$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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — MDW
Dec 5 — Dec 121
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
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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 November 5, 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 November 5, 2026.
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1811:26 am -
1 stop9h 04m
Tue 12/298:35 pm -
1 stop12h 56m
Deal found 11/2![Frontier logo]()
$332
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1811:26 am -
1 stop9h 04m
Sun 12/278:35 pm -
1 stop12h 56m
Deal found 11/2![Frontier logo]()
$380
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/164:05 pm -
1 stop6h 25m
Sat 12/193:40 pm -
1 stop7h 05m
Deal found 11/4![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:25 am -
1 stop11h 25m
Sun 11/298:45 pm -
1 stop11h 00m
Deal found 11/2![Southwest logo]()
$511
This Southwest deal was found by Cheapflights users on 11/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:05 pm -
1 stop6h 25m
Fri 11/207:50 am -
2 stops8h 15m
Deal found 11/1![Southwest logo]()
$542
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/174:05 pm -
1 stop6h 25m
Sat 11/213:40 pm -
1 stop7h 05m
Deal found 11/2![Southwest logo]()
$548
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:25 am -
1 stop8h 05m
Sun 11/298:45 pm -
1 stop11h 00m
Deal found 11/2![Southwest logo]()
$560
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:30 am -
1 stop9h 25m
Sun 11/225:05 am -
1 stop5h 40m
Deal found 11/3![Southwest logo]()
$563
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 November 5, 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 November 5, 2026.
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2111:26 am -
1 stop9h 04m
Tue 12/298:35 pm -
1 stop12h 56m
Deal found 11/2![Frontier logo]()
$332
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/164:05 pm -
1 stop6h 25m
Sat 12/193:40 pm -
1 stop7h 05m
Deal found 11/4![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:25 am -
1 stop11h 25m
Sun 11/298:45 pm -
1 stop11h 00m
Deal found 11/2![Southwest logo]()
$511
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1811:26 am -
2 stops13h 35m
Tue 12/298:35 pm -
1 stop12h 56m
Deal found 11/2![Frontier logo]()
$583
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/184:05 pm -
1 stop6h 25m
Sun 11/227:50 am -
2 stops8h 15m
Deal found 11/3![Southwest logo]()
$542
This Southwest deal was found by Cheapflights users on 11/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:05 pm -
1 stop6h 25m
Fri 11/207:50 am -
2 stops8h 15m
Deal found 11/1![Southwest logo]()
$542
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:05 pm -
2 stops8h 20m
Sun 11/227:50 am -
2 stops8h 15m
Deal found 11/2![Southwest logo]()
$547
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/174:05 pm -
1 stop6h 25m
Sat 11/213:40 pm -
1 stop7h 05m
Deal found 11/2![Southwest logo]()
$548
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:25 am -
1 stop8h 05m
Sun 11/298:45 pm -
1 stop11h 00m
Deal found 11/2![Southwest logo]()
$560
Last-minute flights from Islip to MidwayDiscover last-minute flight deals from Islip to Midway. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Islip to Midway. Data last updated November 5, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 11/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:05 pm -
1 stop6h 25m
Fri 11/207:50 am -
2 stops8h 15m
Deal found 11/1![Southwest logo]()
$542
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/174:05 pm -
1 stop6h 25m
Sat 11/213:40 pm -
1 stop7h 05m
Deal found 11/2![Southwest logo]()
$548
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:30 am -
1 stop9h 25m
Sun 11/225:05 am -
1 stop5h 40m
Deal found 11/3![Southwest logo]()
$563
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:25 am -
1 stop11h 25m
Sun 11/298:45 pm -
1 stop11h 00m
Deal found 11/2![Southwest logo]()
$511
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:25 am -
1 stop8h 05m
Sun 11/298:45 pm -
1 stop11h 00m
Deal found 11/2![Southwest logo]()
$560
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/164:05 pm -
1 stop6h 25m
Sat 12/193:40 pm -
1 stop7h 05m
Deal found 11/4![Southwest logo]()
$418
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1811:26 am -
1 stop9h 04m
Tue 12/298:35 pm -
1 stop12h 56m
Deal found 11/2![Frontier logo]()
$332
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1811:26 am -
1 stop9h 04m
Sun 12/278:35 pm -
1 stop12h 56m
Deal found 11/2![Frontier logo]()
$380
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 November 5, 2026.
Search for one-way flight options from Islip to Midway. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/155:25 pm -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 11/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2512:30 pm -
2 stops8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Fri 1/153:02 pm -
3 stops22h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Fri 12/259:39 am -
3 stops27h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:30 am -
1 stop4h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$474
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/274:40 pm -
2 stops15h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$538
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/287:42 pm -
3 stops49h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$763
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/294:40 pm -
2 stops15h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$973
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 November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $332 (Frontier) |
One-way from | $170 (Southwest) |
Popular in | October |
Cheapest in | January |
Average price | $277 |
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 November 5, 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
Fri 1/15
5:25 pm-11:00 pm
1 stop6h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Fri 12/25
12:30 pm-6:55 pm
1 stop7h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$207
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Mon 12/21
11:26 am-7:30 pm
1 stop9h 04m
Chicago Midway
Tue 12/29
8:35 pm-10:31 am
1 stop12h 56m
$332
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Wed 12/16
4:05 pm-9:30 pm
1 stop6h 25m
Chicago Midway
Sat 12/19
3:40 pm-11:45 pm
1 stop7h 05m
$418
Quickest round-trip
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Sat 11/28
5:30 am-8:55 am
1 stop4h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$474
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Tue 11/24
9:25 am-7:50 pm
1 stop11h 25m
Chicago Midway
Sun 11/29
8:45 pm-8:45 am
1 stop11h 00m
$511
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Fri 11/27
4:40 pm-7:37 am
2 stops15h 57m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$538
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Wed 11/18
4:05 pm-9:30 pm
1 stop6h 25m
Chicago Midway
Sun 11/22
7:50 am-5:05 pm
2 stops8h 15m
$542
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Mon 11/16
4:05 pm-9:30 pm
1 stop6h 25m
Chicago Midway
Fri 11/20
7:50 am-5:05 pm
2 stops8h 15m
$542
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Sat 11/21
5:05 pm-12:25 am
2 stops8h 20m
Chicago Midway
Sun 11/22
7:50 am-5:05 pm
2 stops8h 15m
$547
Showing 1-10 of 14 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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
Merrillville
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Valparaiso
Hammond
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Porter
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