ISP - CHI

Find Cheap Flights from Islip to Chicago

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Islip (ISP)
Chicago All airports
Fri 7/26
Fri 8/2
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Islip Long Island to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Islip Long Island
Flight Price $164
Distance 757 miles
Airlines American Airlines

Good to Know

Average Price:
$374
(avg. price over the last 2 weeks)
Good Deal:
$333
or less (round trip)

When to Book Flights from Islip to Chicago

Estimated round-trip price
Flight prices as travel date approaches
-1 day
-2 days

Top Tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $332 or less.
The cheapest flight from Islip to Chicago was found 86 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
Morning departure is around 24% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Islip to Chicago Flights

How long does a flight from Islip to Chicago take?
There are no direct flights for this route listed on KAYAK, the shortest multi-flight duration is 4h 14m.
Which airlines provide the cheapest flights from Islip to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on American Airlines ($164)
Do I need a passport to fly between Islip and Chicago?
No.
What’s the cheapest day of the week to fly Islip to Chicago?
For Islip to Chicago, Friday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Chicago back to Islip, the best deals are generally found on Saturday, with Sunday being the most expensive.
Which airports will I be using when flying from Islip to Chicago?
When flying out of Islip you will be using Islip Long Island, often referred to as Islip Airport. You will be landing at one of these airports: Chicago O'Hare Intl.

Book cheap flights from Islip to Chicago (round-trip)

Airports
Origin
Islip
$164
only
$164
Destination
Chicago
$164
only
$164
Fri, Oct 25
ISP
Islip Long Island
ORD
Chicago O'Hare Intl
5h 47m
Sat, Oct 26
ORD
Chicago O'Hare Intl
ISP
Islip Long Island
5h 20m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,775 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
CLT
LIT
Excellent 9.2

Pros: On this flight was a female flight attendant who anticipated my every need. I wasn’t flying first class, but still, she went out of her way to treat me very well. Her personality and hospitality made my flight relaxing, made me feel loved and appreciated, and the flight felt like I was already home

FCO
JFK
Okay 5.3

Cons: When my husband retrieved his luggage, it smelled terrible- like dog poop. We had to drive home with the windows down & throw away the baggage when we got home.

BWI
PHL
Mediocre 2.6

Cons: British Airways but the flights were operated by American Airlines who I've always had terrible experiences with. This was no different. TOTAL NIGHTMARE

DFW
ORD
Mediocre 3.3

Pros: They quickly rebooked us after cancelling our original flights

Cons: The British Airways experience was awful. American should be ashamed for selling that business class seat. The seats were confusing, uncomfortable, and tiny. I feel like I paid a full price rate for a stripped down and discounted product. Not flying BA ever again if I have a choice.

LAX
SMF
Excellent 10.0

Pros: I didn’t interact with the crew but they seems nice.

Cons: The trip from HonoluIu to Los Angeles was too warm.

Tue, Aug 20
ISP
Islip Long Island
ORD
Chicago O'Hare Intl
4h 51m
Tue, Aug 27
ORD
Chicago O'Hare Intl
ISP
Islip Long Island
4h 07m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,775 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
HNL
PHX
Excellent 9.0

Pros: The flight was good.

Cons: The seat size could be bigger, and the layover was awful. Sixteen hours is unheard of.

JFK
PIT
Good 6.0

Cons: When my husband retrieved his piece of luggage, it smelled terribly lie dog poop. We had to drive home with the windows all the way down because the stench was so bad and throw away the suitcase I had just bought because of the terrible smell. Just awful to come home to that!

AVL
DFW
Okay 4.8

Pros: Direct flight and good personal service provided by crew.

Cons: Flight was delayed and overbooked causing further delay at departure gate. Plane is small and cramped.

MCO
MIA
Mediocre 2.0

Pros: Nothing other than being able to get off this plane ride as soon as possible.

Cons: Everything. Friendlier crew who could look like they enjoy their job more. Seat and comfort. Seat pitch was awful for a major airline. Some discount airlines seats were more comfortable w/ more space. Boarding was archaic. Climbing stairs down to tarmac, bus ride, climbing up stairs to plane.

CDG
ORD
Good 7.0

Cons: Boarding at gate a47 T2A at CDG was chaotic

Wed, Sep 4
ISP
Islip Long Island
ORD
Chicago O'Hare Intl
6h 09m
Thu, Sep 12
ORD
Chicago O'Hare Intl
ISP
Islip Long Island
6h 26m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,775 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
MCO
MIA
Mediocre 2.0

Pros: Nothing other than being able to get off this plane ride as soon as possible.

Cons: Everything. Friendlier crew who could look like they enjoy their job more. Seat and comfort. Seat pitch was awful for a major airline. Some discount airlines seats were more comfortable w/ more space. Boarding was archaic. Climbing stairs down to tarmac, bus ride, climbing up stairs to plane.

JFK
PIT
Good 6.0

Cons: When my husband retrieved his piece of luggage, it smelled terribly lie dog poop. We had to drive home with the windows all the way down because the stench was so bad and throw away the suitcase I had just bought because of the terrible smell. Just awful to come home to that!

COS
DFW
Mediocre 2.0

Pros: No flight. It was cancelled.

Cons: Find a sooner alternate flight

BWI
PHL
Mediocre 2.6

Cons: British Airways but the flights were operated by American Airlines who I've always had terrible experiences with. This was no different. TOTAL NIGHTMARE

LGA
CLT
Okay 5.6

Pros: Friendliness of crew

Cons: Offered more of an incentive for the inconvenience

Thu, Sep 5
ISP
Islip Long Island
ORD
Chicago O'Hare Intl
7h 22m
Tue, Sep 10
ORD
Chicago O'Hare Intl
ISP
Islip Long Island
6h 06m
Trip: 6 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,775 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
LAX
DEN
Okay 5.0

Pros: Horrible staff at LAX boarding gate. Been treated horribly by incompetent and rude AA staff.

Cons: Hire only friendly people for this type of job. Hire people knows basic math. Train their well on how to communicate with people.

PHX
LHR
Good 6.3

Pros: Friendly crew and relatively new entertainment system

Cons: - Seats are very tight - Pay for luggage even on a transatlantic flight and your seat (if you want to choose) - Food was below average - even for airline standards, ran out of drink options even for dinner (the second time they serve drinks)

ATH
ORD
Excellent 8.6

Pros: The crew was amazing,attentive and courteous.

Cons: Better boarding procedure. Everyone was budding the lines not well organized.

BNA
DFW
Mediocre 2.0

Pros: Embarrassed to say but there wasn’t one thing I enjoyed about this trip. I felt like I down graded to Spirit or Frontier Airlines. The flight was terribly hot, delayed multiple times coming and going. Given, I paid for priority round trip, I was delayed to Main boarding and seated in 7A.

Cons: Adjustments to the above statement. In addition to my next travels plans, I’d like to be seated in First class. My next travel dates with AA are 06/27/2019-07/05/2019. Please feel to contact me directly beau.polley0@gmail.com

COR
MIA
Good 6.3

Pros: Boarding was fine and crew were friendly with one exception. The in flight entertainment is great idea, except that the wifi went down mid flight, mid movie.

Cons: First and foremost seats are very uncomfortable. Would expect American to realize that passengers will be sitting for 9 hours and the seat needs to have some cushion. Could not get comfortable so could not sleep. Most of the crew were friendly and courteous, but was the 1 who was less so. Wifi quit

Sat, Nov 23
ISP
Islip Long Island
ORD
Chicago O'Hare Intl
6h 43m
Fri, Nov 29
ORD
Chicago O'Hare Intl
ISP
Islip Long Island
5h 20m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,775 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
LAX
LAS
Mediocre 3.0

Pros: The crew was nice

Cons: Pilots showing up on time. The flight was delayed 3 hours not due to weather or mechanical issues. Then they boarded us on the plane, let us know it was delayed 1.5 hours, then back onto the plane at that time, then waited another 1.5 hours to leave. Unacceptable. I missed my work meeting from this.

CDG
ORD
Good 7.0

Cons: Boarding at gate a47 T2A at CDG was chaotic

LAX
ORD
Excellent 10.0

Pros: Staff, plane, ride - one of the nicest flights I've had in a long time

Cons: Nothing. Well, if you paid me to fly ;)

BDL
ORD
Mediocre 2.0

Cons: American Airlines consistently proves that customer service is not a priority. Their servicemen/servicewoman make no effort to show customer care at any point whenever a customer is experiencing difficulty with ticketing or boarding. They are routinely late and appear extremely amateur

LAX
SMF
Excellent 10.0

Pros: I didn’t interact with the crew but they seems nice.

Cons: The trip from HonoluIu to Los Angeles was too warm.

Tue, Jul 2
ISP
Islip Long Island
ORD
Chicago O'Hare Intl
4h 52m
Sat, Jul 6
ORD
Chicago O'Hare Intl
ISP
Islip Long Island
4h 07m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,775 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
MCO
MIA
Mediocre 2.0

Pros: Nothing other than being able to get off this plane ride as soon as possible.

Cons: Everything. Friendlier crew who could look like they enjoy their job more. Seat and comfort. Seat pitch was awful for a major airline. Some discount airlines seats were more comfortable w/ more space. Boarding was archaic. Climbing stairs down to tarmac, bus ride, climbing up stairs to plane.

BDL
ORD
Mediocre 2.0

Cons: American Airlines consistently proves that customer service is not a priority. Their servicemen/servicewoman make no effort to show customer care at any point whenever a customer is experiencing difficulty with ticketing or boarding. They are routinely late and appear extremely amateur

AUS
DFW
Good 6.3

Cons: First plane broken, second plane broken, overall 4 hours late, 2 hours of that sitting in a hot plane

ORF
LGA
Okay 4.6

Pros: Crew was kind and attentive

Cons: Flight delayed 3 hours and sat on tarmac in nyc for 45 minutes

DFW
ORD
Mediocre 3.3

Pros: They quickly rebooked us after cancelling our original flights

Cons: The British Airways experience was awful. American should be ashamed for selling that business class seat. The seats were confusing, uncomfortable, and tiny. I feel like I paid a full price rate for a stripped down and discounted product. Not flying BA ever again if I have a choice.

Tue, Jul 2
ISP
Islip Long Island
ORD
Chicago O'Hare Intl
4h 14m
Sat, Jul 6
ORD
Chicago O'Hare Intl
ISP
Islip Long Island
4h 07m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,775 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
PHL
SJU
Excellent 9.3

Pros: Smooth ride

SFO
ORD
Good 7.0

Pros: seat was basic. prefer having tv screens in the seatbacks as opposed to using my tiny phone as a viewing screen.

Cons: prefer having tv screens in the seatbacks as opposed to using my tiny phone as a viewing screen. only food available besides pretzel was pay food.

DEN
ORD
Good 7.3

Pros: The plane was super comfortable

Cons: Long check-in lines in Denver - there were two sky caps outside who had no line which allowed me to reach my gate in time. Otherwise I may have missed my flight

COR
MIA
Good 6.3

Pros: Boarding was fine and crew were friendly with one exception. The in flight entertainment is great idea, except that the wifi went down mid flight, mid movie.

Cons: First and foremost seats are very uncomfortable. Would expect American to realize that passengers will be sitting for 9 hours and the seat needs to have some cushion. Could not get comfortable so could not sleep. Most of the crew were friendly and courteous, but was the 1 who was less so. Wifi quit

BNA
DFW
Mediocre 2.0

Pros: Embarrassed to say but there wasn’t one thing I enjoyed about this trip. I felt like I down graded to Spirit or Frontier Airlines. The flight was terribly hot, delayed multiple times coming and going. Given, I paid for priority round trip, I was delayed to Main boarding and seated in 7A.

Cons: Adjustments to the above statement. In addition to my next travels plans, I’d like to be seated in First class. My next travel dates with AA are 06/27/2019-07/05/2019. Please feel to contact me directly beau.polley0@gmail.com

Fri, Aug 30
ISP
Islip Long Island
ORD
Chicago O'Hare Intl
4h 51m
Sun, Sep 1
ORD
Chicago O'Hare Intl
ISP
Islip Long Island
6h 16m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,775 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
ERI
CLT
Good 6.0

Cons: Had to sit next to someone that was so big she had to put up the arm seat and sit on half my seat. Thank god I’m 110 but sitting next to the window made me very claustrophobic.

PIT
MIA
Good 6.0

Cons: The plane was so small no roller bags could be accommodated. All bags were gate checked. Retrieving all those bags while on the jetway was difficult

LAX
SFO
Good 7.3

Pros: Comfortable

Cons: I was in 10C a So I was able to hear a disgruntled AA employee. Just like office politics. But up in the air. I didn’t need to hear

AVL
DFW
Okay 4.8

Pros: Direct flight and good personal service provided by crew.

Cons: Flight was delayed and overbooked causing further delay at departure gate. Plane is small and cramped.

ORD
MSP
Good 6.3

Pros: Crew

Cons: The delays due to software

Fri, Jun 28
ISP
Islip Long Island
ORD
Chicago O'Hare Intl
4h 52m
Sat, Jul 6
ORD
Chicago O'Hare Intl
ISP
Islip Long Island
4h 07m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,775 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
ATH
ORD
Excellent 8.6

Pros: The crew was amazing,attentive and courteous.

Cons: Better boarding procedure. Everyone was budding the lines not well organized.

PHL
MAD
Mediocre 2.0

Pros: I made it alive

Cons: American airlines will leave you out to dry if there are any issues. Never had so many issues with the same airline.

CYS
DFW
Excellent 8.0

Cons: Offered entertainment

LGA
CLT
Okay 5.6

Pros: Friendliness of crew

Cons: Offered more of an incentive for the inconvenience

CLT
LIT
Excellent 9.2

Pros: On this flight was a female flight attendant who anticipated my every need. I wasn’t flying first class, but still, she went out of her way to treat me very well. Her personality and hospitality made my flight relaxing, made me feel loved and appreciated, and the flight felt like I was already home

Tue, Jul 2
ISP
Islip Long Island
ORD
Chicago O'Hare Intl
4h 14m
Fri, Jul 12
ORD
Chicago O'Hare Intl
ISP
Islip Long Island
4h 07m
Trip: 11 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,775 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
FCO
ORD
Okay 5.0

Pros: I’m home

Cons: Ran almost an hour late with. I explanation of why. No seat power - first class had mediocre seats. No foot rests and not very comfortable

DEN
MIA
Good 6.3

Pros: Crew on the plant was friendly.

Cons: I think at least some small food should be offer even tho it wasn’t dinner time.

ORD
SFO
Okay 4.6

Cons: almost an hour late - and no explanation. First class was about equal to Jet Blue regular class but without seat power.

BWI
JFK
Excellent 8.5

Cons: Larger plane. Had to crouch all the way to my seat. Seat was comfortable enough.

MCO
MIA
Mediocre 2.0

Pros: Nothing other than being able to get off this plane ride as soon as possible.

Cons: Everything. Friendlier crew who could look like they enjoy their job more. Seat and comfort. Seat pitch was awful for a major airline. Some discount airlines seats were more comfortable w/ more space. Boarding was archaic. Climbing stairs down to tarmac, bus ride, climbing up stairs to plane.

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