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Cheap flights from Islip, New York to Chicago from $87

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Islip, New York to Chicago departing on 1/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Islip, New York to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:55 am - 4:58 pmISP-ORD
30h 03m2 stops
Multiple Airlines Logo
8:08 pm - 7:50 pmORD-ISP
22h 42m1 stop
$174Multiple Airlines
Find Deal
dom., ene. 11 - jue., ene. 15
Frontier Logo
8:29 pm - 1:16 pmISP-ORD
17h 47m1 stop
Frontier Logo
2:26 pm - 7:34 pmORD-ISP
28h 08m1 stop
$208Frontier
Find Deal
vie., dic. 5 - lun., dic. 8
Frontier Logo
8:29 pm - 1:16 pmISP-ORD
17h 47m1 stop
Frontier Logo
2:36 pm - 9:13 amORD-ISP
17h 37m1 stop
$212Frontier
Find Deal
vie., dic. 5 - dom., dic. 7
Multiple Airlines Logo
8:40 pm - 5:52 pmISP-ORD
22h 12m1 stop
Multiple Airlines Logo
8:08 pm - 7:50 pmORD-ISP
22h 42m1 stop
$229Multiple Airlines
Find Deal
dom., ene. 11 - jue., ene. 15
Multiple Airlines Logo
10:19 am - 10:24 pmISP-ORD
13h 05m2 stops
Multiple Airlines Logo
12:09 pm - 7:34 pmORD-ISP
30h 25m1 stop
$230Multiple Airlines
Find Deal
sáb., dic. 13 - lun., dic. 15
Frontier Logo
10:19 am - 1:31 pmISP-ORD
28h 12m1 stop
Frontier Logo
2:26 pm - 7:34 pmORD-ISP
28h 08m1 stop
$234Frontier
Find Deal
sáb., dic. 13 - lun., dic. 15
Frontier Logo
8:29 pm - 1:16 pmISP-ORD
17h 47m1 stop
Frontier Logo
2:26 pm - 7:34 pmORD-ISP
28h 08m1 stop
$238Frontier
Find Deal
vie., dic. 5 - lun., dic. 8
Frontier Logo
8:35 pm - 8:47 amISP-ORD
13h 12m1 stop
Frontier Logo
8:27 pm - 7:08 pmORD-ISP
21h 41m1 stop
$242Frontier
Find Deal
dom., dic. 21 - vie., ene. 9
Frontier Logo
8:40 pm - 7:17 pmISP-ORD
23h 37m1 stop
Frontier Logo
8:27 pm - 7:51 pmORD-ISP
22h 24m1 stop
$248Frontier
Find Deal
jue., ene. 8 - dom., ene. 11
Multiple Airlines Logo
10:19 am - 10:24 pmISP-ORD
13h 05m2 stops
Multiple Airlines Logo
12:09 pm - 9:13 amORD-ISP
20h 04m1 stop
$250Multiple Airlines
Find Deal
lun., dic. 8 - vie., dic. 12

Frontier flights from Islip, New York to Chicago

Our best Frontier deals on Islip, New York to Chicago flight tickets
Frontier
Dec 5
ISP8:29 pmIslip Long Island
17h 47m
1 stop
ORD1:16 pmChicago O'Hare Intl
Dec 8
ORD2:26 pmChicago O'Hare Intl
28h 08m
1 stop
ISP7:34 pmIslip Long Island
$208
Find similar
Frontier
Dec 5
ISP8:29 pmIslip Long Island
17h 47m
1 stop
ORD1:16 pmChicago O'Hare Intl
Dec 7
ORD2:36 pmChicago O'Hare Intl
17h 37m
1 stop
ISP9:13 amIslip Long Island
$212
Find similar
Frontier
Dec 13
ISP10:19 amIslip Long Island
28h 12m
1 stop
ORD1:31 pmChicago O'Hare Intl
Dec 15
ORD2:26 pmChicago O'Hare Intl
28h 08m
1 stop
ISP7:34 pmIslip Long Island
$234
Find similar

Southwest flights from Islip, New York to Chicago

Our best Southwest deals on Islip, New York to Chicago flight tickets
Southwest
Jan 11
ISP5:55 amIslip Long Island
9h 50m
2 stops
ORD2:45 pmChicago O'Hare Intl
Jan 15
ORD11:55 amChicago O'Hare Intl
9h 25m
2 stops
ISP10:20 pmIslip Long Island
$374
Find similar
Southwest
Apr 12
ISP1:50 pmIslip Long Island
9h 05m
1 stop
ORD9:55 pmChicago O'Hare Intl
Apr 17
ORD3:05 pmChicago O'Hare Intl
6h 25m
1 stop
ISP10:30 pmIslip Long Island
$407
Find similar
Southwest
Apr 12
ISP11:50 amIslip Long Island
11h 05m
2 stops
ORD9:55 pmChicago O'Hare Intl
Apr 17
ORD3:05 pmChicago O'Hare Intl
6h 25m
1 stop
ISP10:30 pmIslip Long Island
$412
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Islip, New York to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated noviembre 25, 2025.
Use the filters below to find and compare flights from Islip, New York to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

dom. 1/11

11:55 am-4:58 pm

2 stops30h 03m

Chicago O'Hare Intl

jue. 1/15

8:08 pm-7:50 pm

1 stop22h 42m

$174

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

vie. 12/5

8:29 pm-1:16 pm

1 stop17h 47m

Chicago O'Hare Intl

lun. 12/8

2:26 pm-7:34 pm

1 stop28h 08m

$208

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

vie. 12/5

8:29 pm-1:16 pm

1 stop17h 47m

Chicago O'Hare Intl

dom. 12/7

2:36 pm-9:13 am

1 stop17h 37m

$212

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

dom. 1/11

8:40 pm-5:52 pm

1 stop22h 12m

Chicago O'Hare Intl

jue. 1/15

8:08 pm-7:50 pm

1 stop22h 42m

$229

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

sáb. 12/13

10:19 am-10:24 pm

2 stops13h 05m

Chicago O'Hare Intl

lun. 12/15

12:09 pm-7:34 pm

1 stop30h 25m

$230

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

sáb. 12/13

10:19 am-1:31 pm

1 stop28h 12m

Chicago O'Hare Intl

lun. 12/15

2:26 pm-7:34 pm

1 stop28h 08m

$234

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

vie. 12/5

8:29 pm-1:16 pm

1 stop17h 47m

Chicago O'Hare Intl

lun. 12/8

2:26 pm-7:34 pm

1 stop28h 08m

$238

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

dom. 12/21

8:35 pm-8:47 am

1 stop13h 12m

Chicago O'Hare Intl

vie. 1/9

8:27 pm-7:08 pm

1 stop21h 41m

$242

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

jue. 1/8

8:40 pm-7:17 pm

1 stop23h 37m

Chicago O'Hare Intl

dom. 1/11

8:27 pm-7:51 pm

1 stop22h 24m

$248

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

lun. 12/8

10:19 am-10:24 pm

2 stops13h 05m

Chicago O'Hare Intl

vie. 12/12

12:09 pm-9:13 am

1 stop20h 04m

$250

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Islip, New York to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Islip, New York and Chicago?

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $292. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Islip, New York to Chicago for around $384.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Islip, New York to Chicago during this time can be as low as $271. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $367.

When to book flights from Islip, New York to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Islip, New York to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Islip, New York to Chicago (ISP to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Islip, New York to Chicago

Fastest flight time

7h 50m

Direct flights

None
The fastest flight from Islip, New York to Chicago takes 7h 50m
There are no direct flights from Islip, New York to Chicago. There are no popular flight routes from Islip, New York to Chicago.
Search flight deals

  • How far is Islip Long Island to Chicago by plane?

    The distance between Islip Long Island and Chicago is about 751.1 mi. Typically, this will take 7h 10m by plane in normal conditions.

  • When did momondo last update prices for flights from Islip Long Island Airport to Chicago?

    Prices for flights from Islip Long Island Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Islip Long Island Airport to Chicago?

  • How old do you have to be to fly from Islip Long Island Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Islip Long Island Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Islip, New York to Chicago?

Best airlines flying from Islip, New York to Chicago

Compare and see reviews for airlines that fly from Islip, New York to Chicago with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $336Free CancellationRating
8.0
4,254 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Islip to Chicago?

It is quick and easy to find Islip to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Islip to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Islip to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Islip to Chicago?

momondo helps you find the best flight between Islip and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Islip to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Islip are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport