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 according to our data. United Airlines is the first choice among our users, with 39% 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 and Southwest are the most popular carriers 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 October 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 to Chicago

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Cheap round-trip flights

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4:58 pm - 12:26 pmISP-ORD

20h 28m1 stop

6:48 am - 9:07 amORD-ISP

25h 19m1 stop

$167Multiple Airlines

Find Deal

Wed, Nov 12 - Wed, Nov 19

4:58 pm - 11:28 pmISP-ORD

31h 30m2 stops

6:48 am - 9:07 amORD-ISP

25h 19m1 stop

$183Multiple Airlines

Find Deal

Wed, Nov 12 - Wed, Nov 19

11:35 am - 9:23 pmISP-ORD

10h 48m1 stop

7:00 am - 6:40 pmORD-ISP

10h 40m1 stop

$226Multiple Airlines

Find Deal

Sun, Jan 25 - Fri, Jan 30

4:58 pm - 3:08 pmISP-ORD

23h 10m1 stop

6:05 pm - 10:37 amORD-ISP

15h 32m2 stops

$281Frontier

Find Deal

Fri, Oct 31 - Tue, Nov 4

6:37 pm - 12:26 pmISP-ORD

18h 49m1 stop

5:25 am - 10:37 amORD-ISP

28h 12m1 stop

$302Frontier

Find Deal

Thu, Nov 6 - Sun, Nov 9

8:47 am - 9:57 pmISP-ORD

14h 10m1 stop

7:09 pm - 8:02 amORD-ISP

11h 53m1 stop

$310Frontier

Find Deal

Sat, Nov 22 - Sun, Nov 23

2:10 pm - 9:50 pmISP-ORD

8h 40m2 stops

6:05 am - 9:55 pmORD-ISP

14h 50m2 stops

$395Southwest

Find Deal

Sun, Jan 25 - Fri, Jan 30

3:40 pm - 9:50 pmISP-ORD

7h 10m1 stop

6:05 am - 1:50 pmORD-ISP

6h 45m1 stop

$412Southwest

Find Deal

Wed, Dec 24 - Tue, Dec 30

3:40 pm - 9:50 pmISP-ORD

7h 10m1 stop

1:00 pm - 11:55 pmORD-ISP

9h 55m2 stops

$417Southwest

Find Deal

Wed, Dec 24 - Tue, Dec 30

6:05 am - 4:45 pmISP-ORD

11h 40m2 stops

1:45 pm - 9:45 pmORD-ISP

7h 00m2 stops

$419Southwest

Find Deal

Sat, Nov 1 - Sat, Nov 8

Southwest flights from Islip to Chicago

Our best Southwest deals on Islip to Chicago flight tickets

Southwest

Jan 25

ISP2:10 pmIslip Long Island

8h 40m

2 stops

ORD9:50 pmChicago O'Hare Intl

Jan 30

ORD6:05 amChicago O'Hare Intl

14h 50m

2 stops

ISP9:55 pmIslip Long Island

$395

Find similar

Southwest

Dec 24

ISP3:40 pmIslip Long Island

7h 10m

1 stop

ORD9:50 pmChicago O'Hare Intl

Dec 30

ORD6:05 amChicago O'Hare Intl

6h 45m

1 stop

ISP1:50 pmIslip Long Island

$412

Find similar

Southwest

Dec 24

ISP3:40 pmIslip Long Island

7h 10m

1 stop

ORD9:50 pmChicago O'Hare Intl

Dec 30

ORD1:00 pmChicago O'Hare Intl

9h 55m

2 stops

ISP11:55 pmIslip Long Island

$417

Find similar

Frontier flights from Islip to Chicago

Our best Frontier deals on Islip to Chicago flight tickets

Frontier

Oct 23

ISP9:37 pmIslip Long Island

10h 57m

1 stop

ORD7:34 amChicago O'Hare Intl

Oct 26

ORD8:14 amChicago O'Hare Intl

11h 38m

1 stop

ISP8:52 pmIslip Long Island

$279

Find similar

Frontier

Oct 31

ISP4:58 pmIslip Long Island

23h 10m

1 stop

ORD3:08 pmChicago O'Hare Intl

Nov 4

ORD6:05 pmChicago O'Hare Intl

15h 32m

2 stops

ISP10:37 amIslip Long Island

$281

Find similar

Frontier

Nov 6

ISP6:37 pmIslip Long Island

18h 49m

1 stop

ORD12:26 pmChicago O'Hare Intl

Nov 9

ORD5:25 amChicago O'Hare Intl

28h 12m

1 stop

ISP10:37 amIslip Long Island

$302

Find similar

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 11/12

4:58 pm-12:26 pm

1 stop20h 28m

Chicago O'Hare Intl

Wed 11/19

6:48 am-9:07 am

1 stop25h 19m

$167

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 11/12

4:58 pm-11:28 pm

2 stops31h 30m

Chicago O'Hare Intl

Wed 11/19

6:48 am-9:07 am

1 stop25h 19m

$183

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 1/25

11:35 am-9:23 pm

1 stop10h 48m

Chicago O'Hare Intl

Fri 1/30

7:00 am-6:40 pm

1 stop10h 40m

$226

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 10/31

4:58 pm-3:08 pm

1 stop23h 10m

Chicago O'Hare Intl

Tue 11/4

6:05 pm-10:37 am

2 stops15h 32m

$281

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 11/6

6:37 pm-12:26 pm

1 stop18h 49m

Chicago O'Hare Intl

Sun 11/9

5:25 am-10:37 am

1 stop28h 12m

$302

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 11/22

8:47 am-9:57 pm

1 stop14h 10m

Chicago O'Hare Intl

Sun 11/23

7:09 pm-8:02 am

1 stop11h 53m

$310

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 1/25

2:10 pm-9:50 pm

2 stops8h 40m

Chicago O'Hare Intl

Fri 1/30

6:05 am-9:55 pm

2 stops14h 50m

$395

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/24

3:40 pm-9:50 pm

1 stop7h 10m

Chicago O'Hare Intl

Tue 12/30

6:05 am-1:50 pm

1 stop6h 45m

$412

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/24

3:40 pm-9:50 pm

1 stop7h 10m

Chicago O'Hare Intl

Tue 12/30

1:00 pm-11:55 pm

2 stops9h 55m

$417

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 11/1

6:05 am-4:45 pm

2 stops11h 40m

Chicago O'Hare Intl

Sat 11/8

1:45 pm-9:45 pm

2 stops7h 00m

$419

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 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 $294. 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 to Chicago for around $387.

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 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 $366.

When to book flights from Islip to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Islip to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Islip to Chicago (ISP to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Islip to Chicago

Direct flights	None

There are no direct flights from Islip to Chicago. There are no popular flight routes from Islip to Chicago.

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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 55m 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 October 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 to Chicago?
Based on momondo bookings for flights between Islip and Chicago, the leading airline is Southwest, making up 100% of the total bookings.

Best airlines flying from Islip to Chicago

Compare and see reviews for airlines that fly from Islip to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $306	Free Cancellation	Rating 8.0 4,241 reviews		Search Southwest flights

Southwest Flights From Islip to Chicago
Southwest flies from Islip to Chicago around 3 times per week, with 4,241 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Islip to Chicago in the last 72 hours was $306 (round-trip), much lower than the average airfare cost of $604 for Southwest flights on this route.

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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.