$96 Cheap Flights from Chicago (MDW) to Islip (ISP)

View $96 flight on Sun, Apr 19, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to MacArthur Airport (ISP)

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Cheap Flights from Chicago to Islip (MDW-ISP)

Prices were available within the past 7 days and start at $96 for one-way flights and $201 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sun, Apr 19 - Sun, Apr 26
MDW
Chicago
ISP
Islip
$201 Roundtrip, found 1 day ago
$201
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Apr 19 from Chicago to Islip, returning Sun, Apr 26, priced at $201 found 1 day ago
Frontier Airlines
Fri, May 22 - Fri, May 29
MDW
Chicago
ISP
Islip
$225 Roundtrip, found 6 days ago
$225
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, May 22 from Chicago to Islip, returning Fri, May 29, priced at $225 found 6 days ago
Frontier Airlines
Fri, May 29 - Mon, Jun 1
MDW
Chicago
ISP
Islip
$246 Roundtrip, found 3 days ago
$246
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, May 29 from Chicago to Islip, returning Mon, Jun 1, priced at $246 found 3 days ago
Frontier Airlines
Fri, May 22 - Sun, May 24
MDW
Chicago
ISP
Islip
$260 Roundtrip, found 6 days ago
$260
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, May 22 from Chicago to Islip, returning Sun, May 24, priced at $260 found 6 days ago
Frontier Airlines
Mon, Aug 17 - Mon, Aug 31
MDW
Chicago
ISP
Islip
$264 Roundtrip, found 2 days ago
$264
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Aug 17 from Chicago to Islip, returning Mon, Aug 31, priced at $264 found 2 days ago
Frontier Airlines
Fri, May 22 - Thu, May 28
MDW
Chicago
ISP
Islip
$280 Roundtrip, found 6 days ago
$280
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, May 22 from Chicago to Islip, returning Thu, May 28, priced at $280 found 6 days ago
Frontier Airlines
Sun, Apr 19 - Sun, Apr 26
MDW
Chicago
ISP
Islip
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Apr 19 from Chicago to Islip, returning Sun, Apr 26, priced at $289 found 1 day ago
Frontier Airlines
Sun, Apr 19 - Sun, Apr 26
MDW
Chicago
ISP
Islip
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Apr 19 from Chicago to Islip, returning Sun, Apr 26, priced at $299 found 1 day ago
Frontier Airlines
Fri, May 22 - Sun, May 31
MDW
Chicago
ISP
Islip
$300 Roundtrip, found 6 days ago
$300
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, May 22 from Chicago to Islip, returning Sun, May 31, priced at $300 found 6 days ago
Southwest Airlines
Mon, Aug 17 - Mon, Aug 31
MDW
Chicago
ISP
Islip
$308 Roundtrip, found 2 days ago
$308
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Aug 17 from Chicago to Islip, returning Mon, Aug 31, priced at $308 found 2 days ago

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Alternative airports near Islip

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to MacArthur ISP. Cheapest and Closest option available. Average driving time to city center is 14 minutes. Flights from $460
ISP
MacArthur
CheapestClosest
Average driving time to city center14 min
Flights from $460

Frequently asked questions

How much does a flight from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur) cost?
You can find cheap one-way flights from $96 and cheap return flights from $201 Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur) with Expedia. One-way flights usually range from $453 to $632. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur)?
The cheapest month to fly from MDW to ISP is April when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur)?
Enter MDW to ISP and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur)?
Delta and Frontier Airlines are just some of the carriers that fly from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur). Use Expedia's flight search tool to compare airlines on this route and find our cheapest option for your trip. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur)?
To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur)?
The earliest flight from Midway International Airport (MDW) to MacArthur (ISP) usually leaves at 5:00 AM. This flight, operated by Southwest Airlines, gives you a great head start on your day in Islip. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur)?
a Thursday typically has the most flights from Midway Intl. (MDW) to MacArthur (ISP), with approximately 17 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Delta and Frontier Airlines.
What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur)?
The most popular departure times for flights from Chicago (MDW) to Islip (ISP) are in the late morning, from 9am to 12pm. About 52% of passengers prefer this time window. Many major carriers, including Southwest Airlines and Frontier Airlines, offer flights during this window. This timing is favored as it allows you to enjoy your morning in Chicago before heading to the airport.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur)?
Flights from MDW to ISP with one stop typically take around 8 hours 30 minutes, covering approximately 762 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur)?
Select the "Business class" and "First class" filters when looking for MDW to ISP flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur) flight with Expedia?
It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Islip from Midway Intl. (MDW)?
If you're planning to travel to Islip from Midway Intl. (MDW), you can fly into MacArthur (ISP) Some flights may connect through major hubs like Hartsfield-Jackson Atlanta Intl. (ATL), Louisville Intl. (SDF), Charlotte-Douglas Intl. (CLT) before reaching Islip. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur) at the last minute?
Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur) flight and hotel package?
Securing a Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur)?
If you booked your Chicago, IL (MDW-Midway Intl.) to Islip, NY (ISP-MacArthur) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Midway Intl.
Destination airport
MacArthur
Airlines serving
Southwest Airlines
Roundtrip price
$201
Distance
762 mi

Book with confidence

Chicago to Islip Flights

The cheapest times to fly from Chicago to Islip

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Islip are during the month of April. You can find some of the cheapest flights from Chicago to Islip with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Islip

Sunday is one of the best days to book for cheap flights from Chicago to Islip: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Islip

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Islip in 2026. You can also book with separate airlines for your outbound and return journeys, from $96 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Islip flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Islip airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Islip Flights

*Flight schedules are subject to change.

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*Available to One Key members.