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Cheap flights from Islip, New York to Chicago from $121

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 5/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
10:48 am - 11:14 pm
ISP
-
ORD
13h 26m
1 stop
Frontier Logo
4:49 pm - 9:33 am
ORD
-
ISP
15h 44m
1 stop
$222Frontier
Wed, Sep 2 - Wed, Sep 9
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
5:11 pm - 5:17 pm
ORD
-
ISP
23h 06m
1 stop
$280Frontier
Sat, May 30 - Mon, Jun 1
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
5:11 pm - 3:56 pm
ORD
-
ISP
21h 45m
1 stop
$315Frontier
Sat, Jun 6 - Mon, Jun 8
Frontier Logo
9:52 pm - 9:21 am
ISP
-
ORD
12h 29m
1 stop
Frontier Logo
4:59 pm - 8:57 pm
ORD
-
ISP
26h 58m
1 stop
$326Frontier
Sun, Jun 14 - Tue, Jun 16
Frontier Logo
4:13 pm - 8:21 am
ISP
-
ORD
17h 08m
1 stop
Frontier Logo
4:49 pm - 9:33 am
ORD
-
ISP
15h 44m
1 stop
$346Frontier
Thu, Sep 24 - Sun, Sep 27
Frontier Logo
10:48 am - 11:14 pm
ISP
-
ORD
13h 26m
1 stop
Frontier Logo
5:30 pm - 10:03 am
ORD
-
ISP
15h 33m
1 stop
$347Frontier
Sun, Aug 30 - Thu, Sep 3
Frontier Logo
10:48 am - 11:05 pm
ISP
-
ORD
13h 17m
1 stop
Frontier Logo
5:13 pm - 3:56 pm
ORD
-
ISP
21h 43m
1 stop
$348Frontier
Fri, Jul 31 - Mon, Aug 3
Multiple Airlines Logo
2:28 pm - 7:29 pm
ISP
-
ORD
30h 01m
2 stops
Multiple Airlines Logo
5:11 pm - 10:15 am
ORD
-
ISP
16h 04m
1 stop
$360Multiple Airlines
Mon, Jun 1 - Fri, Jun 5
Multiple Airlines Logo
11:57 am - 7:55 am
ISP
-
ORD
44h 58m
2 stops
Multiple Airlines Logo
4:59 pm - 8:57 pm
ORD
-
ISP
26h 58m
1 stop
$364Multiple Airlines
Sat, Jun 6 - Tue, Jun 9
Multiple Airlines Logo
2:28 pm - 7:29 pm
ISP
-
ORD
30h 01m
2 stops
Multiple Airlines Logo
5:11 pm - 10:15 am
ORD
-
ISP
16h 04m
1 stop
$366Multiple Airlines
Mon, Jun 1 - Fri, Jun 5

Frontier flights from Islip, New York to Chicago

Our best Frontier deals on Islip, New York to Chicago flight tickets
Frontier
Sep 2
ISP10:48 amIslip Long Island
13h 26m
1 stop
ORD11:14 pmChicago O'Hare Intl
Sep 9
ORD4:49 pmChicago O'Hare Intl
15h 44m
1 stop
ISP9:33 amIslip Long Island
$222
Frontier
May 30
ISP11:00 amIslip Long Island
13h 13m
1 stop
ORD11:13 pmChicago O'Hare Intl
Jun 1
ORD5:11 pmChicago O'Hare Intl
23h 06m
1 stop
ISP5:17 pmIslip Long Island
$280
Frontier
Jun 6
ISP11:00 amIslip Long Island
13h 13m
1 stop
ORD11:13 pmChicago O'Hare Intl
Jun 8
ORD5:11 pmChicago O'Hare Intl
21h 45m
1 stop
ISP3:56 pmIslip Long Island
$315

Southwest flights from Islip, New York to Chicago

Our best Southwest deals on Islip, New York to Chicago flight tickets
Southwest
May 28
ISP6:50 amIslip Long Island
8h 30m
1 stop
ORD2:20 pmChicago O'Hare Intl
Jun 1
ORD2:40 pmChicago O'Hare Intl
7h 50m
2 stops
ISP11:30 pmIslip Long Island
$380
Southwest
May 28
ISP12:30 pmIslip Long Island
10h 25m
2 stops
ORD9:55 pmChicago O'Hare Intl
Jun 1
ORD2:40 pmChicago O'Hare Intl
7h 50m
2 stops
ISP11:30 pmIslip Long Island
$385
Southwest
May 28
ISP6:50 amIslip Long Island
8h 30m
1 stop
ORD2:20 pmChicago O'Hare Intl
Jun 1
ORD3:05 pmChicago O'Hare Intl
6h 25m
1 stop
ISP10:30 pmIslip Long Island
$401

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 May 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

Cheapest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 9/2

10:48 am-11:14 pm

1 stop13h 26m

Chicago O'Hare Intl

Wed 9/9

4:49 pm-9:33 am

1 stop15h 44m

$222

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 5/30

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

Mon 6/1

5:11 pm-5:17 pm

1 stop23h 06m

$280

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 6/6

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

Mon 6/8

5:11 pm-3:56 pm

1 stop21h 45m

$315

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 6/14

9:52 pm-9:21 am

1 stop12h 29m

Chicago O'Hare Intl

Tue 6/16

4:59 pm-8:57 pm

1 stop26h 58m

$326

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/24

4:13 pm-8:21 am

1 stop17h 08m

Chicago O'Hare Intl

Sun 9/27

4:49 pm-9:33 am

1 stop15h 44m

$346
Quickest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 8/30

10:48 am-11:14 pm

1 stop13h 26m

Chicago O'Hare Intl

Thu 9/3

5:30 pm-10:03 am

1 stop15h 33m

$347

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 7/31

10:48 am-11:05 pm

1 stop13h 17m

Chicago O'Hare Intl

Mon 8/3

5:13 pm-3:56 pm

1 stop21h 43m

$348

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 6/1

2:28 pm-7:29 pm

2 stops30h 01m

Chicago O'Hare Intl

Fri 6/5

5:11 pm-10:15 am

1 stop16h 04m

$360

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 6/6

11:57 am-7:55 am

2 stops44h 58m

Chicago O'Hare Intl

Tue 6/9

4:59 pm-8:57 pm

1 stop26h 58m

$364

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 6/1

2:28 pm-7:29 pm

2 stops30h 01m

Chicago O'Hare Intl

Fri 6/5

5:11 pm-10:15 am

1 stop16h 04m

$366

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 month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Islip, New York, with most prices found around $0. If you’re not able to fly to Chicago in October, then February is your next best option. Flight prices from Islip, New York to Chicago during February average around $0.

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 Saturday when prices can be found for as low as $291. 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 $367.

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 $273. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $361.

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

8h 42m

Direct flights

None
The fastest flight from Islip, New York to Chicago takes 8h 42m
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

Frequently asked questions about flying from Islip, New York to Chicago

  • 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 8h 42m 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 $387Free CancellationRating
8.0
4,302 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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