$109+ Cheap flights from Chicago (CHI) to New Windsor (SWF)
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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SWF
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Stewart 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 Stewart
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to StewartExplore the most affordable flight options available from Chicago to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
Explore the most affordable flight options available from Chicago to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:00 am -
1 stop11h 59m
Sun 12/66:49 pm -
1 stop19h 01m
Deal found 9/8![Multiple Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 am -
1 stop24h 44m
Sun 10/2511:58 am -
1 stop28h 32m
Deal found 9/7![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:04 am -
1 stop25h 59m
Thu 10/2210:38 am -
1 stop29h 52m
Deal found 9/6![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:11 am -
1 stop25h 27m
Sun 10/411:48 am -
1 stop27h 57m
Deal found 9/7![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:38 am -
1 stop22h 51m
Fri 10/28:48 pm -
2 stops16h 11m
Deal found 9/8![Multiple Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:12 am -
1 stop23h 07m
Sun 11/155:37 pm -
2 stops25h 10m
Deal found 9/7![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 12/118:07 pm -
2 stops14h 32m
Sun 12/1311:06 am -
1 stop8h 56m
Deal found 9/9![Multiple Airlines logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/10![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:38 am -
1 stop22h 51m
Sun 10/1111:53 am -
2 stops36h 50m
Deal found 9/7![Multiple Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:42 pm -
2 stops13h 57m
Sun 11/2210:56 am -
1 stop9h 51m
Deal found 9/6![Multiple Airlines logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:07 pm -
1 stop13h 06m
Wed 12/2312:39 pm -
2 stops31h 23m
Deal found 9/8![Multiple Airlines logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/178:07 pm -
2 stops14h 29m
Mon 12/215:46 pm -
1 stop16h 06m
Deal found 9/8![Multiple Airlines logo]()
$582
Best flights from Chicago to StewartDiscover carefully curated flight deals from Chicago to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
Discover carefully curated flight deals from Chicago to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 am -
1 stop24h 44m
Sun 10/2511:58 am -
1 stop28h 32m
Deal found 9/7![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:04 am -
1 stop25h 59m
Thu 10/2210:38 am -
1 stop29h 52m
Deal found 9/6![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:28 pm -
2 stops39h 11m
Sun 10/411:48 am -
1 stop27h 57m
Deal found 9/6![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/3112:39 pm -
2 stops12h 42m
Deal found 9/9![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 am -
1 stop24h 44m
Mon 11/27:01 pm -
2 stops24h 15m
Deal found 9/8![Multiple Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:38 am -
1 stop22h 51m
Fri 10/28:48 pm -
2 stops16h 11m
Deal found 9/8![Multiple Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/10![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:38 am -
1 stop22h 51m
Sun 10/1111:53 am -
2 stops36h 50m
Deal found 9/7![Multiple Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:42 pm -
2 stops13h 57m
Sun 11/2210:56 am -
1 stop9h 51m
Deal found 9/6![Multiple Airlines logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:07 pm -
1 stop13h 06m
Wed 12/2312:39 pm -
2 stops31h 23m
Deal found 9/8![Multiple Airlines logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/218:42 pm -
1 stop12h 34m
Wed 11/259:29 am -
1 stop11h 18m
Deal found 9/9![Multiple Airlines logo]()
$620
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:07 pm -
2 stops14h 32m
Sun 12/611:06 am -
1 stop8h 56m
Deal found 9/7![Multiple Airlines logo]()
$694
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/268:42 pm -
2 stops13h 54m
Sun 11/298:36 am -
1 stop12h 11m
Deal found 9/9![Multiple Airlines logo]()
$1,081
Last-minute flights from Chicago to StewartDiscover last-minute flight deals from Chicago to Stewart. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Stewart. Data last updated September 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:11 am -
1 stop25h 27m
Sun 10/411:48 am -
1 stop27h 57m
Deal found 9/7![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:28 pm -
2 stops39h 11m
Sun 10/411:48 am -
1 stop27h 57m
Deal found 9/6![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:38 am -
1 stop22h 51m
Fri 10/28:48 pm -
2 stops16h 11m
Deal found 9/8![Multiple Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:38 am -
1 stop22h 51m
Sun 10/1111:53 am -
2 stops36h 50m
Deal found 9/7![Multiple Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:04 am -
1 stop25h 59m
Thu 10/2210:38 am -
1 stop29h 52m
Deal found 9/6![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 am -
1 stop24h 44m
Sun 10/2511:58 am -
1 stop28h 32m
Deal found 9/7![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 am -
1 stop24h 44m
Fri 11/65:30 pm -
1 stop16h 16m
Deal found 9/7![Multiple Airlines logo]()
$347
One-way flights from Chicago to StewartSearch for one-way flight options from Chicago to Stewart. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from Chicago to Stewart. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:11 am -
1 stop25h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 am -
1 stop24h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:04 am -
1 stop24h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:25 am -
2 stops27h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 am -
2 stops27h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:10 pm -
1 stop13h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Allegiant Air logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:21 am -
2 stops26h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/9![Multiple Airlines logo]()
$177
Find flight deals from Chicago to Stewart
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 10, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $238 (Kiwi.com) |
One-way from | $109 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $269 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Stewart 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 10, 2026.
Use the filters below to find and compare flights from Chicago to New Windsor that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Sat 10/17
8:04 am-11:03 am
1 stop25h 59m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$141
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Sat 10/24
6:21 am-11:08 am
2 stops27h 47m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$151
Quickest round-trip
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Sun 12/6
6:10 pm-8:52 am
1 stop13h 42m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$165
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 11/11
7:28 pm-11:36 am
3 stops39h 08m
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
Tue 9/29
7:28 pm-9:38 am
2 stops37h 10m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$191
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Thu 11/5
6:42 pm-11:39 am
2 stops39h 57m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$191
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 10/28
7:28 pm-11:36 am
3 stops39h 08m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$193
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Mon 10/19
7:44 pm-11:39 am
3 stops38h 55m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$197
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Tue 10/20
6:00 am-11:39 am
3 stops28h 39m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$198
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Wed 10/14
6:21 am-9:28 am
2 stops26h 07m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$200
Showing 1-10 of 34 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Chicago-New Windsor flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago-New Windsor flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Chicago-New Windsor flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-New Windsor flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Stewart
Have a flexible travel schedule? Discover the best time to fly to Stewart from Chicago with our price prediction graph.
CHI-SWF
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 New Windsor
CHI-SWF
ORD-SWF
MDW-SWF
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Stewart. 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 New Windsor?
Book flights to New Windsor if you plan to visit one of these locationsKingston
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