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 40% 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 November 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.

$65 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.

1:15 pm - 11:05 amISP-ORD

22h 50m1 stop

2:26 pm - 7:34 pmORD-ISP

28h 08m1 stop

$150Frontier

Find Deal

Thu, Dec 4 - Mon, Dec 8

6:00 am - 11:54 amISP-ORD

30h 54m2 stops

2:36 pm - 9:13 amORD-ISP

17h 37m1 stop

$158Frontier

Find Deal

Fri, Dec 5 - Sun, Dec 7

6:00 am - 12:39 pmISP-ORD

7h 39m1 stop

7:20 am - 9:13 amORD-ISP

24h 53m1 stop

$181Multiple Airlines

Find Deal

Fri, Dec 5 - Sun, Dec 7

6:00 am - 4:03 pmISP-ORD

11h 03m1 stop

2:36 pm - 9:13 amORD-ISP

17h 37m1 stop

$188Multiple Airlines

Find Deal

Wed, Dec 3 - Sun, Dec 7

6:00 am - 4:03 pmISP-ORD

11h 03m1 stop

8:00 am - 9:13 amORD-ISP

24h 13m2 stops

$189Multiple Airlines

Find Deal

Wed, Dec 3 - Wed, Dec 10

10:19 am - 1:16 pmISP-ORD

27h 57m1 stop

2:26 pm - 7:34 pmORD-ISP

28h 08m1 stop

$190Frontier

Find Deal

Thu, Dec 11 - Mon, Dec 15

6:00 am - 12:39 pmISP-ORD

7h 39m1 stop

9:14 pm - 7:34 pmORD-ISP

45h 20m2 stops

$197Multiple Airlines

Find Deal

Fri, Dec 5 - Sun, Dec 7

6:00 am - 4:03 pmISP-ORD

11h 03m1 stop

9:14 pm - 7:34 pmORD-ISP

45h 20m2 stops

$204Multiple Airlines

Find Deal

Wed, Dec 3 - Sun, Dec 7

10:19 am - 9:48 pmISP-ORD

12h 29m1 stop

2:26 pm - 7:34 pmORD-ISP

28h 08m1 stop

$205Multiple Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

4:05 pm - 4:08 pmISP-ORD

25h 03m1 stop

2:26 pm - 7:34 pmORD-ISP

28h 08m1 stop

$210Frontier

Find Deal

Sat, Dec 6 - Mon, Dec 8

Frontier flights from Islip, New York to Chicago

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

Frontier

Dec 4

ISP1:15 pmIslip Long Island

22h 50m

1 stop

ORD11:05 amChicago O'Hare Intl

Dec 8

ORD2:26 pmChicago O'Hare Intl

28h 08m

1 stop

ISP7:34 pmIslip Long Island

$150

Find similar

Frontier

Dec 5

ISP6:00 amIslip Long Island

30h 54m

2 stops

ORD11:54 amChicago O'Hare Intl

Dec 7

ORD2:36 pmChicago O'Hare Intl

17h 37m

1 stop

ISP9:13 amIslip Long Island

$158

Find similar

Frontier

Dec 11

ISP10:19 amIslip Long Island

27h 57m

1 stop

ORD1:16 pmChicago O'Hare Intl

Dec 15

ORD2:26 pmChicago O'Hare Intl

28h 08m

1 stop

ISP7:34 pmIslip Long Island

$190

Find similar

Southwest flights from Islip, New York to Chicago

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

Southwest

Dec 11

ISP12:55 pmIslip Long Island

9h 55m

2 stops

ORD9:50 pmChicago O'Hare Intl

Dec 15

ORD6:05 amChicago O'Hare Intl

8h 00m

2 stops

ISP3:05 pmIslip Long Island

$384

Find similar

Southwest

Mar 5

ISP6:00 amIslip Long Island

11h 10m

2 stops

ORD4:10 pmChicago O'Hare Intl

Mar 9

ORD1:35 pmChicago O'Hare Intl

9h 20m

2 stops

ISP11:55 pmIslip Long Island

$397

Find similar

Southwest

Dec 18

ISP1:40 pmIslip Long Island

9h 10m

2 stops

ORD9:50 pmChicago O'Hare Intl

Dec 22

ORD1:00 pmChicago O'Hare Intl

9h 55m

2 stops

ISP11:55 pmIslip Long Island

$402

Find similar

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 12/4

1:15 pm-11:05 am

1 stop22h 50m

Chicago O'Hare Intl

Mon 12/8

2:26 pm-7:34 pm

1 stop28h 08m

$150

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 12/5

6:00 am-11:54 am

2 stops30h 54m

Chicago O'Hare Intl

Sun 12/7

2:36 pm-9:13 am

1 stop17h 37m

$158

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 12/5

6:00 am-12:39 pm

1 stop7h 39m

Chicago O'Hare Intl

Sun 12/7

7:20 am-9:13 am

1 stop24h 53m

$181

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/3

6:00 am-4:03 pm

1 stop11h 03m

Chicago O'Hare Intl

Sun 12/7

2:36 pm-9:13 am

1 stop17h 37m

$188

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/3

6:00 am-4:03 pm

1 stop11h 03m

Chicago O'Hare Intl

Wed 12/10

8:00 am-9:13 am

2 stops24h 13m

$189

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 12/11

10:19 am-1:16 pm

1 stop27h 57m

Chicago O'Hare Intl

Mon 12/15

2:26 pm-7:34 pm

1 stop28h 08m

$190

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 12/5

6:00 am-12:39 pm

1 stop7h 39m

Chicago O'Hare Intl

Sun 12/7

9:14 pm-7:34 pm

2 stops45h 20m

$197

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/3

6:00 am-4:03 pm

1 stop11h 03m

Chicago O'Hare Intl

Sun 12/7

9:14 pm-7:34 pm

2 stops45h 20m

$204

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 12/4

10:19 am-9:48 pm

1 stop12h 29m

Chicago O'Hare Intl

Mon 12/8

2:26 pm-7:34 pm

1 stop28h 08m

$205

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 12/6

4:05 pm-4:08 pm

1 stop25h 03m

Chicago O'Hare Intl

Mon 12/8

2:26 pm-7:34 pm

1 stop28h 08m

$210

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 $292. 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 $384.

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 $271. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $367.

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

Direct flights	None

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 09m 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 November 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 8.0 4,249 reviews		Search Southwest flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

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.