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Cheap flights from Islip (ISP) to Chicago (CHI) from $59

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
ISP — CHI
Apr 28 — May 51
From?
To?
Sun 4/28
Sun 5/5
1 adult, Economy
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Cheap flight deals from Islip to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 23, 2024.

Round-trip from

$222

One-way from

$59
From Islip Long Island to Chicago (CHI)
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One-way flight from Islip Long Island to Chicago (CHI)
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How far in advance should I book a flight from Islip, New York to Chicago?

Users have found that booking a flight from Islip, New York to Chicago at least 48 days early can save you up to 76% on average compared to booking a flight this week. If booking 48 days before your flight isn’t an option for you, users have found flights from Islip, New York to Chicago for as little as $302 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $415 for flights departing within the next 3 days.

What is the cheapest month to fly from Islip, New York to Chicago?

February can be a great time to fly to Chicago from Islip, New York with a flight ticket averaging about $268. Cheapflights users have found deals in the month of February for as cheap as $107. The most expensive prices can be found in the month of June.

When is the cheapest time to fly from Islip, New York to Chicago (ISP - CHI)?

It’s typically best to fly out from Islip, New York to Chicago at noon. Doing so could potentially save you 56% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap Frontier flights from Islip to Chicago

Explore cheap flight options specifically provided by Frontier for the route between Islip and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.
Thu 5/164:49 pmISP - ORD
1 stop9h 19mFrontier
Fri 5/175:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/22$148
Thu 5/96:05 pmISP - ORD
1 stop7h 54mFrontier
Sun 5/125:51 pmORD - ISP
1 stop13h 03mFrontier
Deal found 4/21$168
Fri 9/205:25 pmISP - ORD
1 stop8h 34mFrontier
Sun 9/225:56 pmORD - ISP
1 stop13h 30mFrontier
Deal found 4/21$178
Thu 5/96:05 pmISP - ORD
1 stop7h 54mFrontier
Fri 5/108:25 amORD - ISP
1 stop12h 07mFrontier
Deal found 4/21$188
Thu 5/164:49 pmISP - ORD
1 stop9h 19mFrontier
Mon 5/205:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/22$194
Sat 6/14:49 pmISP - ORD
1 stop9h 09mFrontier
Mon 6/35:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/21$209
Mon 6/104:46 pmISP - ORD
1 stop9h 22mFrontier
Thu 6/137:13 pmORD - ISP
1 stop11h 27mFrontier
Deal found 4/22$221
Fri 5/314:49 pmISP - ORD
1 stop9h 19mFrontier
Sun 6/25:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/22$229
Thu 6/611:37 amISP - ORD
1 stop6h 10mFrontier
Sun 6/911:26 amORD - ISP
1 stop6h 53mFrontier
Deal found 4/22$249

Cheap Islip to Chicago flights in April & May 2024

Find cheap flight options from Islip to Chicago specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,086,534 searches. Prices were last updated on April 23, 2024.
Thu 5/164:49 pmISP - ORD
1 stop9h 19mFrontier
Fri 5/175:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/22$148
Sun 5/56:05 pmISP - ORD
1 stop7h 54mFrontier
Sun 5/125:51 pmORD - ISP
1 stop13h 03mFrontier
Deal found 4/23$158
Thu 5/96:05 pmISP - ORD
1 stop7h 54mFrontier
Sun 5/125:51 pmORD - ISP
1 stop13h 03mFrontier
Deal found 4/21$168
Mon 4/2912:54 pmISP - ORD
1 stop11h 49mFrontier
Thu 5/25:51 pmORD - ISP
1 stop14h 27mFrontier
Deal found 4/22$188
Thu 5/164:49 pmISP - ORD
1 stop9h 19mFrontier
Mon 5/205:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/22$194
Fri 5/314:49 pmISP - ORD
1 stop9h 19mFrontier
Sun 6/25:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/22$229
Sat 5/254:49 pmISP - ORD
1 stop9h 09mFrontier
Tue 5/287:00 amORD - ISP
1 stop12h 23mFrontier
Deal found 4/22$258
Wed 5/224:49 pmISP - ORD
1 stop9h 19mFrontier
Wed 5/295:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/22$259
Fri 5/244:49 pmISP - ORD
1 stop9h 19mFrontier
Sun 5/265:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/22$320

Islip to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Islip and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.
Thu 5/164:49 pmISP - ORD
1 stop9h 19mFrontier
Fri 5/175:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/22$148
Fri 9/135:25 pmISP - ORD
1 stop8h 34mFrontier
Sun 9/155:56 pmORD - ISP
1 stop13h 30mFrontier
Deal found 4/22$157
Sun 5/56:05 pmISP - ORD
1 stop7h 54mFrontier
Sun 5/125:51 pmORD - ISP
1 stop13h 03mFrontier
Deal found 4/23$158
Thu 5/96:05 pmISP - ORD
1 stop7h 54mFrontier
Sun 5/125:51 pmORD - ISP
1 stop13h 03mFrontier
Deal found 4/21$168
Sat 8/2410:00 amISP - ORD
1 stop7h 46mFrontier
Mon 8/265:56 pmORD - ISP
1 stop13h 30mFrontier
Deal found 4/23$178
Mon 4/2912:54 pmISP - ORD
1 stop11h 49mFrontier
Thu 5/25:51 pmORD - ISP
1 stop14h 27mFrontier
Deal found 4/22$188
Thu 5/164:49 pmISP - ORD
1 stop9h 19mFrontier
Mon 5/205:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/22$194
Sat 6/14:49 pmISP - ORD
1 stop9h 09mFrontier
Mon 6/35:56 pmORD - ISP
1 stop13h 17mFrontier
Deal found 4/21$209
Mon 6/104:46 pmISP - ORD
1 stop9h 22mFrontier
Thu 6/137:13 pmORD - ISP
1 stop11h 27mFrontier
Deal found 4/22$221

Islip to Chicago flights leaving soon

Find last-minute flight options from Islip to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.
Mon 4/2912:54 pmISP - ORD
1 stop11h 49mFrontier
Thu 5/25:51 pmORD - ISP
1 stop14h 27mFrontier
Deal found 4/22$188

One-way flights to Chicago from Islip

Search for one-way flight options from Islip to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.
Thu 5/99:50 pmISP - ORD
1 stop26h 53mFrontier
Deal found 4/21$59
Sun 5/126:05 pmISP - ORD
1 stop7h 54mFrontier
Deal found 4/22$79
Tue 6/44:49 pmISP - ORD
1 stop9h 19mFrontier
Deal found 4/22$80
Mon 4/2912:54 pmISP - ORD
1 stop11h 49mFrontier
Deal found 4/22$95
Sun 5/56:05 pmISP - ORD
1 stop7h 54mFrontier
Deal found 4/22$99
Thu 6/611:37 amISP - ORD
1 stop6h 10mFrontier
Deal found 4/21$100
Mon 5/204:49 pmISP - ORD
1 stop9h 19mFrontier
Deal found 4/22$119
Mon 5/274:49 pmISP - ORD
1 stop9h 19mFrontier
Deal found 4/22$129
Sun 4/286:05 pmISP - ORD
1 stop7h 54mFrontier
Deal found 4/22$139

Find flights from Islip to Chicago within your budget

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, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$148 - $488

Route

Depart

Return

Price

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Thu 5/16

1 stop9h 19m

Chicago O'Hare Intl

Fri 5/17

1 stop13h 17m

$148

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Thu 5/9

1 stop7h 54m

Chicago O'Hare Intl

Sun 5/12

1 stop13h 03m

$168

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Fri 9/20

1 stop8h 34m

Chicago O'Hare Intl

Sun 9/22

1 stop13h 30m

$178

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Thu 5/9

1 stop7h 54m

Chicago O'Hare Intl

Fri 5/10

1 stop12h 07m

$188

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Thu 5/16

1 stop9h 19m

Chicago O'Hare Intl

Mon 5/20

1 stop13h 17m

$194

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Sat 6/1

1 stop9h 09m

Chicago O'Hare Intl

Mon 6/3

1 stop13h 17m

$209

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Mon 6/10

1 stop9h 22m

Chicago O'Hare Intl

Thu 6/13

1 stop11h 27m

$221

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Fri 5/31

1 stop9h 19m

Chicago O'Hare Intl

Sun 6/2

1 stop13h 17m

$229

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Thu 6/6

2 stops12h 34m

Chicago O'Hare Intl

Sun 6/9

2 stops17h 50m

$488

Flights are sorted by cheapest first

Deals found on 4/22

When is the cheapest time to fly from Islip, New York to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Islip to Chicago. Price data was last updated on April 21, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Islip, New York to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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Average price of flights to Chicago by month

Plan your trip from Islip to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Islip to Chicago is currently $100 while a round-trip flight costs $225. Price data was last updated on April 21, 2024.

Currently, February is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $245). Flying from Islip, New York to Chicago in June is currently the most expensive (average of $356). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

January

$248

February

$245

March

$280

April

$273

May

$282

June

$356

July

$336

August

$276

September

$258

October

$248

November

$270

December

$248

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 23, 2024.
Frontier
6.3
Okay
4,142 reviews
Check prices

Boarding

6.6

Comfort

5.8

Entertainment

5.0

Crew

7.1

Overall

6.3

Food

5.2

Reviews

1 / 10

My flight is always delayed to Las Vegas And the seats always so uncomfortable

Frontier
6.3
Okay
4,142 reviews
Frontier
6.3
Okay
4,142 reviews
Check prices

Boarding

6.6

Comfort

5.8

Entertainment

5.0

Crew

7.1

Overall

6.3

Food

5.2

Reviews

1 / 10

My flight is always delayed to Las Vegas And the seats always so uncomfortable

Related info for your journey

Find useful and relevant information for your journey from Islip to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Islip to Chicago?

    Most people fly from Islip Long Island (ISP) if they book a flight from Islip to Chicago. On average, Long Island has 0 outbound flights to Chicago per day from 0 airlines. Islip Long Island is conveniently located just 7.2 mi from Islip’s city center.

  • Can I find flights from Islip, New York to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from Islip, New York to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $148, but on average you can expect to pay $274.

  • Are there last-minute flights available from Islip, New York to Chicago for under $200?

    There are currently 1+ open flights from Islip, New York to Chicago within the next 7 days for less than $200.

  • What is the cheapest airline to fly from Islip, New York to Chicago round-trip?

    Cheapflights users have booked flights from Islip, New York to Chicago round-trip from $148.

  • What does ISP to ORD mean?

    ISP and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. ISP to ORD refers to a flight route from Islip Long Island Airport to Chicago O'Hare Intl Airport. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Islip to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Islip to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Islip to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Islip to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Islip to Chicago that include hotel bookings?

    Yes. In addition to deals on Islip to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Islip to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Islip to Chicago.

  • Can I find deals for business class flights from Islip to Chicago?

    Yes. Cheapflights offers flight deals from Islip to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Islip to Chicago that allow pets onboard?

    Many airlines flying from Islip to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Islip to Chicago?

    Yes, you can often find last-minute deals on Islip to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Islip, New York to Chicago flight deals updated?

    The Islip, New York to Chicago flight deals you see on this page were last updated on 4/23.

See more FAQs

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Alternative routes for Islip to Chicago
See prices for flight routes from nearby airports that may be better suited for you.

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Search flights from Islip to Chicago by cabin class

Find flights from Islip to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Islip to Chicago?

Cheapflights makes it easy to find Islip to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Islip to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Islip.

Can Cheapflights find flights from Islip to Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from Islip to Chicago with no change fees.

Can Cheapflights notify me if prices for flights from Islip to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Islip to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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