$84+ Cheap flights from Chicago (CHI) to New Windsor (SWF)
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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SWF
Sep 11 — Sep 181
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
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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 August 12, 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 August 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 10/37:11 am -
1 stop26h 47m
Sat 10/1012:39 pm -
2 stops8h 49m
Deal found 8/8![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 10/77:11 am -
1 stop25h 17m
Sat 10/1012:39 pm -
2 stops8h 49m
Deal found 8/8![Multiple Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 9/38:14 am -
1 stop9h 26m
Sun 9/610:33 am -
1 stop13h 35m
Deal found 8/8![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/38:14 am -
1 stop9h 26m
Mon 9/712:16 pm -
2 stops32h 52m
Deal found 8/11![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/38:14 am -
1 stop9h 26m
Thu 9/1010:56 am -
1 stop13h 03m
Deal found 8/11![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 12/35:00 am -
1 stop11h 59m
Sun 12/66:49 pm -
1 stop19h 01m
Deal found 8/9![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 8/278:05 am -
1 stop9h 36m
Sun 8/307:31 pm -
2 stops37h 22m
Deal found 8/11![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 10/2210:08 am -
1 stop23h 21m
Mon 10/267:01 pm -
2 stops16h 57m
Deal found 8/9![Multiple Airlines logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 10/2210:08 am -
1 stop23h 21m
Sun 10/257:19 pm -
2 stops16h 39m
Deal found 8/9![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:03 pm -
2 stops21h 13m
Sun 11/2210:56 am -
1 stop26h 28m
Deal found 8/8![Multiple Airlines logo]()
$542
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 August 12, 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 August 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/38:14 am -
1 stop9h 26m
Thu 9/1010:56 am -
1 stop13h 03m
Deal found 8/11![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 10/2210:08 am -
1 stop23h 21m
Mon 10/267:01 pm -
2 stops16h 57m
Deal found 8/9![Multiple Airlines logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/38:14 am -
1 stop9h 26m
Mon 9/71:41 pm -
2 stops34h 27m
Deal found 8/12![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 10/2210:08 am -
1 stop23h 21m
Sun 10/257:19 pm -
2 stops16h 39m
Deal found 8/9![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/319:10 pm -
1 stop12h 58m
Thu 9/310:33 am -
1 stop13h 35m
Deal found 8/8![Multiple Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:10 pm -
1 stop12h 58m
Thu 8/277:31 pm -
1 stop18h 19m
Deal found 8/8![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 8/265:59 pm -
1 stop14h 54m
Mon 8/3111:56 am -
2 stops33h 12m
Deal found 8/12![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Sun 8/237:44 pm -
2 stops14h 53m
Thu 8/277:31 pm -
1 stop18h 19m
Deal found 8/10![Multiple Airlines logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 8/295:59 pm -
1 stop14h 54m
Mon 8/3111:56 am -
1 stop12h 12m
Deal found 8/12![Multiple Airlines logo]()
$475
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 8/277:44 pm -
1 stop13h 22m
Sun 8/307:31 pm -
1 stop18h 19m
Deal found 8/11![Multiple Airlines logo]()
$491
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Sat 8/295:59 pm -
1 stop14h 54m
Thu 9/37:30 pm -
1 stop18h 20m
Deal found 8/10![Multiple Airlines logo]()
$565
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Wed 8/265:59 pm -
1 stop14h 54m
Tue 9/111:48 am -
1 stop12h 20m
Deal found 8/10![Multiple Airlines logo]()
$574
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 9/27:44 pm -
1 stop13h 09m
Sat 9/512:05 pm -
2 stops12h 03m
Deal found 8/8![Multiple Airlines logo]()
$646
Last-minute flights from Chicago to StewartDiscover last-minute flight deals from Chicago to Stewart. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Stewart. Data last updated August 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 8/278:05 am -
1 stop9h 36m
Sun 8/307:31 pm -
2 stops37h 22m
Deal found 8/11![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 8/319:10 pm -
1 stop12h 58m
Thu 9/37:30 pm -
2 stops25h 35m
Deal found 8/11![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 9/38:14 am -
1 stop9h 26m
Sun 9/610:33 am -
1 stop13h 35m
Deal found 8/8![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/38:14 am -
1 stop9h 26m
Mon 9/712:16 pm -
2 stops32h 52m
Deal found 8/11![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/38:14 am -
1 stop9h 26m
Thu 9/1010:56 am -
1 stop13h 03m
Deal found 8/11![Multiple Airlines logo]()
$269
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 August 12, 2026.
Search for one-way flight options from Chicago to Stewart. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/11. 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
Deal found 8/11![Multiple Airlines logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 8/12. 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
Deal found 8/12![Multiple Airlines logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 10/37:11 am -
1 stop26h 47m
Deal found 8/12![Multiple Airlines logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 10/77:11 am -
1 stop25h 17m
Deal found 8/9![Multiple Airlines logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 10/108:04 am -
1 stop25h 59m
Deal found 8/12![Multiple Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 10/217:00 am -
2 stops25h 48m
Deal found 8/11![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/38:14 am -
1 stop9h 26m
Deal found 8/10![Multiple Airlines logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:03 pm -
2 stops20h 45m
Deal found 8/12![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/306:25 am -
2 stops26h 13m
Deal found 8/11![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 10/2112:03 pm -
2 stops20h 45m
Deal found 8/11![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/12. 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
Deal found 8/12![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/211:50 am -
2 stops29h 50m
Deal found 8/11![Multiple Airlines logo]()
$149
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 August 12, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $252 (Kiwi.com) |
One-way from | $84 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $259 |
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 2,558,603 searches. Data last updated August 12, 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
Quickest round-trip
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Thu 9/3
8:14 am-6:40 pm
1 stop9h 26m
New Windsor Stewart
Thu 9/10
10:56 am-10:59 pm
1 stop13h 03m
$269
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Thu 10/22
10:08 am-10:29 am
1 stop23h 21m
New Windsor Stewart
Mon 10/26
7:01 pm-10:58 am
2 stops16h 57m
$342
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Thu 9/3
8:14 am-6:40 pm
1 stop9h 26m
New Windsor Stewart
Mon 9/7
1:41 pm-11:08 pm
2 stops34h 27m
$357
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Thu 10/22
10:08 am-10:29 am
1 stop23h 21m
New Windsor Stewart
Sun 10/25
7:19 pm-10:58 am
2 stops16h 39m
$366
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Mon 8/31
9:10 pm-11:08 am
1 stop12h 58m
New Windsor Stewart
Thu 9/3
10:33 am-11:08 pm
1 stop13h 35m
$380
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Mon 8/24
9:10 pm-11:08 am
1 stop12h 58m
New Windsor Stewart
Thu 8/27
7:31 pm-12:50 pm
1 stop18h 19m
$400
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 8/26
5:59 pm-9:53 am
1 stop14h 54m
New Windsor Stewart
Mon 8/31
11:56 am-8:08 pm
2 stops33h 12m
$401
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Sun 8/23
7:44 pm-11:37 am
2 stops14h 53m
New Windsor Stewart
Thu 8/27
7:31 pm-12:50 pm
1 stop18h 19m
$433
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Sat 8/29
5:59 pm-9:53 am
1 stop14h 54m
New Windsor Stewart
Mon 8/31
11:56 am-11:08 pm
1 stop12h 12m
$475
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Thu 8/27
7:44 pm-10:06 am
1 stop13h 22m
New Windsor Stewart
Sun 8/30
7:31 pm-12:50 pm
1 stop18h 19m
$491
Showing 1-10 of 33 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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