What airlines fly to Chicago?

United Airlines, American Airlines and Delta 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 56% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 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 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.

$134 Cheap Flights from Islip, New York to Chicago in 2026/27

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.

4:40 pm - 12:42 amISP Islip Long Island-ORD Chicago O'Hare Intl

9h 02m1 stop Orlando

5:40 am - 3:45 pmORD Chicago O'Hare Intl-ISP Islip Long Island

9h 05m1 stop Orlando

$278Frontier

Fri, Nov 20 - Sun, Nov 22

4:43 pm - 12:42 amISP Islip Long Island-ORD Chicago O'Hare Intl

8h 59m1 stop Orlando

5:40 am - 3:45 pmORD Chicago O'Hare Intl-ISP Islip Long Island

9h 05m1 stop Orlando

$280Frontier

Sat, Nov 21 - Fri, Nov 27

6:25 pm - 7:31 amISP Islip Long Island-ORD Chicago O'Hare Intl

14h 06m1 stop Orlando

9:51 am - 5:31 pmORD Chicago O'Hare Intl-ISP Islip Long Island

6h 40m1 stop Orlando

$299Frontier

Sat, Oct 24 - Sat, Oct 31

6:25 pm - 7:31 amISP Islip Long Island-ORD Chicago O'Hare Intl

14h 06m1 stop Orlando

8:46 am - 5:30 pmORD Chicago O'Hare Intl-ISP Islip Long Island

7h 44m1 stop Orlando

$309Frontier

Sat, Oct 10 - Sat, Oct 17

6:25 pm - 7:31 amISP Islip Long Island-ORD Chicago O'Hare Intl

14h 06m1 stop Orlando

8:26 am - 6:00 pmORD Chicago O'Hare Intl-ISP Islip Long Island

8h 34m1 stop Orlando

$329Frontier

Sat, Oct 17 - Mon, Oct 19

6:55 pm - 7:51 amISP Islip Long Island-ORD Chicago O'Hare Intl

13h 56m1 stop Orlando

8:26 am - 6:00 pmORD Chicago O'Hare Intl-ISP Islip Long Island

8h 34m1 stop Orlando

$350Frontier

Mon, Oct 12 - Mon, Oct 19

6:25 pm - 7:31 amISP Islip Long Island-ORD Chicago O'Hare Intl

14h 06m1 stop Orlando

8:46 am - 5:30 pmORD Chicago O'Hare Intl-ISP Islip Long Island

7h 44m1 stop Orlando

$354Frontier

Sat, Oct 10 - Sat, Oct 17

6:25 pm - 7:31 amISP Islip Long Island-ORD Chicago O'Hare Intl

14h 06m1 stop Orlando

8:26 am - 5:30 pmORD Chicago O'Hare Intl-ISP Islip Long Island

8h 04m1 stop Orlando

$355Frontier

Thu, Oct 15 - Sun, Oct 25

6:55 pm - 7:51 amISP Islip Long Island-ORD Chicago O'Hare Intl

13h 56m1 stop Orlando

6:58 pm - 6:00 pmORD Chicago O'Hare Intl-ISP Islip Long Island

22h 02m1 stop Orlando

$356Frontier

Fri, Oct 16 - Sun, Oct 18

6:55 pm - 7:51 amISP Islip Long Island-ORD Chicago O'Hare Intl

13h 56m1 stop Orlando

8:46 am - 5:30 pmORD Chicago O'Hare Intl-ISP Islip Long Island

7h 44m1 stop Orlando

$375Frontier

Mon, Oct 12 - Sat, Oct 17

Cheap last minute flights

Enter your travel dates to find the best prices.

5:43 pm - 10:20 amISP Islip Long Island-ORD Chicago O'Hare Intl

17h 37m1 stop Orlando

3:50 pm - 4:58 pmORD Chicago O'Hare Intl-ISP Islip Long Island

24h 08m1 stop Orlando

$370Frontier

Wed, Sep 16 - Tue, Sep 22

5:43 pm - 10:59 pmISP Islip Long Island-ORD Chicago O'Hare Intl

30h 16m1 stop Orlando

3:50 pm - 11:20 amORD Chicago O'Hare Intl-ISP Islip Long Island

18h 30m2 stops Orlando Raleigh-Durham

$547Multiple Airlines

Wed, Sep 16 - Tue, Sep 22

11:52 am - 11:51 amISP Islip Long Island-ORD Chicago O'Hare Intl

24h 59m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson

3:50 pm - 4:58 pmORD Chicago O'Hare Intl-ISP Islip Long Island

24h 08m1 stop Orlando

$590Multiple Airlines

Fri, Sep 18 - Mon, Sep 21

5:43 pm - 10:59 pmISP Islip Long Island-ORD Chicago O'Hare Intl

30h 16m1 stop Orlando

3:50 pm - 4:58 pmORD Chicago O'Hare Intl-ISP Islip Long Island

24h 08m1 stop Orlando

$635Frontier

Fri, Sep 18 - Mon, Sep 21

5:43 pm - 10:20 amISP Islip Long Island-ORD Chicago O'Hare Intl

17h 37m1 stop Orlando

3:50 pm - 4:58 pmORD Chicago O'Hare Intl-ISP Islip Long Island

24h 08m1 stop Orlando

$656Frontier

Thu, Sep 17 - Sat, Sep 19

5:43 pm - 10:20 amISP Islip Long Island-ORD Chicago O'Hare Intl

17h 37m1 stop Orlando

4:35 pm - 4:58 pmORD Chicago O'Hare Intl-ISP Islip Long Island

23h 23m2 stops Dallas/Fort Worth Orlando

$750Frontier

Thu, Sep 17 - Sat, Sep 19

5:43 pm - 10:20 amISP Islip Long Island-ORD Chicago O'Hare Intl

17h 37m1 stop Orlando

3:50 pm - 4:58 pmORD Chicago O'Hare Intl-ISP Islip Long Island

24h 08m1 stop Orlando

$790Frontier

Thu, Sep 17 - Sat, Sep 19

7:00 am - 1:45 pmISP Islip Long Island-ORD Chicago O'Hare Intl

7h 45m1 stop Fort Lauderdale

3:50 pm - 4:58 pmORD Chicago O'Hare Intl-ISP Islip Long Island

24h 08m1 stop Orlando

$847Multiple Airlines

Fri, Sep 18 - Fri, Sep 25

5:43 pm - 10:20 amISP Islip Long Island-ORD Chicago O'Hare Intl

17h 37m1 stop Orlando

4:35 pm - 4:58 pmORD Chicago O'Hare Intl-ISP Islip Long Island

23h 23m2 stops Dallas/Fort Worth Orlando

$880Frontier

Thu, Sep 17 - Sat, Sep 19

7:00 am - 1:45 pmISP Islip Long Island-ORD Chicago O'Hare Intl

7h 45m1 stop Fort Lauderdale

3:00 pm - 11:22 pmORD Chicago O'Hare Intl-ISP Islip Long Island

7h 22m1 stop Fort Lauderdale

$963JetBlue

Sat, Sep 19 - Wed, Sep 23

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JetBlue flights from Islip, New York to Chicago

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

JetBlue

Oct 3

ISP7:00 amIslip Long Island

7h 45m

1 stop

ORD1:45 pmChicago O'Hare Intl

Oct 6

ORD3:00 pmChicago O'Hare Intl

7h 22m

1 stop

ISP11:22 pmIslip Long Island

$545

JetBlue

Oct 3

ISP7:00 amIslip Long Island

17h 08m

1 stop

ORD11:08 pmChicago O'Hare Intl

Oct 6

ORD6:00 amChicago O'Hare Intl

16h 22m

1 stop

ISP11:22 pmIslip Long Island

$592

JetBlue

Sep 27

ISP7:00 amIslip Long Island

7h 45m

1 stop

ORD1:45 pmChicago O'Hare Intl

Oct 5

ORD3:00 pmChicago O'Hare Intl

7h 22m

1 stop

ISP11:22 pmIslip Long Island

$773

Frontier flights from Islip, New York to Chicago

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

Frontier

Nov 20

ISP4:40 pmIslip Long Island

9h 02m

1 stop

ORD12:42 amChicago O'Hare Intl

Nov 22

ORD5:40 amChicago O'Hare Intl

9h 05m

1 stop

ISP3:45 pmIslip Long Island

$278

Frontier

Nov 21

ISP4:43 pmIslip Long Island

8h 59m

1 stop

ORD12:42 amChicago O'Hare Intl

Nov 27

ORD5:40 amChicago O'Hare Intl

9h 05m

1 stop

ISP3:45 pmIslip Long Island

$280

Frontier

Oct 24

ISP6:25 pmIslip Long Island

14h 06m

1 stop

ORD7:31 amChicago O'Hare Intl

Oct 31

ORD9:51 amChicago O'Hare Intl

6h 40m

1 stop

ISP5:31 pmIslip Long Island

$299

momondo Fare Finder

Use the filters below to find and compare flights from Islip, New York to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Fri 11/20

4:40 pm-12:42 am

1 stop9h 02m

Chicago O'Hare Intl

Sun 11/22

5:40 am-3:45 pm

1 stop9h 05m

$278

Quickest round-trip

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sat 11/21

4:43 pm-12:42 am

1 stop8h 59m

Chicago O'Hare Intl

Fri 11/27

5:40 am-3:45 pm

1 stop9h 05m

$280

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sat 10/24

6:25 pm-7:31 am

1 stop14h 06m

Chicago O'Hare Intl

Sat 10/31

9:51 am-5:31 pm

1 stop6h 40m

$299

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sat 10/10

6:25 pm-7:31 am

1 stop14h 06m

Chicago O'Hare Intl

Sat 10/17

8:46 am-5:30 pm

1 stop7h 44m

$309

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sat 10/17

6:25 pm-7:31 am

1 stop14h 06m

Chicago O'Hare Intl

Mon 10/19

8:26 am-6:00 pm

1 stop8h 34m

$329

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Mon 10/12

6:55 pm-7:51 am

1 stop13h 56m

Chicago O'Hare Intl

Mon 10/19

8:26 am-6:00 pm

1 stop8h 34m

$350

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sat 10/10

6:25 pm-7:31 am

1 stop14h 06m

Chicago O'Hare Intl

Sat 10/17

8:46 am-5:30 pm

1 stop7h 44m

$354

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 10/15

6:25 pm-7:31 am

1 stop14h 06m

Chicago O'Hare Intl

Sun 10/25

8:26 am-5:30 pm

1 stop8h 04m

$355

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Fri 10/16

6:55 pm-7:51 am

1 stop13h 56m

Chicago O'Hare Intl

Sun 10/18

6:58 pm-6:00 pm

1 stop22h 02m

$356

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Mon 10/12

6:55 pm-7:51 am

1 stop13h 56m

Chicago O'Hare Intl

Sat 10/17

8:46 am-5:30 pm

1 stop7h 44m

$375

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 typical price of a round-trip flight between Islip, New York and Chicago?

Prices are currently typical for flights on this route.

Typical prices usually range from $267 to $334.
The lowest price recently found on this route was $278.

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Islip, New York, with most prices found around $0. If you’re not able to fly to Chicago in February, then August is your next best option. Flight prices from Islip, New York to Chicago during August average around $187.

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 Saturday when prices can be found for as low as $331. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Islip, New York to Chicago for around $411.

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 $325. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $373.

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

Best Price Found	$134
Fastest flight time	5h 35m
Direct flights	None

The best one-way flight to Chicago from Islip, New York in the past 72 hours is $134. The best round-trip flight deal from Islip, New York to Chicago found on momondo in the last 72 hours is $278.

The fastest flight from Islip, New York to Chicago takes 5h 35m

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

Frequently asked questions about flying from Islip, New York to Chicago

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 35m 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 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.

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Lansing

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Schererville

Munster

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Monticello

Porter

Crown Point

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.

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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Islip, New York to Chicago from $134

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Islip, New York to Chicago departing on 10/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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JetBlue flights from Islip, New York to Chicago

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

Frontier flights from Islip, New York to Chicago

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

momondo Fare Finder

Use the filters below to find and compare flights from Islip, New York to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Islip, New York to Chicago

What is the typical price of a round-trip flight between Islip, New York and Chicago?

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest airline that flies from Islip Long Island to Chicago?

What airlines fly to Chicago?

When to book flights from Islip, New York to Chicago

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

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Islip, New York to Chicago

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

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According to popular flight searches on momondo this year

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