ISP - ORD

$84 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 9/25. 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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Flight 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

Thu, Oct 2 - Sun, Oct 5
Frontier Logo
11:40 am - 7:44 pmISP-ORD
9h 04m1 stop
Frontier Logo
8:49 pm - 10:40 amORD-ISP
12h 51m1 stop
$168Frontier
Find Deal
Thu, Oct 9 - Sun, Oct 12
Frontier Logo
9:37 pm - 7:34 amISP-ORD
10h 57m1 stop
Frontier Logo
8:14 am - 8:52 pmORD-ISP
11h 38m1 stop
$184Frontier
Find Deal
Thu, Oct 2 - Sun, Oct 5
Frontier Logo
11:40 am - 11:20 pmISP-ORD
12h 40m2 stops
Frontier Logo
8:49 pm - 10:40 amORD-ISP
12h 51m1 stop
$197Frontier
Find Deal
Thu, Oct 9 - Sun, Oct 12
Frontier Logo
9:37 pm - 7:34 amISP-ORD
10h 57m1 stop
Frontier Logo
8:14 am - 8:52 pmORD-ISP
11h 38m1 stop
$200Frontier
Find Deal
Sun, Sep 28 - Sun, Oct 5
Frontier Logo
11:25 am - 7:44 pmISP-ORD
9h 19m1 stop
Frontier Logo
8:49 pm - 10:40 amORD-ISP
12h 51m1 stop
$224Frontier
Find Deal
Mon, Nov 3 - Thu, Nov 6
Multiple Airlines Logo
2:25 pm - 11:28 pmISP-ORD
10h 03m1 stop
Multiple Airlines Logo
1:50 pm - 1:45 pmORD-ISP
22h 55m1 stop
$235Multiple Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Southwest Logo
6:00 am - 12:45 pmISP-ORD
7h 45m2 stops
Southwest Logo
6:00 am - 4:05 pmORD-ISP
9h 05m2 stops
$336Southwest
Find Deal
Sat, Dec 6 - Mon, Dec 8
Southwest Logo
1:30 pm - 9:50 pmISP-ORD
9h 20m2 stops
Southwest Logo
11:55 am - 10:05 pmORD-ISP
9h 10m2 stops
$344Southwest
Find Deal
Tue, Oct 7 - Wed, Oct 8
Southwest Logo
6:00 am - 11:50 amISP-ORD
6h 50m1 stop
Southwest Logo
6:00 am - 4:20 pmORD-ISP
9h 20m1 stop
$365Southwest
Find Deal
Tue, Oct 7 - Wed, Oct 8
Southwest Logo
6:00 am - 12:45 pmISP-ORD
7h 45m2 stops
Southwest Logo
6:00 am - 4:20 pmORD-ISP
9h 20m1 stop
$371Southwest
Find Deal

Everything you should know

Top airlines
Frontier
Cheapest • from $168 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$168
Frontier
Thu 10/2Sun 10/5
ISP - ORD • 1 stop
Cheapest one-way
$84
Frontier
Thu 9/25
ISP - ORD • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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 ($168) and Southwest ($336).

Good to know

Cheapest flight$84
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 $84 for a one-way ticket and $168 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 4242 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

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

Information on your arrival and departure airports

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