Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Islip, New York to Chicago from $119

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
6:25 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
$236Frontier
Sat, Oct 24 - 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
9:51 am - 5:31 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
6h 40m1 stop Orlando
$238Frontier
Sat, Oct 24 - Sat, Oct 31
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
$251Frontier
Thu, Sep 24 - Fri, Sep 25
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
$257Frontier
Thu, Oct 22 - 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
8:26 am - 6:00 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
8h 34m1 stop Orlando
$260Frontier
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
6:58 pm - 6:00 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
22h 02m1 stop Orlando
$277Frontier
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
8:26 am - 5:30 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
8h 04m1 stop Orlando
$279Frontier
Thu, Oct 8 - Sun, Oct 11
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
$280Frontier
Sat, Sep 12 - Tue, Sep 22
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
$281Frontier
Thu, Oct 8 - Sun, Oct 11
Frontier Logo
6:25 pm - 7:02 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
25h 37m1 stop Orlando
Frontier Logo
6:58 pm - 6:00 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
22h 02m1 stop Orlando
$291Frontier
Thu, Oct 15 - Sun, Oct 18

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Frontier flights from Islip, New York to Chicago

Our best Frontier deals on Islip, New York to Chicago flight tickets
Frontier
Oct 24
ISP6:25 pmIslip Long Island
14h 06m
1 stop
ORD7:31 amChicago O'Hare Intl
Oct 31
ORD9:51 amChicago O'Hare Intl
6h 40m
1 stop
ISP5:31 pmIslip Long Island
$236
Frontier
Oct 10
ISP6:25 pmIslip Long Island
14h 06m
1 stop
ORD7:31 amChicago O'Hare Intl
Oct 16
ORD8:11 pmChicago O'Hare Intl
20h 19m
1 stop
ISP5:30 pmIslip Long Island
$237
Frontier
Oct 24
ISP6:25 pmIslip Long Island
14h 06m
1 stop
ORD7:31 amChicago O'Hare Intl
Oct 31
ORD9:51 amChicago O'Hare Intl
6h 40m
1 stop
ISP5:31 pmIslip Long Island
$238

JetBlue flights from Islip, New York to Chicago

Our best JetBlue deals on Islip, New York to Chicago flight tickets
JetBlue
Oct 27
ISP6:00 amIslip Long Island
18h 57m
1 stop
ORD11:57 pmChicago O'Hare Intl
Oct 29
ORD2:42 pmChicago O'Hare Intl
29h 55m
1 stop
ISP9:37 pmIslip Long Island
$489
JetBlue
Sep 21
ISP7:00 amIslip Long Island
7h 45m
1 stop
ORD1:45 pmChicago O'Hare Intl
Sep 25
ORD3:00 pmChicago O'Hare Intl
7h 22m
1 stop
ISP11:22 pmIslip Long Island
$527
JetBlue
Oct 28
ISP6:00 amIslip Long Island
8h 44m
1 stop
ORD1:44 pmChicago O'Hare Intl
Oct 30
ORD7:00 amChicago O'Hare Intl
13h 37m
1 stop
ISP9:37 pmIslip Long Island
$539

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sat 10/24

6:25 pm-7:31 am

1 stop14h 06m

Chicago O'Hare Intl

Sat 10/31

9:51 am-5:31 pm

1 stop6h 40m

$236

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sat 10/24

6:25 pm-7:31 am

1 stop14h 06m

Chicago O'Hare Intl

Sat 10/31

9:51 am-5:31 pm

1 stop6h 40m

$238

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 9/24

5:43 pm-10:20 am

1 stop17h 37m

Chicago O'Hare Intl

Fri 9/25

3:50 pm-4:58 pm

1 stop24h 08m

$251

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

Sat 10/24

8:46 am-5:30 pm

1 stop7h 44m

$257

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

$260

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

6:58 pm-6:00 pm

1 stop22h 02m

$277

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 10/8

6:25 pm-7:31 am

1 stop14h 06m

Chicago O'Hare Intl

Sun 10/11

8:26 am-5:30 pm

1 stop8h 04m

$279

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sat 9/12

5:43 pm-10:20 am

1 stop17h 37m

Chicago O'Hare Intl

Tue 9/22

3:50 pm-4:58 pm

1 stop24h 08m

$280

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 10/8

6:25 pm-7:31 am

1 stop14h 06m

Chicago O'Hare Intl

Sun 10/11

8:26 am-5:30 pm

1 stop8h 04m

$281

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 10/15

6:25 pm-7:02 pm

1 stop25h 37m

Chicago O'Hare Intl

Sun 10/18

6:58 pm-6:00 pm

1 stop22h 02m

$291

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 October 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 October, then February is your next best option. Flight prices from Islip, New York to Chicago during February average around $0.

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 $327. 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 $320. 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

$119

Fastest flight time

5h 58m

Direct flights

None
The best one-way flight to Chicago from Islip, New York in the past 72 hours is $119. 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 5h 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 5h 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
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 10/2
Fri 10/9
By creating a price alert you accept our terms of use and privacy policy.

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