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Cheap flights from Islip, New York to Chicago from $96

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 5/27. 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
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
6:02 pm - 11:13 pm
ISP
-
ORD
30h 11m
1 stop
Frontier Logo
5:11 pm - 10:05 am
ORD
-
ISP
15h 54m
1 stop
$203Frontier
Tue, May 26 - Thu, May 28
Frontier Logo
4:07 pm - 1:15 pm
ISP
-
ORD
22h 08m
1 stop
Frontier Logo
6:00 am - 11:00 am
ORD
-
ISP
28h 00m
1 stop
$218Frontier
Thu, Apr 30 - Mon, May 4
Multiple Airlines Logo
11:12 am - 10:14 pm
ISP
-
ORD
12h 02m
1 stop
Multiple Airlines Logo
3:55 pm - 10:05 am
ORD
-
ISP
17h 10m
1 stop
$239Multiple Airlines
Thu, May 14 - Tue, May 19
Multiple Airlines Logo
11:00 am - 10:14 pm
ISP
-
ORD
12h 14m
1 stop
Multiple Airlines Logo
6:55 am - 11:00 am
ORD
-
ISP
27h 05m
2 stops
$241Multiple Airlines
Wed, May 13 - Mon, May 18
Multiple Airlines Logo
8:31 pm - 6:20 pm
ISP
-
ORD
22h 49m
1 stop
Multiple Airlines Logo
2:10 pm - 11:00 am
ORD
-
ISP
19h 50m
2 stops
$245Multiple Airlines
Thu, Apr 30 - Mon, May 4
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
1:50 pm - 5:17 pm
ORD
-
ISP
26h 27m
2 stops
$253Frontier
Fri, May 29 - Mon, Jun 1
Multiple Airlines Logo
8:31 pm - 6:20 pm
ISP
-
ORD
22h 49m
1 stop
Multiple Airlines Logo
7:15 am - 10:05 am
ORD
-
ISP
25h 50m
2 stops
$254Multiple Airlines
Fri, May 1 - Tue, May 5
Multiple Airlines Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Multiple Airlines Logo
8:30 am - 5:58 pm
ORD
-
ISP
8h 28m
1 stop
$259Multiple Airlines
Fri, May 29 - Mon, Jun 1
Multiple Airlines Logo
11:12 am - 10:14 pm
ISP
-
ORD
12h 02m
1 stop
Multiple Airlines Logo
6:55 am - 10:05 am
ORD
-
ISP
26h 10m
2 stops
$263Multiple Airlines
Thu, May 14 - Tue, May 19
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
5:11 pm - 10:05 am
ORD
-
ISP
15h 54m
1 stop
$268Frontier
Fri, May 29 - Fri, Jun 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
May 26
ISP6:02 pmIslip Long Island
30h 11m
1 stop
ORD11:13 pmChicago O'Hare Intl
May 28
ORD5:11 pmChicago O'Hare Intl
15h 54m
1 stop
ISP10:05 amIslip Long Island
$203
Frontier
Apr 30
ISP4:07 pmIslip Long Island
22h 08m
1 stop
ORD1:15 pmChicago O'Hare Intl
May 4
ORD6:00 amChicago O'Hare Intl
28h 00m
1 stop
ISP11:00 amIslip Long Island
$218
Frontier
May 29
ISP11:00 amIslip Long Island
13h 13m
1 stop
ORD11:13 pmChicago O'Hare Intl
Jun 1
ORD1:50 pmChicago O'Hare Intl
26h 27m
2 stops
ISP5:17 pmIslip Long Island
$253

Southwest flights from Islip, New York to Chicago

Our best Southwest deals on Islip, New York to Chicago flight tickets
Southwest
May 13
ISP12:30 pmIslip Long Island
10h 25m
2 stops
ORD9:55 pmChicago O'Hare Intl
May 20
ORD11:55 amChicago O'Hare Intl
9h 15m
2 stops
ISP10:10 pmIslip Long Island
$345
Southwest
May 26
ISP6:55 amIslip Long Island
12h 30m
1 stop
ORD6:25 pmChicago O'Hare Intl
May 28
ORD3:05 pmChicago O'Hare Intl
6h 25m
1 stop
ISP10:30 pmIslip Long Island
$360
Southwest
May 26
ISP2:30 pmIslip Long Island
8h 25m
2 stops
ORD9:55 pmChicago O'Hare Intl
May 28
ORD2:40 pmChicago O'Hare Intl
7h 50m
2 stops
ISP11:30 pmIslip Long Island
$365

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 April 18, 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 - ORD

ISPORD

Islip Long Island

Tue 5/26

6:02 pm-11:13 pm

1 stop30h 11m

Chicago O'Hare Intl

Thu 5/28

5:11 pm-10:05 am

1 stop15h 54m

$203

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 4/30

4:07 pm-1:15 pm

1 stop22h 08m

Chicago O'Hare Intl

Mon 5/4

6:00 am-11:00 am

1 stop28h 00m

$218

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 5/14

11:12 am-10:14 pm

1 stop12h 02m

Chicago O'Hare Intl

Tue 5/19

3:55 pm-10:05 am

1 stop17h 10m

$239

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 5/13

11:00 am-10:14 pm

1 stop12h 14m

Chicago O'Hare Intl

Mon 5/18

6:55 am-11:00 am

2 stops27h 05m

$241

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 4/30

8:31 pm-6:20 pm

1 stop22h 49m

Chicago O'Hare Intl

Mon 5/4

2:10 pm-11:00 am

2 stops19h 50m

$245

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 5/29

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

Mon 6/1

1:50 pm-5:17 pm

2 stops26h 27m

$253

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 5/1

8:31 pm-6:20 pm

1 stop22h 49m

Chicago O'Hare Intl

Tue 5/5

7:15 am-10:05 am

2 stops25h 50m

$254
Quickest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 5/29

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

Mon 6/1

8:30 am-5:58 pm

1 stop8h 28m

$259

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 5/14

11:12 am-10:14 pm

1 stop12h 02m

Chicago O'Hare Intl

Tue 5/19

6:55 am-10:05 am

2 stops26h 10m

$263

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 5/29

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

Fri 6/5

5:11 pm-10:05 am

1 stop15h 54m

$268

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 typical price of a round-trip flight between Islip, New York and Chicago?

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 $290. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Islip, New York to Chicago for around $366.

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 $271. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $360.

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

6h 55m

Direct flights

None
The fastest flight from Islip, New York to Chicago takes 6h 55m
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 6h 55m 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 many operators does momondo search for flights from Islip Long Island Airport to Chicago?

  • 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?

Best airlines flying from Islip, New York to Chicago

Compare and see reviews for airlines that fly from Islip, New York to Chicago with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $387Free CancellationRating
8.0
4,330 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Chesterton
Monticello
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