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Cheap flights from Islip, New York to Chicago from $92

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 12/15. 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, New York to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Islip, New York to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Islip, New York to Chicago.

Cheap last minute flights

Planning a quick getaway from Islip, New York to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Islip, New York to Chicago

Find recent round-trip train or bus tickets from Islip, New York to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
3:25 pm - 1:54 pmISP-ORD
23h 29m1 stop
10:02 pm - 11:43 amORD-ISP
12h 41m1 stop
$119Frontier
Find Deal
Wed, Jan 8 - Fri, Jan 17
7:52 pm - 12:46 pmISP-ORD
17h 54m1 stop
4:02 pm - 6:08 pmORD-ISP
25h 06m1 stop
$268Frontier
Find Deal
Mon, Dec 16 - Mon, Dec 23
11:31 am - 6:24 pmISP-ORD
7h 53m1 stop
10:35 am - 7:02 pmORD-ISP
7h 27m1 stop
$313Frontier
Find Deal
Thu, Jan 2 - Thu, Jan 9
11:31 am - 6:24 pmISP-ORD
7h 53m1 stop
10:33 am - 7:12 pmORD-ISP
7h 39m1 stop
$314Frontier
Find Deal
Thu, Jan 2 - Thu, Jan 23
6:15 am - 2:04 pmISP-ORD
8h 49m1 stop
6:30 am - 7:45 pmORD-ISP
12h 15m1 stop
$338Frontier
Find Deal
Sat, Dec 21 - Thu, Jan 2
5:45 pm - 9:30 pmISP-ORD
4h 45m1 stop
7:00 am - 12:10 pmORD-ISP
4h 10m1 stop
$366Southwest
Find Deal
Mon, Jan 20 - Thu, Jan 23
11:25 am - 10:20 pmISP-ORD
11h 55m2 stops
7:00 am - 12:10 pmORD-ISP
4h 10m1 stop
$371Southwest
Find Deal
Mon, Jan 20 - Thu, Jan 23
8:55 pm - 11:56 pmISP-ORD
28h 01m1 stop
7:29 pm - 7:50 amORD-ISP
11h 21m1 stop
$384Frontier
Find Deal
Fri, Dec 20 - Sun, Dec 22
5:55 am - 10:20 pmISP-ORD
17h 25m3 stops
7:00 am - 12:10 pmORD-ISP
4h 10m1 stop
$489Southwest
Find Deal
Mon, Jan 20 - Thu, Jan 23
7:25 pm - 10:55 pmISP-ORD
28h 30m3 stops
5:35 am - 5:59 pmORD-ISP
11h 24m1 stop
Wed, Jan 8 - Fri, Jan 17
8:12 pm - 9:54 amISP-ORD
14h 42m1 stop
$92Frontier
Find Deal
Sun, Dec 15
9:38 pm - 10:04 amISP-ORD
13h 26m1 stop
$119Frontier
Find Deal
Wed, Dec 18
11:31 am - 6:24 pmISP-ORD
7h 53m1 stop
$182Frontier
Find Deal
Thu, Dec 19
9:25 pm - 9:24 amISP-ORD
12h 59m1 stop
$190Frontier
Find Deal
Tue, Dec 24
9:38 pm - 10:28 amISP-ORD
13h 50m1 stop
$195Frontier
Find Deal
Mon, Dec 30
11:31 am - 6:24 pmISP-ORD
7h 53m1 stop
$210Frontier
Find Deal
Thu, Dec 19
11:31 am - 6:24 pmISP-ORD
7h 53m1 stop
$211Frontier
Find Deal
Thu, Dec 19
5:35 am - 3:00 pmISP-ORD
10h 25m2 stops
$218Southwest
Find Deal
Sun, Dec 15
6:25 am - 1:00 pmISP-ORD
7h 35m2 stops
$238Southwest
Find Deal
Wed, Jan 1
6:25 am - 2:00 pmISP-ORD
8h 35m1 stop
$239Southwest
Find Deal
Wed, Jan 1
5:45 am - 1:20 pmISP-ORD
8h 35m1 stop
8:57 am - 5:57 pmORD-ISP
8h 00m1 stop
Wed, Nov 27 - Sat, Nov 30
4:05 pm - 11:52 amISP-ORD
20h 47m3 stops
7:49 am - 5:11 pmORD-ISP
8h 22m1 stop
Wed, Nov 27 - Sat, Nov 30
5:30 am - 2:00 pmISP-ORD
9h 30m1 stop
11:25 am - 11:55 pmORD-ISP
11h 30m2 stops
$901Southwest
Find Deal
Wed, Nov 27 - Sat, Nov 30
4:05 pm - 11:52 amISP-ORD
20h 47m3 stops
7:39 pm - 1:17 pmORD-ISP
16h 38m2 stops
Wed, Nov 27 - Sat, Nov 30
4:05 pm - 11:52 amISP-ORD
20h 47m3 stops
5:15 pm - 6:54 pmORD-ISP
24h 39m3 stops
$1,037
Find Deal
Wed, Nov 27 - Sat, Nov 30

Frontier flights from Islip, New York to Chicago

Our best Frontier deals on Islip, New York to Chicago flight tickets
Frontier
Jan 8
ISP3:25 pmIslip Long Island
23h 29m
1 stop
ORD1:54 pmChicago O'Hare Intl
Jan 17
ORD10:02 pmChicago O'Hare Intl
12h 41m
1 stop
ISP11:43 amIslip Long Island
Frontier
Dec 16
ISP7:52 pmIslip Long Island
17h 54m
1 stop
ORD12:46 pmChicago O'Hare Intl
Dec 23
ORD4:02 pmChicago O'Hare Intl
25h 06m
1 stop
ISP6:08 pmIslip Long Island
Frontier
Jan 2
ISP11:31 amIslip Long Island
7h 53m
1 stop
ORD6:24 pmChicago O'Hare Intl
Jan 9
ORD10:35 amChicago O'Hare Intl
7h 27m
1 stop
ISP7:02 pmIslip Long Island

Southwest flights from Islip, New York to Chicago

Our best Southwest deals on Islip, New York to Chicago flight tickets
Southwest
Jan 20
ISP5:45 pmIslip Long Island
4h 45m
1 stop
ORD9:30 pmChicago O'Hare Intl
Jan 23
ORD7:00 amChicago O'Hare Intl
4h 10m
1 stop
ISP12:10 pmIslip Long Island
Southwest
Jan 20
ISP11:25 amIslip Long Island
11h 55m
2 stops
ORD10:20 pmChicago O'Hare Intl
Jan 23
ORD7:00 amChicago O'Hare Intl
4h 10m
1 stop
ISP12:10 pmIslip Long Island
Southwest
Jan 20
ISP5:55 amIslip Long Island
17h 25m
3 stops
ORD10:20 pmChicago O'Hare Intl
Jan 23
ORD7:00 amChicago O'Hare Intl
4h 10m
1 stop
ISP12:10 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 month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Islip, New York, with most prices found around $176. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Islip, New York to Chicago during January average around $196.

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 Tuesday when prices can be found for as low as $201. 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 $270.

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 $214. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $263.

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Islip, New York is 55 days out, which is when prices tend to be around $228. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $166.

Can stopping save me money on Islip, New York to Chicago flights?

You could potentially save up to 57% on your flight if you consider stops on a Islip, New York to Chicago flight.

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

$92

Fastest flight time

4h 45m

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 $92. The best round-trip flight deal from Islip, New York to Chicago found on momondo in the last 72 hours is $119.
The fastest flight from Islip, New York to Chicago takes 4h 45m
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 4h 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.


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
FrontierPriceFrom $243Free CancellationRating
6.1
3,524 reviews
Search Frontier flights

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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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago