ISP - ORD

$101 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 11/7. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$130
Frontier
Thu 11/13Thu 11/20
ISP - ORD • 1 stop
Cheapest one-way
$94
Frontier
Fri 11/7
ISP - ORD • 1 stop
Top airlines
Frontier
Cheapest • from $130 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
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, Nov 13 - Thu, Nov 20
Frontier Logo
6:37 pm - 12:26 pmISP-ORD
18h 49m1 stop
Frontier Logo
3:37 pm - 11:59 pmORD-ISP
7h 22m1 stop
$130Frontier
Find Deal
Wed, Nov 12 - Sun, Nov 16
Frontier Logo
4:58 pm - 12:26 pmISP-ORD
20h 28m1 stop
Frontier Logo
7:05 am - 9:09 amORD-ISP
25h 04m1 stop
$172Frontier
Find Deal
Mon, Nov 10 - Thu, Nov 13
Frontier Logo
8:02 pm - 3:08 pmISP-ORD
20h 06m1 stop
Frontier Logo
5:25 am - 10:37 amORD-ISP
28h 12m1 stop
$178Frontier
Find Deal
Tue, Dec 2 - Fri, Dec 5
Multiple Airlines Logo
8:29 pm - 4:03 pmISP-ORD
20h 34m1 stop
Multiple Airlines Logo
12:09 pm - 9:13 amORD-ISP
20h 04m1 stop
$188Multiple Airlines
Find Deal
Thu, Nov 20 - Mon, Nov 24
Frontier Logo
10:02 am - 7:26 amISP-ORD
22h 24m1 stop
Frontier Logo
6:15 pm - 10:18 amORD-ISP
15h 03m1 stop
$190Frontier
Find Deal
Mon, Nov 10 - Thu, Nov 13
Multiple Airlines Logo
9:54 am - 3:39 pmISP-ORD
30h 45m2 stops
Multiple Airlines Logo
6:48 am - 5:42 pmORD-ISP
9h 54m1 stop
$194Multiple Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Southwest Logo
12:55 pm - 9:50 pmISP-ORD
9h 55m2 stops
Southwest Logo
1:45 pm - 11:50 pmORD-ISP
9h 05m2 stops
$407Southwest
Find Deal
Fri, Nov 21 - Sun, Nov 23
Southwest Logo
11:05 am - 9:50 pmISP-ORD
11h 45m2 stops
Southwest Logo
1:45 pm - 11:50 pmORD-ISP
9h 05m2 stops
$458Southwest
Find Deal
Wed, Dec 24 - Mon, Dec 29
Southwest Logo
12:55 pm - 9:50 pmISP-ORD
9h 55m2 stops
Southwest Logo
6:05 am - 2:00 pmORD-ISP
6h 55m1 stop
$519Southwest
Find Deal
Wed, Dec 24 - Mon, Dec 29
Southwest Logo
12:55 pm - 9:50 pmISP-ORD
9h 55m2 stops
Southwest Logo
1:45 pm - 11:55 pmORD-ISP
9h 10m2 stops
$524Southwest
Find Deal
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 ($130) and Southwest ($407).

Which airlines fly non-stop between Islip and Chicago O'Hare Intl Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Islip to Chicago O'Hare Intl Airport.

There is just one airline that flies from Islip to Chicago O'Hare Intl Airport direct and that is Southwest. The best round-trip deal found from Southwest for the route is $336.

Good to know

Cheapest flight$94
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 $94 for a one-way ticket and $130 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 4243 reviews
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

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

Information on your arrival and departure airports

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