$122+ Cheap flights from Newburgh, NY to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Oct 8 — Oct 151
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 September 8, 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 September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 11/226:48 pm -
1 stop18h 50m
Thu 12/35:00 am -
1 stop11h 59m
Deal found 9/7![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 12/66:49 pm -
1 stop19h 01m
Thu 12/105:00 am -
1 stop11h 59m
Deal found 9/3![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Thu 10/1510:18 am -
1 stop30h 12m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/5![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Sun 10/1811:53 am -
1 stop28h 37m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/4![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/810:18 am -
1 stop30h 12m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/7![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/196:48 pm -
1 stop18h 50m
Mon 11/235:01 am -
1 stop28h 08m
Deal found 9/8![Multiple Airlines logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/1012:39 pm -
2 stops45h 42m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/4![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 10/197:01 pm -
1 stop13h 50m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/3![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/1510:18 am -
1 stop30h 12m
Tue 10/207:44 pm -
2 stops37h 04m
Deal found 9/3![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 10/1510:56 am -
1 stop22h 03m
Mon 10/1910:39 am -
1 stop6h 32m
Deal found 9/4![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 10/224:59 pm -
1 stop27h 07m
Sun 10/255:35 pm -
1 stop16h 04m
Deal found 9/4![Allegiant Air logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Fri 12/2510:40 am -
1 stop7h 36m
Thu 1/75:06 pm -
1 stop14h 45m
Deal found 9/5![Allegiant Air logo]()
$419
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 September 8, 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 September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 12/66:49 pm -
1 stop19h 01m
Thu 12/105:00 am -
1 stop11h 59m
Deal found 9/3![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 10/224:59 pm -
1 stop27h 07m
Sun 10/255:35 pm -
1 stop16h 04m
Deal found 9/4![Allegiant Air logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Thu 10/1510:18 am -
1 stop30h 12m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/5![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Sun 10/411:48 am -
2 stops22h 32m
Wed 10/77:11 am -
1 stop25h 17m
Deal found 9/4![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/2210:38 am -
1 stop29h 52m
Thu 10/297:50 pm -
2 stops38h 49m
Deal found 9/7![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/810:18 am -
1 stop30h 12m
Tue 10/137:44 pm -
2 stops36h 44m
Deal found 9/7![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Mon 9/285:38 pm -
1 stop20h 13m
Thu 10/15:30 pm -
1 stop15h 59m
Deal found 9/5![Allegiant Air logo]()
$488
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/167:04 pm -
2 stops24h 12m
Thu 11/198:00 am -
1 stop8h 58m
Deal found 9/8![Multiple Airlines logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Wed 10/2812:39 pm -
2 stops21h 07m
Sat 10/318:00 am -
1 stop27h 08m
Deal found 9/4![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2510:48 am -
2 stops13h 11m
Wed 9/307:11 am -
1 stop25h 27m
Deal found 9/3![Multiple Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/712:39 pm -
2 stops19h 52m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/7![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/196:48 pm -
1 stop18h 50m
Sat 11/2111:53 pm -
2 stops17h 05m
Deal found 9/8![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 -
1 stop6h 49m
Mon 11/235:07 pm -
1 stop24h 35m
Deal found 9/8![Allegiant Air logo]()
$766
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 10/1510:56 am -
1 stop22h 03m
Mon 10/1910:39 am -
1 stop6h 32m
Deal found 9/4![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 10/2210:56 am -
2 stops13h 47m
Sun 10/258:38 am -
1 stop25h 01m
Deal found 9/4![Multiple Airlines logo]()
$482
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/1910:56 am -
2 stops13h 51m
Sun 11/228:42 pm -
1 stop12h 57m
Deal found 9/8![Multiple Airlines logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/1812:39 pm -
2 stops12h 08m
Sat 11/218:42 pm -
1 stop12h 34m
Deal found 9/8![Multiple Airlines logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/167:04 pm -
2 stops17h 18m
Sat 11/218:42 pm -
1 stop12h 34m
Deal found 9/8![Multiple Airlines logo]()
$555
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/2210:56 am -
1 stop9h 51m
Mon 11/238:42 pm -
2 stops19h 13m
Deal found 9/8![Multiple Airlines logo]()
$658
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/167:04 pm -
2 stops17h 18m
Thu 11/195:57 pm -
1 stop23h 15m
Deal found 9/8![Multiple Airlines logo]()
$658
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Thu 10/810:56 am -
2 stops13h 47m
Sun 10/1111:38 am -
1 stop22h 51m
Deal found 9/5![Multiple Airlines logo]()
$768
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 -
1 stop6h 49m
Mon 11/236:38 pm -
2 stops21h 17m
Deal found 9/8![Multiple Airlines logo]()
$773
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 11/2511:06 am -
1 stop9h 41m
Fri 11/278:42 pm -
2 stops13h 57m
Deal found 9/7![Multiple Airlines logo]()
$1,207
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Wed 11/2511:06 am -
1 stop9h 41m
Sat 11/288:42 pm -
1 stop10h 14m
Deal found 9/4![Multiple Airlines logo]()
$1,498
Last-minute flights from Newburgh to ChicagoDiscover last-minute flight deals from Newburgh to Chicago. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Newburgh to Chicago. Data last updated September 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/110:28 am -
2 stops15h 17m
Sat 10/37:11 am -
1 stop26h 47m
Deal found 9/3![Multiple Airlines logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/28:48 pm -
2 stops22h 35m
Sat 10/178:04 am -
1 stop25h 59m
Deal found 9/4![Multiple Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/28:48 pm -
2 stops16h 11m
Sun 10/411:08 am -
1 stop23h 11m
Deal found 9/8![Multiple Airlines logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Wed 10/712:39 pm -
2 stops30h 52m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/4![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/810:18 am -
1 stop30h 12m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/7![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/1012:39 pm -
2 stops45h 42m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/4![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Thu 10/1510:18 am -
1 stop30h 12m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/5![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/1510:18 am -
1 stop30h 12m
Tue 10/207:44 pm -
2 stops37h 04m
Deal found 9/3![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 10/1510:56 am -
1 stop22h 03m
Mon 10/1910:39 am -
1 stop6h 32m
Deal found 9/4![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Sun 10/1811:53 am -
1 stop28h 37m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/4![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 10/197:01 pm -
1 stop13h 50m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/3![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 10/224:59 pm -
1 stop27h 07m
Sun 10/255:35 pm -
1 stop16h 04m
Deal found 9/4![Allegiant Air logo]()
$400
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 September 8, 2026.
Search for one-way flight options from Newburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/2910:38 am -
1 stop29h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 10/2210:38 am -
1 stop29h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 11/226:48 pm -
1 stop30h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 11/196:48 pm -
1 stop18h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/110:28 am -
1 stop29h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sun 10/411:48 am -
1 stop27h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sun 10/411:48 am -
2 stops31h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/1510:56 am -
1 stop22h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Mon 10/267:01 pm -
2 stops23h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/2511:58 am -
2 stops36h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Wed 11/412:39 pm -
3 stops21h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 10/57:13 pm -
2 stops23h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$185
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 September 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $261 (Kiwi.com) |
One-way from | $122 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $289 |
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 7,457,451 searches. Data last updated September 8, 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 New Windsor Stewart - MDW Chicago Midway
SWFMDW
New Windsor Stewart
Sun 10/25
11:58 am-11:43 pm
2 stops36h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Wed 10/14
12:39 pm-6:31 pm
2 stops30h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$181
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Sat 10/31
12:39 pm-10:17 am
2 stops46h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$184
New WindsorChicago
SWF New Windsor Stewart - RFD Chicago Greater Rockford
SWFRFD
New Windsor Stewart
Thu 9/24
10:56 am-8:52 am
1 stop22h 56m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$188
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Wed 9/23
12:39 pm-2:45 pm
2 stops51h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$192
New WindsorChicago
SWF New Windsor Stewart - MDW Chicago Midway
SWFMDW
New Windsor Stewart
Wed 11/18
12:39 pm-5:47 pm
2 stops30h 08m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$197
New WindsorChicago
SWF New Windsor Stewart - MDW Chicago Midway
SWFMDW
New Windsor Stewart
Wed 9/23
12:39 pm-11:44 pm
3 stops36h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$204
New WindsorChicago
SWF New Windsor Stewart - RFD Chicago Greater Rockford
SWFRFD
New Windsor Stewart
Fri 11/13
11:09 am-11:54 am
1 stop25h 45m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$208
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Thu 10/15
10:18 am-9:21 am
2 stops24h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$208
New WindsorChicago
SWF New Windsor Stewart - RFD Chicago Greater Rockford
SWFRFD
New Windsor Stewart
Thu 10/22
10:56 am-7:54 am
1 stop21h 58m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$211
Showing 1-10 of 50 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-MDW
SWF-RFD
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-MDW
SWF-RFD
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 September 8, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 25% 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 September 5, 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
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.
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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 September 8, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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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 September 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$44 | Average$175 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$74 | Average$375 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$122 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$148 | Average$332 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$354 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$177 | Average$319 | FlexibilityNo cancel fee | On-time63% |