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.

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

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 January 2026, 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.

$88 Cheap Flights from Islip to Chicago in 2026

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Find the cheapest flights from Islip, New York to Chicago

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:43 pm - 7:41 pm

ISP

ORD

24h 58m1 stop

10:48 am - 8:47 pm

ORD

ISP

8h 59m1 stop

$167Multiple Airlines

Mon, Feb 2 - Fri, Feb 6

9:25 am - 10:41 am

ISP

ORD

26h 16m1 stop

7:21 pm - 6:40 pm

ORD

ISP

22h 19m1 stop

$190Multiple Airlines

Sun, Jan 25 - Thu, Jan 29

7:20 pm - 9:43 am

ISP

ORD

15h 23m1 stop

8:43 pm - 8:40 am

ORD

ISP

34h 57m2 stops

$194Multiple Airlines

Mon, Feb 2 - Fri, Feb 6

9:25 am - 10:41 am

ISP

ORD

26h 16m1 stop

7:20 am - 6:48 pm

ORD

ISP

10h 28m2 stops

$197Multiple Airlines

Sun, Jan 25 - Thu, Jan 29

7:43 pm - 10:35 am

ISP

ORD

15h 52m1 stop

12:21 pm - 6:48 pm

ORD

ISP

29h 27m1 stop

$219Frontier

Thu, Jan 22 - Sun, Jan 25

3:34 pm - 3:35 pm

ISP

ORD

25h 01m1 stop

1:17 pm - 7:38 am

ORD

ISP

17h 21m1 stop

$254Frontier

Fri, Feb 20 - Sun, Feb 22

8:00 am - 6:24 pm

ISP

ORD

35h 24m2 stops

7:00 am - 6:40 pm

ORD

ISP

10h 40m1 stop

$270Multiple Airlines

Tue, Jan 13 - Fri, Jan 16

8:45 pm - 4:58 pm

ISP

ORD

21h 13m1 stop

10:07 am - 11:10 am

ORD

ISP

24h 03m2 stops

$281Multiple Airlines

Fri, Jan 16 - Tue, Jan 20

7:43 pm - 9:03 pm

ISP

ORD

26h 20m2 stops

5:15 am - 8:47 pm

ORD

ISP

14h 32m2 stops

$289Multiple Airlines

Mon, Feb 2 - Fri, Feb 6

8:45 pm - 4:58 pm

ISP

ORD

21h 13m1 stop

7:21 pm - 6:55 pm

ORD

ISP

22h 34m1 stop

$314Multiple Airlines

Fri, Jan 16 - Tue, Jan 20

Frontier flights from Islip, New York to Chicago

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

Frontier

Jan 22

ISP7:43 pmIslip Long Island

15h 52m

1 stop

ORD10:35 amChicago O'Hare Intl

Jan 25

ORD12:21 pmChicago O'Hare Intl

29h 27m

1 stop

ISP6:48 pmIslip Long Island

$219

Find similar

Frontier

Jan 10

ISP7:56 pmIslip Long Island

24h 21m

1 stop

ORD7:17 pmChicago O'Hare Intl

Jan 17

ORD3:49 pmChicago O'Hare Intl

16h 06m

1 stop

ISP8:55 amIslip Long Island

$244

Find similar

Frontier

Feb 20

ISP3:34 pmIslip Long Island

25h 01m

1 stop

ORD3:35 pmChicago O'Hare Intl

Feb 22

ORD1:17 pmChicago O'Hare Intl

17h 21m

1 stop

ISP7:38 amIslip Long Island

$254

Find similar

Southwest flights from Islip, New York to Chicago

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

Southwest

Feb 2

ISP12:40 pmIslip Long Island

10h 10m

2 stops

ORD9:50 pmChicago O'Hare Intl

Feb 6

ORD11:55 amChicago O'Hare Intl

9h 25m

2 stops

ISP10:20 pmIslip Long Island

$375

Find similar

Southwest

May 1

ISP6:50 amIslip Long Island

8h 30m

1 stop

ORD2:20 pmChicago O'Hare Intl

May 3

ORD1:35 pmChicago O'Hare Intl

9h 10m

1 stop

ISP11:45 pmIslip Long Island

$407

Find similar

Southwest

May 1

ISP12:30 pmIslip Long Island

10h 25m

2 stops

ORD9:55 pmChicago O'Hare Intl

May 3

ORD1:35 pmChicago O'Hare Intl

9h 10m

1 stop

ISP11:45 pmIslip Long Island

$412

Find similar

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 2/2

7:43 pm-7:41 pm

1 stop24h 58m

Chicago O'Hare Intl

Fri 2/6

10:48 am-8:47 pm

1 stop8h 59m

$167

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 1/25

9:25 am-10:41 am

1 stop26h 16m

Chicago O'Hare Intl

Thu 1/29

7:21 pm-6:40 pm

1 stop22h 19m

$190

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 2/2

7:20 pm-9:43 am

1 stop15h 23m

Chicago O'Hare Intl

Fri 2/6

8:43 pm-8:40 am

2 stops34h 57m

$194

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 1/25

9:25 am-10:41 am

1 stop26h 16m

Chicago O'Hare Intl

Thu 1/29

7:20 am-6:48 pm

2 stops10h 28m

$197

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 1/22

7:43 pm-10:35 am

1 stop15h 52m

Chicago O'Hare Intl

Sun 1/25

12:21 pm-6:48 pm

1 stop29h 27m

$219

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/20

3:34 pm-3:35 pm

1 stop25h 01m

Chicago O'Hare Intl

Sun 2/22

1:17 pm-7:38 am

1 stop17h 21m

$254

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 1/13

8:00 am-6:24 pm

2 stops35h 24m

Chicago O'Hare Intl

Fri 1/16

7:00 am-6:40 pm

1 stop10h 40m

$270

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 1/16

8:45 pm-4:58 pm

1 stop21h 13m

Chicago O'Hare Intl

Tue 1/20

10:07 am-11:10 am

2 stops24h 03m

$281

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 2/2

7:43 pm-9:03 pm

2 stops26h 20m

Chicago O'Hare Intl

Fri 2/6

5:15 am-8:47 pm

2 stops14h 32m

$289

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 1/16

8:45 pm-4:58 pm

1 stop21h 13m

Chicago O'Hare Intl

Tue 1/20

7:21 pm-6:55 pm

1 stop22h 34m

$314

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 $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 $368.

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 $269. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $365.

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 19m
Direct flights	None

The fastest flight from Islip, New York to Chicago takes 7h 19m

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 19m 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 January 2026, 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 8.0 4,254 reviews		Search Southwest flights

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.