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$85+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Mar 4 — Mar 111
Wed 3/4
Wed 3/11
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 February 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/30. 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 4/2311:45 am
SWF
-
ORD
1 stop10h 32m
Multiple Airlines
Tue 4/287:20 pm
ORD
-
SWF
2 stops38h 35m
Multiple Airlines
Deal found 1/30$281
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/511:48 am
SWF
-
ORD
1 stop8h 53m
Multiple Airlines
Tue 2/106:07 pm
ORD
-
SWF
2 stops39h 45m
Multiple Airlines
Deal found 2/1$365
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Wed 2/185:46 pm
SWF
-
ORD
1 stop18h 00m
Multiple Airlines
Thu 2/193:40 pm
ORD
-
SWF
2 stops17h 34m
Multiple Airlines
Deal found 2/2$391
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Thu 2/1912:22 pm
SWF
-
ORD
1 stop9h 51m
Multiple Airlines
Sun 2/2212:44 pm
ORD
-
SWF
2 stops21h 47m
Multiple Airlines
Deal found 1/31$422
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/115:46 pm
SWF
-
ORD
1 stop18h 00m
Multiple Airlines
Thu 2/124:42 pm
ORD
-
SWF
2 stops16h 32m
Multiple Airlines
Deal found 2/1$476
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 7/3010:28 am
SWF
-
ORD
1 stop14h 13m
Multiple Airlines
Mon 8/312:41 pm
ORD
-
SWF
1 stop21h 27m
Multiple Airlines
Deal found 2/1$480
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Thu 6/259:38 am
SWF
-
ORD
1 stop13h 30m
Multiple Airlines
Mon 6/294:10 pm
ORD
-
SWF
1 stop17h 58m
Multiple Airlines
Deal found 1/31$501
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Fri 7/107:41 pm
SWF
-
RFD
1 stop21h 38m
Multiple Airlines
Thu 7/1611:27 am
RFD
-
SWF
2 stops23h 08m
Multiple Airlines
Deal found 1/31$566
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 6/265:55 pm
SWF
-
RFD
2 stops41h 42m
Multiple Airlines
Wed 7/14:47 pm
RFD
-
SWF
1 stop17h 08m
Multiple Airlines
Deal found 2/1$584
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 7/3011:45 am
SWF
-
RFD
1 stop21h 04m
Multiple Airlines
Mon 8/37:50 pm
RFD
-
SWF
1 stop14h 18m
Multiple Airlines
Deal found 2/1$607
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Fri 3/67:36 pm
SWF
-
RFD
1 stop14h 28m
Allegiant Air
Sun 3/87:39 pm
RFD
-
SWF
1 stop22h 07m
Allegiant Air
Deal found 2/2$714
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 6/267:28 pm
SWF
-
RFD
1 stop21h 57m
Allegiant Air
Wed 7/14:47 pm
RFD
-
SWF
1 stop17h 08m
Allegiant Air
Deal found 2/1$716

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 February 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(Kiwi.com)

One-way from

$85
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$186
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
Search Deals
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. 9% potential increase in price ($24 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 February 2026
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 February 2, 2026.
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 4/23

11:45 am-9:17 pm

1 stop10h 32m

Chicago O'Hare Intl

Tue 4/28

7:20 pm-10:55 am

2 stops38h 35m

$281

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Wed 2/18

5:46 pm-10:46 am

1 stop18h 00m

Chicago O'Hare Intl

Thu 2/19

3:40 pm-10:14 am

2 stops17h 34m

$391

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Wed 7/29

7:46 pm-7:59 am

1 stop13h 13m

Chicago O'Hare Intl

Sat 8/1

5:32 pm-9:38 am

1 stop15h 06m

$422

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 2/19

12:22 pm-9:13 pm

1 stop9h 51m

Chicago O'Hare Intl

Sun 2/22

12:44 pm-11:31 am

2 stops21h 47m

$422

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 7/30

10:28 am-11:41 pm

1 stop14h 13m

Chicago O'Hare Intl

Mon 8/3

12:41 pm-11:08 am

1 stop21h 27m

$480

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 6/25

9:38 am-10:08 pm

1 stop13h 30m

Chicago O'Hare Intl

Mon 6/29

4:10 pm-11:08 am

1 stop17h 58m

$501

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Fri 7/10

7:41 pm-4:19 pm

1 stop21h 38m

Chicago Greater Rockford

Thu 7/16

11:27 am-11:35 am

2 stops23h 08m

$566

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Fri 6/26

5:55 pm-10:37 am

2 stops41h 42m

Chicago Greater Rockford

Wed 7/1

4:47 pm-10:55 am

1 stop17h 08m

$584

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 7/30

11:45 am-7:49 am

1 stop21h 04m

Chicago Greater Rockford

Mon 8/3

7:50 pm-11:08 am

1 stop14h 18m

$607

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Fri 3/6

7:36 pm-9:04 am

1 stop14h 28m

Chicago Greater Rockford

Sun 3/8

7:39 pm-6:46 pm

1 stop22h 07m

$714

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

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, December is the cheapest month in which you can book a flight from Newburgh to Chicago (average of $48). Flying from Newburgh to Chicago in July is currently the most expensive (average of $119). 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 February 2, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 33% 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 January 31, 2026.

Travelers seeking maximum savings on their Newburgh to Chicago flight should consider departing on Tuesday at noon 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 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 February 2, 2026.

The most flights from N3W to CHI are scheduled on a Friday (44 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (33 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 14h 28m. 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 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: SAUDIA (75%), WestJet (74%), Endeavor Airlines( 71%).

  • What are the cheapest flights from Newburgh to Chicago?

    The cheapest flight price from Newburgh to Chicago is $40. On average you can expect to pay $602. The most popular route, (New Windsor Stewart - Chicago O'Hare Intl), can usually be booked for $281.

  • 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, December is the cheapest month in which you can book a flight from Newburgh to Chicago (average of $48). Flying from Newburgh to Chicago in July is currently the most expensive (average of $119). 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 February 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$184FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$56Average$148FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$74Average$222FlexibilityNo cancel feeOn-time62%
DeltaCheapest$79Average$336FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$140Average$297FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$156Average$332FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$158Average$274FlexibilityNo cancel feeOn-time63%

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