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Cheap flights from Islip, New York to Chicago from $141

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
3:30 pm - 10:40 pmISP  Islip Long Island-MDW Chicago Midway
8h 10m1 stop Baltimore/Washington
Southwest Logo
7:55 am - 6:15 pmMDW  Chicago Midway-ISP Islip Long Island
9h 20m2 stops Hartford Bradley Intl Baltimore/Washington
$293Southwest
Sat, Feb 27 - Mon, Mar 1
Frontier Logo
11:59 am - 7:42 pmISP  Islip Long Island-MDW Chicago Midway
8h 43m1 stop Orlando
Frontier Logo
8:47 pm - 11:04 amMDW  Chicago Midway-ISP Islip Long Island
13h 17m1 stop Orlando
$304Frontier
Sat, Feb 27 - Mon, Mar 1
Frontier Logo
4:40 pm - 12:43 amISP  Islip Long Island-ORD Chicago O'Hare Intl
9h 03m1 stop Orlando
Frontier Logo
5:40 am - 3:45 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
9h 05m1 stop Orlando
$349Frontier
Mon, Nov 23 - Sat, Nov 28
Frontier Logo
6:55 pm - 7:51 amISP  Islip Long Island-ORD Chicago O'Hare Intl
13h 56m1 stop Orlando
Frontier Logo
8:46 am - 5:30 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
7h 44m1 stop Orlando
$356Frontier
Mon, Oct 19 - Sat, Oct 24
Frontier Logo
6:55 pm - 7:51 amISP  Islip Long Island-ORD Chicago O'Hare Intl
13h 56m1 stop Orlando
Frontier Logo
8:11 pm - 5:30 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
20h 19m1 stop Orlando
$358Frontier
Mon, Oct 19 - Fri, Oct 23
Southwest Logo
4:05 pm - 9:30 pmISP  Islip Long Island-MDW Chicago Midway
6h 25m1 stop Baltimore/Washington
Southwest Logo
7:50 am - 5:05 pmMDW  Chicago Midway-ISP Islip Long Island
8h 15m2 stops Buffalo Baltimore/Washington
$365Southwest
Wed, Nov 11 - Thu, Nov 12
Frontier Logo
6:54 pm - 8:46 amISP  Islip Long Island-ORD Chicago O'Hare Intl
14h 52m1 stop Orlando
Frontier Logo
9:51 am - 5:31 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
6h 40m1 stop Orlando
$370Frontier
Fri, Oct 30 - Sun, Nov 1
Southwest Logo
5:35 am - 8:40 amISP  Islip Long Island-MDW Chicago Midway
4h 05m1 stop Baltimore/Washington
Southwest Logo
6:10 pm - 11:35 pmMDW  Chicago Midway-ISP Islip Long Island
4h 25m1 stop Baltimore/Washington
$370Southwest
Sun, Nov 1 - Thu, Nov 5
Frontier Logo
4:40 pm - 12:43 amISP  Islip Long Island-ORD Chicago O'Hare Intl
9h 03m1 stop Orlando
Frontier Logo
5:40 am - 3:45 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
9h 05m1 stop Orlando
$374Frontier
Fri, Nov 20 - Mon, Nov 23
Southwest Logo
1:35 pm - 10:55 pmISP  Islip Long Island-MDW Chicago Midway
10h 20m2 stops West Palm Beach President Donald J. Trump Intl Orlando
Southwest Logo
6:10 pm - 11:35 pmMDW  Chicago Midway-ISP Islip Long Island
4h 25m1 stop Baltimore/Washington
$375Southwest
Sun, Nov 1 - Thu, Nov 5

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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
Feb 27
ISP11:59 amIslip Long Island
8h 43m
1 stop
MDW7:42 pmChicago Midway
Mar 1
MDW8:47 pmChicago Midway
13h 17m
1 stop
ISP11:04 amIslip Long Island
$304
Frontier
Oct 26
ISP6:55 pmIslip Long Island
24h 50m
2 stops
ORD6:45 pmChicago O'Hare Intl
Oct 28
ORD7:28 pmChicago O'Hare Intl
21h 03m
2 stops
ISP5:31 pmIslip Long Island
$332
Frontier
Nov 23
ISP4:40 pmIslip Long Island
9h 03m
1 stop
ORD12:43 amChicago O'Hare Intl
Nov 28
ORD5:40 amChicago O'Hare Intl
9h 05m
1 stop
ISP3:45 pmIslip Long Island
$349

JetBlue flights from Islip, New York to Chicago

Our best JetBlue deals on Islip, New York to Chicago flight tickets
JetBlue
Nov 11
ISP6:00 amIslip Long Island
18h 36m
1 stop
ORD11:36 pmChicago O'Hare Intl
Nov 12
ORD7:00 amChicago O'Hare Intl
13h 37m
1 stop
ISP9:37 pmIslip Long Island
$486
JetBlue
Nov 2
ISP6:00 amIslip Long Island
18h 57m
1 stop
ORD11:57 pmChicago O'Hare Intl
Nov 9
ORD2:59 pmChicago O'Hare Intl
29h 38m
1 stop
ISP9:37 pmIslip Long Island
$492
JetBlue
Oct 31
ISP6:00 amIslip Long Island
18h 57m
1 stop
ORD11:57 pmChicago O'Hare Intl
Nov 3
ORD7:00 amChicago O'Hare Intl
13h 37m
1 stop
ISP9:37 pmIslip Long Island
$493

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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Depart

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Price

Cheapest round-trip

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sat 2/27

3:30 pm-10:40 pm

1 stop8h 10m

Chicago Midway

Mon 3/1

7:55 am-6:15 pm

2 stops9h 20m

$293

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sat 2/27

11:59 am-7:42 pm

1 stop8h 43m

Chicago Midway

Mon 3/1

8:47 pm-11:04 am

1 stop13h 17m

$304

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Mon 11/23

4:40 pm-12:43 am

1 stop9h 03m

Chicago O'Hare Intl

Sat 11/28

5:40 am-3:45 pm

1 stop9h 05m

$349

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Mon 10/19

6:55 pm-7:51 am

1 stop13h 56m

Chicago O'Hare Intl

Sat 10/24

8:46 am-5:30 pm

1 stop7h 44m

$356

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Mon 10/19

6:55 pm-7:51 am

1 stop13h 56m

Chicago O'Hare Intl

Fri 10/23

8:11 pm-5:30 pm

1 stop20h 19m

$358

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Wed 11/11

4:05 pm-9:30 pm

1 stop6h 25m

Chicago Midway

Thu 11/12

7:50 am-5:05 pm

2 stops8h 15m

$365

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Fri 10/30

6:54 pm-8:46 am

1 stop14h 52m

Chicago O'Hare Intl

Sun 11/1

9:51 am-5:31 pm

1 stop6h 40m

$370
Quickest round-trip

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sun 11/1

5:35 am-8:40 am

1 stop4h 05m

Chicago Midway

Thu 11/5

6:10 pm-11:35 pm

1 stop4h 25m

$370

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Fri 11/20

4:40 pm-12:43 am

1 stop9h 03m

Chicago O'Hare Intl

Mon 11/23

5:40 am-3:45 pm

1 stop9h 05m

$374

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Sun 11/1

1:35 pm-10:55 pm

2 stops10h 20m

Chicago Midway

Thu 11/5

6:10 pm-11:35 pm

1 stop4h 25m

$375

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 $336. 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 $416.

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 $335. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $376.

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

$141

Fastest flight time

8h 42m

Direct flights

None
The best one-way flight to Chicago from Islip, New York in the past 72 hours is $141. The best round-trip flight deal from Islip, New York to Chicago found on momondo in the last 72 hours is $293.
The fastest flight from Islip, New York to Chicago takes 8h 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 8h 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?

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
Benton Harbor
Lansing
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