ORD - ISP

$144 Find Cheap Flights from Chicago to Islip

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Islip departing on 8/24. 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
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Islip

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

Cheap Flights from Chicago to Islip (ORD-ISP)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Islip 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Islip

Wed, Jul 9 - Sat, Jul 12
Southwest Logo
11:25 am - 9:45 pmORD-ISP
9h 20m1 stop
Southwest Logo
6:30 am - 3:20 pmISP-ORD
9h 50m1 stop
$297Southwest
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Thu, Aug 28 - Thu, Sep 4
Frontier Logo
7:30 am - 8:06 pmORD-ISP
11h 36m1 stop
Frontier Logo
11:27 am - 12:57 pmISP-ORD
26h 30m1 stop
$301Frontier
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Sat, Jul 26 - Sat, Aug 2
Frontier Logo
9:08 am - 7:42 pmORD-ISP
9h 34m1 stop
Frontier Logo
8:37 pm - 3:43 pmISP-ORD
20h 06m1 stop
$307Frontier
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Thu, Aug 28 - Mon, Sep 1
Frontier Logo
7:30 am - 8:06 pmORD-ISP
11h 36m1 stop
Frontier Logo
8:59 am - 6:41 pmISP-ORD
10h 42m1 stop
$312Frontier
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Wed, Aug 6 - Sat, Aug 9
Southwest Logo
1:50 pm - 10:05 pmORD-ISP
7h 15m1 stop
Southwest Logo
5:40 am - 11:50 amISP-ORD
7h 10m1 stop
$319Southwest
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Thu, Jul 10 - Mon, Jul 14
Frontier Logo
4:37 pm - 7:42 pmORD-ISP
26h 05m1 stop
Frontier Logo
8:38 pm - 10:14 amISP-ORD
14h 36m1 stop
$322Frontier
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Fri, Jul 25 - Fri, Aug 1
Frontier Logo
4:26 pm - 7:42 pmORD-ISP
26h 16m1 stop
Frontier Logo
8:37 pm - 8:07 amISP-ORD
12h 30m1 stop
$326Frontier
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Tue, Jul 1 - Tue, Jul 8
Frontier Logo
11:28 am - 7:36 pmORD-ISP
7h 08m1 stop
Frontier Logo
8:00 am - 10:14 amISP-ORD
27h 14m1 stop
$327Frontier
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Wed, Jul 9 - Sat, Jul 12
Southwest Logo
11:25 am - 9:45 pmORD-ISP
9h 20m1 stop
Southwest Logo
6:00 am - 3:20 pmISP-ORD
10h 20m2 stops
$337Southwest
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Wed, Jun 25 - Sun, Jun 29
Logo
4:45 pm - 6:59 pmORD-ISP
25h 14m2 stops
Logo
7:39 pm - 11:45 pmISP-ORD
29h 06m3 stops
$644
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Useful Info

KAYAK's insights & trends for Chicago to Islip flights

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

Which airlines provide the cheapest flights from Chicago to Islip?

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 Chicago to Islip were found on Southwest ($297) and Frontier ($301).

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Good to know

Cheapest flight$144
Flight from Chicago to Islip

When to book flights from Chicago to Islip

Are your dates flexible? Find out the best times to travel from Chicago to Islip 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 Chicago to Islip flights

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

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Islip was $144 for a one-way ticket and $297 for a round-trip.

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

    No

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

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

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

    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 Chicago to Islip.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Islip from Chicago 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 Chicago to Islip?

    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 Islip with an airline and back to Chicago with another airline. Booking your flights between Chicago and ISP 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 Chicago to Islip?

    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 Islip from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top airline flying from Chicago to Islip

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Islip. 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 Chicago to Islip? 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 4287 reviews
7.6Entertainment
8.2Boarding
7.1Food
8.6Crew
8.0Comfort
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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

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

Information on your arrival and departure airports

Chicago (ORD)
Islip (ISP)

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