Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Islip, New York to Chicago from $78

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 5/3. 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

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

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
8:31 pm - 1:09 am
ISP
-
ORD
29h 38m
1 stop
Frontier Logo
2:05 pm - 9:13 am
ORD
-
ISP
18h 08m
1 stop
$182Frontier
dom., abr. 19 - jue., abr. 23
Frontier Logo
8:31 pm - 1:09 am
ISP
-
ORD
29h 38m
1 stop
Frontier Logo
2:05 pm - 9:13 am
ORD
-
ISP
18h 08m
1 stop
$201Frontier
dom., abr. 19 - jue., abr. 23
Multiple Airlines Logo
4:07 pm - 1:00 pm
ISP
-
ORD
21h 53m
1 stop
Multiple Airlines Logo
1:27 pm - 10:05 am
ORD
-
ISP
43h 38m
2 stops
$203Multiple Airlines
lun., abr. 27 - lun., may. 4
Frontier Logo
8:31 pm - 1:09 am
ISP
-
ORD
29h 38m
1 stop
Frontier Logo
2:05 pm - 9:13 am
ORD
-
ISP
18h 08m
1 stop
$223Frontier
dom., abr. 19 - jue., abr. 23
Frontier Logo
8:31 pm - 10:37 am
ISP
-
ORD
15h 06m
1 stop
Frontier Logo
4:57 pm - 9:13 am
ORD
-
ISP
15h 16m
1 stop
$254Frontier
vie., abr. 17 - dom., abr. 19
Multiple Airlines Logo
8:43 pm - 11:13 pm
ISP
-
ORD
27h 30m
2 stops
Multiple Airlines Logo
5:30 pm - 11:00 am
ORD
-
ISP
16h 30m
1 stop
$262Multiple Airlines
lun., may. 11 - lun., may. 18
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
9:42 pm - 10:05 am
ORD
-
ISP
35h 23m
2 stops
$265Frontier
vie., may. 15 - lun., may. 18
Multiple Airlines Logo
7:34 pm - 4:56 pm
ISP
-
ORD
22h 22m
1 stop
Multiple Airlines Logo
8:52 pm - 11:10 am
ORD
-
ISP
13h 18m
2 stops
$267Multiple Airlines
lun., abr. 13 - vie., abr. 17
Multiple Airlines Logo
8:35 pm - 6:20 pm
ISP
-
ORD
22h 45m
1 stop
Multiple Airlines Logo
11:28 am - 11:00 am
ORD
-
ISP
46h 32m
2 stops
$275Multiple Airlines
dom., abr. 26 - dom., may. 3
Multiple Airlines Logo
6:02 pm - 10:14 pm
ISP
-
ORD
29h 12m
1 stop
Multiple Airlines Logo
6:55 am - 3:56 pm
ORD
-
ISP
32h 01m
2 stops
$280Multiple Airlines
mar., jun. 2 - lun., jun. 8

Frontier flights from Islip, New York to Chicago O'Hare Intl Airport

Our best Frontier deals on Islip, New York to Chicago O'Hare Intl Airport flight tickets
Frontier
Apr 19
ISP8:31 pmIslip Long Island
29h 38m
1 stop
ORD1:09 amChicago O'Hare Intl
Apr 23
ORD2:05 pmChicago O'Hare Intl
18h 08m
1 stop
ISP9:13 amIslip Long Island
$182
Frontier
Apr 19
ISP8:31 pmIslip Long Island
29h 38m
1 stop
ORD1:09 amChicago O'Hare Intl
Apr 23
ORD2:05 pmChicago O'Hare Intl
18h 08m
1 stop
ISP9:13 amIslip Long Island
$201
Frontier
Apr 19
ISP8:31 pmIslip Long Island
29h 38m
1 stop
ORD1:09 amChicago O'Hare Intl
Apr 23
ORD2:05 pmChicago O'Hare Intl
18h 08m
1 stop
ISP9:13 amIslip Long Island
$223

Southwest flights from Islip, New York to Chicago O'Hare Intl Airport

Our best Southwest deals on Islip, New York to Chicago O'Hare Intl Airport flight tickets
Southwest
Apr 25
ISP4:25 pmIslip Long Island
6h 30m
1 stop
ORD9:55 pmChicago O'Hare Intl
May 2
ORD6:00 amChicago O'Hare Intl
8h 45m
1 stop
ISP3:45 pmIslip Long Island
$375
Southwest
Apr 29
ISP6:55 amIslip Long Island
12h 30m
1 stop
ORD6:25 pmChicago O'Hare Intl
May 1
ORD3:05 pmChicago O'Hare Intl
6h 25m
1 stop
ISP10:30 pmIslip Long Island
$376
Southwest
Apr 25
ISP5:30 amIslip Long Island
11h 00m
2 stops
ORD3:30 pmChicago O'Hare Intl
May 2
ORD6:00 amChicago O'Hare Intl
9h 00m
2 stops
ISP4:00 pmIslip Long Island
$385

momondo Fare Finder

 
Customize your flight search to find flights from Islip, New York to Chicago O'Hare Intl Airport 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 abril 1, 2026.
Use the filters below to find and compare flights from Islip, New York to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

dom. 4/19

8:31 pm-1:09 am

1 stop29h 38m

Chicago O'Hare Intl

jue. 4/23

2:05 pm-9:13 am

1 stop18h 08m

$182

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

dom. 4/19

8:31 pm-1:09 am

1 stop29h 38m

Chicago O'Hare Intl

jue. 4/23

2:05 pm-9:13 am

1 stop18h 08m

$201

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

lun. 4/27

4:07 pm-1:00 pm

1 stop21h 53m

Chicago O'Hare Intl

lun. 5/4

1:27 pm-10:05 am

2 stops43h 38m

$203

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

dom. 4/19

8:31 pm-1:09 am

1 stop29h 38m

Chicago O'Hare Intl

jue. 4/23

2:05 pm-9:13 am

1 stop18h 08m

$223
Quickest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

vie. 4/17

8:31 pm-10:37 am

1 stop15h 06m

Chicago O'Hare Intl

dom. 4/19

4:57 pm-9:13 am

1 stop15h 16m

$254

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

lun. 5/11

8:43 pm-11:13 pm

2 stops27h 30m

Chicago O'Hare Intl

lun. 5/18

5:30 pm-11:00 am

1 stop16h 30m

$262

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

vie. 5/15

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

lun. 5/18

9:42 pm-10:05 am

2 stops35h 23m

$265

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

lun. 4/13

7:34 pm-4:56 pm

1 stop22h 22m

Chicago O'Hare Intl

vie. 4/17

8:52 pm-11:10 am

2 stops13h 18m

$267

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

dom. 4/26

8:35 pm-6:20 pm

1 stop22h 45m

Chicago O'Hare Intl

dom. 5/3

11:28 am-11:00 am

2 stops46h 32m

$275

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mar. 6/2

6:02 pm-10:14 pm

1 stop29h 12m

Chicago O'Hare Intl

lun. 6/8

6:55 am-3:56 pm

2 stops32h 01m

$280

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 O'Hare Intl Airport

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 day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday 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. On the other hand, Sunday is the most expensive day to depart from Islip, New York because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $367.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Islip, New York in the evening is the least expensive time of day to depart. momondo users have found prices as low as $273 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $361. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Islip, New York to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Islip, New York to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport (ISP to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Islip, New York to Chicago O'Hare Intl Airport

Fastest flight time

10h 25m

Direct flights

None
The fastest flight from Islip, New York to Chicago O'Hare Intl Airport takes 10h 25m
There are no direct flights from Islip, New York to Chicago O'Hare Intl Airport. There are no popular flight routes from Islip, New York to Chicago O'Hare Intl Airport.
Search flight deals

  • How far is Islip Long Island to Chicago O'Hare Intl by plane?

    Chicago O'Hare Intl is 765.5 mi away from Islip Long Island. In terms of flight time, this usually takes a little over 10h 25m.

  • When did momondo last update prices for flights from Islip Long Island Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Islip Long Island Airport to Chicago O'Hare Intl Airport are updated daily.

  • How many operators does momondo search for flights from Islip Long Island Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Islip Long Island Airport to Chicago O'Hare Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Islip Long Island Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Islip, New York to Chicago O'Hare Intl Airport?

Best airlines flying from Islip, New York to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Islip, New York to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $366Free CancellationRating
8.0
4,335 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Janesville
Aurora
Racine
Hammond
Elgin
Tinley Park
South Holland

Why use momondo?

Why should I use momondo to find a flight deal from Islip to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Islip.

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 provides multiple filters to help you find the best flight to Chicago from Islip. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Islip to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Islip to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago O'Hare Intl Airport 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
vie. 5/1
vie. 5/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago