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Cheap flights from Islip, New York to Chicago from $138

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.
Southwest Logo
4:05 pm - 9:30 pmISP  Islip Long Island-MDW Chicago Midway
6h 25m1 stop Baltimore/Washington
Southwest Logo
6:00 am - 11:45 amMDW  Chicago Midway-ISP Islip Long Island
4h 45m1 stop Baltimore/Washington
$339Southwest
Tue, Nov 17 - Wed, Dec 2
Southwest Logo
3:30 pm - 7:40 pmISP  Islip Long Island-MDW Chicago Midway
5h 10m1 stop Baltimore/Washington
Southwest Logo
7:45 am - 2:55 pmMDW  Chicago Midway-ISP Islip Long Island
6h 10m2 stops Greater Rochester Intl Baltimore/Washington
$344Southwest
Sat, Nov 7 - Sat, Nov 14
Southwest Logo
12:45 pm - 5:20 pmISP  Islip Long Island-MDW Chicago Midway
5h 35m2 stops Baltimore/Washington Columbus
Southwest Logo
7:45 am - 2:55 pmMDW  Chicago Midway-ISP Islip Long Island
6h 10m2 stops Greater Rochester Intl Baltimore/Washington
$349Southwest
Sat, Nov 7 - Sat, Nov 14
Frontier Logo
4:43 pm - 12:43 amISP  Islip Long Island-ORD Chicago O'Hare Intl
9h 00m1 stop Orlando
Frontier Logo
5:40 am - 3:45 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
9h 05m1 stop Orlando
$355Frontier
Sat, Nov 21 - Fri, Nov 27
Southwest Logo
5:35 am - 12:20 pmISP  Islip Long Island-MDW Chicago Midway
7h 45m1 stop Orlando
Southwest Logo
5:10 am - 12:00 pmMDW  Chicago Midway-ISP Islip Long Island
5h 50m1 stop Baltimore/Washington
$357Southwest
Fri, Dec 18 - Mon, Jan 18
Frontier Logo
6:25 pm - 7:31 amISP  Islip Long Island-ORD Chicago O'Hare Intl
14h 06m1 stop Orlando
Frontier Logo
9:51 am - 5:31 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
6h 40m1 stop Orlando
$358Frontier
Sun, Oct 25 - Thu, Oct 29
Frontier Logo
6:55 pm - 5:03 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
23h 08m1 stop Orlando
Frontier Logo
9:51 am - 5:56 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
7h 05m1 stop Orlando
$358Frontier
Mon, Oct 26 - Fri, Oct 30
Southwest Logo
5:35 am - 12:25 pmISP  Islip Long Island-MDW Chicago Midway
7h 50m2 stops Orlando Columbus
Southwest Logo
5:10 am - 12:00 pmMDW  Chicago Midway-ISP Islip Long Island
5h 50m1 stop Baltimore/Washington
$362Southwest
Fri, Dec 18 - Mon, Jan 18
Southwest Logo
12:45 pm - 5:20 pmISP  Islip Long Island-MDW Chicago Midway
5h 35m2 stops Baltimore/Washington Columbus
Southwest Logo
4:00 pm - 11:35 pmMDW  Chicago Midway-ISP Islip Long Island
6h 35m2 stops Nashville Intl Baltimore/Washington
$367Southwest
Sat, Nov 7 - Mon, Nov 9
Southwest Logo
12:30 pm - 7:45 pmISP  Islip Long Island-MDW Chicago Midway
8h 15m2 stops Baltimore/Washington Buffalo
Southwest Logo
8:35 pm - 8:45 amMDW  Chicago Midway-ISP Islip Long Island
11h 10m1 stop Orlando
$368Southwest
Fri, Dec 25 - Tue, Dec 29

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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
Nov 21
ISP4:43 pmIslip Long Island
9h 00m
1 stop
ORD12:43 amChicago O'Hare Intl
Nov 27
ORD5:40 amChicago O'Hare Intl
9h 05m
1 stop
ISP3:45 pmIslip Long Island
$355
Frontier
Oct 25
ISP6:25 pmIslip Long Island
14h 06m
1 stop
ORD7:31 amChicago O'Hare Intl
Oct 29
ORD9:51 amChicago O'Hare Intl
6h 40m
1 stop
ISP5:31 pmIslip Long Island
$358
Frontier
Oct 30
ISP6:54 pmIslip Long Island
14h 52m
1 stop
ORD8:46 amChicago O'Hare Intl
Nov 1
ORD9:51 amChicago O'Hare Intl
6h 40m
1 stop
ISP5:31 pmIslip Long Island
$394

JetBlue flights from Islip, New York to Chicago

Our best JetBlue deals on Islip, New York to Chicago flight tickets
JetBlue
Nov 17
ISP6:00 amIslip Long Island
18h 36m
1 stop
ORD11:36 pmChicago O'Hare Intl
Dec 2
ORD7:00 amChicago O'Hare Intl
14h 40m
1 stop
ISP10:40 pmIslip Long Island
$468
JetBlue
Oct 29
ISP6:00 amIslip Long Island
18h 57m
1 stop
ORD11:57 pmChicago O'Hare Intl
Nov 4
ORD7:00 amChicago O'Hare Intl
13h 37m
1 stop
ISP9:37 pmIslip Long Island
$520
JetBlue
Nov 13
ISP6:00 amIslip Long Island
18h 36m
1 stop
ORD11:36 pmChicago O'Hare Intl
Nov 16
ORD2:59 pmChicago O'Hare Intl
29h 38m
1 stop
ISP9:37 pmIslip Long Island
$558

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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Route

Depart

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Price

Cheapest round-trip
Quickest round-trip

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Tue 11/17

4:05 pm-9:30 pm

1 stop6h 25m

Chicago Midway

Wed 12/2

6:00 am-11:45 am

1 stop4h 45m

$339

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sat 11/7

3:30 pm-7:40 pm

1 stop5h 10m

Chicago Midway

Sat 11/14

7:45 am-2:55 pm

2 stops6h 10m

$344

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sat 11/7

12:45 pm-5:20 pm

2 stops5h 35m

Chicago Midway

Sat 11/14

7:45 am-2:55 pm

2 stops6h 10m

$349

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sat 11/21

4:43 pm-12:43 am

1 stop9h 00m

Chicago O'Hare Intl

Fri 11/27

5:40 am-3:45 pm

1 stop9h 05m

$355

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Fri 12/18

5:35 am-12:20 pm

1 stop7h 45m

Chicago Midway

Mon 1/18

5:10 am-12:00 pm

1 stop5h 50m

$357

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sun 10/25

6:25 pm-7:31 am

1 stop14h 06m

Chicago O'Hare Intl

Thu 10/29

9:51 am-5:31 pm

1 stop6h 40m

$358

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Mon 10/26

6:55 pm-5:03 pm

1 stop23h 08m

Chicago O'Hare Intl

Fri 10/30

9:51 am-5:56 pm

1 stop7h 05m

$358

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Fri 12/18

5:35 am-12:25 pm

2 stops7h 50m

Chicago Midway

Mon 1/18

5:10 am-12:00 pm

1 stop5h 50m

$362

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sat 11/7

12:45 pm-5:20 pm

2 stops5h 35m

Chicago Midway

Mon 11/9

4:00 pm-11:35 pm

2 stops6h 35m

$367

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Fri 12/25

12:30 pm-7:45 pm

2 stops8h 15m

Chicago Midway

Tue 12/29

8:35 pm-8:45 am

1 stop11h 10m

$368

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 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 $338. 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 $420.

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 $337. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $379.

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

$138

Fastest flight time

7h 39m

Direct flights

None
The best one-way flight to Chicago from Islip, New York in the past 72 hours is $138. The best round-trip flight deal from Islip, New York to Chicago found on momondo in the last 72 hours is $339.
The fastest flight from Islip, New York to Chicago takes 7h 39m
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 39m 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
Saint Joseph
Lansing
Benton Harbor
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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.

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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