Title: £260 Cheap Flights from Islip to Chicago (ISP to ORD) - Expedia.co.uk ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # £260 Cheap Flights from Islip (ISP) to Chicago (ORD) [View £260 flight on Tue, 27 Jan 2026](https://expedia.co.uk/Flights-Search?trip=oneway&leg1=from:ISP,to:ORD,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:259.60&airProductToken=AQpaCikIuZYBEgMyMTQYyHwgwZMBKLrJgwMwmMqDAzhCQABYAWoCRVJyA0JJUAotCMJsEgM4MTEYwZMBIK4cKPPKgwMwr8yDAzhVQAFYAWoCQU5yCFVJMlFCRVk1EgoIARABGAEqAkI2GAEiBAgBEAEoAigDKAQwAQ) - [Return](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## Popular airlines from MacArthur Airport (ISP) to Chicago O'Hare International Airport (ORD) - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:ISP,to:ORD,departure:01/01/2026TANYT&leg2=from:ORD,to:ISP,departure:08/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:ISP,to:ORD,departure:01/01/2026TANYT&leg2=from:ORD,to:ISP,departure:08/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.co.uk/Flights-Search?leg1=from:ISP,to:ORD,departure:01/01/2026TANYT&leg2=from:ORD,to:ISP,departure:08/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![notification illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 25% on select hotels after you book a flight\* - ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.co.uk/login) ## Cheap Flights from Islip (ISP) to Chicago (ORD) Prices were available within the past 7 days and start at £260 for one-way flights and £435 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Return ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Tue, 27 Jan - Tue, 3 Feb ISP Islip ORD Chicago £435 Return found 5 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:27/01/2026TANYT&leg2=from:ORD,to:ISP,departure:03/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:435.00&airProductToken=AQpaCikIuZYBEgMyMTAYyHwgwZMBKInHgwMw58eDAzhCQABYAWoCRVJyA0JJUAotCMJsEgM4MTEYwZMBIK4cKPPKgwMwr8yDAzhVQAFYAWoCQU5yCFVJM0FSRVk1CosBCi0IwmwSBDEzMDYYrhwgqVEorJeEAzC0mIQDOFBAAFgBagJBTnIIUEk5UUJTWTUKLAjCbBIDMzgzGKlRIMxwKNybhAMwmJ2EAzhQQAFYAWoCQU5yCFBJMlFCRVk1CiwIwmwSAzU0NhjMcCDIfCjDoIQDMOChhAM4UEABWAFqAkFOcghQSTRQVUVZNRIKCAEQARgBKgJCNhgBIgQIARABKAIoAygEMAE) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Tue, 27 Jan - Tue, 3 Feb ISP Islip ORD Chicago £511 Return found 5 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:27/01/2026TANYT&leg2=from:ORD,to:ISP,departure:03/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:510.60&airProductToken=AQpaCikIuZYBEgMyMTQYyHwgwZMBKLrJgwMwmMqDAzhCQABYAWoCRVJyA0JJUAotCMJsEgM4MTEYwZMBIK4cKPPKgwMwr8yDAzhVQAFYAWoCQU5yCFVJM0FSRVk1CloKLQjCbBIDMzEyGK4cIMGTASi5loQDMMqXhAM4VUAAWAFqAkFOcghVSTNBUkVZNQopCLmWARIDMjE3GMGTASDIfCj3moQDMM2bhAM4QkABWAFqAkVScgNCSVASCggBEAEYASoCQjYYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from Islip (ISP) to Chicago (ORD) ### February is typically the cheapest month to fly From £83 - £583 per traveller. ## Frequently asked questions ### How much is a flight from MacArthur Airport to O'Hare Airport? ### Do I need to pay a cancellation fee if I cancel my flight from MacArthur Airport to O'Hare Airport? ### How do I find cheap flights from ISP to O'Hare Airport that have flexible change policies? ### How far is the flight from MacArthur Airport (ISP) to O'Hare Airport? ### Which airlines fly direct from MacArthur Airport to O'Hare Intl. Airport (ORD)? ### Are MacArthur Airport to ORD flight tickets cheaper when they're purchased at the last minute? ## Travel information | Origin airport | MacArthur | | ------------------- | ------------ | | Destination airport | O'Hare Intl. | | Return price | £435 | | Distance | 1233 km | ## Book with confidence # Compare flights from Islip to Chicago easily and book with confidence For travelling on business or for pleasure, Expedia makes it easy to book your flights from Islip to Chicago. Operating between them flights per day, 4 airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from MacArthur to O'Hare Intl.. To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. Grab a great deal on your flight from MacArthur (ISP) to O'Hare Intl. (ORD) The easiest way to view the best deals on flights from Islip to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from MacArthur to O'Hare Intl. start at just £435 and range up to £511\. To find an even better deal, try - being flexible on your dates – midweek flights can be cheaper - looking for other airports near Islip and Chicago - booking your flight during January, the cheapest month on this route - varying your flight times – early morning and late at night are sometimes cheaper Why you should book your Islip to Chicago flight with Expedia! We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from MacArthur to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you. Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. 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