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Cheap flights from Islip, New York to Chicago from $140

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
4:40 pm - 3:52 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
24h 12m1 stop Orlando
Frontier Logo
1:19 pm - 1:22 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
23h 03m1 stop Orlando
$261Frontier
Mon, Nov 23 - Wed, Dec 2
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
$280Frontier
Sat, Nov 21 - Tue, Nov 24
Southwest Logo
4:05 pm - 9:30 pmISP  Islip Long Island-MDW Chicago Midway
6h 25m1 stop Baltimore/Washington
Southwest Logo
8:50 am - 4:15 pmMDW  Chicago Midway-ISP Islip Long Island
6h 25m1 stop Baltimore/Washington
$303Southwest
Wed, Dec 16 - Fri, Jan 1
Southwest Logo
4:05 pm - 9:30 pmISP  Islip Long Island-MDW Chicago Midway
6h 25m1 stop Baltimore/Washington
Southwest Logo
8:10 am - 4:15 pmMDW  Chicago Midway-ISP Islip Long Island
7h 05m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington
$308Southwest
Wed, Dec 16 - Fri, Jan 1
Southwest Logo
6:05 am - 12:55 pmISP  Islip Long Island-MDW Chicago Midway
7h 50m2 stops Baltimore/Washington Nashville Intl
Southwest Logo
8:10 am - 4:15 pmMDW  Chicago Midway-ISP Islip Long Island
7h 05m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington
$313Southwest
Wed, Dec 16 - Fri, Jan 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
$320Frontier
Sun, Nov 22 - Tue, Nov 24
Southwest Logo
4:05 pm - 9:30 pmISP  Islip Long Island-MDW Chicago Midway
6h 25m1 stop Baltimore/Washington
Southwest Logo
8:50 am - 4:15 pmMDW  Chicago Midway-ISP Islip Long Island
6h 25m1 stop Baltimore/Washington
$376Southwest
Tue, Dec 1 - Thu, Dec 3
Southwest Logo
4:45 pm - 11:00 pmISP  Islip Long Island-MDW Chicago Midway
7h 15m1 stop Orlando
Southwest Logo
8:50 am - 4:15 pmMDW  Chicago Midway-ISP Islip Long Island
6h 25m1 stop Baltimore/Washington
$376Southwest
Mon, Nov 23 - Wed, Dec 2
Southwest Logo
5:40 pm - 11:10 pmISP  Islip Long Island-MDW Chicago Midway
6h 30m1 stop Baltimore/Washington
Southwest Logo
1:15 pm - 9:45 pmMDW  Chicago Midway-ISP Islip Long Island
7h 30m2 stops Cincinnati Cinci./N. Kentucky Baltimore/Washington
$381Southwest
Mon, Nov 23 - Wed, Dec 2
Southwest Logo
4:05 pm - 10:45 pmISP  Islip Long Island-MDW Chicago Midway
7h 40m2 stops Baltimore/Washington Nashville Intl
Southwest Logo
8:50 am - 4:15 pmMDW  Chicago Midway-ISP Islip Long Island
6h 25m1 stop Baltimore/Washington
$381Southwest
Tue, Dec 1 - Thu, Dec 3

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JetBlue flights from Islip, New York to Chicago

Our best JetBlue deals on Islip, New York to Chicago flight tickets
JetBlue
Nov 18
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
Nov 17
ISP6:00 amIslip Long Island
18h 36m
1 stop
ORD11:36 pmChicago O'Hare Intl
Dec 3
ORD7:00 amChicago O'Hare Intl
14h 40m
1 stop
ISP10:40 pmIslip Long Island
$495
JetBlue
Jan 4
ISP6:20 pmIslip Long Island
30h 22m
1 stop
ORD11:42 pmChicago O'Hare Intl
Jan 12
ORD7:45 pmChicago O'Hare Intl
25h 11m
1 stop
ISP9:56 pmIslip Long Island
$570

Frontier flights from Islip, New York to Chicago

Our best Frontier deals on Islip, New York to Chicago flight tickets
Frontier
Nov 23
ISP4:40 pmIslip Long Island
24h 12m
1 stop
ORD3:52 pmChicago O'Hare Intl
Dec 2
ORD1:19 pmChicago O'Hare Intl
23h 03m
1 stop
ISP1:22 pmIslip Long Island
$261
Frontier
Nov 21
ISP4:43 pmIslip Long Island
9h 00m
1 stop
ORD12:43 amChicago O'Hare Intl
Nov 24
ORD5:40 amChicago O'Hare Intl
9h 05m
1 stop
ISP3:45 pmIslip Long Island
$280
Frontier
Nov 22
ISP4:40 pmIslip Long Island
9h 03m
1 stop
ORD12:43 amChicago O'Hare Intl
Nov 24
ORD5:40 amChicago O'Hare Intl
9h 05m
1 stop
ISP3:45 pmIslip Long Island
$320

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

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Mon 11/23

4:40 pm-3:52 pm

1 stop24h 12m

Chicago O'Hare Intl

Wed 12/2

1:19 pm-1:22 pm

1 stop23h 03m

$261

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

Tue 11/24

5:40 am-3:45 pm

1 stop9h 05m

$280
Quickest round-trip

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Wed 12/16

4:05 pm-9:30 pm

1 stop6h 25m

Chicago Midway

Fri 1/1

8:50 am-4:15 pm

1 stop6h 25m

$303

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Wed 12/16

4:05 pm-9:30 pm

1 stop6h 25m

Chicago Midway

Fri 1/1

8:10 am-4:15 pm

2 stops7h 05m

$308

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Wed 12/16

6:05 am-12:55 pm

2 stops7h 50m

Chicago Midway

Fri 1/1

8:10 am-4:15 pm

2 stops7h 05m

$313

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sun 11/22

4:40 pm-12:43 am

1 stop9h 03m

Chicago O'Hare Intl

Tue 11/24

5:40 am-3:45 pm

1 stop9h 05m

$320

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Tue 12/1

4:05 pm-9:30 pm

1 stop6h 25m

Chicago Midway

Thu 12/3

8:50 am-4:15 pm

1 stop6h 25m

$376

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Mon 11/23

4:45 pm-11:00 pm

1 stop7h 15m

Chicago Midway

Wed 12/2

8:50 am-4:15 pm

1 stop6h 25m

$376

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Mon 11/23

5:40 pm-11:10 pm

1 stop6h 30m

Chicago Midway

Wed 12/2

1:15 pm-9:45 pm

2 stops7h 30m

$381

IslipChicago

ISP Islip Long Island - MDW Chicago Midway

ISPMDW

Islip Long Island

Tue 12/1

4:05 pm-10:45 pm

2 stops7h 40m

Chicago Midway

Thu 12/3

8:50 am-4:15 pm

1 stop6h 25m

$381

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 $342. 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 $341. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $381.

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

$140

Fastest flight time

7h 59m

Direct flights

None
The best one-way flight to Chicago from Islip, New York in the past 72 hours is $140. The best round-trip flight deal from Islip, New York to Chicago found on momondo in the last 72 hours is $261.
The fastest flight from Islip, New York to Chicago takes 7h 59m
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 59m 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