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Cheap flights from Islip, New York to Chicago from $124

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Islip, New York to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:55 pm - 7:51 amISP  Islip Long Island-ORD Chicago O'Hare Intl
13h 56m1 stop Orlando
Frontier Logo
8:26 am - 6:00 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
8h 34m1 stop Orlando
$236Frontier
Fri, Oct 16 - Mon, Oct 19
Frontier Logo
6:25 pm - 7:31 amISP  Islip Long Island-ORD Chicago O'Hare Intl
14h 06m1 stop Orlando
Frontier Logo
8:26 am - 6:00 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
8h 34m1 stop Orlando
$258Frontier
Thu, Oct 15 - Mon, Oct 19
Frontier Logo
6:25 pm - 7:31 amISP  Islip Long Island-ORD Chicago O'Hare Intl
14h 06m1 stop Orlando
Frontier Logo
8:26 am - 6:00 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
8h 34m1 stop Orlando
$258Frontier
Sat, Oct 17 - Mon, Oct 19
Frontier Logo
6:55 pm - 7:51 amISP  Islip Long Island-ORD Chicago O'Hare Intl
13h 56m1 stop Orlando
Frontier Logo
6:58 pm - 6:00 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
22h 02m1 stop Orlando
$265Frontier
Fri, Oct 16 - Sun, Oct 18
Frontier Logo
5:43 pm - 10:20 amISP  Islip Long Island-ORD Chicago O'Hare Intl
17h 37m1 stop Orlando
Frontier Logo
3:50 pm - 4:58 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
24h 08m1 stop Orlando
$272Frontier
Wed, Sep 23 - Sun, Sep 27
Frontier Logo
6:55 pm - 7:51 amISP  Islip Long Island-ORD Chicago O'Hare Intl
13h 56m1 stop Orlando
Frontier Logo
6:58 pm - 6:00 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
22h 02m1 stop Orlando
$280Frontier
Fri, Oct 16 - Sun, Oct 18
Frontier Logo
6:25 pm - 7:31 amISP  Islip Long Island-ORD Chicago O'Hare Intl
14h 06m1 stop Orlando
Frontier Logo
8:26 am - 5:30 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
8h 04m1 stop Orlando
$298Frontier
Thu, Oct 22 - Sun, Oct 25
Frontier Logo
6:33 pm - 8:46 amISP  Islip Long Island-ORD Chicago O'Hare Intl
15h 13m1 stop Orlando
Frontier Logo
9:51 am - 5:31 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
6h 40m1 stop Orlando
$298Frontier
Thu, Oct 29 - Sat, Oct 31
Frontier Logo
6:25 pm - 7:31 amISP  Islip Long Island-ORD Chicago O'Hare Intl
14h 06m1 stop Orlando
Frontier Logo
8:26 am - 5:30 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
8h 04m1 stop Orlando
$309Frontier
Thu, Oct 15 - Sun, Oct 18
Frontier Logo
6:25 pm - 7:31 amISP  Islip Long Island-ORD Chicago O'Hare Intl
14h 06m1 stop Orlando
Frontier Logo
8:46 am - 5:30 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
7h 44m1 stop Orlando
$309Frontier
Thu, Oct 15 - Sat, Oct 17

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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
Oct 16
ISP6:55 pmIslip Long Island
13h 56m
1 stop
ORD7:51 amChicago O'Hare Intl
Oct 19
ORD8:26 amChicago O'Hare Intl
8h 34m
1 stop
ISP6:00 pmIslip Long Island
$236
Frontier
Oct 15
ISP6:25 pmIslip Long Island
14h 06m
1 stop
ORD7:31 amChicago O'Hare Intl
Oct 19
ORD8:26 amChicago O'Hare Intl
8h 34m
1 stop
ISP6:00 pmIslip Long Island
$258
Frontier
Oct 16
ISP6:55 pmIslip Long Island
13h 56m
1 stop
ORD7:51 amChicago O'Hare Intl
Oct 18
ORD6:58 pmChicago O'Hare Intl
22h 02m
1 stop
ISP6:00 pmIslip Long Island
$265

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
$527
JetBlue
Sep 27
ISP7:00 amIslip Long Island
7h 45m
1 stop
ORD1:45 pmChicago O'Hare Intl
Sep 29
ORD3:00 pmChicago O'Hare Intl
7h 22m
1 stop
ISP11:22 pmIslip Long Island
$546
JetBlue
Sep 19
ISP7:00 amIslip Long Island
7h 45m
1 stop
ORD1:45 pmChicago O'Hare Intl
Sep 21
ORD3:00 pmChicago O'Hare Intl
7h 22m
1 stop
ISP11:22 pmIslip Long Island
$781

momondo Fare Finder

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

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Price

Cheapest round-trip

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

Mon 10/19

8:26 am-6:00 pm

1 stop8h 34m

$236

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

Mon 10/19

8:26 am-6:00 pm

1 stop8h 34m

$258

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

$258

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

$265

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Wed 9/23

5:43 pm-10:20 am

1 stop17h 37m

Chicago O'Hare Intl

Sun 9/27

3:50 pm-4:58 pm

1 stop24h 08m

$272

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

$280

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 10/22

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

$298

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 10/29

6:33 pm-8:46 am

1 stop15h 13m

Chicago O'Hare Intl

Sat 10/31

9:51 am-5:31 pm

1 stop6h 40m

$298

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 10/18

8:26 am-5:30 pm

1 stop8h 04m

$309
Quickest round-trip

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

Sat 10/17

8:46 am-5:30 pm

1 stop7h 44m

$309

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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

Prices are currently low for flights on this route.

Typical prices usually range from $267 to $334.
The lowest price recently found on this route was $236.

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 $328. 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 $410.

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 $323. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $372.

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

$124

Fastest flight time

7h 45m

Direct flights

None
The best one-way flight to Chicago from Islip, New York in the past 72 hours is $124. The best round-trip flight deal from Islip, New York to Chicago found on momondo in the last 72 hours is $236.
The fastest flight from Islip, New York to Chicago takes 7h 45m
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 45m 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?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport