Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Islip, New York to Chicago from $95

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 5/28. 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

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.

Find the cheapest flights from Islip, New York to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Islip, New York to Chicago.
Frontier Logo
9:06 pm - 8:22 amISP-ORD
12h 16m1 stop
Frontier Logo
5:03 pm - 7:26 pmORD-ISP
25h 23m1 stop
$181Frontier
Find Deal
Sat, May 24 - Wed, May 28
Frontier Logo
9:06 pm - 8:22 amISP-ORD
12h 16m1 stop
Frontier Logo
9:17 am - 7:26 pmORD-ISP
9h 09m1 stop
$188Frontier
Find Deal
Sat, May 24 - Thu, May 29
Frontier Logo
7:15 pm - 11:32 pmISP-ORD
29h 17m1 stop
Frontier Logo
4:15 pm - 11:26 amORD-ISP
18h 11m1 stop
$191Frontier
Find Deal
Wed, May 14 - Mon, May 19
Frontier Logo
8:26 pm - 12:10 amISP-ORD
28h 44m1 stop
Frontier Logo
5:08 pm - 7:41 pmORD-ISP
25h 33m1 stop
$195Frontier
Find Deal
Thu, Jun 5 - Sat, Jun 7
Frontier Logo
9:40 pm - 8:05 amISP-ORD
11h 25m1 stop
Frontier Logo
9:00 am - 4:33 pmORD-ISP
6h 33m1 stop
$198Frontier
Find Deal
Thu, May 8 - Fri, May 16
Southwest Logo
6:00 am - 11:50 amISP-ORD
6h 50m1 stop
Southwest Logo
1:50 pm - 10:55 pmORD-ISP
8h 05m1 stop
$292Southwest
Find Deal
Tue, Jun 10 - Wed, Jun 11
Southwest Logo
6:00 am - 4:25 pmISP-ORD
11h 25m2 stops
Southwest Logo
1:50 pm - 10:55 pmORD-ISP
8h 05m1 stop
$314Southwest
Find Deal
Tue, Jun 10 - Wed, Jun 11
Southwest Logo
5:05 am - 11:50 amISP-ORD
7h 45m1 stop
Southwest Logo
12:40 pm - 11:10 pmORD-ISP
9h 30m2 stops
$340Southwest
Find Deal
Thu, Jul 10 - Sat, Jul 12
Southwest Logo
6:00 am - 4:25 pmISP-ORD
11h 25m2 stops
Southwest Logo
11:25 am - 11:10 pmORD-ISP
10h 45m2 stops
$351Southwest
Find Deal
Thu, Jul 10 - Sat, Jul 12
 Logo
7:39 pm - 11:29 pmISP-ORD
28h 50m2 stops
 Logo
5:05 am - 8:42 amORD-ISP
26h 37m2 stops
Thu, Jun 5 - Sat, Jun 7

Frontier flights from Islip, New York to Chicago

Our best Frontier deals on Islip, New York to Chicago flight tickets
Frontier
May 24
ISP9:06 pmIslip Long Island
12h 16m
1 stop
ORD8:22 amChicago O'Hare Intl
May 28
ORD5:03 pmChicago O'Hare Intl
25h 23m
1 stop
ISP7:26 pmIslip Long Island
Frontier
May 24
ISP9:06 pmIslip Long Island
12h 16m
1 stop
ORD8:22 amChicago O'Hare Intl
May 29
ORD9:17 amChicago O'Hare Intl
9h 09m
1 stop
ISP7:26 pmIslip Long Island
Frontier
May 14
ISP7:15 pmIslip Long Island
29h 17m
1 stop
ORD11:32 pmChicago O'Hare Intl
May 19
ORD4:15 pmChicago O'Hare Intl
18h 11m
1 stop
ISP11:26 amIslip Long Island

Southwest flights from Islip, New York to Chicago

Our best Southwest deals on Islip, New York to Chicago flight tickets
Southwest
Jun 10
ISP6:00 amIslip Long Island
6h 50m
1 stop
ORD11:50 amChicago O'Hare Intl
Jun 11
ORD1:50 pmChicago O'Hare Intl
8h 05m
1 stop
ISP10:55 pmIslip Long Island
Southwest
Jun 10
ISP6:00 amIslip Long Island
11h 25m
2 stops
ORD4:25 pmChicago O'Hare Intl
Jun 11
ORD1:50 pmChicago O'Hare Intl
8h 05m
1 stop
ISP10:55 pmIslip Long Island
Southwest
Jul 10
ISP5:05 amIslip Long Island
7h 45m
1 stop
ORD11:50 amChicago O'Hare Intl
Jul 12
ORD12:40 pmChicago O'Hare Intl
9h 30m
2 stops
ISP11:10 pmIslip Long Island

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 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 $291. 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 $376.

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 $236. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $341.

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

$95

Fastest flight time

6h 50m

Direct flights

None

Airports in Chicago

1 airport
The best one-way flight to Chicago from Islip, New York in the past 72 hours is $95. The best round-trip flight deal from Islip, New York to Chicago found on momondo in the last 72 hours is $181.
The fastest flight from Islip, New York to Chicago takes 6h 50m
There are no direct flights from Islip, New York to Chicago. Popular non-direct route for this connection is Islip Long Island Airport - Chicago O'Hare Intl Airport.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

  • 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 50m 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 $296Free CancellationRating
8.0
4,286 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
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Wed 4/30
Wed 5/7

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