$90 Cheap Flights from Chicago (MDW) to Islip (ISP)

View $90 flight on Thu, Oct 23, 2025Opens in a new window

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

Cheap Flights from Chicago to Islip (MDW-ISP)

Prices were available within the past 7 days and start at $90 for one-way flights and $212 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, Sep 5 - Sun, Sep 7
MDW
Chicago
ISP
Islip
$212 Roundtrip, found 3 days ago
$212
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Sep 5 from Chicago to Islip, returning Sun, Sep 7, priced at $212 found 3 days ago
Frontier Airlines
Fri, Sep 5 - Sun, Sep 7
MDW
Chicago
ISP
Islip
$229 Roundtrip, found 6 days ago
$229
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Sep 5 from Chicago to Islip, returning Sun, Sep 7, priced at $229 found 6 days ago
Frontier Airlines
Fri, Sep 26 - Sun, Sep 28
MDW
Chicago
ISP
Islip
$233 Roundtrip, found 2 days ago
$233
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Sep 26 from Chicago to Islip, returning Sun, Sep 28, priced at $233 found 2 days ago
Frontier Airlines
Fri, Sep 12 - Mon, Sep 15
MDW
Chicago
ISP
Islip
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Sep 12 from Chicago to Islip, returning Mon, Sep 15, priced at $237 found 5 days ago
Frontier Airlines
Thu, Nov 13 - Wed, Nov 19
MDW
Chicago
ISP
Islip
$238 Roundtrip, found 6 hours ago
$238
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Chicago to Islip, returning Wed, Nov 19, priced at $238 found 6 hours ago
Frontier Airlines
Thu, Sep 4 - Sun, Sep 7
MDW
Chicago
ISP
Islip
$240 Roundtrip, found 3 days ago
$240
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Chicago to Islip, returning Sun, Sep 7, priced at $240 found 3 days ago
Frontier Airlines
Fri, Sep 5 - Sun, Sep 7
MDW
Chicago
ISP
Islip
$246 Roundtrip, found 3 days ago
$246
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Sep 5 from Chicago to Islip, returning Sun, Sep 7, priced at $246 found 3 days ago
Frontier Airlines
Thu, Nov 13 - Mon, Nov 17
MDW
Chicago
ISP
Islip
$248 Roundtrip, found 6 hours ago
$248
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Chicago to Islip, returning Mon, Nov 17, priced at $248 found 6 hours ago
Frontier Airlines
Thu, Sep 11 - Sun, Sep 14
MDW
Chicago
ISP
Islip
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Chicago to Islip, returning Sun, Sep 14, priced at $257 found 2 days ago
Southwest Airlines
Tue, Sep 30 - Sat, Oct 4
MDW
Chicago
ISP
Islip
$284 Roundtrip, found 3 days ago
$284
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Sep 30 from Chicago to Islip, returning Sat, Oct 4, priced at $284 found 3 days ago

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 $238
ISP
MacArthur
CheapestClosest
Average driving time to city center14 min
Flights from $238
Flights from Chicago (MDW) to Islip (ISP)
Origin airport
Midway Intl.
Destination airport
MacArthur
Airlines serving
Frontier Airlines, Southwest Airlines
Roundtrip price
$212
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 September. 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 $90 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?
Snag a cheap one-way flight from $90 or cheap return flight from $212 from Midway Intl. Airport (MDW) to MacArthur Airport (ISP) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to MacArthur Airport (ISP)?
The cheapest month to fly from MDW to ISP is September, when demand is low. Off-peak months are usually when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to MacArthur Airport (ISP)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to ISP. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
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.