ISP - ORD

$90 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 5/11. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$210
Frontier
Wed 5/13Fri 5/15
ISP - ORD • 1 stop
Cheapest one-way
$90
Frontier
Mon 5/11
ISP - ORD • 1 stop
Top airlines
Frontier
Cheapest • from $210 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Islip and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Baltimore (BWI)
Cheapest • Avg $392 (round-trip)
Baltimore (BWI)
Shortest trip • 7h 28m (one-way)
Insights
Insights
Insights
Insights
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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

Wed, May 13 - Fri, May 15
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
5:30 pm - 10:05 am
ORD
-
ISP
15h 35m
1 stop
$210Frontier
Thu, Apr 16 - Sat, Apr 25
Frontier Logo
4:07 pm - 5:09 pm
ISP
-
ORD
26h 02m
1 stop
Frontier Logo
8:00 am - 9:13 am
ORD
-
ISP
24h 13m
1 stop
$222Frontier
Wed, May 27 - Thu, May 28
Frontier Logo
10:03 am - 11:41 pm
ISP
-
ORD
14h 38m
1 stop
Frontier Logo
5:14 pm - 9:08 am
ORD
-
ISP
14h 54m
1 stop
$255Frontier
Wed, May 27 - Mon, Jun 1
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
5:30 pm - 5:17 pm
ORD
-
ISP
22h 47m
1 stop
$268Frontier
Wed, Apr 8 - Wed, Apr 15
Frontier Logo
8:00 am - 12:24 pm
ISP
-
ORD
29h 24m
1 stop
Frontier Logo
6:08 pm - 9:13 am
ORD
-
ISP
38h 05m
2 stops
$284Frontier
Thu, Jun 4 - Sun, Jun 7
Frontier Logo
10:03 am - 11:41 pm
ISP
-
ORD
14h 38m
1 stop
Frontier Logo
7:00 am - 2:34 pm
ORD
-
ISP
6h 34m
1 stop
$290Frontier
Wed, Apr 8 - Wed, Apr 15
Multiple Airlines Logo
8:00 am - 6:26 pm
ISP
-
ORD
11h 26m
1 stop
Multiple Airlines Logo
6:08 pm - 9:13 am
ORD
-
ISP
38h 05m
2 stops
$301Multiple Airlines
Thu, Jun 18 - Tue, Jun 23
Frontier Logo
10:03 am - 11:41 pm
ISP
-
ORD
14h 38m
1 stop
Frontier Logo
5:14 pm - 9:08 am
ORD
-
ISP
14h 54m
1 stop
$310Frontier
Wed, Apr 8 - Wed, Apr 15
Frontier Logo
8:00 am - 12:24 pm
ISP
-
ORD
29h 24m
1 stop
Frontier Logo
6:08 pm - 9:13 am
ORD
-
ISP
38h 05m
2 stops
$314Frontier
Sat, May 16 - Mon, May 18
Multiple Airlines Logo
11:57 am - 12:54 pm
ISP
-
ORD
25h 57m
1 stop
Multiple Airlines Logo
7:00 am - 7:51 pm
ORD
-
ISP
11h 51m
1 stop
$326Multiple Airlines
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 ($210) and Southwest ($342).

Find deals

Good to know

Cheapest flight$90
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 $90 for a one-way ticket and $210 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 4318 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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)