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Cheap flights from Islip, New York to Chicago from $145

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
$363Southwest
Tue, Dec 8 - Tue, Dec 15
Southwest Logo
4:05 pm - 9:30 pmISP  Islip Long Island-MDW Chicago Midway
6h 25m1 stop Baltimore/Washington
Southwest Logo
6:15 am - 4:15 pmMDW  Chicago Midway-ISP Islip Long Island
9h 00m2 stops Tampa Baltimore/Washington
$368Southwest
Tue, Dec 8 - Tue, Dec 15
Southwest Logo
12:30 pm - 7:45 pmISP  Islip Long Island-MDW Chicago Midway
8h 15m2 stops Baltimore/Washington Buffalo
Southwest Logo
5:20 am - 4:15 pmMDW  Chicago Midway-ISP Islip Long Island
9h 55m2 stops Orlando Baltimore/Washington
$373Southwest
Tue, Dec 8 - Tue, Dec 15
Frontier Logo
11:26 am - 7:30 pmISP  Islip Long Island-MDW Chicago Midway
9h 04m1 stop Orlando
Frontier Logo
8:35 pm - 10:31 amMDW  Chicago Midway-ISP Islip Long Island
12h 56m1 stop Orlando
$385Frontier
Fri, Dec 18 - Sun, Dec 20
Southwest Logo
5:40 pm - 11:10 pmISP  Islip Long Island-MDW Chicago Midway
6h 30m1 stop Baltimore/Washington
Southwest Logo
6:35 am - 11:50 amMDW  Chicago Midway-ISP Islip Long Island
4h 15m1 stop Baltimore/Washington
$393Southwest
Mon, Jan 4 - Wed, Jan 13
Southwest Logo
12:25 pm - 4:00 pmISP  Islip Long Island-MDW Chicago Midway
4h 35m1 stop Baltimore/Washington
Southwest Logo
1:30 pm - 9:35 pmMDW  Chicago Midway-ISP Islip Long Island
7h 05m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington
$398Southwest
Mon, Jan 4 - Wed, Jan 13
Southwest Logo
5:40 pm - 10:45 pmISP  Islip Long Island-MDW Chicago Midway
6h 05m2 stops Baltimore/Washington Lambert-St Louis
Southwest Logo
8:15 am - 3:45 pmMDW  Chicago Midway-ISP Islip Long Island
6h 30m2 stops Greater Rochester Intl Baltimore/Washington
$403Southwest
Mon, Jan 4 - Wed, Jan 13
Frontier Logo
4:40 pm - 7:47 pmISP  Islip Long Island-MDW Chicago Midway
28h 07m1 stop Orlando
Frontier Logo
8:42 pm - 3:45 pmMDW  Chicago Midway-ISP Islip Long Island
18h 03m1 stop Orlando
$465Frontier
Mon, Nov 23 - Fri, Nov 27
Southwest Logo
5:40 pm - 11:10 pmISP  Islip Long Island-MDW Chicago Midway
6h 30m1 stop Baltimore/Washington
Southwest Logo
7:50 am - 5:05 pmMDW  Chicago Midway-ISP Islip Long Island
8h 15m2 stops Cleveland Hopkins Intl Baltimore/Washington
$482Southwest
Sun, Dec 6 - Sun, Dec 13
Southwest Logo
12:25 pm - 8:05 pmISP  Islip Long Island-MDW Chicago Midway
8h 40m2 stops Baltimore/Washington Charlotte Douglas
Southwest Logo
7:50 am - 5:05 pmMDW  Chicago Midway-ISP Islip Long Island
8h 15m2 stops Buffalo Baltimore/Washington
$487Southwest
Sun, Dec 6 - Sun, Dec 13

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Southwest flights from Islip, New York to Chicago

Our best Southwest deals on Islip, New York to Chicago flight tickets
Southwest
Dec 8
ISP4:05 pmIslip Long Island
6h 25m
1 stop
MDW9:30 pmChicago Midway
Dec 15
MDW6:00 amChicago Midway
4h 45m
1 stop
ISP11:45 amIslip Long Island
$363
Southwest
Dec 8
ISP4:05 pmIslip Long Island
6h 25m
1 stop
MDW9:30 pmChicago Midway
Dec 15
MDW6:15 amChicago Midway
9h 00m
2 stops
ISP4:15 pmIslip Long Island
$368
Southwest
Dec 8
ISP12:30 pmIslip Long Island
8h 15m
2 stops
MDW7:45 pmChicago Midway
Dec 15
MDW5:20 amChicago Midway
9h 55m
2 stops
ISP4:15 pmIslip Long Island
$373

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
28h 07m
1 stop
MDW7:47 pmChicago Midway
Nov 23
MDW8:42 pmChicago Midway
18h 03m
1 stop
ISP3:45 pmIslip Long Island
$350
Frontier
Nov 19
ISP6:33 pmIslip Long Island
26h 14m
1 stop
MDW7:47 pmChicago Midway
Nov 23
MDW8:42 pmChicago Midway
18h 03m
1 stop
ISP3:45 pmIslip Long Island
$362
Frontier
Nov 20
ISP4:40 pmIslip Long Island
28h 07m
1 stop
MDW7:47 pmChicago Midway
Nov 22
MDW8:42 pmChicago Midway
18h 03m
1 stop
ISP3:45 pmIslip Long Island
$370

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 - MDW Chicago Midway

ISPMDW

Islip Long Island

Tue 12/8

4:05 pm-9:30 pm

1 stop6h 25m

Chicago Midway

Tue 12/15

6:00 am-11:45 am

1 stop4h 45m

$363

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Tue 12/8

4:05 pm-9:30 pm

1 stop6h 25m

Chicago Midway

Tue 12/15

6:15 am-4:15 pm

2 stops9h 00m

$368

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Tue 12/8

12:30 pm-7:45 pm

2 stops8h 15m

Chicago Midway

Tue 12/15

5:20 am-4:15 pm

2 stops9h 55m

$373

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 12/20

8:35 pm-10:31 am

1 stop12h 56m

$385
Quickest round-trip

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Mon 1/4

5:40 pm-11:10 pm

1 stop6h 30m

Chicago Midway

Wed 1/13

6:35 am-11:50 am

1 stop4h 15m

$393

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Mon 1/4

12:25 pm-4:00 pm

1 stop4h 35m

Chicago Midway

Wed 1/13

1:30 pm-9:35 pm

2 stops7h 05m

$398

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Mon 1/4

5:40 pm-10:45 pm

2 stops6h 05m

Chicago Midway

Wed 1/13

8:15 am-3:45 pm

2 stops6h 30m

$403

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Mon 11/23

4:40 pm-7:47 pm

1 stop28h 07m

Chicago Midway

Fri 11/27

8:42 pm-3:45 pm

1 stop18h 03m

$465

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sun 12/6

5:40 pm-11:10 pm

1 stop6h 30m

Chicago Midway

Sun 12/13

7:50 am-5:05 pm

2 stops8h 15m

$482

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sun 12/6

12:25 pm-8:05 pm

2 stops8h 40m

Chicago Midway

Sun 12/13

7:50 am-5:05 pm

2 stops8h 15m

$487

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 Friday when prices can be found for as low as $348. 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 $427.

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 $353. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $389.

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

$145

Fastest flight time

7h 58m

Direct flights

None
The best one-way flight to Chicago from Islip, New York in the past 72 hours is $145. The best round-trip flight deal from Islip, New York to Chicago found on momondo in the last 72 hours is $363.
The fastest flight from Islip, New York to Chicago takes 7h 58m
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 58m 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
Lansing
Benton Harbor
Saint Joseph
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