ORD - ISP

$124 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 9/8. 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

Sat, Sep 27 - Tue, Sep 30
Southwest Logo
1:30 pm - 9:40 pmORD-ISP
7h 10m1 stop
Southwest Logo
5:30 am - 1:05 pmISP-ORD
8h 35m1 stop
$237Southwest
Find Deal
Mon, Sep 8 - Thu, Sep 11
Southwest Logo
1:50 pm - 10:55 pmORD-ISP
8h 05m1 stop
Southwest Logo
6:25 am - 11:50 amISP-ORD
6h 25m1 stop
$242Southwest
Find Deal
Tue, Sep 2 - Thu, Sep 4
Southwest Logo
6:00 am - 3:15 pmORD-ISP
8h 15m2 stops
Southwest Logo
6:25 am - 4:25 pmISP-ORD
11h 00m2 stops
$247Southwest
Find Deal
Sat, Sep 27 - Tue, Sep 30
Southwest Logo
1:30 pm - 9:40 pmORD-ISP
7h 10m1 stop
Southwest Logo
6:05 am - 9:30 pmISP-ORD
16h 25m2 stops
$248Southwest
Find Deal
Tue, Aug 12 - Fri, Aug 15
Frontier Logo
11:28 am - 9:58 pmORD-ISP
9h 30m1 stop
Frontier Logo
8:37 pm - 8:07 amISP-ORD
12h 30m1 stop
$252Frontier
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Tue, Sep 2 - Thu, Sep 4
Southwest Logo
1:50 pm - 10:05 pmORD-ISP
7h 15m1 stop
Southwest Logo
6:25 am - 11:50 amISP-ORD
6h 25m1 stop
$259Southwest
Find Deal
Wed, Jul 30 - Fri, Aug 1
Frontier Logo
11:28 am - 7:52 pmORD-ISP
7h 24m1 stop
Frontier Logo
8:37 pm - 8:07 amISP-ORD
12h 30m1 stop
$264Frontier
Find Deal
Thu, Aug 28 - Thu, Sep 4
Frontier Logo
7:30 am - 8:06 pmORD-ISP
11h 36m1 stop
Frontier Logo
11:25 am - 7:40 pmISP-ORD
9h 15m1 stop
$269Frontier
Find Deal
Thu, Aug 28 - Thu, Sep 4
Frontier Logo
7:30 am - 8:06 pmORD-ISP
11h 36m1 stop
Frontier Logo
11:25 am - 7:40 pmISP-ORD
9h 15m1 stop
$270Frontier
Find Deal
Wed, Jul 30 - Sun, Aug 3
 Logo
11:28 am - 7:52 pmORD-ISP
7h 24m1 stop
 Logo
6:00 am - 3:31 pmISP-ORD
10h 31m1 stop
Booking Insights

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 ($237) and Frontier ($252).

Good to know

Cheapest flight$124
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 $124 for a one-way ticket and $237 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.

Reviews of the 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 4239 reviews
7.0Food
8.1Boarding
8.6Crew
7.6Entertainment
8.0Comfort
Airline reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

4.0 OkayGreg, Jul 2025PDX - DEN
Read more Southwest reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

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

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