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

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Cheap Flights from MDW to ISP starting at $76 One Way, $407 Round Trip

Prices starting at $407 for return flights and $76 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, Jul 10 - Tue, Jul 14
MDW
Chicago
ISP
Islip
$407 Roundtrip, found 12 hours ago
$407
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Fri, Jul 10 from Chicago to Islip, returning Tue, Jul 14, priced at $407 found 12 hours ago
Fri, Jul 10 - Tue, Jul 14
MDW
Chicago
ISP
Islip
$412 Roundtrip, found 12 hours ago
$412
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Fri, Jul 10 from Chicago to Islip, returning Tue, Jul 14, priced at $412 found 12 hours ago
Sat, Jul 11 - Mon, Jul 13
MDW
Chicago
ISP
Islip
$417 Roundtrip, found 2 days ago
$417
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Jul 11 from Chicago to Islip, returning Mon, Jul 13, priced at $417 found 2 days ago
Fri, Jul 10 - Tue, Jul 14
MDW
Chicago
ISP
Islip
$417 Roundtrip, found 12 hours ago
$417
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Fri, Jul 10 from Chicago to Islip, returning Tue, Jul 14, priced at $417 found 12 hours ago
Fri, Jul 10 - Tue, Jul 14
MDW
Chicago
ISP
Islip
$422 Roundtrip, found 12 hours ago
$422
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Fri, Jul 10 from Chicago to Islip, returning Tue, Jul 14, priced at $422 found 12 hours 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
$92 nightly
The price is $105 total per night from Mar 29 to Mar 30
$105 total
Mar 29 - Mar 30
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 (1,522 reviews)
The room met expectations, especially for the price. Convenient to airport and food runs

Reviewed on Mar 25, 2026

La Quinta Inn & Suites by Wyndham Islip - 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 Apr 8 to Apr 9
$174 total
Apr 8 - Apr 9
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! (601 reviews)
Clean room with microwave, staff was accommodating, and friendly.

Reviewed on Mar 18, 2026

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

Courtyard by Marriott Long Island MacArthur Airport

3 out of 5
5000 Express Dr S Ronkonkoma NY
$119 nightly
The price is $136 total per night from Mar 30 to Mar 31
$136 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 a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,005 reviews)
Please Google or go to Yelp and find Mesoyios Restaurant. Best tasting Greek food with large portion sizes and excellent prices!!! Super close to the hotel. The hotel was amazing with super clean hot tub and very warm pool.

Reviewed on Mar 23, 2026

Courtyard by Marriott Long Island 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

Courtyard by Marriott Long Island MacArthur Airport

Courtyard by Marriott Long Island MacArthur Airport

3 out of 5
5000 Express Dr S Ronkonkoma NY
$119 nightly
The price is $136 total per night from Mar 30 to Mar 31
$136 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 a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,005 reviews)
Please Google or go to Yelp and find Mesoyios Restaurant. Best tasting Greek food with large portion sizes and excellent prices!!! Super close to the hotel. The hotel was amazing with super clean hot tub and very warm pool.

Reviewed on Mar 23, 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 Apr 8 to Apr 9
$174 total
Apr 8 - Apr 9
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! (601 reviews)
Clean room with microwave, staff was accommodating, and friendly.

Reviewed on Mar 18, 2026

Homewood Suites by Hilton Ronkonkoma
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 Apr 26 to Apr 27
$106 total
Apr 26 - Apr 27
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 ...
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.

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
$119 nightly
The price is $136 total per night from Mar 30 to Mar 31
$136 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 a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,005 reviews)
Please Google or go to Yelp and find Mesoyios Restaurant. Best tasting Greek food with large portion sizes and excellent prices!!! Super close to the hotel. The hotel was amazing with super clean hot tub and very warm pool.

Reviewed on Mar 23, 2026

Courtyard by Marriott Long Island 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

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 Apr 26 to Apr 27
$106 total
Apr 26 - Apr 27
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 ...
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

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 Apr 26 to Apr 27
$106 total
Apr 26 - Apr 27
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 ...
Rodeway Inn 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
$119 nightly
The price is $136 total per night from Mar 30 to Mar 31
$136 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 a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,005 reviews)
Please Google or go to Yelp and find Mesoyios Restaurant. Best tasting Greek food with large portion sizes and excellent prices!!! Super close to the hotel. The hotel was amazing with super clean hot tub and very warm pool.

Reviewed on Mar 23, 2026

Courtyard by Marriott Long Island 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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