$141+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SWF
Oct 5 — Oct 121
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
Last-minute
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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 September 5, 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 September 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:10 pm -
1 stop13h 42m
Thu 12/1011:06 am -
1 stop8h 56m
Deal found 9/1![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 12/106:10 pm -
1 stop13h 42m
Sun 12/136:49 pm -
2 stops19h 10m
Deal found 9/3![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:08 am -
1 stop23h 21m
Mon 10/267:01 pm -
2 stops23h 26m
Deal found 8/31![Multiple Airlines logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 12/178:07 pm -
1 stop21h 18m
Mon 12/215:46 pm -
1 stop16h 06m
Deal found 9/2![Multiple Airlines logo]()
$552
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 12/198:07 pm -
1 stop13h 19m
Mon 12/215:46 pm -
1 stop16h 06m
Deal found 8/30![Multiple Airlines logo]()
$614
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:07 pm -
2 stops14h 29m
Sun 12/611:06 am -
1 stop8h 56m
Deal found 8/31![Multiple Airlines logo]()
$636
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 12/268:07 pm -
1 stop13h 19m
Sat 1/27:46 pm -
2 stops21h 29m
Deal found 9/4![Multiple Airlines logo]()
$653
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/208:07 pm -
1 stop22h 53m
Thu 12/2411:06 am -
1 stop8h 56m
Deal found 9/1![Multiple Airlines logo]()
$686
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.
Fri 12/48:07 pm -
2 stops14h 32m
Sun 12/611:06 am -
1 stop8h 56m
Deal found 9/4![Multiple Airlines logo]()
$694
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 September 5, 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 September 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:08 am -
1 stop23h 21m
Mon 10/267:01 pm -
2 stops23h 26m
Deal found 8/31![Multiple Airlines logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:38 am -
1 stop22h 51m
Thu 10/86:45 pm -
2 stops17h 51m
Deal found 9/3![Allegiant Air logo]()
$698
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:07 pm -
2 stops14h 29m
Sun 12/611:06 am -
1 stop8h 56m
Deal found 8/31![Multiple Airlines logo]()
$636
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:18 am -
1 stop24h 11m
Sun 10/187:14 pm -
2 stops18h 22m
Deal found 9/1![Allegiant Air logo]()
$715
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.
Thu 11/268:42 pm -
2 stops13h 54m
Sun 11/298:36 am -
1 stop12h 11m
Deal found 9/4![Multiple Airlines logo]()
$1,257
Last-minute flights from Midway to StewartDiscover last-minute flight deals from Midway to Stewart. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Stewart. Data last updated September 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:38 am -
1 stop22h 51m
Thu 10/86:45 pm -
2 stops17h 51m
Deal found 9/3![Allegiant Air logo]()
$698
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:18 am -
1 stop24h 11m
Sun 10/187:14 pm -
2 stops18h 22m
Deal found 9/1![Allegiant Air logo]()
$715
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:08 am -
1 stop23h 21m
Mon 10/267:01 pm -
2 stops23h 26m
Deal found 8/31![Multiple Airlines logo]()
$429
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 September 5, 2026.
Search for one-way flight options from Midway to Stewart. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
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 10/36:25 am -
2 stops27h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$141
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 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/145:26 pm -
1 stop15h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Allegiant Air logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 1/105:26 pm -
1 stop14h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Allegiant Air logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:38 am -
1 stop22h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Allegiant Air logo]()
$168
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.
Sun 11/810:42 am -
1 stop23h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Allegiant Air logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/266:25 am -
2 stops26h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:16 am -
2 stops26h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$178
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 September 5, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $429 (Kiwi.com) |
One-way from | $141 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $269 |
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 September 5, 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
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
$150
Quickest round-trip
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Thu 1/14
5:26 pm-10:11 am
1 stop15h 45m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$154
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Sat 10/3
6:25 am-10:58 am
2 stops27h 33m
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
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
$190
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Sun 11/1
10:38 am-10:39 am
1 stop23h 01m
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
Fri 10/2
6:46 pm-10:58 am
2 stops39h 12m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$200
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Mon 10/26
6:15 am-11:39 am
3 stops52h 24m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$205
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Tue 10/13
6:21 am-11:39 am
2 stops28h 18m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$206
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Wed 10/21
6:21 am-9:48 am
2 stops26h 27m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$212
ChicagoNew Windsor
MDW Chicago Midway - SWF New Windsor Stewart
MDWSWF
Chicago Midway
Thu 10/29
6:42 pm-11:39 am
2 stops39h 57m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$218
Showing 1-10 of 17 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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