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 42% 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.

$74 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

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

3:34 pm - 8:12 pm

ISP

ORD

29h 38m

1 stop

11:55 am - 2:39 pm

ORD

ISP

25h 44m

1 stop

$162Frontier

Thu, Feb 19 - Thu, Feb 26

3:34 pm - 10:47 pm

ISP

ORD

8h 13m

1 stop

8:15 am - 7:28 pm

ORD

ISP

10h 13m

1 stop

$195Frontier

Fri, Feb 27 - Sat, Feb 28

5:07 pm - 9:40 pm

ISP

ORD

29h 33m

1 stop

11:55 am - 12:47 pm

ORD

ISP

23h 52m

1 stop

$196Frontier

Thu, Feb 26 - Thu, Mar 5

11:50 am - 10:51 am

ISP

ORD

24h 01m

2 stops

1:17 pm - 7:38 am

ORD

ISP

17h 21m

1 stop

$229Multiple Airlines

Wed, Feb 11 - Sun, Feb 15

3:34 pm - 10:46 am

ISP

ORD

20h 12m

2 stops

11:55 am - 7:38 am

ORD

ISP

18h 43m

1 stop

$266Frontier

Thu, Feb 19 - Thu, Feb 26

11:59 am - 8:13 am

ISP

ORD

21h 14m

1 stop

12:44 pm - 12:47 pm

ORD

ISP

23h 03m

1 stop

$274Multiple Airlines

Tue, Mar 3 - Thu, Mar 5

11:59 am - 8:13 am

ISP

ORD

21h 14m

1 stop

8:42 pm - 1:31 pm

ORD

ISP

15h 49m

2 stops

$277Multiple Airlines

Tue, Mar 3 - Thu, Mar 5

12:45 pm - 10:08 pm

ISP

ORD

10h 23m

1 stop

4:42 pm - 7:06 pm

ORD

ISP

25h 24m

2 stops

$293Multiple Airlines

Tue, Feb 10 - Sat, Feb 14

2:03 pm - 9:44 pm

ISP

ORD

8h 41m

1 stop

1:17 pm - 7:38 am

ORD

ISP

17h 21m

1 stop

$309Multiple Airlines

Wed, Feb 11 - Sun, Feb 15

6:00 am - 2:45 pm

ISP

ORD

9h 45m

2 stops

2:00 pm - 11:55 pm

ORD

ISP

8h 55m

2 stops

$340Southwest

Tue, Mar 3 - Thu, Mar 5

Southwest flights from Islip, New York to Chicago

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

Southwest

Mar 3

ISP6:00 amIslip Long Island

9h 45m

2 stops

ORD2:45 pmChicago O'Hare Intl

Mar 5

ORD2:00 pmChicago O'Hare Intl

8h 55m

2 stops

ISP11:55 pmIslip Long Island

$340

Southwest

Apr 9

ISP12:30 pmIslip Long Island

10h 25m

2 stops

ORD9:55 pmChicago O'Hare Intl

Apr 13

ORD2:40 pmChicago O'Hare Intl

7h 50m

2 stops

ISP11:30 pmIslip Long Island

$374

Southwest

Feb 19

ISP2:10 pmIslip Long Island

8h 40m

2 stops

ORD9:50 pmChicago O'Hare Intl

Feb 26

ORD6:05 amChicago O'Hare Intl

9h 55m

2 stops

ISP5:00 pmIslip Long Island

$394

Frontier flights from Islip, New York to Chicago

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

Frontier

Feb 19

ISP3:34 pmIslip Long Island

29h 38m

1 stop

ORD8:12 pmChicago O'Hare Intl

Feb 26

ORD11:55 amChicago O'Hare Intl

25h 44m

1 stop

ISP2:39 pmIslip Long Island

$162

Frontier

Feb 27

ISP3:34 pmIslip Long Island

8h 13m

1 stop

ORD10:47 pmChicago O'Hare Intl

Feb 28

ORD8:15 amChicago O'Hare Intl

10h 13m

1 stop

ISP7:28 pmIslip Long Island

$195

Frontier

Feb 26

ISP5:07 pmIslip Long Island

29h 33m

1 stop

ORD9:40 pmChicago O'Hare Intl

Mar 5

ORD11:55 amChicago O'Hare Intl

23h 52m

1 stop

ISP12:47 pmIslip Long Island

$196

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 2/19

3:34 pm-8:12 pm

1 stop29h 38m

Chicago O'Hare Intl

Thu 2/26

11:55 am-2:39 pm

1 stop25h 44m

$162

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/27

3:34 pm-10:47 pm

1 stop8h 13m

Chicago O'Hare Intl

Sat 2/28

8:15 am-7:28 pm

1 stop10h 13m

$195

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 2/26

5:07 pm-9:40 pm

1 stop29h 33m

Chicago O'Hare Intl

Thu 3/5

11:55 am-12:47 pm

1 stop23h 52m

$196

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 2/11

11:50 am-10:51 am

2 stops24h 01m

Chicago O'Hare Intl

Sun 2/15

1:17 pm-7:38 am

1 stop17h 21m

$229

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 2/19

3:34 pm-10:46 am

2 stops20h 12m

Chicago O'Hare Intl

Thu 2/26

11:55 am-7:38 am

1 stop18h 43m

$266

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 3/3

11:59 am-8:13 am

1 stop21h 14m

Chicago O'Hare Intl

Thu 3/5

12:44 pm-12:47 pm

1 stop23h 03m

$274

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 3/3

11:59 am-8:13 am

1 stop21h 14m

Chicago O'Hare Intl

Thu 3/5

8:42 pm-1:31 pm

2 stops15h 49m

$277

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 2/10

12:45 pm-10:08 pm

1 stop10h 23m

Chicago O'Hare Intl

Sat 2/14

4:42 pm-7:06 pm

2 stops25h 24m

$293

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 2/11

2:03 pm-9:44 pm

1 stop8h 41m

Chicago O'Hare Intl

Sun 2/15

1:17 pm-7:38 am

1 stop17h 21m

$309

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 3/3

6:00 am-2:45 pm

2 stops9h 45m

Chicago O'Hare Intl

Thu 3/5

2:00 pm-11:55 pm

2 stops8h 55m

$340

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 $289. 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 $361.

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 $268. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $363.

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	9h 50m
Direct flights	None

The fastest flight from Islip, New York to Chicago takes 9h 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 9h 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?
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 $366	Free Cancellation	Rating 8.0 4,267 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.