$168+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — MDW
Oct 7 — Oct 141
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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Best
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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 7, 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 7, 2026.
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:56 am -
1 stop10h 06m
Sun 12/68:07 pm -
1 stop11h 54m
Deal found 9/4![Frontier logo]()
$281
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:55 am -
1 stop7h 50m
Sat 10/316:45 am -
1 stop4h 10m
Deal found 9/3![Southwest logo]()
$297
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:40 pm -
2 stops8h 25m
Thu 10/85:00 am -
1 stop5h 45m
Deal found 9/3![Southwest logo]()
$382
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:00 am -
1 stop5h 35m
Sun 10/185:10 am -
1 stop4h 10m
Deal found 9/3![Southwest logo]()
$385
This Southwest deal was found by Cheapflights users on 9/7. 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 10/136:05 am -
1 stop6h 15m
Sat 10/176:45 am -
2 stops8h 25m
Deal found 9/7![Southwest logo]()
$392
This Southwest deal was found by Cheapflights users on 9/7. 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 10/115:40 am -
1 stop5h 35m
Wed 10/144:45 pm -
1 stop4h 55m
Deal found 9/7![Southwest logo]()
$402
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:10 pm -
1 stop6h 15m
Sun 10/185:10 am -
1 stop4h 10m
Deal found 9/3![Southwest logo]()
$404
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 7, 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 7, 2026.
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:56 am -
1 stop10h 06m
Sun 12/68:07 pm -
1 stop11h 54m
Deal found 9/4![Frontier logo]()
$281
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:55 am -
1 stop7h 50m
Sat 10/316:45 am -
1 stop4h 10m
Deal found 9/3![Southwest logo]()
$297
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:40 pm -
2 stops8h 25m
Thu 10/85:00 am -
1 stop5h 45m
Deal found 9/3![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 9/7. 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 10/1312:50 pm -
1 stop4h 15m
Sat 10/172:40 pm -
1 stop6h 10m
Deal found 9/7![Southwest logo]()
$387
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:40 pm -
1 stop6h 25m
Sat 11/144:25 pm -
1 stop4h 20m
Deal found 9/4![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 9/7. 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 11/131:35 pm -
2 stops10h 20m
Sat 11/144:25 pm -
1 stop4h 20m
Deal found 9/7![Southwest logo]()
$392
Last-minute flights from Islip to MidwayDiscover last-minute flight deals from Islip to Midway. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Islip to Midway. Data last updated September 7, 2026 and is based on user searches.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:40 pm -
2 stops8h 25m
Thu 10/85:00 am -
1 stop5h 45m
Deal found 9/3![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 9/7. 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 10/115:40 am -
1 stop5h 35m
Wed 10/144:45 pm -
1 stop4h 55m
Deal found 9/7![Southwest logo]()
$402
This Southwest deal was found by Cheapflights users on 9/7. 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 10/136:05 am -
1 stop6h 15m
Sat 10/176:45 am -
2 stops8h 25m
Deal found 9/7![Southwest logo]()
$392
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:00 am -
1 stop5h 35m
Sun 10/185:10 am -
1 stop4h 10m
Deal found 9/3![Southwest logo]()
$385
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:10 pm -
1 stop6h 15m
Sun 10/185:10 am -
1 stop4h 10m
Deal found 9/3![Southwest logo]()
$404
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:55 am -
1 stop7h 50m
Sat 10/316:45 am -
1 stop4h 10m
Deal found 9/3![Southwest logo]()
$297
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 7, 2026.
Search for one-way flight options from Islip to Midway. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:25 pm -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$168
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:40 pm -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/1612:00 pm -
2 stops30h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$230
This Southwest deal was found by Cheapflights users on 9/5. 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 9/184:05 pm -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Southwest logo]()
$249
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:40 am -
2 stops7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 9/1811:52 am -
3 stops30h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 9/7. 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 9/163:20 pm -
1 stop6h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$394
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 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (Frontier) |
One-way from | $168 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $289 |
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 7, 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 11/13
1:35 pm-10:55 pm
2 stops10h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$173
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Sun 11/15
5:40 pm-11:05 pm
1 stop6h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$209
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Wed 9/16
12:00 pm-5:46 pm
2 stops30h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$230
Quickest round-trip
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Fri 9/18
4:05 pm-9:00 pm
1 stop5h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$249
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Sun 10/25
5:40 am-12:10 pm
2 stops7h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$265
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Thu 12/3
9:56 am-7:02 pm
1 stop10h 06m
Chicago Midway
Sun 12/6
8:07 pm-9:01 am
1 stop11h 54m
$281
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Thu 10/29
6:55 am-1:45 pm
1 stop7h 50m
Chicago Midway
Sat 10/31
6:45 am-11:55 am
1 stop4h 10m
$297
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Fri 9/18
11:52 am-5:51 pm
3 stops30h 59m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$362
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Thu 10/1
5:40 pm-1:05 am
2 stops8h 25m
Chicago Midway
Thu 10/8
5:00 am-11:45 am
1 stop5h 45m
$382
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Tue 10/13
12:50 pm-4:05 pm
1 stop4h 15m
Chicago Midway
Sat 10/17
2:40 pm-9:50 pm
1 stop6h 10m
$387
Showing 1-10 of 13 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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