$170+ Cheap flights from Islip, NY (ISP) to Midway (MDW)
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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — MDW
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Find cheap flights from Islip to Midway 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 Islip to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Islip to MidwayExplore the most affordable flight options available from Islip to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
Explore the most affordable flight options available from Islip to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
This Southwest deal was found by Cheapflights users on 9/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/204:20 pm -
1 stop6h 40m
Tue 10/275:30 am -
1 stop5h 40m
Deal found 9/20![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:10 pm -
1 stop6h 15m
Sat 10/316:45 am -
1 stop4h 10m
Deal found 9/19![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:10 pm -
2 stops5h 55m
Wed 10/281:40 pm -
2 stops5h 20m
Deal found 9/21![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:25 pm -
1 stop7h 35m
Sun 11/155:05 am -
1 stop5h 40m
Deal found 9/21![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:40 pm -
1 stop5h 20m
Fri 10/236:25 pm -
1 stop4h 15m
Deal found 9/21![Southwest logo]()
$391
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:40 pm -
1 stop6h 25m
Fri 11/64:00 pm -
1 stop6h 35m
Deal found 9/19![Southwest logo]()
$406
Best flights from Islip to MidwayDiscover carefully curated flight deals from Islip to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
Discover carefully curated flight deals from Islip to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:40 pm -
1 stop5h 20m
Wed 10/284:45 pm -
1 stop4h 55m
Deal found 9/21![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 9/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/204:20 pm -
1 stop6h 40m
Tue 10/275:30 am -
1 stop5h 40m
Deal found 9/20![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 9/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
1 stop3h 50m
Wed 11/41:15 pm -
1 stop7h 00m
Deal found 9/18![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:25 pm -
1 stop7h 35m
Sun 11/155:05 am -
1 stop5h 40m
Deal found 9/21![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 9/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:35 pm -
2 stops10h 25m
Sun 11/85:05 am -
1 stop5h 40m
Deal found 9/20![Southwest logo]()
$411
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:25 pm -
2 stops8h 40m
Sun 11/155:05 am -
1 stop5h 40m
Deal found 9/19![Southwest logo]()
$411
Last-minute flights from Islip to MidwayDiscover last-minute flight deals from Islip to Midway. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Islip to Midway. Data last updated September 23, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:40 pm -
1 stop5h 20m
Sun 10/185:10 am -
1 stop4h 10m
Deal found 9/20![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 9/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/204:20 pm -
1 stop6h 40m
Tue 10/275:30 am -
1 stop5h 40m
Deal found 9/20![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:10 pm -
2 stops5h 55m
Wed 10/281:40 pm -
2 stops5h 20m
Deal found 9/21![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:40 pm -
1 stop5h 20m
Fri 10/236:25 pm -
1 stop4h 15m
Deal found 9/21![Southwest logo]()
$391
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:10 pm -
1 stop6h 15m
Sat 10/316:45 am -
1 stop4h 10m
Deal found 9/19![Southwest logo]()
$357
One-way flights from Islip to MidwaySearch for one-way flight options from Islip to Midway. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
Search for one-way flight options from Islip to Midway. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:40 pm -
1 stop5h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 9/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:00 am -
1 stop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/193:02 pm -
3 stops33h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Fri 10/303:02 pm -
3 stops27h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$285
This Southwest deal was found by Cheapflights users on 9/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:10 pm -
1 stop6h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/93:02 pm -
2 stops33h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$402
Find flight deals from Islip to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) to Midway (MDW). 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 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $330 (Frontier) |
One-way from | $170 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $308 |
Cheapflights Fare Finder
Customize your flight search to find flights from Islip to Midway 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 23, 2026.
Use the filters below to find and compare flights from Islip to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Mon 10/19
5:40 pm-10:00 pm
1 stop5h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
Quickest round-trip
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Fri 10/30
6:00 am-8:50 am
1 stop3h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$188
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Mon 10/19
3:02 pm-11:43 pm
3 stops33h 41m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$260
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Fri 10/30
3:02 pm-5:47 pm
3 stops27h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$285
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Fri 10/9
7:10 pm-12:25 am
1 stop6h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Thu 10/22
5:40 pm-10:00 pm
1 stop5h 20m
Chicago Midway
Wed 10/28
4:45 pm-10:40 pm
1 stop4h 55m
$339
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Tue 10/20
4:20 pm-10:00 pm
1 stop6h 40m
Chicago Midway
Tue 10/27
5:30 am-12:10 pm
1 stop5h 40m
$339
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Thu 10/29
6:00 am-8:50 am
1 stop3h 50m
Chicago Midway
Wed 11/4
1:15 pm-9:15 pm
1 stop7h 00m
$339
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Thu 11/12
4:25 pm-11:00 pm
1 stop7h 35m
Chicago Midway
Sun 11/15
5:05 am-11:45 am
1 stop5h 40m
$388
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Fri 10/9
3:02 pm-11:43 pm
2 stops33h 41m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$402
Showing 1-10 of 12 resultsSorted by cheapest first
Compare providers for flights from Islip to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Islip to Midway in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Islip, New York-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Islip, New York-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip, New York-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Islip, New York-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub 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 Islip, New York-Chicago Midway Airport 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 Islip to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Islip with our price prediction graph.
ISP-MDW
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 Islip to Midway. 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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