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Cheap flights from Islip, New York to Chicago from $64

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 3/4. 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.
Frontier Logo
8:23 am - 11:15 pm
ISP
-
ORD
15h 52m
1 stop
Frontier Logo
3:11 pm - 11:06 am
ORD
-
ISP
18h 55m
1 stop
$202Frontier
Mon, Feb 23 - Fri, Feb 27
Frontier Logo
8:33 am - 8:12 pm
ISP
-
ORD
12h 39m
1 stop
Frontier Logo
8:30 am - 8:40 am
ORD
-
ISP
23h 10m
1 stop
$216Frontier
Fri, Feb 20 - Tue, Feb 24
Multiple Airlines Logo
8:33 am - 5:46 pm
ISP
-
ORD
10h 13m
1 stop
Multiple Airlines Logo
12:44 pm - 8:40 am
ORD
-
ISP
18h 56m
1 stop
$218Multiple Airlines
Fri, Feb 20 - Tue, Feb 24
Multiple Airlines Logo
4:07 pm - 11:12 pm
ISP
-
ORD
8h 05m
1 stop
Multiple Airlines Logo
10:25 am - 9:13 am
ORD
-
ISP
21h 48m
1 stop
$228Multiple Airlines
Fri, Apr 24 - Sun, Apr 26
Multiple Airlines Logo
6:49 pm - 2:47 pm
ISP
-
ORD
20h 58m
1 stop
Multiple Airlines Logo
10:25 am - 9:13 am
ORD
-
ISP
21h 48m
1 stop
$230Multiple Airlines
Wed, Apr 22 - Sun, Apr 26
Multiple Airlines Logo
3:34 pm - 7:54 am
ISP
-
ORD
17h 20m
2 stops
Multiple Airlines Logo
12:44 pm - 8:40 am
ORD
-
ISP
18h 56m
1 stop
$233Multiple Airlines
Fri, Feb 20 - Tue, Feb 24
Multiple Airlines Logo
11:41 am - 7:47 pm
ISP
-
ORD
9h 06m
1 stop
Multiple Airlines Logo
5:58 pm - 2:39 pm
ORD
-
ISP
19h 41m
2 stops
$239Multiple Airlines
Sat, Feb 21 - Wed, Feb 25
Multiple Airlines Logo
11:41 am - 7:47 pm
ISP
-
ORD
9h 06m
1 stop
Multiple Airlines Logo
10:44 am - 2:39 pm
ORD
-
ISP
26h 55m
1 stop
$240Multiple Airlines
Sat, Feb 21 - Wed, Feb 25
Multiple Airlines Logo
2:31 pm - 11:37 pm
ISP
-
ORD
10h 06m
1 stop
Multiple Airlines Logo
12:01 pm - 11:06 am
ORD
-
ISP
22h 05m
2 stops
$249Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
4:07 pm - 11:12 pm
ISP
-
ORD
8h 05m
1 stop
Multiple Airlines Logo
5:32 pm - 9:13 am
ORD
-
ISP
14h 41m
2 stops
$261Multiple Airlines
Fri, Apr 24 - Sun, Apr 26

Frontier flights from Islip, New York to Chicago

Our best Frontier deals on Islip, New York to Chicago flight tickets
Frontier
Feb 23
ISP3:59 pmIslip Long Island
24h 53m
1 stop
ORD3:52 pmChicago O'Hare Intl
Feb 27
ORD3:11 pmChicago O'Hare Intl
18h 55m
1 stop
ISP11:06 amIslip Long Island
$202
Frontier
May 8
ISP3:50 pmIslip Long Island
20h 53m
1 stop
ORD11:43 amChicago O'Hare Intl
May 10
ORD10:25 amChicago O'Hare Intl
21h 48m
1 stop
ISP9:13 amIslip Long Island
$325
Frontier
Mar 6
ISP1:42 pmIslip Long Island
28h 10m
1 stop
ORD4:52 pmChicago O'Hare Intl
Mar 8
ORD5:05 pmChicago O'Hare Intl
15h 58m
1 stop
ISP10:03 amIslip Long Island
$448

Southwest flights from Islip, New York to Chicago

Our best Southwest deals on Islip, New York to Chicago flight tickets
Southwest
Mar 10
ISP5:45 amIslip Long Island
11h 20m
2 stops
ORD4:05 pmChicago O'Hare Intl
Mar 17
ORD2:40 pmChicago O'Hare Intl
7h 10m
2 stops
ISP10:50 pmIslip Long Island
$329
Southwest
Mar 10
ISP6:10 amIslip Long Island
13h 25m
1 stop
ORD6:35 pmChicago O'Hare Intl
Mar 17
ORD1:35 pmChicago O'Hare Intl
8h 05m
1 stop
ISP10:40 pmIslip Long Island
$358
Southwest
Apr 19
ISP11:50 amIslip Long Island
11h 05m
2 stops
ORD9:55 pmChicago O'Hare Intl
Apr 22
ORD5:55 amChicago O'Hare Intl
11h 35m
2 stops
ISP6:30 pmIslip Long Island
$363

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 February 9, 2026.
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

Mon 2/23

8:23 am-11:15 pm

1 stop15h 52m

Chicago O'Hare Intl

Fri 2/27

3:11 pm-11:06 am

1 stop18h 55m

$202

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/20

8:33 am-8:12 pm

1 stop12h 39m

Chicago O'Hare Intl

Tue 2/24

8:30 am-8:40 am

1 stop23h 10m

$216

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/20

8:33 am-5:46 pm

1 stop10h 13m

Chicago O'Hare Intl

Tue 2/24

12:44 pm-8:40 am

1 stop18h 56m

$218

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 4/24

4:07 pm-11:12 pm

1 stop8h 05m

Chicago O'Hare Intl

Sun 4/26

10:25 am-9:13 am

1 stop21h 48m

$228

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 4/22

6:49 pm-2:47 pm

1 stop20h 58m

Chicago O'Hare Intl

Sun 4/26

10:25 am-9:13 am

1 stop21h 48m

$230

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/20

3:34 pm-7:54 am

2 stops17h 20m

Chicago O'Hare Intl

Tue 2/24

12:44 pm-8:40 am

1 stop18h 56m

$233

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 2/21

11:41 am-7:47 pm

1 stop9h 06m

Chicago O'Hare Intl

Wed 2/25

5:58 pm-2:39 pm

2 stops19h 41m

$239

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 2/21

11:41 am-7:47 pm

1 stop9h 06m

Chicago O'Hare Intl

Wed 2/25

10:44 am-2:39 pm

1 stop26h 55m

$240

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 2/23

2:31 pm-11:37 pm

1 stop10h 06m

Chicago O'Hare Intl

Fri 2/27

12:01 pm-11:06 am

2 stops22h 05m

$249

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 4/24

4:07 pm-11:12 pm

1 stop8h 05m

Chicago O'Hare Intl

Sun 4/26

5:32 pm-9:13 am

2 stops14h 41m

$261

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 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 $290. 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 $364.

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 $267. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $362.

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

6h 50m

Direct flights

None
The fastest flight from Islip, New York to Chicago takes 6h 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 6h 50m 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 $366Free CancellationRating
8.0
4,282 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
Munster
Crown Point
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