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

Southwest is the most popular carrier operating from Islip Long Island to Chicago

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.

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.

$170 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.

11:26 am - 7:30 pmISP Islip Long Island-MDW Chicago Midway

9h 04m1 stop Orlando

8:35 pm - 10:31 amMDW Chicago Midway-ISP Islip Long Island

12h 56m1 stop Orlando

$332Frontier

Fri, Dec 18 - Tue, Dec 29

11:26 am - 7:30 pmISP Islip Long Island-MDW Chicago Midway

9h 04m1 stop Orlando

8:35 pm - 10:31 amMDW Chicago Midway-ISP Islip Long Island

12h 56m1 stop Orlando

$344Frontier

Mon, Dec 21 - Tue, Dec 29

11:26 am - 7:30 pmISP Islip Long Island-MDW Chicago Midway

9h 04m1 stop Orlando

8:35 pm - 10:31 amMDW Chicago Midway-ISP Islip Long Island

12h 56m1 stop Orlando

$380Frontier

Fri, Dec 18 - Sun, Dec 27

4:55 pm - 12:20 amISP Islip Long Island-MDW Chicago Midway

8h 25m2 stops Baltimore/Washington Nashville Intl

4:05 pm - 11:50 pmMDW Chicago Midway-ISP Islip Long Island

6h 45m1 stop Baltimore/Washington

$411Southwest

Mon, Dec 21 - Tue, Dec 29

5:45 am - 8:55 amISP Islip Long Island-MDW Chicago Midway

4h 10m1 stop Baltimore/Washington

6:00 am - 4:15 pmMDW Chicago Midway-ISP Islip Long Island

9h 15m1 stop Baltimore/Washington

$413Southwest

Thu, Nov 26 - Thu, Dec 3

5:45 am - 1:00 pmISP Islip Long Island-MDW Chicago Midway

8h 15m2 stops Baltimore/Washington Atlanta Hartsfield-Jackson

8:10 am - 4:15 pmMDW Chicago Midway-ISP Islip Long Island

7h 05m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington

$418Southwest

Thu, Nov 26 - Thu, Dec 3

9:25 am - 4:30 pmISP Islip Long Island-MDW Chicago Midway

8h 05m1 stop Tampa

4:05 pm - 11:50 pmMDW Chicago Midway-ISP Islip Long Island

6h 45m1 stop Baltimore/Washington

$442Southwest

Sun, Dec 20 - Tue, Dec 29

4:55 pm - 12:20 amISP Islip Long Island-MDW Chicago Midway

8h 25m2 stops Baltimore/Washington Nashville Intl

3:05 pm - 11:50 pmMDW Chicago Midway-ISP Islip Long Island

7h 45m2 stops Nashville Intl Baltimore/Washington

$445Southwest

Mon, Dec 21 - Tue, Dec 29

4:55 pm - 11:40 pmISP Islip Long Island-MDW Chicago Midway

7h 45m2 stops Baltimore/Washington Atlanta Hartsfield-Jackson

4:05 pm - 11:50 pmMDW Chicago Midway-ISP Islip Long Island

6h 45m1 stop Baltimore/Washington

$447Southwest

Sun, Dec 20 - Tue, Dec 29

4:55 pm - 8:40 pmISP Islip Long Island-MDW Chicago Midway

4h 45m1 stop Baltimore/Washington

4:05 pm - 11:50 pmMDW Chicago Midway-ISP Islip Long Island

6h 45m1 stop Baltimore/Washington

$472Southwest

Sun, Dec 20 - Mon, Dec 28

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Frontier flights from Islip, New York to Chicago

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

Frontier

Dec 18

ISP11:26 amIslip Long Island

9h 04m

1 stop

MDW7:30 pmChicago Midway

Dec 29

MDW8:35 pmChicago Midway

12h 56m

1 stop

ISP10:31 amIslip Long Island

$332

Frontier

Dec 21

ISP11:26 amIslip Long Island

9h 04m

1 stop

MDW7:30 pmChicago Midway

Dec 29

MDW8:35 pmChicago Midway

12h 56m

1 stop

ISP10:31 amIslip Long Island

$344

Frontier

Dec 18

ISP11:26 amIslip Long Island

9h 04m

1 stop

MDW7:30 pmChicago Midway

Dec 27

MDW8:35 pmChicago Midway

12h 56m

1 stop

ISP10:31 amIslip Long Island

$380

Southwest flights from Islip, New York to Chicago

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

Southwest

Dec 21

ISP4:55 pmIslip Long Island

8h 25m

2 stops

MDW12:20 amChicago Midway

Dec 29

MDW4:05 pmChicago Midway

6h 45m

1 stop

ISP11:50 pmIslip Long Island

$411

Southwest

Nov 26

ISP5:45 amIslip Long Island

4h 10m

1 stop

MDW8:55 amChicago Midway

Dec 3

MDW6:00 amChicago Midway

9h 15m

1 stop

ISP4:15 pmIslip Long Island

$413

Southwest

Nov 26

ISP5:45 amIslip Long Island

8h 15m

2 stops

MDW1:00 pmChicago Midway

Dec 3

MDW8:10 amChicago Midway

7h 05m

2 stops

ISP4:15 pmIslip Long Island

$418

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Fri 12/18

11:26 am-7:30 pm

1 stop9h 04m

Chicago Midway

Tue 12/29

8:35 pm-10:31 am

1 stop12h 56m

$332

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Mon 12/21

11:26 am-7:30 pm

1 stop9h 04m

Chicago Midway

Tue 12/29

8:35 pm-10:31 am

1 stop12h 56m

$344

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Fri 12/18

11:26 am-7:30 pm

1 stop9h 04m

Chicago Midway

Sun 12/27

8:35 pm-10:31 am

1 stop12h 56m

$380

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Mon 12/21

4:55 pm-12:20 am

2 stops8h 25m

Chicago Midway

Tue 12/29

4:05 pm-11:50 pm

1 stop6h 45m

$411

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Thu 11/26

5:45 am-8:55 am

1 stop4h 10m

Chicago Midway

Thu 12/3

6:00 am-4:15 pm

1 stop9h 15m

$413

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Thu 11/26

5:45 am-1:00 pm

2 stops8h 15m

Chicago Midway

Thu 12/3

8:10 am-4:15 pm

2 stops7h 05m

$418

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sun 12/20

9:25 am-4:30 pm

1 stop8h 05m

Chicago Midway

Tue 12/29

4:05 pm-11:50 pm

1 stop6h 45m

$442

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Mon 12/21

4:55 pm-12:20 am

2 stops8h 25m

Chicago Midway

Tue 12/29

3:05 pm-11:50 pm

2 stops7h 45m

$445

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sun 12/20

4:55 pm-11:40 pm

2 stops7h 45m

Chicago Midway

Tue 12/29

4:05 pm-11:50 pm

1 stop6h 45m

$447

Quickest round-trip

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sun 12/20

4:55 pm-8:40 pm

1 stop4h 45m

Chicago Midway

Mon 12/28

4:05 pm-11:50 pm

1 stop6h 45m

$472

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 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 $346. 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 $425.

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 $349. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $386.

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	$170
Fastest flight time	7h 42m
Direct flights	None

The best one-way flight to Chicago from Islip, New York in the past 72 hours is $170. The best round-trip flight deal from Islip, New York to Chicago found on momondo in the last 72 hours is $332.

The fastest flight from Islip, New York to Chicago takes 7h 42m

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 7h 42m 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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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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Cheap flights from Islip, New York to Chicago from $170

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 1/15. 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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Frontier flights from Islip, New York to Chicago

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

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

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

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