HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$123+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Newburgh to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/2312:05 pm
SWF
-
ORD
2 stops36h 08m
Multiple Airlines
Wed 5/275:11 pm
ORD
-
SWF
1 stop14h 47m
Multiple Airlines
Deal found 5/4$262
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 8/277:31 pm
SWF
-
ORD
1 stop17h 54m
Multiple Airlines
Tue 9/11:50 pm
ORD
-
SWF
2 stops20h 35m
Multiple Airlines
Deal found 5/3$311
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 8/231:00 pm
SWF
-
ORD
1 stop24h 25m
Multiple Airlines
Tue 9/11:50 pm
ORD
-
SWF
2 stops20h 35m
Multiple Airlines
Deal found 5/3$314
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 7/511:45 am
SWF
-
RFD
1 stop21h 04m
Allegiant Air
Sat 7/1110:05 am
RFD
-
SWF
1 stop6h 49m
Allegiant Air
Deal found 5/3$334
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Mon 5/1811:45 am
SWF
-
ORD
1 stop12h 28m
Multiple Airlines
Wed 5/275:11 pm
ORD
-
SWF
1 stop14h 47m
Multiple Airlines
Deal found 5/2$339
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 7/210:28 am
SWF
-
ORD
2 stops22h 35m
Multiple Airlines
Wed 7/88:05 am
ORD
-
SWF
1 stop24h 33m
Multiple Airlines
Deal found 5/3$343
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 9/212:05 pm
SWF
-
ORD
2 stops12h 09m
Multiple Airlines
Sun 9/67:55 am
ORD
-
SWF
1 stop9h 45m
Multiple Airlines
Deal found 5/5$346
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 6/2810:28 am
SWF
-
ORD
2 stops22h 35m
Multiple Airlines
Wed 7/158:05 am
ORD
-
SWF
1 stop24h 33m
Multiple Airlines
Deal found 5/3$351
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 8/201:00 pm
SWF
-
ORD
1 stop24h 25m
Multiple Airlines
Thu 8/277:55 am
ORD
-
SWF
1 stop9h 46m
Multiple Airlines
Deal found 5/3$355
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 7/37:41 pm
SWF
-
RFD
1 stop21h 38m
Allegiant Air
Sat 7/1110:05 am
RFD
-
SWF
1 stop6h 49m
Allegiant Air
Deal found 5/3$356
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 7/511:45 am
SWF
-
RFD
1 stop21h 04m
Allegiant Air
Fri 7/107:50 pm
RFD
-
SWF
1 stop21h 04m
Allegiant Air
Deal found 5/3$358
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Mon 5/1811:45 am
SWF
-
ORD
1 stop12h 28m
Multiple Airlines
Tue 5/266:55 am
ORD
-
SWF
2 stops27h 30m
Multiple Airlines
Deal found 5/2$364

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 May 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$262
(Kiwi.com)

One-way from

$123
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$266
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 May 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 May 6, 2026.
Use the filters below to find and compare flights from Newburgh to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sat 5/23

12:05 pm-6:24 am

2 stops43h 19m

Chicago O'Hare Intl

Wed 5/27

5:11 pm-8:58 am

1 stop14h 47m

$368

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 7/30

10:28 am-12:25 pm

1 stop26h 57m

Chicago O'Hare Intl

Sat 8/1

5:13 pm-8:58 am

1 stop14h 45m

$377

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Fri 7/3

7:41 pm-4:19 pm

1 stop21h 38m

Chicago Greater Rockford

Fri 7/10

7:50 pm-5:54 pm

1 stop21h 04m

$380

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 6/14

6:33 pm-12:24 pm

2 stops18h 51m

Chicago O'Hare Intl

Sat 6/20

7:07 pm-9:38 am

1 stop13h 31m

$391

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 6/21

10:28 am-8:03 am

2 stops22h 35m

Chicago O'Hare Intl

Tue 6/23

4:59 pm-7:06 pm

1 stop25h 07m

$408

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Wed 7/29

7:46 pm-11:05 pm

1 stop28h 19m

Chicago O'Hare Intl

Sat 8/1

5:13 pm-8:58 am

1 stop14h 45m

$409

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Fri 7/3

7:41 pm-4:19 pm

1 stop21h 38m

Chicago Greater Rockford

Wed 7/8

10:03 am-6:56 pm

1 stop7h 53m

$415

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sun 5/31

8:10 pm-7:45 am

1 stop12h 35m

Chicago Greater Rockford

Fri 6/5

7:53 pm-11:25 am

2 stops14h 32m

$423

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 7/2

11:45 am-7:49 am

1 stop21h 04m

Chicago Greater Rockford

Fri 7/10

7:50 pm-5:54 pm

1 stop21h 04m

$424

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 5/18

11:45 am-11:13 pm

1 stop12h 28m

Chicago O'Hare Intl

Mon 5/25

5:11 pm-11:25 am

2 stops41h 14m

$424

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 53 resultsSorted by cheapest first
1
2
3
...
6

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 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 May 6, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 31% 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 May 2, 2026.

Travelers seeking maximum savings on their Newburgh to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Thursday 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 May 6, 2026.

The most flights from N3W to CHI are scheduled on a Tuesday (44 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 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 21h 38m. 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: Atlas Air (100%), Malaysia Airlines (100%), Gulf Air( 83%).

  • What are the cheapest flights from Newburgh to Chicago?

    The cheapest flight price from Newburgh to Chicago is $88. On average you can expect to pay $441. The most popular route, (New Windsor Stewart - Chicago O'Hare Intl), can usually be booked for $291.

  • 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 May 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$47Average$166FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$61Average$151FlexibilityNo cancel feeOn-time65%
DeltaCheapest$74Average$328FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$88Average$234FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$139Average$310FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$339FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$164Average$302FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.