$65+ Cheap flights from Islip, NY (ISP) to Chicago (CHI)
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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Islip to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 January 21, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $105 (Frontier) |
One-way from | $65 (Cheapflightsfares) |
Find flight deals from Islip to Chicago
Cheapest flights from Islip to ChicagoExplore the most affordable flight options available from Islip to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.
Explore the most affordable flight options available from Islip to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.
This Frontier deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 2,558,603 searches. Data last updated January 21, 2025.
Fly from
Fly to
Route
Depart
Return
Price
IslipChicago
ISP - ORD
ISPORD
Islip Long Island
Wed 2/19
9:04 pm-7:09 am
1 stop11h 05m
Chicago O'Hare Intl
Wed 2/26
7:25 am-6:05 pm
1 stop9h 40m
IslipChicago
ISP - ORD
ISPORD
Islip Long Island
Wed 4/30
6:10 am-11:50 am
1 stop6h 40m
Chicago O'Hare Intl
Thu 5/1
1:50 pm-8:20 pm
1 stop5h 30m
IslipChicago
ISP - ORD
ISPORD
Islip Long Island
Fri 2/7
12:56 pm-9:34 am
3 stops21h 38m
Chicago O'Hare Intl
Sun 2/9
5:11 am-6:40 pm
2 stops12h 29m
IslipChicago
ISP - ORD
ISPORD
Islip Long Island
Fri 2/21
9:07 am-3:53 pm
1 stop7h 46m
IslipChicago
ISP - ORD
ISPORD
Islip Long Island
Sat 5/31
6:00 am-10:03 am
1 stop5h 03m
Compare providers for flights from Islip to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Islip to Chicago in January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Islip, New York-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Islip, New York-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip, New York-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Islip, New York-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Islip, New York-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Islip to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Islip with our price prediction graph.
Travel insights for flights from Islip to Chicago
Get recent, data-driven insights about flights from Islip to Chicago including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from Islip, New York to Chicago?
Currently, August 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 March is currently the most expensive (average of $320). 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.
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 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 January 21, 2025.
Comfort
Food
Boarding
Overall
Crew
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Food
Boarding
Overall
Crew
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Food
Boarding
Overall
Crew
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Food
Boarding
Overall
Crew
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
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.
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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.
Top airline flying from Islip to Chicago
Discover the top airline that operate flights from Islip to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$243 | Average$328 | FlexibilityNo cancel fee | On-time62% |