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$85+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JFK
Mar 8 — Mar 151
Sun 3/8
Sun 3/15
1 adult, Economy
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Cheap 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 February 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/144:43 pm
ORD
-
SWF
1 stop17h 09m
Multiple Airlines
Sun 2/2211:48 am
SWF
-
ORD
1 stop30h 58m
Multiple Airlines
Deal found 2/4$310
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Wed 2/184:43 pm
ORD
-
SWF
1 stop17h 49m
Multiple Airlines
Sun 2/2211:52 am
SWF
-
ORD
2 stops21h 02m
Multiple Airlines
Deal found 2/3$366
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 6/143:49 pm
ORD
-
SWF
1 stop16h 00m
Multiple Airlines
Thu 6/1810:28 am
SWF
-
ORD
1 stop10h 20m
Multiple Airlines
Deal found 2/6$384
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/209:07 pm
ORD
-
SWF
1 stop14h 32m
Multiple Airlines
Mon 2/2312:11 pm
SWF
-
ORD
2 stops32h 36m
Multiple Airlines
Deal found 2/3$401
This Kiwi.com deal was found by Cheapflights users on 2/5. 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.
Sat 2/148:00 am
MDW
-
SWF
1 stop26h 08m
Multiple Airlines
Sun 2/2211:52 am
SWF
-
MDW
2 stops26h 16m
Multiple Airlines
Deal found 2/5$404
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 6/275:32 pm
ORD
-
SWF
1 stop15h 06m
Multiple Airlines
Tue 7/711:48 am
SWF
-
ORD
1 stop21h 11m
Multiple Airlines
Deal found 2/4$468
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/207:30 am
MDW
-
SWF
1 stop28h 09m
Multiple Airlines
Mon 2/2312:11 pm
SWF
-
MDW
2 stops9h 16m
Multiple Airlines
Deal found 2/3$483
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Fri 2/1310:44 am
ORD
-
SWF
1 stop24h 55m
Multiple Airlines
Mon 2/1612:11 pm
SWF
-
ORD
2 stops34h 02m
Multiple Airlines
Deal found 2/4$507
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 6/47:41 pm
MDW
-
SWF
2 stops14h 54m
Multiple Airlines
Sun 6/79:38 am
SWF
-
MDW
1 stop9h 58m
Multiple Airlines
Deal found 2/6$604

Find flight deals from Chicago to Newburgh

Keep the following information in mind while searching for Chicago to Newburgh flight deals. Data was last updated February 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$366
(Kiwi.com)

One-way from

$85
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$177
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
Search Deals
From Chicago (CHI) to Newburgh
Search Deals
One-way flight from Chicago (CHI) to Newburgh
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 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 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 February 6, 2026.
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

Wed 2/18

4:43 pm-11:32 am

1 stop17h 49m

New Windsor Stewart

Sun 2/22

11:52 am-7:54 am

2 stops21h 02m

$366

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 2/20

9:07 pm-12:39 pm

1 stop14h 32m

New Windsor Stewart

Mon 2/23

12:11 pm-7:47 pm

2 stops32h 36m

$401

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 6/14

3:49 pm-11:35 am

2 stops18h 46m

New Windsor Stewart

Thu 6/18

10:28 am-7:48 pm

1 stop10h 20m

$444

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 6/27

5:32 pm-9:38 am

1 stop15h 06m

New Windsor Stewart

Tue 7/7

11:48 am-7:59 am

1 stop21h 11m

$468

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 2/20

7:30 am-12:39 pm

1 stop28h 09m

New Windsor Stewart

Mon 2/23

12:11 pm-8:27 pm

2 stops9h 16m

$483

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 7/18

4:10 pm-8:58 am

1 stop15h 48m

New Windsor Stewart

Sat 7/25

12:05 pm-10:08 pm

2 stops11h 03m

$487

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 6/4

3:49 pm-11:35 am

2 stops18h 46m

New Windsor Stewart

Sun 6/7

10:28 am-7:48 pm

1 stop10h 20m

$549

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 6/24

11:21 am-8:58 am

2 stops20h 37m

New Windsor Stewart

Sat 6/27

8:00 pm-7:59 am

1 stop12h 59m

$559

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Mon 6/29

12:41 pm-11:08 am

1 stop21h 27m

New Windsor Stewart

Mon 7/6

5:49 pm-7:59 am

2 stops39h 10m

$582

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 6/4

7:41 pm-11:35 am

2 stops14h 54m

New Windsor Stewart

Sun 6/7

9:38 am-6:36 pm

1 stop9h 58m

$604

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 32 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 $103). 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 February 6, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 35% 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 January 31, 2026.

Travelers seeking maximum savings on their Chicago to Newburgh flight should consider departing on Tuesday afternoons 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 February 6, 2026.

The most flights from CHI to N3W are scheduled on a Friday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 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 Qantas Airways (100%), Iberia (80%) and GOL (75%).

  • What are the cheapest flights from Chicago to Newburgh?

    Looking for the cheapest flight from Chicago to Newburgh? While on average our users pay $751, our data indicates the cheapest price to be $35. The most popular route (Chicago O'Hare Intl - New Windsor Stewart), is priced around $401.

  • 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 $103). 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 February 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$151FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$40Average$128FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$199FlexibilityNo cancel feeOn-time62%
DeltaCheapest$87Average$239FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$138Average$278FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$148Average$305FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$289FlexibilityNo cancel feeOn-time63%

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