ISP - ORD

$119 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 8/22. 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 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 Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Islip to Chicago

Fri, Aug 15 - Sat, Aug 16
Frontier Logo
2:05 pm - 12:25 amISP-ORD
11h 20m1 stop
Frontier Logo
9:08 am - 7:42 pmORD-ISP
9h 34m1 stop
$228Frontier
Find Deal
Thu, Aug 28 - Sun, Aug 31
Frontier Logo
6:05 am - 6:41 pmISP-ORD
13h 36m1 stop
Frontier Logo
6:10 am - 8:06 pmORD-ISP
12h 56m1 stop
$238Frontier
Find Deal
Thu, Aug 28 - Sun, Aug 31
Frontier Logo
7:33 pm - 6:41 pmISP-ORD
24h 08m1 stop
Frontier Logo
6:10 am - 8:06 pmORD-ISP
12h 56m1 stop
$239Frontier
Find Deal
Fri, Nov 14 - Sun, Nov 16
Frontier Logo
8:48 pm - 2:53 pmISP-ORD
19h 05m1 stop
Frontier Logo
6:10 am - 10:37 amORD-ISP
27h 27m1 stop
$245Frontier
Find Deal
Thu, Aug 21 - Sat, Aug 23
Frontier Logo
1:04 pm - 8:37 amISP-ORD
20h 33m1 stop
Frontier Logo
7:46 pm - 11:59 pmORD-ISP
27h 13m1 stop
$281Frontier
Find Deal
Tue, Sep 23 - Fri, Sep 26
Southwest Logo
5:30 am - 1:05 pmISP-ORD
8h 35m1 stop
Southwest Logo
1:50 pm - 10:55 pmORD-ISP
8h 05m1 stop
$286Southwest
Find Deal
Wed, Sep 24 - Fri, Sep 26
Southwest Logo
6:05 am - 5:55 pmISP-ORD
12h 50m2 stops
Southwest Logo
1:50 pm - 10:55 pmORD-ISP
8h 05m1 stop
$292Southwest
Find Deal
Wed, Sep 24 - Sun, Sep 28
Southwest Logo
6:05 am - 11:50 amISP-ORD
6h 45m1 stop
Southwest Logo
1:50 pm - 7:50 pmORD-ISP
5h 00m1 stop
$302Southwest
Find Deal
Tue, Sep 23 - Fri, Sep 26
Southwest Logo
6:05 am - 11:50 amISP-ORD
6h 45m1 stop
Southwest Logo
11:25 am - 10:55 pmORD-ISP
10h 30m2 stops
$307Southwest
Find Deal
Tue, Aug 19 - Fri, Aug 22
 Logo
1:55 pm - 10:31 amISP-ORD
21h 36m3 stops
 Logo
5:21 pm - 1:32 pmORD-ISP
19h 11m2 stops
Booking Insights

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 ($228) and Southwest ($286).

Good to know

Cheapest flight$119
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 $119 for a one-way ticket and $228 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.

Reviews of the 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 4246 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

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.

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

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