chicago by exploring options for tickets in the evening.

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 13, 2025.

Travelers seeking maximum savings on their Newburgh to Chicago flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday afternoons 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 December 18, 2025.

The most flights from N3W to CHI are scheduled on a Thursday (41 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 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 12h 06m. The distance from Newburgh to Chicago is about 772 mi.

  • What are the most popular routes from Newburgh to Chicago?

    Most travelers choose New Windsor Stewart - Chicago Greater Rockford, New Windsor Stewart - Chicago O'Hare Intl 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: China Airlines (85%), LATAM Airlines (81%), Delta( 76%).

  • What are the cheapest flights from Newburgh to Chicago?

    The cheapest flight price from Newburgh to Chicago is $45. On average you can expect to pay $557. The most popular route, (New Windsor Stewart - Chicago Greater Rockford), can usually be booked for $675.

  • 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, May is the cheapest month in which you can book a flight from Newburgh to Chicago (average of $55). Flying from Newburgh to Chicago in July is currently the most expensive (average of $126). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$203FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$186FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$87Average$229FlexibilityNo cancel feeOn-time62%
DeltaCheapest$101Average$353FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$118Average$301FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$329FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$153Average$272FlexibilityNo cancel feeOn-time63%

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