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Cheap flights from Islip, New York to Chicago from $118

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Islip, New York to Chicago departing on 11/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
10:57 am - 11:08 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
13h 11m1 stop Orlando
Frontier Logo
7:44 pm - 9:53 amORD  Chicago O'Hare Intl-ISP Islip Long Island
13h 09m1 stop Orlando
$236Frontier
Tue, Sep 1 - Sat, Sep 5
Frontier Logo
4:13 pm - 8:21 amISP  Islip Long Island-ORD Chicago O'Hare Intl
17h 08m1 stop Orlando
Frontier Logo
4:44 pm - 10:33 amORD  Chicago O'Hare Intl-ISP Islip Long Island
16h 49m1 stop Orlando
$246Frontier
Thu, Oct 29 - Sat, Oct 31
Frontier Logo
10:57 am - 11:08 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
13h 11m1 stop Orlando
Frontier Logo
7:44 pm - 9:53 amORD  Chicago O'Hare Intl-ISP Islip Long Island
13h 09m1 stop Orlando
$247Frontier
Thu, Sep 3 - Sat, Sep 5
Frontier Logo
10:57 am - 11:08 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
13h 11m1 stop Orlando
Frontier Logo
9:10 pm - 9:53 amORD  Chicago O'Hare Intl-ISP Islip Long Island
11h 43m1 stop Orlando
$257Frontier
Wed, Sep 2 - Fri, Sep 4
Frontier Logo
10:57 am - 11:08 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
13h 11m1 stop Orlando
Frontier Logo
7:44 pm - 9:53 amORD  Chicago O'Hare Intl-ISP Islip Long Island
13h 09m1 stop Orlando
$258Frontier
Tue, Sep 1 - Sat, Sep 5
Frontier Logo
4:13 pm - 11:55 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
8h 42m1 stop Orlando
Frontier Logo
6:05 am - 9:33 amORD  Chicago O'Hare Intl-ISP Islip Long Island
26h 28m1 stop Orlando
$267Frontier
Thu, Oct 8 - Sun, Oct 11
Frontier Logo
10:57 am - 11:08 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
13h 11m1 stop Orlando
Frontier Logo
9:10 pm - 6:14 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
20h 04m1 stop Orlando
$268Frontier
Thu, Sep 3 - Fri, Sep 4
Frontier Logo
7:09 pm - 11:08 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
28h 59m1 stop Orlando
Frontier Logo
11:15 am - 4:58 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
28h 43m1 stop Orlando
$269Frontier
Mon, Sep 7 - Mon, Sep 14
Frontier Logo
10:57 am - 11:08 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
13h 11m1 stop Orlando
Frontier Logo
9:10 pm - 9:53 amORD  Chicago O'Hare Intl-ISP Islip Long Island
11h 43m1 stop Orlando
$270Frontier
Sat, Sep 5 - Mon, Sep 7
Multiple Airlines Logo
7:00 am - 1:45 pmISP  Islip Long Island-ORD Chicago O'Hare Intl
7h 45m1 stop Fort Lauderdale
Multiple Airlines Logo
3:50 pm - 4:58 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
24h 08m1 stop Orlando
$274Multiple Airlines
Thu, Sep 24 - Tue, Sep 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
Sep 1
ISP10:57 amIslip Long Island
13h 11m
1 stop
ORD11:08 pmChicago O'Hare Intl
Sep 5
ORD7:44 pmChicago O'Hare Intl
13h 09m
1 stop
ISP9:53 amIslip Long Island
$236
Frontier
Oct 29
ISP4:13 pmIslip Long Island
17h 08m
1 stop
ORD8:21 amChicago O'Hare Intl
Oct 31
ORD4:44 pmChicago O'Hare Intl
16h 49m
1 stop
ISP10:33 amIslip Long Island
$246
Frontier
Sep 3
ISP10:57 amIslip Long Island
13h 11m
1 stop
ORD11:08 pmChicago O'Hare Intl
Sep 5
ORD7:44 pmChicago O'Hare Intl
13h 09m
1 stop
ISP9:53 amIslip Long Island
$247

JetBlue flights from Islip, New York to Chicago

Our best JetBlue deals on Islip, New York to Chicago flight tickets
JetBlue
Sep 19
ISP7:00 amIslip Long Island
7h 45m
1 stop
ORD1:45 pmChicago O'Hare Intl
Sep 20
ORD3:00 pmChicago O'Hare Intl
7h 22m
1 stop
ISP11:22 pmIslip Long Island
$291
JetBlue
Sep 6
ISP6:00 amIslip Long Island
8h 49m
1 stop
ORD1:49 pmChicago O'Hare Intl
Sep 10
ORD3:00 pmChicago O'Hare Intl
7h 22m
1 stop
ISP11:22 pmIslip Long Island
$319
JetBlue
Sep 25
ISP7:00 amIslip Long Island
7h 45m
1 stop
ORD1:45 pmChicago O'Hare Intl
Sep 27
ORD3:00 pmChicago O'Hare Intl
7h 22m
1 stop
ISP11:22 pmIslip Long Island
$346

momondo Fare Finder

 
Customize your flight search to find flights from Islip, New York to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 9, 2026.
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

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Tue 9/1

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Sat 9/5

7:44 pm-9:53 am

1 stop13h 09m

$236

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 10/29

4:13 pm-8:21 am

1 stop17h 08m

Chicago O'Hare Intl

Sat 10/31

4:44 pm-10:33 am

1 stop16h 49m

$246

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 9/3

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Sat 9/5

7:44 pm-9:53 am

1 stop13h 09m

$247
Quickest round-trip

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Wed 9/2

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Fri 9/4

9:10 pm-9:53 am

1 stop11h 43m

$257

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Tue 9/1

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Sat 9/5

7:44 pm-9:53 am

1 stop13h 09m

$258

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 10/8

4:13 pm-11:55 pm

1 stop8h 42m

Chicago O'Hare Intl

Sun 10/11

6:05 am-9:33 am

1 stop26h 28m

$267

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 9/3

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Fri 9/4

9:10 pm-6:14 pm

1 stop20h 04m

$268

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Mon 9/7

7:09 pm-11:08 pm

1 stop28h 59m

Chicago O'Hare Intl

Mon 9/14

11:15 am-4:58 pm

1 stop28h 43m

$269

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Sat 9/5

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Mon 9/7

9:10 pm-9:53 am

1 stop11h 43m

$270

IslipChicago

ISP Islip Long Island - ORD Chicago O'Hare Intl

ISPORD

Islip Long Island

Thu 9/24

7:00 am-1:45 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 9/29

3:50 pm-4:58 pm

1 stop24h 08m

$274

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 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 $323. 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 $405.

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 $311. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $373.

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

Fastest flight time

7h 45m

Direct flights

None
The fastest flight from Islip, New York to Chicago takes 7h 45m
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 45m 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
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

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport