ISP - ORD

$74 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 2/23. 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
$162
Frontier
Thu 2/19Thu 2/26
ISP - ORD • 1 stop
Cheapest one-way
$74
Frontier
Mon 2/23
ISP - ORD • 1 stop
Top airlines
Frontier
Cheapest • from $162 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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!
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, Feb 19 - Thu, Feb 26
Frontier Logo
3:34 pm - 8:12 pm
ISP
-
ORD
29h 38m
1 stop
Frontier Logo
11:55 am - 2:39 pm
ORD
-
ISP
25h 44m
1 stop
$162Frontier
Fri, Feb 27 - Sat, Feb 28
Frontier Logo
3:34 pm - 10:47 pm
ISP
-
ORD
8h 13m
1 stop
Frontier Logo
8:15 am - 7:28 pm
ORD
-
ISP
10h 13m
1 stop
$195Frontier
Thu, Feb 26 - Thu, Mar 5
Frontier Logo
5:07 pm - 9:40 pm
ISP
-
ORD
29h 33m
1 stop
Frontier Logo
11:55 am - 12:47 pm
ORD
-
ISP
23h 52m
1 stop
$196Frontier
Wed, Feb 11 - Sun, Feb 15
Multiple Airlines Logo
11:50 am - 10:51 am
ISP
-
ORD
24h 01m
2 stops
Multiple Airlines Logo
1:17 pm - 7:38 am
ORD
-
ISP
17h 21m
1 stop
$229Multiple Airlines
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
3:34 pm - 10:46 am
ISP
-
ORD
20h 12m
2 stops
Frontier Logo
11:55 am - 7:38 am
ORD
-
ISP
18h 43m
1 stop
$266Frontier
Tue, Mar 3 - Thu, Mar 5
Multiple Airlines Logo
11:59 am - 8:13 am
ISP
-
ORD
21h 14m
1 stop
Multiple Airlines Logo
12:44 pm - 12:47 pm
ORD
-
ISP
23h 03m
1 stop
$274Multiple Airlines
Tue, Mar 3 - Thu, Mar 5
Multiple Airlines Logo
11:59 am - 8:13 am
ISP
-
ORD
21h 14m
1 stop
Multiple Airlines Logo
8:42 pm - 1:31 pm
ORD
-
ISP
15h 49m
2 stops
$277Multiple Airlines
Tue, Feb 10 - Sat, Feb 14
Multiple Airlines Logo
12:45 pm - 10:08 pm
ISP
-
ORD
10h 23m
1 stop
Multiple Airlines Logo
4:42 pm - 7:06 pm
ORD
-
ISP
25h 24m
2 stops
$293Multiple Airlines
Wed, Feb 11 - Sun, Feb 15
Multiple Airlines Logo
2:03 pm - 9:44 pm
ISP
-
ORD
8h 41m
1 stop
Multiple Airlines Logo
1:17 pm - 7:38 am
ORD
-
ISP
17h 21m
1 stop
$309Multiple Airlines
Tue, Mar 3 - Thu, Mar 5
Southwest Logo
6:00 am - 2:45 pm
ISP
-
ORD
9h 45m
2 stops
Southwest Logo
2:00 pm - 11:55 pm
ORD
-
ISP
8h 55m
2 stops
$340Southwest
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 ($162) and Southwest ($340).

Find deals

Good to know

Cheapest flight$74
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 $74 for a one-way ticket and $162 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 4268 reviews
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

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

Information on your arrival and departure airports

Islip (ISP)
O'Hare Intl (ORD)