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 37% 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 September 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.

$84 Cheap Flights from Islip to Chicago in 2025/26

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Islip to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

11:40 am - 7:44 pmISP-ORD

9h 04m1 stop

8:49 pm - 10:55 amORD-ISP

13h 06m1 stop

$168Frontier

Find Deal

Thu, Sep 25 - Fri, Sep 26

11:40 am - 7:44 pmISP-ORD

9h 04m1 stop

8:49 pm - 10:40 amORD-ISP

12h 51m1 stop

$184Frontier

Find Deal

Thu, Sep 25 - Sun, Sep 28

11:25 am - 9:58 pmISP-ORD

11h 33m1 stop

8:49 pm - 10:55 amORD-ISP

13h 06m1 stop

$207

Find Deal

Tue, Sep 30 - Fri, Oct 3

9:37 pm - 5:53 pmISP-ORD

21h 16m1 stop

6:58 pm - 8:42 pmORD-ISP

24h 44m1 stop

$218

Find Deal

Tue, Oct 7 - Wed, Oct 22

11:25 am - 7:44 pmISP-ORD

9h 19m1 stop

8:49 pm - 10:40 amORD-ISP

12h 51m1 stop

$224Frontier

Find Deal

Sun, Sep 28 - Thu, Oct 2

9:47 pm - 11:18 amISP-ORD

14h 31m2 stops

3:12 pm - 9:04 amORD-ISP

16h 52m2 stops

$227Frontier

Find Deal

Sun, Oct 19 - Wed, Oct 22

1:30 pm - 9:50 pmISP-ORD

9h 20m2 stops

11:55 am - 10:05 pmORD-ISP

9h 10m2 stops

$344Southwest

Find Deal

Sat, Dec 6 - Mon, Dec 8

6:00 am - 4:25 pmISP-ORD

11h 25m2 stops

6:00 am - 4:05 pmORD-ISP

9h 05m2 stops

$362Southwest

Find Deal

Tue, Oct 7 - Wed, Oct 22

5:40 am - 2:45 pmISP-ORD

10h 05m2 stops

11:55 am - 10:05 pmORD-ISP

9h 10m2 stops

$365Southwest

Find Deal

Fri, Dec 5 - Mon, Dec 8

6:05 am - 5:55 pmISP-ORD

12h 50m2 stops

11:25 am - 11:45 pmORD-ISP

11h 20m2 stops

$457Southwest

Find Deal

Tue, Sep 30 - Fri, Oct 3

Frontier flights from Islip to Chicago

Our best Frontier deals on Islip to Chicago flight tickets

Frontier

Sep 25

ISP11:40 amIslip Long Island

9h 04m

1 stop

ORD7:44 pmChicago O'Hare Intl

Sep 26

ORD8:49 pmChicago O'Hare Intl

13h 06m

1 stop

ISP10:55 amIslip Long Island

$168

Find similar

Frontier

Sep 25

ISP11:40 amIslip Long Island

9h 04m

1 stop

ORD7:44 pmChicago O'Hare Intl

Sep 28

ORD8:49 pmChicago O'Hare Intl

12h 51m

1 stop

ISP10:40 amIslip Long Island

$184

Find similar

Frontier

Sep 28

ISP11:25 amIslip Long Island

9h 19m

1 stop

ORD7:44 pmChicago O'Hare Intl

Oct 2

ORD8:49 pmChicago O'Hare Intl

12h 51m

1 stop

ISP10:40 amIslip Long Island

$224

Find similar

Southwest flights from Islip to Chicago

Our best Southwest deals on Islip to Chicago flight tickets

Southwest

Dec 6

ISP1:30 pmIslip Long Island

9h 20m

2 stops

ORD9:50 pmChicago O'Hare Intl

Dec 8

ORD11:55 amChicago O'Hare Intl

9h 10m

2 stops

ISP10:05 pmIslip Long Island

$344

Find similar

Southwest

Oct 7

ISP6:00 amIslip Long Island

11h 25m

2 stops

ORD4:25 pmChicago O'Hare Intl

Oct 22

ORD6:00 amChicago O'Hare Intl

9h 05m

2 stops

ISP4:05 pmIslip Long Island

$362

Find similar

Southwest

Dec 5

ISP5:40 amIslip Long Island

10h 05m

2 stops

ORD2:45 pmChicago O'Hare Intl

Dec 8

ORD11:55 amChicago O'Hare Intl

9h 10m

2 stops

ISP10:05 pmIslip Long Island

$365

Find similar

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/25

11:40 am-7:44 pm

1 stop9h 04m

Chicago O'Hare Intl

Fri 9/26

8:49 pm-10:55 am

1 stop13h 06m

$168

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/25

11:40 am-7:44 pm

1 stop9h 04m

Chicago O'Hare Intl

Sun 9/28

8:49 pm-10:40 am

1 stop12h 51m

$184

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 9/30

11:25 am-9:58 pm

1 stop11h 33m

Chicago O'Hare Intl

Fri 10/3

8:49 pm-10:55 am

1 stop13h 06m

$207

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 10/7

9:37 pm-5:53 pm

1 stop21h 16m

Chicago O'Hare Intl

Wed 10/22

6:58 pm-8:42 pm

1 stop24h 44m

$218

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 9/28

11:25 am-7:44 pm

1 stop9h 19m

Chicago O'Hare Intl

Thu 10/2

8:49 pm-10:40 am

1 stop12h 51m

$224

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 10/19

9:47 pm-11:18 am

2 stops14h 31m

Chicago O'Hare Intl

Wed 10/22

3:12 pm-9:04 am

2 stops16h 52m

$227

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 12/6

1:30 pm-9:50 pm

2 stops9h 20m

Chicago O'Hare Intl

Mon 12/8

11:55 am-10:05 pm

2 stops9h 10m

$344

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 10/7

6:00 am-4:25 pm

2 stops11h 25m

Chicago O'Hare Intl

Wed 10/22

6:00 am-4:05 pm

2 stops9h 05m

$362

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 12/5

5:40 am-2:45 pm

2 stops10h 05m

Chicago O'Hare Intl

Mon 12/8

11:55 am-10:05 pm

2 stops9h 10m

$365

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 9/30

6:05 am-5:55 pm

2 stops12h 50m

Chicago O'Hare Intl

Fri 10/3

11:25 am-11:45 pm

2 stops11h 20m

$457

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 $295. 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 $389.

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 $261. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $368.

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.

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 5h 26m 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 September 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 4,242 reviews		Search Southwest flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

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.