ISP - ORD

$105 Find Cheap Flights from Islip to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Islip to Chicago departing on 5/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Islip to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Islip to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flight Deals from Islip to Chicago (ISP-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Islip to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Islip to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Islip to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
8:21 pm - 8:22 amISP-ORD
13h 01m1 stop
Frontier Logo
1:02 pm - 8:42 pmORD-ISP
6h 40m1 stop
$201Frontier
Find Deal
Wed, May 28 - Sat, May 31
Frontier Logo
8:21 pm - 8:22 amISP-ORD
13h 01m1 stop
Frontier Logo
5:03 pm - 7:41 pmORD-ISP
25h 38m1 stop
$208Frontier
Find Deal
Wed, May 28 - Wed, Jun 4
Frontier Logo
9:40 pm - 8:05 amISP-ORD
11h 25m1 stop
Frontier Logo
6:55 am - 3:33 pmORD-ISP
7h 38m1 stop
$210Frontier
Find Deal
Thu, May 15 - Mon, May 19
Frontier Logo
6:48 pm - 11:32 pmISP-ORD
29h 44m1 stop
Frontier Logo
4:15 pm - 11:26 amORD-ISP
18h 11m1 stop
$211Frontier
Find Deal
Fri, May 16 - Mon, May 19
Frontier Logo
8:51 am - 7:56 pmISP-ORD
12h 05m1 stop
Frontier Logo
5:08 pm - 7:41 pmORD-ISP
25h 33m1 stop
$218Frontier
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Fri, Jun 6 - Sat, Jun 7
Southwest Logo
8:20 am - 5:55 pmISP-ORD
10h 35m2 stops
Southwest Logo
1:50 pm - 8:20 pmORD-ISP
5h 30m1 stop
$276Southwest
Find Deal
Wed, May 28 - Wed, Jun 4
Southwest Logo
6:00 am - 11:50 amISP-ORD
6h 50m1 stop
Southwest Logo
12:40 pm - 12:05 amORD-ISP
10h 25m2 stops
$316Southwest
Find Deal
Wed, Jul 30 - Fri, Aug 1
Logo
6:48 pm - 8:55 amISP-ORD
15h 07m2 stops
Logo
9:17 am - 7:34 pmORD-ISP
9h 17m1 stop
$318
Find Deal
Sun, May 18 - Thu, May 22
Southwest Logo
6:00 am - 4:25 pmISP-ORD
11h 25m2 stops
Southwest Logo
6:00 am - 5:00 pmORD-ISP
10h 00m2 stops
$321Southwest
Find Deal
Wed, Jul 16 - Wed, Jul 23
Southwest Logo
6:00 am - 4:25 pmISP-ORD
11h 25m2 stops
Southwest Logo
1:50 pm - 10:55 pmORD-ISP
8h 05m1 stop
$322Southwest
Find Deal
Wed, Jul 16 - Wed, Jul 23
Useful Info

KAYAK's insights & trends for Islip to Chicago flights

Get data-powered insights and trends into flights from Islip to Chicago to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Islip to Chicago?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Islip to Chicago were found on Frontier ($201) and Southwest ($276).

Find deals

Good to know

Cheapest flight$105
Flight from Islip to Chicago

When to book flights from Islip to Chicago

Are your dates flexible? Find out the best times to travel from Islip to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Islip to Chicago flights

  • What is the cheapest flight from Islip to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Islip to Chicago O'Hare Intl Airport was $105 for a one-way ticket and $201 for a round-trip.

  • Do I need a passport to fly between Islip and Chicago?

    A passport is not required to fly from Islip to Chicago.

  • Which airports will I be using when flying from Islip to Chicago?

    When flying out of Islip you will be using Islip Long Island. You will be landing at Chicago, also known as Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Islip to Chicago?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Islip to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Islip to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Islip to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Islip is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Islip to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Islip with another airline. Booking your flights between Islip and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Islip to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Islip up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top airline flying from Islip to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Islip to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Islip to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Everything you need to know for your flight from Islip to Chicago

Information on your arrival and departure airports

O'Hare Intl (ORD)
Islip (ISP)

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