What is the cheapest airline that flies from Islip Long Island to Chicago?

Frontier is the most popular carrier operating from Islip Long Island to Chicago

What airlines fly to Chicago?

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Islip, New York according to our data. United Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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?

As of December 2025, there is 1 operator available to choose from 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.

$86 Cheap Flights from Islip to Chicago in 2025/26

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Find the cheapest flights from Islip, New York to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:25 am - 10:41 am

ISP

ORD

26h 16m1 stop

8:15 am - 7:48 am

ORD

ISP

22h 33m1 stop

$249Frontier

Sun, Feb 1 - Sat, Feb 14

5:07 pm - 9:40 pm

ISP

ORD

29h 33m1 stop

1:17 pm - 2:39 pm

ORD

ISP

24h 22m1 stop

$263Frontier

Thu, Feb 19 - Sun, Feb 22

5:08 pm - 11:38 pm

ISP

ORD

7h 30m1 stop

4:18 pm - 12:47 pm

ORD

ISP

19h 29m1 stop

$322Frontier

Thu, Mar 12 - Sun, Mar 15

8:35 pm - 9:02 am

ISP

ORD

13h 27m1 stop

7:01 pm - 4:37 pm

ORD

ISP

20h 36m1 stop

$344Frontier

Mon, Dec 29 - Tue, Dec 30

5:27 pm - 10:18 am

ISP

ORD

17h 51m1 stop

8:09 pm - 1:09 pm

ORD

ISP

16h 00m1 stop

$357Frontier

Wed, Dec 31 - Sun, Jan 4

12:20 pm - 8:52 am

ISP

ORD

21h 32m1 stop

3:49 pm - 8:55 am

ORD

ISP

16h 06m1 stop

$362Frontier

Thu, Jan 1 - Sat, Jan 17

8:35 pm - 6:52 pm

ISP

ORD

23h 17m2 stops

7:20 am - 4:37 pm

ORD

ISP

8h 17m1 stop

$419Multiple Airlines

Mon, Dec 22 - Wed, Dec 31

5:27 pm - 10:18 am

ISP

ORD

17h 51m1 stop

8:09 pm - 1:45 pm

ORD

ISP

16h 36m2 stops

$435Multiple Airlines

Wed, Dec 31 - Sun, Jan 4

8:35 pm - 8:47 am

ISP

ORD

13h 12m1 stop

12:25 pm - 11:59 pm

ORD

ISP

10h 34m1 stop

$438Frontier

Sun, Dec 28 - Mon, Jan 5

12:20 pm - 8:52 am

ISP

ORD

21h 32m1 stop

8:09 pm - 1:09 pm

ORD

ISP

16h 00m1 stop

$442Frontier

Thu, Jan 1 - Sun, Jan 4

Frontier flights from Islip, New York to Chicago

Our best Frontier deals on Islip, New York to Chicago flight tickets

Frontier

Feb 19

ISP5:07 pmIslip Long Island

29h 33m

1 stop

ORD9:40 pmChicago O'Hare Intl

Feb 22

ORD1:17 pmChicago O'Hare Intl

24h 22m

1 stop

ISP2:39 pmIslip Long Island

$263

Find similar

Frontier

Dec 17

ISP6:00 amIslip Long Island

29h 18m

1 stop

ORD10:18 amChicago O'Hare Intl

Jan 15

ORD8:51 pmChicago O'Hare Intl

22h 18m

1 stop

ISP8:09 pmIslip Long Island

$312

Find similar

Frontier

Mar 12

ISP5:08 pmIslip Long Island

7h 30m

1 stop

ORD11:38 pmChicago O'Hare Intl

Mar 15

ORD4:18 pmChicago O'Hare Intl

19h 29m

1 stop

ISP12:47 pmIslip Long Island

$322

Find similar

Southwest flights from Islip, New York to Chicago

Our best Southwest deals on Islip, New York to Chicago flight tickets

Southwest

May 9

ISP4:25 pmIslip Long Island

6h 30m

1 stop

ORD9:55 pmChicago O'Hare Intl

May 12

ORD1:35 pmChicago O'Hare Intl

8h 05m

1 stop

ISP10:40 pmIslip Long Island

$387

Find similar

Southwest

May 9

ISP6:00 amIslip Long Island

10h 30m

2 stops

ORD3:30 pmChicago O'Hare Intl

May 12

ORD1:35 pmChicago O'Hare Intl

8h 05m

1 stop

ISP10:40 pmIslip Long Island

$392

Find similar

Southwest

May 9

ISP6:00 amIslip Long Island

10h 30m

2 stops

ORD3:30 pmChicago O'Hare Intl

May 12

ORD10:30 amChicago O'Hare Intl

10h 40m

2 stops

ISP10:10 pmIslip Long Island

$397

Find similar

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 2/1

9:25 am-10:41 am

1 stop26h 16m

Chicago O'Hare Intl

Sat 2/14

8:15 am-7:48 am

1 stop22h 33m

$249

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 2/19

5:07 pm-9:40 pm

1 stop29h 33m

Chicago O'Hare Intl

Sun 2/22

1:17 pm-2:39 pm

1 stop24h 22m

$263

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 3/12

5:08 pm-11:38 pm

1 stop7h 30m

Chicago O'Hare Intl

Sun 3/15

4:18 pm-12:47 pm

1 stop19h 29m

$322

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 12/29

8:35 pm-9:02 am

1 stop13h 27m

Chicago O'Hare Intl

Tue 12/30

7:01 pm-4:37 pm

1 stop20h 36m

$344

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/31

5:27 pm-10:18 am

1 stop17h 51m

Chicago O'Hare Intl

Sun 1/4

8:09 pm-1:09 pm

1 stop16h 00m

$357

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 1/1

12:20 pm-8:52 am

1 stop21h 32m

Chicago O'Hare Intl

Sat 1/17

3:49 pm-8:55 am

1 stop16h 06m

$362

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 12/22

8:35 pm-6:52 pm

2 stops23h 17m

Chicago O'Hare Intl

Wed 12/31

7:20 am-4:37 pm

1 stop8h 17m

$419

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/31

5:27 pm-10:18 am

1 stop17h 51m

Chicago O'Hare Intl

Sun 1/4

8:09 pm-1:45 pm

2 stops16h 36m

$435

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 12/28

8:35 pm-8:47 am

1 stop13h 12m

Chicago O'Hare Intl

Mon 1/5

12:25 pm-11:59 pm

1 stop10h 34m

$438

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 1/1

12:20 pm-8:52 am

1 stop21h 32m

Chicago O'Hare Intl

Sun 1/4

8:09 pm-1:09 pm

1 stop16h 00m

$442

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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 $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 $372.

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 $270. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $366.

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 30m
Direct flights	None

The fastest flight from Islip, New York to Chicago takes 6h 30m

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 30m 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?
As of December 2025, there is 1 operator available to choose from 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?
Based on momondo bookings for flights between Islip, New York and Chicago, the leading airline is Southwest, making up 100% of the total bookings.

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
Southwest	PriceFrom $336	Free Cancellation	Rating 7.9 4,250 reviews		Search Southwest flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

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.