$88+ Cheap flights from Chicago (CHI) to Newburgh, NY
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JFK
Jun 6 — Jun 131
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Newburgh with Cheapflights
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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
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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 May 7, 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 May 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 8/197:55 am
ORD
- SWF
1 stop27h 15m
Multiple Airlines
Mon 8/245:39 pm
SWF
- ORD
1 stop30h 35m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 7/17:52 am
ORD
- SWF
1 stop24h 46m
Multiple Airlines
Sun 7/1210:28 am
SWF
- ORD
2 stops46h 25m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Wed 7/88:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Sun 7/1210:28 am
SWF
- ORD
1 stop26h 57m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Sat 7/47:52 am
ORD
- SWF
1 stop24h 46m
Multiple Airlines
Sun 7/1210:28 am
SWF
- ORD
2 stops46h 25m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Sat 7/188:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Wed 7/2212:05 pm
SWF
- ORD
2 stops12h 00m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Wed 5/275:11 pm
ORD
- SWF
1 stop14h 47m
Multiple Airlines
Fri 5/299:41 am
SWF
- ORD
1 stop14h 32m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 8/277:55 am
ORD
- SWF
1 stop9h 46m
Multiple Airlines
Sun 8/309:38 am
SWF
- ORD
1 stop14h 36m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 11/110:38 am
MDW
- SWF
1 stop23h 01m
Multiple Airlines
Wed 11/412:39 pm
SWF
- MDW
2 stops10h 14m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$445
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 May 7, 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 May 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Sat 7/188:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Wed 7/2212:05 pm
SWF
- ORD
2 stops12h 00m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Wed 5/275:11 pm
ORD
- SWF
1 stop14h 47m
Multiple Airlines
Fri 5/299:41 am
SWF
- ORD
1 stop14h 32m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Sat 7/47:52 am
ORD
- SWF
1 stop24h 46m
Multiple Airlines
Sun 7/1210:28 am
SWF
- ORD
1 stop26h 57m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Wed 7/85:13 pm
ORD
- SWF
1 stop14h 45m
Multiple Airlines
Thu 7/1610:28 am
SWF
- ORD
1 stop26h 57m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 7/225:13 pm
ORD
- SWF
1 stop14h 45m
Multiple Airlines
Sun 7/2610:28 am
SWF
- ORD
2 stops22h 25m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$436
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 11/110:38 am
MDW
- SWF
1 stop23h 01m
Multiple Airlines
Wed 11/412:39 pm
SWF
- MDW
2 stops10h 14m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/315:11 pm
ORD
- SWF
1 stop14h 40m
Multiple Airlines
Sun 6/78:04 pm
SWF
- ORD
2 stops24h 25m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Wed 5/131:59 pm
ORD
- SWF
2 stops17h 59m
Multiple Airlines
Mon 5/1811:45 am
SWF
- ORD
1 stop12h 28m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$486
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/203:55 pm
ORD
- SWF
1 stop16h 03m
Multiple Airlines
Mon 5/259:41 am
SWF
- ORD
1 stop14h 32m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$513
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/134:59 pm
ORD
- SWF
1 stop14h 59m
Multiple Airlines
Sun 6/2110:28 am
SWF
- ORD
1 stop26h 56m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 5/203:55 pm
ORD
- SWF
1 stop16h 03m
Multiple Airlines
Sun 5/249:38 am
SWF
- ORD
1 stop14h 35m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:13 pm
ORD
- SWF
1 stop14h 45m
Multiple Airlines
Sat 7/2512:05 pm
SWF
- ORD
2 stops44h 48m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$554
Last-minute flights from Chicago to NewburghDiscover last-minute flight deals from Chicago to Newburgh. Data last updated May 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Newburgh. Data last updated May 7, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 5/151:59 pm
ORD
- SWF
2 stops20h 26m
Multiple Airlines
Mon 5/1811:45 am
SWF
- ORD
1 stop12h 28m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Wed 5/275:11 pm
ORD
- SWF
1 stop14h 47m
Multiple Airlines
Fri 5/299:41 am
SWF
- ORD
1 stop14h 32m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/285:11 pm
ORD
- SWF
2 stops17h 26m
Multiple Airlines
Sun 5/319:38 am
SWF
- ORD
1 stop14h 35m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/315:11 pm
ORD
- SWF
1 stop14h 40m
Multiple Airlines
Sun 6/78:04 pm
SWF
- ORD
2 stops24h 25m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Wed 6/35:11 pm
ORD
- SWF
1 stop14h 47m
Multiple Airlines
Sun 6/78:04 pm
SWF
- ORD
2 stops24h 25m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Thu 6/45:11 pm
ORD
- SWF
1 stop14h 38m
Multiple Airlines
Sun 6/78:04 pm
SWF
- ORD
2 stops24h 25m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Sat 6/65:11 pm
ORD
- SWF
1 stop14h 47m
Multiple Airlines
Sun 6/78:04 pm
SWF
- ORD
2 stops24h 25m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 6/104:59 pm
ORD
- SWF
1 stop14h 59m
Multiple Airlines
Sun 6/148:04 pm
SWF
- ORD
2 stops36h 59m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$434
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/114:59 pm
ORD
- SWF
1 stop14h 50m
Multiple Airlines
Sun 6/148:04 pm
SWF
- ORD
2 stops36h 59m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 6/264:59 pm
ORD
- SWF
1 stop25h 11m
Multiple Airlines
Sun 7/510:28 am
SWF
- ORD
1 stop26h 57m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Tue 6/304:59 pm
ORD
- SWF
2 stops17h 26m
Multiple Airlines
Sun 7/510:28 am
SWF
- ORD
1 stop26h 57m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$431
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 May 7, 2026.
Search for one-way flight options from Chicago to Newburgh. Find affordable one-way fares based on user searches. Data last updated May 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 7/88:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 7/17:52 am
ORD
- SWF
1 stop24h 46m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Wed 7/158:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 6/177:52 am
ORD
- SWF
1 stop24h 46m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 7/228:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/285:11 pm
ORD
- SWF
2 stops17h 26m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 7/86:00 am
MDW
- SWF
2 stops26h 38m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/35:11 pm
ORD
- SWF
1 stop14h 47m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 6/45:11 pm
ORD
- SWF
1 stop14h 38m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Sat 7/411:59 am
MDW
- SWF
2 stops20h 39m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 7/34:59 pm
ORD
- SWF
1 stop23h 55m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Sat 7/188:05 am
ORD
- SWF
1 stop24h 33m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$131
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 May 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $189 (Kiwi.com) |
One-way from | $88 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $208 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Newburgh that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 7, 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
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 7/18
8:05 am-9:38 am
1 stop24h 33m
New Windsor Stewart
Wed 7/22
12:05 pm-11:05 pm
2 stops12h 00m
$303
Quickest round-trip
ChicagoNew Windsor
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 5/27
5:11 pm-8:58 am
1 stop14h 47m
New Windsor Stewart
Fri 5/29
9:41 am-11:13 pm
1 stop14h 32m
$316
ChicagoNew Windsor
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 7/4
7:52 am-9:38 am
1 stop24h 46m
New Windsor Stewart
Sun 7/12
10:28 am-12:25 pm
1 stop26h 57m
$322
ChicagoNew Windsor
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 7/8
5:13 pm-8:58 am
1 stop14h 45m
New Windsor Stewart
Thu 7/16
10:28 am-12:25 pm
1 stop26h 57m
$391
ChicagoNew Windsor
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 7/22
5:13 pm-8:58 am
1 stop14h 45m
New Windsor Stewart
Sun 7/26
10:28 am-7:53 am
2 stops22h 25m
$436
ChicagoNew Windsor
MDW - SWF
MDWSWF
Chicago Midway
Sun 11/1
10:38 am-10:39 am
1 stop23h 01m
New Windsor Stewart
Wed 11/4
12:39 pm-9:53 pm
2 stops10h 14m
$445
ChicagoNew Windsor
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sun 5/31
5:11 pm-8:51 am
1 stop14h 40m
New Windsor Stewart
Sun 6/7
8:04 pm-7:29 pm
2 stops24h 25m
$447
ChicagoNew Windsor
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 5/13
1:59 pm-8:58 am
2 stops17h 59m
New Windsor Stewart
Mon 5/18
11:45 am-11:13 pm
1 stop12h 28m
$486
ChicagoNew Windsor
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 5/20
3:55 pm-8:58 am
1 stop16h 03m
New Windsor Stewart
Mon 5/25
9:41 am-11:13 pm
1 stop14h 32m
$513
ChicagoNew Windsor
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 6/13
4:59 pm-8:58 am
1 stop14h 59m
New Windsor Stewart
Sun 6/21
10:28 am-12:24 pm
1 stop26h 56m
$535
Showing 1-10 of 36 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.
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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
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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 May 7, 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 evening.
What is the cheapest day to fly from Chicago to Newburgh?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Newburgh. Price data was last updated on May 2, 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.
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 May 7, 2026.
The most flights from CHI to N3W are scheduled on a Thursday (52 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (21 on average).
Related info for your journey
Find useful and relevant information for your journey from Chicago to Newburgh. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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 May 7, 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 May 7, 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 7 airlines flying from Chicago to Newburgh
Discover the top 7 airlines that operate flights from Chicago to Newburgh. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$40 | Average$147 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$42 | Average$136 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$81 | Average$242 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$86 | Average$197 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$139 | Average$289 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$150 | Average$343 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$169 | Average$350 | FlexibilityNo cancel fee | On-time63% |