$109+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Sep 4 — Sep 111
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Newburgh to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Newburgh to Chicago
Cheapest
Best
Last-minute
One-way
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 August 5, 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 August 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 -
1 stop18h 19m
Thu 9/38:14 am -
1 stop9h 26m
Deal found 8/1![Multiple Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 08m
Sun 10/189:33 pm -
2 stops19h 38m
Deal found 8/3![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 -
2 stops37h 23m
Sun 9/68:05 am -
1 stop9h 35m
Deal found 7/31![Multiple Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 -
1 stop18h 19m
Mon 8/319:10 pm -
1 stop12h 58m
Deal found 8/1![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 8/1. 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
Mon 10/2610:44 am -
1 stop6h 27m
Deal found 8/1![Allegiant Air logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 10/2311:19 am -
1 stop29h 44m
Fri 10/308:44 am -
1 stop7h 05m
Deal found 8/1![Allegiant Air logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/310:33 am -
1 stop13h 35m
Sat 9/58:45 am -
2 stops32h 55m
Deal found 7/31![Multiple Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 10/211:19 am -
1 stop24h 33m
Mon 10/510:44 am -
1 stop6h 39m
Deal found 8/3![Allegiant Air logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:09 am -
1 stop25h 45m
Mon 11/910:38 am -
1 stop6h 36m
Deal found 8/2![Allegiant Air logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 8/1. 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
Fri 10/308:44 am -
1 stop7h 05m
Deal found 8/1![Allegiant Air logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 10/257:19 pm -
1 stop22h 46m
Fri 10/308:44 am -
1 stop7h 05m
Deal found 8/1![Allegiant Air logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 11/611:09 am -
1 stop25h 45m
Sun 11/85:37 pm -
1 stop16h 52m
Deal found 8/3![Allegiant Air logo]()
$345
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 August 5, 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 August 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 08m
Sun 10/189:33 pm -
2 stops19h 38m
Deal found 8/3![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 8/1. 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
Mon 10/2610:44 am -
1 stop6h 27m
Deal found 8/1![Allegiant Air logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:31 pm -
1 stop18h 19m
Mon 8/319:10 pm -
1 stop12h 58m
Deal found 8/3![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 10/211:19 am -
1 stop24h 33m
Mon 10/510:44 am -
1 stop6h 39m
Deal found 8/3![Allegiant Air logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 -
1 stop18h 20m
Sun 9/68:05 am -
1 stop9h 35m
Deal found 7/31![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 10/257:19 pm -
1 stop22h 46m
Fri 10/308:44 am -
1 stop7h 05m
Deal found 8/1![Allegiant Air logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/310:33 am -
1 stop13h 35m
Sat 9/58:45 am -
2 stops32h 55m
Deal found 7/31![Multiple Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 10/257:19 pm -
1 stop22h 46m
Thu 10/294:45 pm -
1 stop16h 44m
Deal found 8/1![Allegiant Air logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:31 pm -
1 stop18h 19m
Wed 9/27:44 pm -
1 stop13h 09m
Deal found 8/3![Multiple Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:31 pm -
1 stop18h 19m
Mon 8/319:10 pm -
1 stop12h 58m
Deal found 8/3![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 -
1 stop18h 20m
Tue 9/85:29 pm -
2 stops17h 10m
Deal found 7/31![Multiple Airlines logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 10/2112:39 pm -
2 stops10h 19m
Sun 10/2510:38 am -
1 stop23h 01m
Deal found 8/4![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 stops12h 02m
Thu 10/2910:08 am -
1 stop23h 21m
Deal found 8/1![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/1611:45 am -
1 stop21h 04m
Thu 8/2010:44 am -
1 stop23h 22m
Deal found 8/1![Allegiant Air logo]()
$972
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/911:45 am -
1 stop21h 04m
Mon 8/106:26 pm -
1 stop15h 42m
Deal found 8/1![Multiple Airlines logo]()
$731
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/76:01 pm -
2 stops41h 46m
Mon 8/106:26 pm -
1 stop15h 42m
Deal found 8/1![Multiple Airlines logo]()
$775
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/911:45 am -
1 stop21h 04m
Thu 8/1311:37 am -
2 stops28h 34m
Deal found 8/3![Multiple Airlines logo]()
$1,067
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 12/2711:06 am -
1 stop8h 56m
Sat 1/25:20 pm -
2 stops16h 57m
Deal found 8/4![Multiple Airlines logo]()
$1,523
Last-minute flights from Newburgh to ChicagoDiscover last-minute flight deals from Newburgh to Chicago. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from Newburgh to Chicago. Data last updated August 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/611:45 am -
1 stop21h 04m
Mon 8/106:26 pm -
1 stop15h 42m
Deal found 8/1![Multiple Airlines logo]()
$828
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/76:01 pm -
2 stops41h 46m
Mon 8/106:26 pm -
1 stop15h 42m
Deal found 8/1![Multiple Airlines logo]()
$775
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/84:40 pm -
2 stops20h 54m
Mon 8/106:26 pm -
1 stop15h 42m
Deal found 8/1![Multiple Airlines logo]()
$866
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/911:45 am -
1 stop21h 04m
Mon 8/106:26 pm -
1 stop15h 42m
Deal found 8/1![Multiple Airlines logo]()
$731
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/911:45 am -
1 stop21h 04m
Thu 8/1311:37 am -
2 stops28h 34m
Deal found 8/3![Multiple Airlines logo]()
$1,067
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/1611:45 am -
1 stop21h 04m
Thu 8/2010:44 am -
1 stop23h 22m
Deal found 8/1![Allegiant Air logo]()
$972
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 -
1 stop18h 19m
Thu 9/38:14 am -
1 stop9h 26m
Deal found 8/1![Multiple Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 -
1 stop18h 19m
Mon 8/319:10 pm -
1 stop12h 58m
Deal found 8/1![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 -
2 stops37h 23m
Sun 9/68:05 am -
1 stop9h 35m
Deal found 7/31![Multiple Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/310:33 am -
1 stop13h 35m
Sat 9/58:45 am -
2 stops32h 55m
Deal found 7/31![Multiple Airlines logo]()
$313
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 August 5, 2026.
Search for one-way flight options from Newburgh to Chicago. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 08m
Deal found 8/3![Multiple Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/1. 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
Deal found 8/1![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 -
1 stop18h 19m
Deal found 7/31![Multiple Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 11/111:58 am -
1 stop28h 26m
Deal found 8/3![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:06 am -
1 stop12h 53m
Deal found 8/2![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 8/2612:05 pm -
2 stops12h 03m
Deal found 8/4![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/1. 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
Deal found 8/1![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 10/17:36 pm -
1 stop24h 36m
Deal found 8/4![Allegiant Air logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 -
1 stop22h 56m
Deal found 8/1![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/4. 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.
Mon 8/3111:56 am -
1 stop7h 18m
Deal found 8/4![Allegiant Air logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:31 pm -
2 stops28h 16m
Deal found 8/3![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 9/145:46 pm -
1 stop20h 05m
Deal found 8/1![Allegiant Air logo]()
$149
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 August 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $219 (Kiwi.com) |
One-way from | $109 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $292 |
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 August 5, 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 10/15
10:18 am-3:26 pm
1 stop30h 08m
Chicago O'Hare Intl
Sun 10/18
9:33 pm-6:11 pm
2 stops19h 38m
$286
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Thu 8/27
7:31 pm-12:50 pm
1 stop18h 19m
Chicago O'Hare Intl
Mon 8/31
9:10 pm-11:08 am
1 stop12h 58m
$307
New WindsorChicago
SWF - RFD
SWFRFD
New Windsor Stewart
Thu 10/22
4:59 pm-7:06 pm
1 stop27h 07m
Chicago Greater Rockford
Mon 10/26
10:44 am-6:11 pm
1 stop6h 27m
$308
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Thu 9/3
7:30 pm-12:50 pm
1 stop18h 20m
Chicago O'Hare Intl
Sun 9/6
8:05 am-6:40 pm
1 stop9h 35m
$311
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Thu 9/3
10:33 am-11:08 pm
1 stop13h 35m
Chicago O'Hare Intl
Sat 9/5
8:45 am-6:40 pm
2 stops32h 55m
$313
New WindsorChicago
SWF - RFD
SWFRFD
New Windsor Stewart
Fri 10/2
11:19 am-10:52 am
1 stop24h 33m
Chicago Greater Rockford
Mon 10/5
10:44 am-6:23 pm
1 stop6h 39m
$328
New WindsorChicago
SWF - RFD
SWFRFD
New Windsor Stewart
Sun 10/25
7:19 pm-5:05 pm
1 stop22h 46m
Chicago Greater Rockford
Fri 10/30
8:44 am-4:49 pm
1 stop7h 05m
$337
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Sun 8/30
7:31 pm-12:50 pm
1 stop18h 19m
Chicago O'Hare Intl
Wed 9/2
7:44 pm-9:53 am
1 stop13h 09m
$337
New WindsorChicago
SWF - ORD
SWFORD
New Windsor Stewart
Sun 8/30
7:31 pm-12:50 pm
1 stop18h 19m
Chicago O'Hare Intl
Mon 8/31
9:10 pm-11:08 am
1 stop12h 58m
$339
New WindsorChicago
SWF - RFD
SWFRFD
New Windsor Stewart
Sun 10/25
7:19 pm-5:05 pm
1 stop22h 46m
Chicago Greater Rockford
Thu 10/29
4:45 pm-10:29 am
1 stop16h 44m
$353
Showing 1-10 of 48 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-RFD
SWF-ORD
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-RFD
SWF-ORD
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 August 5, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 27% 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 August 5, 2026.
The most flights from N3W to CHI are scheduled on a Monday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 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 August 1, 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
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.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
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 August 5, 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 August 5, 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 2,558,603 searches. Data last updated August 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$44 | Average$173 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$74 | Average$352 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$122 | Average$250 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$148 | Average$326 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$353 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$164 | Average$316 | FlexibilityNo cancel fee | On-time63% |