$70+ Cheap flights from Chicago (CHI) to Newburgh, NY
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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JFK
Oct 19 — Oct 261
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Newburgh 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 Chicago to Newburgh
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Cheapest flights from Chicago to NewburghExplore 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 September 19, 2026.
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 September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/35:00 am -
1 stop11h 59m
Sun 12/66:49 pm -
1 stop20h 10m
Deal found 9/16![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/218:04 am -
1 stop24h 44m
Sun 10/2511:58 am -
2 stops22h 23m
Deal found 9/16![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/48:00 am -
2 stops26h 39m
Sun 12/66:49 pm -
1 stop20h 10m
Deal found 9/18![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/218:04 am -
1 stop24h 44m
Fri 10/235:39 pm -
1 stop15h 12m
Deal found 9/16![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Wed 12/25:24 pm -
1 stop16h 02m
Sun 12/66:49 pm -
1 stop20h 10m
Deal found 9/18![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/148:04 am -
1 stop24h 24m
Wed 10/2112:39 pm -
2 stops30h 14m
Deal found 9/16![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/36:10 am -
1 stop10h 49m
Sat 12/512:39 pm -
2 stops8h 37m
Deal found 9/15![Multiple Airlines logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/38:07 pm -
1 stop13h 06m
Sun 12/611:06 am -
1 stop8h 56m
Deal found 9/15![Multiple Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/36:10 pm -
1 stop13h 42m
Mon 12/712:16 pm -
2 stops9h 26m
Deal found 9/18![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/106:10 pm -
1 stop13h 42m
Sun 12/136:49 pm -
2 stops21h 06m
Deal found 9/16![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/110:38 am -
1 stop22h 51m
Sun 10/411:48 am -
2 stops31h 03m
Deal found 9/16![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sun 10/411:08 am -
1 stop23h 11m
Wed 10/1412:39 pm -
2 stops12h 04m
Deal found 9/15![Multiple Airlines logo]()
$417
Best flights from Chicago to NewburghDiscover carefully curated flight deals from Chicago to Newburgh that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 19, 2026.
Discover carefully curated flight deals from Chicago to Newburgh that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/36:10 am -
1 stop10h 49m
Sun 12/66:49 pm -
1 stop20h 10m
Deal found 9/16![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/48:00 am -
2 stops26h 39m
Sun 12/66:49 pm -
1 stop20h 10m
Deal found 9/18![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/218:04 am -
1 stop24h 44m
Fri 10/235:39 pm -
1 stop15h 12m
Deal found 9/16![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/36:10 am -
1 stop10h 49m
Sat 12/512:39 pm -
2 stops8h 37m
Deal found 9/15![Multiple Airlines logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/36:10 pm -
1 stop13h 42m
Mon 12/712:16 pm -
2 stops9h 26m
Deal found 9/18![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 12/106:10 am -
1 stop10h 49m
Sun 12/136:49 pm -
2 stops29h 08m
Deal found 9/17![Multiple Airlines logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 11/198:00 am -
1 stop8h 58m
Sun 11/226:48 pm -
1 stop18h 50m
Deal found 9/17![Multiple Airlines logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/106:10 pm -
1 stop13h 42m
Sun 12/136:49 pm -
2 stops26h 29m
Deal found 9/15![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/110:38 am -
1 stop22h 51m
Mon 10/57:13 pm -
2 stops23h 33m
Deal found 9/16![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/35:00 am -
1 stop11h 59m
Mon 12/711:03 am -
1 stop15h 06m
Deal found 9/14![Multiple Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/110:38 am -
1 stop22h 51m
Sun 10/411:48 am -
2 stops31h 03m
Deal found 9/15![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 2/101:18 pm -
2 stops19h 58m
Wed 2/173:46 pm -
1 stop25h 36m
Deal found 9/16![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Sun 12/136:10 am -
1 stop10h 49m
Wed 12/1612:39 pm -
2 stops25h 11m
Deal found 9/18![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/105:00 am -
1 stop11h 59m
Sat 12/1212:39 pm -
2 stops8h 37m
Deal found 9/15![Multiple Airlines logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/36:10 pm -
1 stop13h 42m
Sun 12/611:06 am -
1 stop8h 56m
Deal found 9/14![Multiple Airlines logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 1/78:47 pm -
2 stops13h 10m
Sun 1/1010:56 am -
1 stop9h 46m
Deal found 9/17![Multiple Airlines logo]()
$469
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/119:37 pm -
2 stops13h 02m
Sun 12/1311:06 am -
1 stop10h 36m
Deal found 9/18![Multiple Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/1111:38 am -
1 stop22h 51m
Wed 10/1412:39 pm -
2 stops12h 04m
Deal found 9/16![Multiple Airlines logo]()
$503
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/110:38 am -
1 stop22h 51m
Fri 10/28:48 pm -
2 stops16h 11m
Deal found 9/16![Multiple Airlines logo]()
$508
Last-minute flights from Chicago to NewburghDiscover last-minute flight deals from Chicago to Newburgh. Data last updated September 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Newburgh. Data last updated September 19, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/110:38 am -
1 stop22h 51m
Sun 10/411:48 am -
2 stops31h 03m
Deal found 9/16![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/110:38 am -
1 stop22h 51m
Fri 10/28:48 pm -
2 stops16h 11m
Deal found 9/16![Multiple Airlines logo]()
$508
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sun 10/411:08 am -
1 stop23h 11m
Wed 10/1412:39 pm -
2 stops12h 04m
Deal found 9/15![Multiple Airlines logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/1111:38 am -
1 stop22h 51m
Wed 10/1412:39 pm -
2 stops12h 04m
Deal found 9/16![Multiple Airlines logo]()
$503
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/148:04 am -
1 stop24h 24m
Wed 10/2112:39 pm -
2 stops30h 14m
Deal found 9/16![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/148:04 am -
1 stop24h 24m
Mon 10/1912:16 pm -
2 stops44h 35m
Deal found 9/16![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/168:11 pm -
2 stops14h 28m
Mon 10/197:01 pm -
1 stop13h 50m
Deal found 9/15![Multiple Airlines logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/178:04 am -
1 stop25h 59m
Mon 10/197:01 pm -
1 stop13h 50m
Deal found 9/15![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/218:04 am -
1 stop24h 44m
Sun 10/2511:58 am -
2 stops22h 23m
Deal found 9/16![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/218:04 am -
1 stop24h 44m
Fri 10/235:39 pm -
1 stop15h 12m
Deal found 9/16![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Wed 10/218:04 am -
1 stop24h 44m
Sat 10/2412:39 pm -
2 stops12h 45m
Deal found 9/18![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Sat 10/318:00 am -
1 stop27h 08m
Wed 11/412:39 pm -
2 stops21h 07m
Deal found 9/18![Multiple Airlines logo]()
$307
One-way flights from Chicago to NewburghSearch for one-way flight options from Chicago to Newburgh. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
Search for one-way flight options from Chicago to Newburgh. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/218:04 am -
1 stop24h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/148:04 am -
1 stop24h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Sat 10/318:00 am -
1 stop27h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Sat 10/317:25 am -
2 stops27h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Sat 10/246:21 am -
2 stops27h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/286:16 am -
2 stops26h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Wed 12/210:21 am -
2 stops30h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Wed 10/216:21 am -
2 stops26h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 10/276:42 pm -
2 stops38h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$155
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 September 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $233 (Kiwi.com) |
One-way from | $70 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $306 |
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 7,457,451 searches. Data last updated September 19, 2026.
Use the filters below to find and compare flights from Chicago to Newburgh that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Wed 12/2
10:21 am-5:59 pm
2 stops30h 38m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$150
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Tue 10/20
8:46 am-11:39 am
2 stops25h 53m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Tue 10/27
7:15 am-11:39 am
3 stops27h 24m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$167
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Thu 11/12
7:50 pm-11:39 am
3 stops38h 49m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$173
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Tue 10/20
3:30 pm-9:48 am
2 stops41h 18m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Fri 10/30
7:50 pm-12:08 pm
2 stops39h 18m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$183
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 10/21
7:44 pm-11:36 am
3 stops38h 52m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Wed 11/11
6:42 pm-11:36 am
3 stops39h 54m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Tue 10/13
6:00 am-11:39 am
2 stops28h 39m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$192
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Sat 11/14
8:00 am-11:10 am
1 stop26h 10m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$192
Showing 1-10 of 41 resultsSorted by cheapest first
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.
ORD-SWF
MDW-SWF
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
CHI-N3W
ORD-SWF
MDW-SWF
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 September 19, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 34% on flights from Chicago to Newburgh by exploring options for tickets in the morning.
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 September 19, 2026.
The most flights from CHI to N3W are scheduled on a Wednesday (56 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (38 on average).
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 September 12, 2026.
Travelers seeking maximum savings on their Chicago to Newburgh flight should consider departing on Monday mornings 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.
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.
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.
Complete your trip
Complete your trip to Newburgh by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Newburgh by cabin class
Find flights from Chicago to Newburgh, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Newburgh flights
Browse other Chicago and Newburgh flight options. Last updated on September 19, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Newburgh flights
Consider these flights traveling from Chicago to Newburgh.
Top 6 airlines flying from Chicago to Newburgh
Discover the top 6 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 7,457,451 searches. Data last updated September 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$38 | Average$184 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$78 | Average$241 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$98 | Average$228 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$146 | Average$333 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$158 | Average$327 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$185 | Average$396 | FlexibilityNo cancel fee | On-time63% |