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Cheap flights from Islip to Chicago from $84

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 to Chicago departing on 9/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Islip to Chicago

Cheap round-trip flights

Frontier Logo
11:25 am - 7:44 pmISP-ORD
9h 19m1 stop
Frontier Logo
8:49 pm - 10:40 amORD-ISP
12h 51m1 stop
$168Frontier
Find Deal
jue., sep. 11 - lun., sep. 15
Frontier Logo
5:05 pm - 3:17 pmISP-ORD
23h 12m1 stop
Frontier Logo
8:49 pm - 10:40 amORD-ISP
12h 51m1 stop
$175Frontier
Find Deal
vie., sep. 26 - lun., sep. 29
Frontier Logo
11:40 am - 7:44 pmISP-ORD
9h 04m1 stop
Frontier Logo
8:49 pm - 10:40 amORD-ISP
12h 51m1 stop
$184Frontier
Find Deal
jue., sep. 25 - dom., sep. 28
Frontier Logo
11:40 am - 7:44 pmISP-ORD
9h 04m1 stop
Frontier Logo
8:05 am - 4:27 pmORD-ISP
7h 22m1 stop
$190Frontier
Find Deal
jue., sep. 25 - dom., sep. 28
Logo
11:35 am - 4:12 pmISP-ORD
29h 37m1 stop
Logo
5:17 pm - 10:40 amORD-ISP
16h 23m1 stop
$209
Find Deal
mié., sep. 17 - sáb., sep. 20
Logo
5:05 pm - 3:17 pmISP-ORD
23h 12m1 stop
Logo
5:17 pm - 10:40 amORD-ISP
16h 23m1 stop
$215
Find Deal
vie., sep. 12 - mar., sep. 16
Frontier Logo
4:58 pm - 3:39 pmISP-ORD
23h 41m1 stop
Frontier Logo
6:23 pm - 8:42 pmORD-ISP
25h 19m1 stop
$217Frontier
Find Deal
vie., oct. 17 - lun., oct. 20
Logo
11:35 am - 10:31 amISP-ORD
23h 56m2 stops
Logo
5:17 pm - 10:40 amORD-ISP
16h 23m1 stop
$218
Find Deal
mié., sep. 17 - sáb., sep. 20
Southwest Logo
11:40 am - 11:05 pmISP-ORD
12h 25m2 stops
Southwest Logo
7:30 am - 10:05 pmORD-ISP
13h 35m2 stops
$330Southwest
Find Deal
mié., oct. 15 - mié., oct. 22
Southwest Logo
3:40 pm - 9:50 pmISP-ORD
7h 10m1 stop
Southwest Logo
1:45 pm - 11:50 pmORD-ISP
9h 05m2 stops
$337Southwest
Find Deal
mar., nov. 11 - dom., nov. 16

Frontier flights from Islip to Chicago

Our best Frontier deals on Islip to Chicago flight tickets
Frontier
Sep 11
ISP11:25 amIslip Long Island
9h 19m
1 stop
ORD7:44 pmChicago O'Hare Intl
Sep 15
ORD8:49 pmChicago O'Hare Intl
12h 51m
1 stop
ISP10:40 amIslip Long Island
$168
Find similar
Frontier
Sep 26
ISP5:05 pmIslip Long Island
23h 12m
1 stop
ORD3:17 pmChicago O'Hare Intl
Sep 29
ORD8:49 pmChicago O'Hare Intl
12h 51m
1 stop
ISP10:40 amIslip Long Island
$175
Find similar
Frontier
Sep 25
ISP11:40 amIslip Long Island
9h 04m
1 stop
ORD7:44 pmChicago O'Hare Intl
Sep 28
ORD8:49 pmChicago O'Hare Intl
12h 51m
1 stop
ISP10:40 amIslip Long Island
$184
Find similar

Southwest flights from Islip to Chicago

Our best Southwest deals on Islip to Chicago flight tickets
Southwest
Oct 15
ISP11:40 amIslip Long Island
12h 25m
2 stops
ORD11:05 pmChicago O'Hare Intl
Oct 22
ORD7:30 amChicago O'Hare Intl
13h 35m
2 stops
ISP10:05 pmIslip Long Island
$330
Find similar
Southwest
Nov 11
ISP3:40 pmIslip Long Island
7h 10m
1 stop
ORD9:50 pmChicago O'Hare Intl
Nov 16
ORD1:45 pmChicago O'Hare Intl
9h 05m
2 stops
ISP11:50 pmIslip Long Island
$337
Find similar
Southwest
Aug 30
ISP5:40 amIslip Long Island
7h 10m
1 stop
ORD11:50 amChicago O'Hare Intl
Sep 1
ORD1:50 pmChicago O'Hare Intl
8h 05m
1 stop
ISP10:55 pmIslip Long Island
$892
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Islip 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 agosto 28, 2025.
Use the filters below to find and compare flights from Islip to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

jue. 9/11

11:25 am-7:44 pm

1 stop9h 19m

Chicago O'Hare Intl

lun. 9/15

8:49 pm-10:40 am

1 stop12h 51m

$168

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

vie. 9/26

5:05 pm-3:17 pm

1 stop23h 12m

Chicago O'Hare Intl

lun. 9/29

8:49 pm-10:40 am

1 stop12h 51m

$175

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

jue. 9/25

11:40 am-7:44 pm

1 stop9h 04m

Chicago O'Hare Intl

dom. 9/28

8:49 pm-10:40 am

1 stop12h 51m

$184

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

jue. 9/25

11:40 am-7:44 pm

1 stop9h 04m

Chicago O'Hare Intl

dom. 9/28

8:05 am-4:27 pm

1 stop7h 22m

$190

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mié. 9/17

11:35 am-4:12 pm

1 stop29h 37m

Chicago O'Hare Intl

sáb. 9/20

5:17 pm-10:40 am

1 stop16h 23m

$209

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

vie. 9/12

5:05 pm-3:17 pm

1 stop23h 12m

Chicago O'Hare Intl

mar. 9/16

5:17 pm-10:40 am

1 stop16h 23m

$215

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

vie. 10/17

4:58 pm-3:39 pm

1 stop23h 41m

Chicago O'Hare Intl

lun. 10/20

6:23 pm-8:42 pm

1 stop25h 19m

$217

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mié. 9/17

11:35 am-10:31 am

2 stops23h 56m

Chicago O'Hare Intl

sáb. 9/20

5:17 pm-10:40 am

1 stop16h 23m

$218

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mié. 10/15

11:40 am-11:05 pm

2 stops12h 25m

Chicago O'Hare Intl

mié. 10/22

7:30 am-10:05 pm

2 stops13h 35m

$330

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mar. 11/11

3:40 pm-9:50 pm

1 stop7h 10m

Chicago O'Hare Intl

dom. 11/16

1:45 pm-11:50 pm

2 stops9h 05m

$337

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 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 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 Wednesday when prices can be found for as low as $294. 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 to Chicago for around $386.

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 to Chicago during this time can be as low as $254. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $362.

When to book flights from Islip to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Islip to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Islip to Chicago (ISP to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Islip to Chicago

Direct flights

None
There are no direct flights from Islip to Chicago. There are no popular flight routes from Islip to Chicago.
Search flight deals

  • 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 10m 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 to Chicago?

Best airlines flying from Islip to Chicago

Compare and see reviews for airlines that fly from Islip to Chicago with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $336Free CancellationRating
8.0
4,242 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
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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