$110 Cheap Flights from Chicago (MDW) to Islip (ISP)

View $110 flight on Thu, May 1, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Islip (MDW-ISP)

Prices were available within the past 7 days and start at $110 for one-way flights and $198 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, May 1 - Wed, May 7
MDW
Chicago
ISP
Islip
$198 Roundtrip, found 2 days ago
$198
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 1 from Chicago to Islip, returning Wed, May 7, priced at $198 found 2 days ago
Frontier Airlines
Thu, May 1 - Thu, May 8
MDW
Chicago
ISP
Islip
$208 Roundtrip, found 2 days ago
$208
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 1 from Chicago to Islip, returning Thu, May 8, priced at $208 found 2 days ago
Frontier Airlines
Fri, May 16 - Sat, May 17
MDW
Chicago
ISP
Islip
$210 Roundtrip, found 1 day ago
$210
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, May 16 from Chicago to Islip, returning Sat, May 17, priced at $210 found 1 day ago
Frontier Airlines
Thu, May 8 - Wed, May 14
MDW
Chicago
ISP
Islip
$218 Roundtrip, found 8 hours ago
$218
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, May 8 from Chicago to Islip, returning Wed, May 14, priced at $218 found 8 hours ago
Frontier Airlines
Thu, May 8 - Sun, May 18
MDW
Chicago
ISP
Islip
$220 Roundtrip, found 8 hours ago
$220
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, May 8 from Chicago to Islip, returning Sun, May 18, priced at $220 found 8 hours ago
Frontier Airlines
Thu, May 8 - Thu, May 15
MDW
Chicago
ISP
Islip
$228 Roundtrip, found 8 hours ago
$228
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, May 8 from Chicago to Islip, returning Thu, May 15, priced at $228 found 8 hours ago
Frontier Airlines
Thu, May 22 - Sat, Jun 7
MDW
Chicago
ISP
Islip
$230 Roundtrip, found 2 days ago
$230
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 22 from Chicago to Islip, returning Sat, Jun 7, priced at $230 found 2 days ago
Frontier Airlines
Thu, May 29 - Wed, Jun 18
MDW
Chicago
ISP
Islip
$231 Roundtrip, found 2 days ago
$231
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 29 from Chicago to Islip, returning Wed, Jun 18, priced at $231 found 2 days ago
Frontier Airlines
Thu, May 8 - Wed, May 21
MDW
Chicago
ISP
Islip
$238 Roundtrip, found 1 day ago
$238
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 8 from Chicago to Islip, returning Wed, May 21, priced at $238 found 1 day ago
Southwest Airlines
Tue, May 13 - Thu, May 15
MDW
Chicago
ISP
Islip
$292 Roundtrip, found 4 days ago
$292
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, May 13 from Chicago to Islip, returning Thu, May 15, priced at $292 found 4 days ago
Flights from Chicago (MDW) to Islip (ISP)
Origin airport
Midway Intl.
Destination airport
MacArthur
Airlines serving
Frontier Airlines, Southwest Airlines
Roundtrip price
$198
Distance
762 mi

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 May. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $110 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to MacArthur Airport (ISP) cost?
Discover the latest flight deals from MDW to ISP by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to ISP?
The cheapest flights from MDW to ISP are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to ISP?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MDW to ISP. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to MacArthur Airport (ISP)?
There are no daily direct flights departing from Midway Intl. Airport (MDW) to MacArthur Airport (ISP). But you can opt for flights with layovers. Filter your search results on Expedia to include one or two stops, and you’ll be on your way in no time at all.
What day of the week has the most flights from MDW to ISP?
Typically you’ll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to MacArthur Airport (ISP)?
To avoid possible delays on the Midway Intl. Airport (MDW) to MacArthur Airport (ISP) route, travel before 3 PM. Later flights have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Islip from Midway Intl. Airport (MDW)?
Explore your flight options from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA). This is the only airport in Islip you can fly into if you’re taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to MacArthur Airport (ISP) last-minute?
Holding off until right before your break to book a ticket from MDW to ISP often results in higher prices. While you may find some last-minute offers, they aren’t always guaranteed. Be flexible with your itinerary for a better chance of landing a bargain.
Is it cheaper to book a MDW to ISP flight and hotel package?
You’ll generally save money by securing a MDW to ISP flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s simple to manage it all in one convenient place. After selecting your ideal accommodations and flights, consider adding extras such as tours, activities and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to MacArthur Airport (ISP)?
In most instances, you can cancel or modify your MDW to ISP flight. However, there may be additional fees, especially if your booking was made more than 24 hours ago. Double-check your itinerary for the airline’s policies and fees on flight changes, or if you need further information, head to our Customer Service portal.

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*Available to One Key members.