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.

$80 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.

8:23 am - 11:15 pm

ISP

ORD

15h 52m

1 stop

8:30 am - 8:40 am

ORD

ISP

23h 10m

1 stop

$160Frontier

Mon, Mar 2 - Tue, Mar 3

8:33 am - 7:47 pm

ISP

ORD

12h 14m

1 stop

10:19 am - 11:10 am

ORD

ISP

23h 51m

2 stops

$203Multiple Airlines

Fri, Feb 20 - Tue, Feb 24

8:33 am - 8:12 pm

ISP

ORD

12h 39m

1 stop

8:30 am - 8:40 am

ORD

ISP

23h 10m

1 stop

$216Frontier

Fri, Feb 20 - Tue, Feb 24

3:59 pm - 11:15 pm

ISP

ORD

8h 16m

1 stop

8:15 am - 7:28 pm

ORD

ISP

10h 13m

1 stop

$221Frontier

Mon, Feb 23 - Sat, Feb 28

3:34 pm - 3:37 pm

ISP

ORD

25h 03m

1 stop

7:35 am - 7:38 am

ORD

ISP

23h 03m

1 stop

$230Frontier

Fri, Feb 27 - Sun, Mar 1

9:43 pm - 4:40 pm

ISP

ORD

19h 57m

1 stop

12:21 pm - 6:48 pm

ORD

ISP

29h 27m

1 stop

$270Frontier

Fri, Jan 30 - Sun, Feb 1

1:42 pm - 11:38 pm

ISP

ORD

10h 56m

1 stop

12:05 pm - 11:10 am

ORD

ISP

46h 05m

2 stops

$284Multiple Airlines

Fri, Mar 6 - Mon, Mar 9

10:58 am - 11:19 pm

ISP

ORD

13h 21m

1 stop

4:21 pm - 11:55 pm

ORD

ISP

6h 34m

1 stop

$289Frontier

Mon, Mar 30 - Thu, Apr 2

3:50 pm - 11:58 pm

ISP

ORD

9h 08m

1 stop

8:00 am - 9:13 am

ORD

ISP

24h 13m

1 stop

$290Frontier

Mon, Apr 20 - Sat, Apr 25

7:20 pm - 9:43 am

ISP

ORD

15h 23m

1 stop

4:38 pm - 6:55 pm

ORD

ISP

25h 17m

1 stop

$305Multiple Airlines

Mon, Feb 2 - Tue, Feb 3

Southwest flights from Islip, New York to Chicago

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

Southwest

Mar 6

ISP6:00 amIslip Long Island

7h 50m

2 stops

ORD12:50 pmChicago O'Hare Intl

Mar 9

ORD2:40 pmChicago O'Hare Intl

8h 15m

2 stops

ISP11:55 pmIslip Long Island

$375

Southwest

Apr 17

ISP6:00 amIslip Long Island

7h 50m

2 stops

ORD12:50 pmChicago O'Hare Intl

Apr 20

ORD7:35 pmChicago O'Hare Intl

15h 20m

2 stops

ISP11:55 amIslip Long Island

$380

Southwest

Apr 17

ISP6:50 amIslip Long Island

8h 30m

1 stop

ORD2:20 pmChicago O'Hare Intl

Apr 20

ORD7:35 pmChicago O'Hare Intl

15h 20m

2 stops

ISP11:55 amIslip Long Island

$395

Frontier flights from Islip, New York to Chicago

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

Frontier

Mar 26

ISP5:08 pmIslip Long Island

17h 12m

1 stop

ORD9:20 amChicago O'Hare Intl

Mar 29

ORD9:47 pmChicago O'Hare Intl

11h 26m

1 stop

ISP10:13 amIslip Long Island

$520

Frontier

Mar 16

ISP1:22 pmIslip Long Island

11h 16m

1 stop

ORD11:38 pmChicago O'Hare Intl

Mar 19

ORD8:05 amChicago O'Hare Intl

6h 44m

1 stop

ISP3:49 pmIslip Long Island

$588

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 3/2

8:23 am-11:15 pm

1 stop15h 52m

Chicago O'Hare Intl

Tue 3/3

8:30 am-8:40 am

1 stop23h 10m

$160

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/20

8:33 am-7:47 pm

1 stop12h 14m

Chicago O'Hare Intl

Tue 2/24

10:19 am-11:10 am

2 stops23h 51m

$203

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/20

8:33 am-8:12 pm

1 stop12h 39m

Chicago O'Hare Intl

Tue 2/24

8:30 am-8:40 am

1 stop23h 10m

$216

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 2/23

3:59 pm-11:15 pm

1 stop8h 16m

Chicago O'Hare Intl

Sat 2/28

8:15 am-7:28 pm

1 stop10h 13m

$221

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/27

3:34 pm-3:37 pm

1 stop25h 03m

Chicago O'Hare Intl

Sun 3/1

7:35 am-7:38 am

1 stop23h 03m

$230

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 1/30

9:43 pm-4:40 pm

1 stop19h 57m

Chicago O'Hare Intl

Sun 2/1

12:21 pm-6:48 pm

1 stop29h 27m

$270

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 3/6

1:42 pm-11:38 pm

1 stop10h 56m

Chicago O'Hare Intl

Mon 3/9

12:05 pm-11:10 am

2 stops46h 05m

$284

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 3/30

10:58 am-11:19 pm

1 stop13h 21m

Chicago O'Hare Intl

Thu 4/2

4:21 pm-11:55 pm

1 stop6h 34m

$289

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 4/20

3:50 pm-11:58 pm

1 stop9h 08m

Chicago O'Hare Intl

Sat 4/25

8:00 am-9:13 am

1 stop24h 13m

$290

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 2/2

7:20 pm-9:43 am

1 stop15h 23m

Chicago O'Hare Intl

Tue 2/3

4:38 pm-6:55 pm

1 stop25h 17m

$305

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 $267. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $364.

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	6h 50m
Direct flights	None

The fastest flight from Islip, New York to Chicago takes 6h 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 6h 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 4,268 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.