$103+ 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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Jul 20 — Jul 271
Round-trip
1 adult, Economy
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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
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Cheapest flights from Newburgh to ChicagoExplore 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 June 20, 2026.
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 June 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/18. 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
Sun 8/308:05 am
ORD
- SWF
1 stop9h 36m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 7/2610:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Sat 8/18:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Thu 7/3010:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Sat 8/18:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/2511:48 am
SWF
- ORD
1 stop12h 26m
Multiple Airlines
Sun 8/308:05 am
ORD
- SWF
1 stop9h 36m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 7/1610:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Sat 7/188:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Thu 8/277:31 pm
SWF
- ORD
1 stop17h 54m
Multiple Airlines
Mon 8/315:30 pm
ORD
- SWF
1 stop16h 38m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 9/37:30 pm
SWF
- ORD
1 stop18h 30m
Multiple Airlines
Sat 9/57:44 pm
ORD
- SWF
1 stop13h 09m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/1610:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Wed 8/197:44 pm
ORD
- SWF
1 stop13h 09m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/2610:28 am
SWF
- ORD
2 stops22h 25m
Multiple Airlines
Wed 7/298:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Fri 7/177:41 pm
SWF
- RFD
1 stop21h 38m
Allegiant Air
Fri 7/247:50 pm
RFD
- SWF
1 stop21h 04m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 10/86:15 pm
SWF
- RFD
1 stop25h 57m
Allegiant Air
Mon 10/126:13 pm
RFD
- SWF
1 stop16h 35m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 11/2011:29 am
SWF
- RFD
1 stop6h 49m
Allegiant Air
Mon 11/235:07 pm
RFD
- SWF
1 stop24h 05m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$549
Best flights from Newburgh to ChicagoDiscover carefully curated flight deals from Newburgh to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
Discover carefully curated flight deals from Newburgh to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 8/277:31 pm
SWF
- ORD
1 stop18h 29m
Multiple Airlines
Sun 8/307:55 am
ORD
- SWF
1 stop9h 46m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Fri 7/177:41 pm
SWF
- RFD
1 stop21h 38m
Allegiant Air
Fri 7/247:50 pm
RFD
- SWF
1 stop21h 04m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Thu 7/3010:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Sat 8/18:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/2511:48 am
SWF
- ORD
1 stop12h 26m
Multiple Airlines
Sun 8/308:05 am
ORD
- SWF
1 stop9h 36m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Thu 8/277:31 pm
SWF
- ORD
1 stop17h 54m
Multiple Airlines
Mon 8/315:30 pm
ORD
- SWF
1 stop16h 38m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 10/86:15 pm
SWF
- RFD
1 stop25h 57m
Allegiant Air
Mon 10/126:13 pm
RFD
- SWF
1 stop16h 35m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 9/37:30 pm
SWF
- ORD
1 stop17h 55m
Multiple Airlines
Sat 9/55:30 pm
ORD
- SWF
1 stop15h 23m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/1610:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Sat 7/188:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/1610:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Thu 8/207:44 pm
ORD
- SWF
2 stops14h 53m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Fri 11/2011:29 am
SWF
- RFD
1 stop6h 49m
Allegiant Air
Mon 11/235:07 pm
RFD
- SWF
1 stop24h 05m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 9/1010:56 am
SWF
- ORD
1 stop13h 59m
Multiple Airlines
Sun 9/134:49 pm
ORD
- SWF
1 stop16h 42m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/2610:28 am
SWF
- ORD
2 stops22h 25m
Multiple Airlines
Sat 8/18:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$367
Last-minute flights from Newburgh to ChicagoDiscover last-minute flight deals from Newburgh to Chicago. Data last updated June 20, 2026 and is based on user searches.
Discover last-minute flight deals from Newburgh to Chicago. Data last updated June 20, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 6/218:04 pm
SWF
- RFD
1 stop12h 41m
Allegiant Air
Wed 6/2410:07 am
RFD
- SWF
1 stop7h 59m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$558
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Tue 6/236:19 pm
SWF
- RFD
1 stop22h 33m
Allegiant Air
Sat 6/2710:07 am
RFD
- SWF
1 stop8h 03m
Allegiant Air
Deal found 6/15![Allegiant Air logo]()
$610
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 6/258:04 pm
SWF
- RFD
1 stop12h 41m
Multiple Airlines
Mon 6/297:48 pm
RFD
- SWF
1 stop14h 20m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$552
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 6/258:04 pm
SWF
- RFD
1 stop12h 41m
Allegiant Air
Sat 6/2710:07 am
RFD
- SWF
1 stop8h 03m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$590
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 6/288:04 pm
SWF
- RFD
1 stop12h 41m
Allegiant Air
Fri 7/37:50 pm
RFD
- SWF
1 stop21h 04m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$602
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 7/1610:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Sat 7/188:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/1610:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Fri 7/248:58 pm
ORD
- SWF
2 stops35h 40m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 7/1610:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Thu 7/235:13 pm
ORD
- SWF
2 stops17h 24m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$444
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Fri 7/177:41 pm
SWF
- RFD
1 stop21h 38m
Allegiant Air
Fri 7/247:50 pm
RFD
- SWF
1 stop21h 04m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 7/2610:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Sat 8/18:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/2610:28 am
SWF
- ORD
2 stops22h 25m
Multiple Airlines
Wed 7/298:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Thu 7/3010:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Sat 8/18:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$269
One-way flights from Newburgh to ChicagoSearch for one-way flight options from Newburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
Search for one-way flight options from Newburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 stop26h 47m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 8/201:00 pm
SWF
- ORD
1 stop24h 25m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/1310:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 8/231:00 pm
SWF
- ORD
1 stop24h 25m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 10/1811:53 am
SWF
- ORD
1 stop28h 33m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 8/210:28 am
SWF
- ORD
1 stop26h 47m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Fri 10/211:19 am
SWF
- RFD
1 stop24h 33m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 9/46:32 pm
SWF
- RFD
1 stop18h 19m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 9/2411:13 am
SWF
- RFD
1 stop30h 02m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/1310:28 am
SWF
- MDW
2 stops29h 31m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Fri 10/911:19 am
SWF
- RFD
1 stop29h 44m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 8/1610:28 am
SWF
- MDW
2 stops29h 31m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$157
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 June 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $223 (Kiwi.com) |
One-way from | $103 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $322 |
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 June 20, 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
Cheapest round-trip
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Thu 8/27
7:31 pm-1:00 pm
1 stop18h 29m
Chicago O'Hare Intl
Sun 8/30
7:55 am-6:41 pm
1 stop9h 46m
$230
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Thu 7/30
10:28 am-12:15 pm
1 stop26h 47m
Chicago O'Hare Intl
Sat 8/1
8:05 am-9:38 am
1 stop24h 33m
$269
Quickest round-trip
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Tue 8/25
11:48 am-11:14 pm
1 stop12h 26m
Chicago O'Hare Intl
Sun 8/30
8:05 am-6:41 pm
1 stop9h 36m
$276
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Thu 8/27
7:31 pm-12:25 pm
1 stop17h 54m
Chicago O'Hare Intl
Mon 8/31
5:30 pm-11:08 am
1 stop16h 38m
$302
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Thu 9/3
7:30 pm-12:25 pm
1 stop17h 55m
Chicago O'Hare Intl
Sat 9/5
5:30 pm-9:53 am
1 stop15h 23m
$312
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Thu 7/16
10:28 am-12:15 pm
1 stop26h 47m
Chicago O'Hare Intl
Sat 7/18
8:05 am-9:38 am
1 stop24h 33m
$317
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Sun 8/16
10:28 am-12:15 pm
1 stop26h 47m
Chicago O'Hare Intl
Thu 8/20
7:44 pm-11:37 am
2 stops14h 53m
$343
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Thu 9/10
10:56 am-11:55 pm
1 stop13h 59m
Chicago O'Hare Intl
Sun 9/13
4:49 pm-10:31 am
1 stop16h 42m
$359
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Sun 7/26
10:28 am-7:53 am
2 stops22h 25m
Chicago O'Hare Intl
Sat 8/1
8:05 am-9:38 am
1 stop24h 33m
$367
New WindsorChicago
SWF - RFD
SWFRFD
New Windsor Stewart
Fri 7/17
7:41 pm-4:19 pm
1 stop21h 38m
Chicago Greater Rockford
Fri 7/24
7:50 pm-5:54 pm
1 stop21h 04m
$400
Showing 1-10 of 42 resultsSorted by cheapest first
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.
SWF-ORD
SWF-RFD
SWF-MDW
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
N3W-CHI
SWF-ORD
SWF-RFD
SWF-MDW
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 June 20, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 29% on flights from Newburgh to Chicago by exploring options for tickets in the evening.
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 June 20, 2026.
The most flights from N3W to CHI are scheduled on a Thursday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 on average).
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 June 13, 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.
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
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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.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 20, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Newburgh to Chicago by cabin class
Find flights from Newburgh to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Newburgh and Chicago flights
Browse other Newburgh and Chicago flight options. Last updated on June 20, 2026.
Popular flight searches
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Newburgh to Chicago flights
Consider these flights traveling from Newburgh to Chicago.
Top 6 airlines flying from Newburgh to Chicago
Discover the top 6 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 June 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$39 | Average$166 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$74 | Average$332 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$89 | Average$245 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$147 | Average$320 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$347 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$164 | Average$313 | FlexibilityNo cancel fee | On-time63% |