$119 Cheap Flights from Islip (ISP) to Chicago (MDW)

View $119 flight on Mon, Oct 20, 2025Opens in a new window

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

Cheap Flights from Islip to Chicago (ISP-MDW)

Prices were available within the past 7 days and start at $119 for one-way flights and $228 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Oct 22 - Sat, Oct 25
ISP
Islip
MDW
Chicago
$228 Roundtrip, found 6 days ago
$228
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Oct 22 from Islip to Chicago, returning Sat, Oct 25, priced at $228 found 6 days ago
Southwest Airlines
Sat, Sep 6 - Tue, Sep 9
ISP
Islip
MDW
Chicago
$237 Roundtrip, found 21 hours ago
$237
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Sat, Sep 6 from Islip to Chicago, returning Tue, Sep 9, priced at $237 found 21 hours ago
Frontier Airlines
Sat, Aug 23 - Sun, Aug 31
ISP
Islip
MDW
Chicago
$238 Roundtrip, found 6 days ago
$238
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Aug 23 from Islip to Chicago, returning Sun, Aug 31, priced at $238 found 6 days ago
Southwest Airlines
Sat, Nov 8 - Mon, Nov 10
ISP
Islip
MDW
Chicago
$246 Roundtrip, found 6 days ago
$246
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Nov 8 from Islip to Chicago, returning Mon, Nov 10, priced at $246 found 6 days ago
Southwest Airlines
Wed, Sep 3 - Sat, Sep 6
ISP
Islip
MDW
Chicago
$247 Roundtrip, found 3 days ago
$247
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Sep 3 from Islip to Chicago, returning Sat, Sep 6, priced at $247 found 3 days ago
Southwest Airlines
Sat, Nov 8 - Mon, Nov 10
ISP
Islip
MDW
Chicago
$251 Roundtrip, found 6 days ago
$251
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Nov 8 from Islip to Chicago, returning Mon, Nov 10, priced at $251 found 6 days ago
Southwest Airlines
Wed, Sep 3 - Sat, Sep 6
ISP
Islip
MDW
Chicago
$252 Roundtrip, found 3 days ago
$252
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Sep 3 from Islip to Chicago, returning Sat, Sep 6, priced at $252 found 3 days ago
Southwest Airlines
Fri, Oct 3 - Sat, Oct 4
ISP
Islip
MDW
Chicago
$259 Roundtrip, found 3 hours ago
$259
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Fri, Oct 3 from Islip to Chicago, returning Sat, Oct 4, priced at $259 found 3 hours ago
Southwest Airlines
Mon, Oct 20 - Fri, Oct 24
ISP
Islip
MDW
Chicago
$264 Roundtrip, found 2 hours ago
$264
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Mon, Oct 20 from Islip to Chicago, returning Fri, Oct 24, priced at $264 found 2 hours ago
Southwest Airlines
Mon, Oct 27 - Fri, Oct 31
ISP
Islip
MDW
Chicago
$267 Roundtrip, found 6 days ago
$267
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Islip to Chicago, returning Fri, Oct 31, priced at $267 found 6 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $390
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $390
Flights from Islip (ISP) to Chicago (MDW)
Origin airport
MacArthur
Destination airport
Midway Intl.
Airlines serving
Frontier Airlines, Southwest Airlines
Roundtrip price
$228
Distance
762 mi

Islip to Chicago Flights

The cheapest times to fly from Islip to Chicago

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 Islip to Chicago are during the month of October. You can find some of the cheapest flights from Islip to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Islip to Chicago

Sunday is one of the best days to book for cheap flights from Islip to Chicago: 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 Islip to Chicago

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 Islip to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $119 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 Islip to Chicago 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 Islip to Chicago 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 MacArthur Airport (ISP) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $119 or cheap return flight from $228 from MacArthur Airport (ISP) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from MacArthur Airport (ISP) to Midway Intl. Airport (MDW)?
October is the most affordable month to fly from ISP to MDW. Timing your trip outside of the busy season is often the key to finding better deals on flights.
What is the cheapest airline that flies from MacArthur Airport (ISP) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, travel time and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest ISP to MDW flight.
How many flights per day from MacArthur Airport (ISP) to Midway Intl. Airport (MDW)?
Direct flights from MacArthur Airport (ISP) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ISP to MDW?
Generally you'll find the widest variety of flight choices on a Friday. Tuesdays are often the quietest.* However, this can vary depending on the airline, season 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 MacArthur Airport (ISP) to Midway Intl. Airport (MDW)?
To avoid possible delays on the MacArthur Airport (ISP) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Later departures 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.
Is it cheaper to buy a plane ticket from MacArthur Airport (ISP) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from ISP to MDW right before your getaway is usually more expensive. But if you're flexible with your schedule, you could land a cheap last-minute fare.
Is it cheaper to book an ISP to MDW flight and hotel package?
You'll typically save money by booking an ISP to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one convenient place. After choosing your ideal flights and accommodations, consider adding extras such as car rentals, activities and tours.
Can I cancel or change the date of my flight from MacArthur Airport (ISP) to Midway Intl. Airport (MDW)?
You can usually reschedule or cancel your ISP to MDW flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more information on our Customer Service portal.

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*Available to One Key members.