Cheap flights from MDW to ISP (Midway Intl. to MacArthur)

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Cheap Flights from MDW to ISP starting at $86 One Way, $267 Round Trip

Prices starting at $267 for return flights and $86 for one-way flights to MacArthur were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Apr 17 - Sun, Apr 19
MDW
Chicago
ISP
Islip
$267 Roundtrip, found 2 days ago
$267
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Apr 17 from Chicago to Islip, returning Sun, Apr 19, priced at $267 found 2 days ago
Fri, Apr 17 - Sun, Apr 19
MDW
Chicago
ISP
Islip
$272 Roundtrip, found 2 days ago
$272
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Apr 17 from Chicago to Islip, returning Sun, Apr 19, priced at $272 found 2 days ago
Fri, Apr 17 - Sun, Apr 19
MDW
Chicago
ISP
Islip
$278 Roundtrip, found 2 days ago
$278
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Apr 17 from Chicago to Islip, returning Sun, Apr 19, priced at $278 found 2 days ago
Fri, Apr 17 - Sun, Apr 19
MDW
Chicago
ISP
Islip
$284 Roundtrip, found 2 days ago
$284
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Apr 17 from Chicago to Islip, returning Sun, Apr 19, priced at $284 found 2 days ago
Fri, Apr 17 - Sun, Apr 19
MDW
Chicago
ISP
Islip
$290 Roundtrip, found 2 days ago
$290
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Apr 17 from Chicago to Islip, returning Sun, Apr 19, priced at $290 found 2 days ago

Hotel Ideas near MacArthur

Airport Hotels near MacArthur

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

3 out of 5
10 Aero Rd Bohemia NY
$94 nightly
The price is $108 total per night from Mar 8 to Mar 9
$108 total
Mar 8 - Mar 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Bohemia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.8/10 (1,510 reviews)
👍

Reviewed on Feb 27, 2026

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
Clarion Hotel & Conference Center

Clarion Hotel & Conference Center

3 out of 5
3845 Veterans Memorial Hwy Ronkonkoma NY
$91 nightly
The price is $104 total per night from Mar 5 to Mar 6
$104 total
Mar 5 - Mar 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Ronkonkoma. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the clean rooms in our ...
5/10 (1,001 reviews)
This hotel made me pay for a room my daughter and I never got to sleep in. They refuse to refund me for the room because I didn't have the deposit $100. My daughter and I ended up sleeping in the car that night, so much for kindness and command courtesy....... The receptionist was rude and had no ...

Reviewed on Feb 22, 2026

Clarion Hotel & Conference Center
Hilton Garden Inn Islip/MacArthur Airport

Hilton Garden Inn Islip/MacArthur Airport

3 out of 5
3485 Veterans Memorial Hwy Ronkonkoma NY
$110 nightly
The price is $126 total per night from Mar 30 to Mar 31
$126 total
Mar 30 - Mar 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Ronkonkoma. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,010 reviews)
Yes

Reviewed on Feb 22, 2026

Hilton Garden Inn Islip/MacArthur Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Islip

Hilton Garden Inn Islip/MacArthur Airport

Hilton Garden Inn Islip/MacArthur Airport

3 out of 5
3485 Veterans Memorial Hwy Ronkonkoma NY
$110 nightly
The price is $126 total per night from Mar 30 to Mar 31
$126 total
Mar 30 - Mar 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Ronkonkoma. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,010 reviews)
Yes

Reviewed on Feb 22, 2026

Hilton Garden Inn Islip/MacArthur Airport
Courtyard by Marriott Long Island MacArthur Airport

Courtyard by Marriott Long Island MacArthur Airport

3 out of 5
5000 Express Dr S Ronkonkoma NY
$127 nightly
The price is $145 total per night from Mar 6 to Mar 7
$145 total
Mar 6 - Mar 7
Total with taxes and fees
Book a stay at this business-friendly hotel in Ronkonkoma. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,000 reviews)
Nice room

Reviewed on Feb 24, 2026

Courtyard by Marriott Long Island MacArthur Airport
Homewood Suites by Hilton Ronkonkoma

Homewood Suites by Hilton Ronkonkoma

3 out of 5
65 Union Avenue Ronkonkoma NY
$152 nightly
The price is $174 total per night from Mar 5 to Mar 6
$174 total
Mar 5 - Mar 6
Total with taxes and fees
Stay at this hotel in Ronkonkoma. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (590 reviews)
For a Hilton Property I expect a better experience. The room had a broken toilet paper holder, The TV was not a smart TV, The hallway had a pungent smell.

Reviewed on Feb 27, 2026

Homewood Suites by Hilton Ronkonkoma
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Islip Hotels With Airport Transportation

Courtyard by Marriott Long Island MacArthur Airport

Courtyard by Marriott Long Island MacArthur Airport

3 out of 5
5000 Express Dr S Ronkonkoma NY
$127 nightly
The price is $145 total per night from Mar 6 to Mar 7
$145 total
Mar 6 - Mar 7
Total with taxes and fees
Book a stay at this business-friendly hotel in Ronkonkoma. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,000 reviews)
Nice room

Reviewed on Feb 24, 2026

Courtyard by Marriott Long Island MacArthur Airport
Clarion Hotel & Conference Center

Clarion Hotel & Conference Center

3 out of 5
3845 Veterans Memorial Hwy Ronkonkoma NY
$91 nightly
The price is $104 total per night from Mar 5 to Mar 6
$104 total
Mar 5 - Mar 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Ronkonkoma. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the clean rooms in our ...
5/10 (1,001 reviews)
This hotel made me pay for a room my daughter and I never got to sleep in. They refuse to refund me for the room because I didn't have the deposit $100. My daughter and I ended up sleeping in the car that night, so much for kindness and command courtesy....... The receptionist was rude and had no ...

Reviewed on Feb 22, 2026

Clarion Hotel & Conference Center
Hilton Garden Inn Islip/MacArthur Airport

Hilton Garden Inn Islip/MacArthur Airport

3 out of 5
3485 Veterans Memorial Hwy Ronkonkoma NY
$110 nightly
The price is $126 total per night from Mar 30 to Mar 31
$126 total
Mar 30 - Mar 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Ronkonkoma. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,010 reviews)
Yes

Reviewed on Feb 22, 2026

Hilton Garden Inn Islip/MacArthur Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Islip Hotels

Clarion Hotel & Conference Center

Clarion Hotel & Conference Center

3 out of 5
3845 Veterans Memorial Hwy Ronkonkoma NY
$91 nightly
The price is $104 total per night from Mar 5 to Mar 6
$104 total
Mar 5 - Mar 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Ronkonkoma. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the clean rooms in our ...
5/10 (1,001 reviews)
This hotel made me pay for a room my daughter and I never got to sleep in. They refuse to refund me for the room because I didn't have the deposit $100. My daughter and I ended up sleeping in the car that night, so much for kindness and command courtesy....... The receptionist was rude and had no ...

Reviewed on Feb 22, 2026

Clarion Hotel & Conference Center
Hilton Garden Inn Islip/MacArthur Airport

Hilton Garden Inn Islip/MacArthur Airport

3 out of 5
3485 Veterans Memorial Hwy Ronkonkoma NY
$110 nightly
The price is $126 total per night from Mar 30 to Mar 31
$126 total
Mar 30 - Mar 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Ronkonkoma. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,010 reviews)
Yes

Reviewed on Feb 22, 2026

Hilton Garden Inn Islip/MacArthur Airport
Rodeway Inn Macarthur Airport

Rodeway Inn Macarthur Airport

2 out of 5
3055 Veterans Memorial Hwy Ronkonkoma NY
$93 nightly
The price is $106 total per night from Mar 29 to Mar 30
$106 total
Mar 29 - Mar 30
Total with taxes and fees
Stay at this hotel in Ronkonkoma. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
7/10 Good! (1,000 reviews)
Always a great stay

Reviewed on Feb 16, 2026

Rodeway Inn Macarthur Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Islip

Hilton Garden Inn Islip/MacArthur Airport

Hilton Garden Inn Islip/MacArthur Airport

3 out of 5
3485 Veterans Memorial Hwy Ronkonkoma NY
$110 nightly
The price is $126 total per night from Mar 30 to Mar 31
$126 total
Mar 30 - Mar 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Ronkonkoma. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,010 reviews)
Yes

Reviewed on Feb 22, 2026

Hilton Garden Inn Islip/MacArthur Airport
Clarion Hotel & Conference Center

Clarion Hotel & Conference Center

3 out of 5
3845 Veterans Memorial Hwy Ronkonkoma NY
$91 nightly
The price is $104 total per night from Mar 5 to Mar 6
$104 total
Mar 5 - Mar 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Ronkonkoma. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the clean rooms in our ...
5/10 (1,001 reviews)
This hotel made me pay for a room my daughter and I never got to sleep in. They refuse to refund me for the room because I didn't have the deposit $100. My daughter and I ended up sleeping in the car that night, so much for kindness and command courtesy....... The receptionist was rude and had no ...

Reviewed on Feb 22, 2026

Clarion Hotel & Conference Center
Rodeway Inn Macarthur Airport

Rodeway Inn Macarthur Airport

2 out of 5
3055 Veterans Memorial Hwy Ronkonkoma NY
$93 nightly
The price is $106 total per night from Mar 29 to Mar 30
$106 total
Mar 29 - Mar 30
Total with taxes and fees
Stay at this hotel in Ronkonkoma. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
7/10 Good! (1,000 reviews)
Always a great stay

Reviewed on Feb 16, 2026

Rodeway Inn Macarthur Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

MDW to ISP Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago
ISP Address & GPS
Address:
100 Arrivals Avenue
Islip NY, 11779
United States
IATA Code:
ISP
Longitude:
-73.097546
Latitude:
40.789314
Time Zone:
America/New_York

Frequently asked questions

What is the shortest flight from Chicago Airport to ISP?
Getting from Chicago Airport to MacArthur Airport (ISP) takes at least 5 hours. Indulge in a wine and watch a flick or two — this is a great chance to sit back and chill out.
How many hours flight from Chicago Airport to MacArthur Airport?
It usually takes around 5 hours and 5 minutes to fly from Midway Intl. Airport (MDW) to MacArthur Airport. You'll be in the sky for a good amount of time, so contemplate bringing your own entertainment, like an audiobook or a few podcasts.
What airlines have the most flights from Chicago Airport to MacArthur Airport?
You won't be able to find any airlines that fly direct between MDW and MacArthur Airport (ISP). Plan ahead and reserve a multi-stop or one-stop plane ticket.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

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