$140+ Cheap flights from Midway (MDW) 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SWF
Nov 19 — Nov 261
Round-trip
1 adult, Economy
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Find cheap flights from Midway 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
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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 Midway to Stewart
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Best
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Cheapest flights from Midway to StewartExplore the most affordable flight options available from Midway to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
Explore the most affordable flight options available from Midway to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 12/66:49 pm -
2 stops22h 17m
Deal found 10/19![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 12/45:02 pm -
2 stops17h 37m
Sun 12/611:06 am -
1 stop9h 36m
Deal found 10/19![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:16 am -
2 stops26h 23m
Mon 11/236:32 pm -
1 stop15h 10m
Deal found 10/16![Multiple Airlines logo]()
$450
This Kiwi.com deal was found by Cheapflights users on 10/19. 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
Thu 12/1011:06 am -
1 stop9h 36m
Deal found 10/19![Multiple Airlines logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
1 stop12h 34m
Sun 11/226:48 pm -
2 stops18h 33m
Deal found 10/16![Multiple Airlines logo]()
$456
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/136:08 am -
2 stops28h 31m
Mon 11/236:32 pm -
1 stop15h 10m
Deal found 10/19![Multiple Airlines logo]()
$458
Best flights from Midway to StewartDiscover carefully curated flight deals from Midway to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
Discover carefully curated flight deals from Midway to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 12/45:02 pm -
2 stops17h 37m
Sun 12/611:06 am -
1 stop9h 36m
Deal found 10/19![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/121:18 pm -
2 stops21h 21m
Sun 1/1710:56 am -
1 stop9h 46m
Deal found 10/16![Multiple Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:10 pm -
1 stop13h 42m
Sun 12/611:06 am -
1 stop9h 36m
Deal found 10/16![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:53 pm -
1 stop15h 57m
Thu 12/3112:07 pm -
2 stops12h 54m
Deal found 10/16![Multiple Airlines logo]()
$458
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
1 stop12h 34m
Sun 11/226:48 pm -
2 stops18h 33m
Deal found 10/16![Multiple Airlines logo]()
$469
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:16 am -
2 stops26h 23m
Mon 11/236:32 pm -
1 stop15h 10m
Deal found 10/18![Multiple Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/221:18 pm -
2 stops21h 21m
Sun 1/2410:56 am -
1 stop9h 46m
Deal found 10/17![Multiple Airlines logo]()
$484
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 12/198:35 pm -
1 stop12h 51m
Wed 12/2312:39 pm -
2 stops31h 51m
Deal found 10/19![Multiple Airlines logo]()
$512
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:16 am -
2 stops26h 23m
Sun 11/2210:56 am -
1 stop9h 51m
Deal found 10/18![Multiple Airlines logo]()
$518
Last-minute flights from Midway to StewartDiscover last-minute flight deals from Midway to Stewart. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Stewart. Data last updated October 20, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/136:08 am -
2 stops28h 31m
Mon 11/236:32 pm -
1 stop15h 10m
Deal found 10/19![Multiple Airlines logo]()
$458
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/136:08 am -
2 stops28h 31m
Sun 11/2210:56 am -
1 stop9h 51m
Deal found 10/19![Multiple Airlines logo]()
$498
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/176:08 am -
2 stops28h 31m
Sun 11/2210:56 am -
1 stop9h 51m
Deal found 10/19![Multiple Airlines logo]()
$495
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/186:08 am -
2 stops27h 08m
Mon 11/236:32 pm -
1 stop15h 10m
Deal found 10/19![Multiple Airlines logo]()
$479
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:16 am -
2 stops26h 23m
Mon 11/236:32 pm -
1 stop15h 10m
Deal found 10/16![Multiple Airlines logo]()
$450
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/208:16 am -
2 stops26h 23m
Sun 11/2210:56 am -
1 stop9h 51m
Deal found 10/19![Multiple Airlines logo]()
$508
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
1 stop12h 34m
Sun 11/226:48 pm -
2 stops18h 33m
Deal found 10/16![Multiple Airlines logo]()
$456
One-way flights from Midway to StewartSearch for one-way flight options from Midway to Stewart. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
Search for one-way flight options from Midway to Stewart. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:28 pm -
2 stops20h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 12/812:28 pm -
2 stops22h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:10 pm -
1 stop13h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Allegiant Air logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/126:42 pm -
2 stops39h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:02 pm -
2 stops17h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/131:18 pm -
2 stops21h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/166:42 pm -
2 stops39h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1610:40 am -
2 stops23h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
2 stops27h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$162
Find flight deals from Midway to Stewart
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) 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 October 20, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $394 (Kiwi.com) |
One-way from | $140 (Kiwi.com) |
Popular in | October |
Cheapest in | January |
Average price | $312 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway 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 October 20, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to New Windsor that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Wed 2/3
1:18 pm-11:39 am
2 stops21h 21m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Fri 12/4
5:02 pm-11:39 am
2 stops17h 37m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$162
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Sun 1/31
1:18 pm-10:57 am
3 stops20h 39m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Fri 11/13
6:08 am-11:39 am
2 stops28h 31m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$189
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Tue 11/10
6:42 pm-10:16 am
2 stops38h 34m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$196
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Thu 11/19
6:42 pm-11:39 am
2 stops39h 57m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$196
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Tue 12/1
12:28 pm-11:39 am
2 stops22h 11m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$197
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Mon 11/9
6:42 pm-11:39 am
2 stops39h 57m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$213
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Fri 11/20
8:16 am-11:39 am
2 stops26h 23m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$223
Quickest round-trip
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Thu 2/4
8:47 pm-10:57 am
2 stops13h 10m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$224
Showing 1-10 of 19 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Chicago Midway Airport-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 Midway Airport-New Windsor flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Chicago Midway Airport-New Windsor flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-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 Midway Airport-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 Midway to Stewart
Have a flexible travel schedule? Discover the best time to fly to Stewart from Midway with our price prediction graph.
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.
Related info for your journey
Find useful and relevant information for your journey from Midway 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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