Title: Cheap Flights from Islip (ISP) to Chicago (ORD) - Expedia.ca ![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) # Cheap Flights from Islip (ISP) to Chicago (ORD) - [Roundtrip](?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) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:isp,to:ord,departure:10/11/2025TANYT&leg2=from:ord,to:isp,departure:17/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:isp,to:ord,departure:10/11/2025TANYT&leg2=from:ord,to:isp,departure:17/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:isp,to:ord,departure:10/11/2025TANYT&leg2=from:ord,to:isp,departure:17/11/2025TANYT&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 30% 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.ca/login) ## Cheap flights from Islip (ISP) to Chicago (ORD) Prices were available within the past 7 days and start at for one-way flights and CA $1,148 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,148 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1148.00&airProductToken=AQpaCikIuZYBEgMyMTAYyHwgwZMBKK77_AIwjPz8AjhTQABYAWoCRVJyA1NJUAotCMJsEgM4MTEYwZMBIK4cKKf__AIw24D9AjhPQAFYAWoCQU5yCE9JNEFSRVk1CokBCi0IwmwSBDEzMDYYrhwgqVEo_Mr9AjCDzP0COFBAAFgBagJBTnIIUEk0UUJFWTUKLQjCbBIDNjE4GKlRIMGTASjzzf0CMMDO_QI4UEABWAFqAkFOcghQSTRRQkVZNQopCLmWARIDMjE3GMGTASDIfCiXz_0CMO3P_QI4U0ABWAFqAkVScgNTSVASCggBEAEYASoCQjYYASIECAEQASgCKAMoBDAB) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,181 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1180.50&airProductToken=AQpjCikIuZYBEgMyMTAYyHwgwZMBKK77_AIwjPz8AjhTQABYAWoCRVJyA1NJUAo2CMSYARIEMjY3ORjBkwEgrhwo6f38AjCf__wCOFhAAVgBaglNQUlOQ0xBU0NyCFhBVVNYME1FCmMKNgjEmAESBDE2MDIYrhwgwZMBKLbK_QIwx8v9AjhUQABYAWoJTUFJTkNMQVNDcghURFZOWDBNTAopCLmWARIDMjEzGMGTASDIfCi7zf0CMJvO_QI4U0ABWAFqAkVScgNTSVASCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,195 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1194.50&airProductToken=AQpaCikIuZYBEgMyMTQYyHwgwZMBKOT9_AIwwv78AjhTQABYAWoCRVJyA1NJUAotCMJsEgM4MTEYwZMBIK4cKKf__AIw24D9AjhPQAFYAWoCQU5yCE9JNEFSRVk1CloKLQjCbBIDMzEyGK4cIMGTASj0zP0CMIbO_QI4TUAAWAFqAkFOcghNSTdBUkVZNQopCLmWARIDMjE3GMGTASDIfCiXz_0CMO3P_QI4U0ABWAFqAkVScgNTSVASCggBEAEYASoCQjYYASIECAEQASgCKAMoBDAB) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,208 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1207.40&airProductToken=AQpdCikIuZYBEgMyMTAYyHwgwZMBKK77_AIwjPz8AjhTQABYAWoCRVJyA1NJUAowCMGCARIDODMyGMGTASCuHCii_vwCMNr__AI4UUABWAFqBE1BSU5yCFFVQUpYU00zCl4KMQjBggESBDM3MTAYrhwgwZMBKPDJ_QIwgMv9AjhOQABYAWoETUFJTnIITlVESFpOTTMKKQi5lgESAzIxMxjBkwEgyHwou839AjCbzv0COFNAAVgBagJFUnIDU0lQEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwAQ) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,237 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1236.20&airProductToken=AQpeCikIuZYBEgMyMTIYyHwgwZMBKMP8_AIwmP38AjhTQABYAWoCRVJyA1NJUAoxCMGCARIEMjUwNBjBkwEgrhwo84D9AjCtgv0COFFAAVgBagRNQUlOcghRVUFKWFNNMwqPAQovCMGCARIDOTcwGK4cIO9ZKJ_K_QIwk8v9AjhOQABYAWoETUFJTnIITjdBSlpTTTMKMQjBggESBDI2MTUY71kgwZMBKODL_QIwssz9AjhOQAFYAWoETUFJTnIITjdBSlpTTTMKKQi5lgESAzIxMxjBkwEgyHwou839AjCbzv0COFNAAVgBagJFUnIDU0lQEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwAQ) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,262 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1261.10&airProductToken=AQpeCikIuZYBEgMyMTQYyHwgwZMBKOT9_AIwwv78AjhTQABYAWoCRVJyA1NJUAoxCMGCARIENDM5MhjBkwEgrhworv_8AjD4gP0COFNAAVgBagRNQUlOcghTN0FaWlNNMwpeCjEIwYIBEgQzNzEwGK4cIMGTASjwyf0CMIDL_QI4TkAAWAFqBE1BSU5yCE5VREhaTk0zCikIuZYBEgMyMTMYwZMBIMh8KLvN_QIwm879AjhTQAFYAWoCRVJyA1NJUBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAE) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,264 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1263.30&airProductToken=AQpdCikIuZYBEgMyMTAYyHwgwZMBKK77_AIwjPz8AjhTQABYAWoCRVJyA1NJUAowCMGCARIDODMyGMGTASCuHCii_vwCMNr__AI4UUABWAFqBE1BSU5yCFFVQUpYU00zCl4KMQjBggESBDQ2MDYYrhwgwZMBKKPK_QIwtsv9AjhHQABYAWoETUFJTnIIR1VBSlpTTTMKKQi5lgESAzIxMxjBkwEgyHwou839AjCbzv0COFNAAVgBagJFUnIDU0lQEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwAQ) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,289 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1288.80&airProductToken=AQpeCikIuZYBEgMyMTQYyHwgwZMBKOT9_AIwwv78AjhTQABYAWoCRVJyA1NJUAoxCMGCARIENDM5MhjBkwEgrhworv_8AjD4gP0COFNAAVgBagRNQUlOcghTN0FaWlNNMwqPAQovCMGCARIDOTcwGK4cIO9ZKJ_K_QIwk8v9AjhOQABYAWoETUFJTnIITjdBSlpTTTMKMQjBggESBDI2MTUY71kgwZMBKODL_QIwssz9AjhOQAFYAWoETUFJTnIITjdBSlpTTTMKKQi5lgESAzIxMxjBkwEgyHwou839AjCbzv0COFNAAVgBagJFUnIDU0lQEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwAQ) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,291 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1290.10&airProductToken=AQpeCikIuZYBEgMyMTAYyHwgwZMBKK77_AIwjPz8AjhTQABYAWoCRVJyA1NJUAoxCMGCARIEMzc5ORjBkwEgrhwow_z8AjD7_fwCOEdAAVgBagRNQUlOcghHVUJKWlNNMwpeCjEIwYIBEgQzNzEwGK4cIMGTASjwyf0CMIDL_QI4TkAAWAFqBE1BSU5yCE5VREhaTk0zCikIuZYBEgMyMTMYwZMBIMh8KLvN_QIwm879AjhTQAFYAWoCRVJyA1NJUBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAE) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,317 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1317.00&airProductToken=AQpeCikIuZYBEgMyMTQYyHwgwZMBKOT9_AIwwv78AjhTQABYAWoCRVJyA1NJUAoxCMGCARIENDM5MhjBkwEgrhworv_8AjD4gP0COFNAAVgBagRNQUlOcghTN0FaWlNNMwpeCjEIwYIBEgQ0NjA2GK4cIMGTASijyv0CMLbL_QI4R0AAWAFqBE1BSU5yCEdVQUpaU00zCikIuZYBEgMyMTMYwZMBIMh8KLvN_QIwm879AjhTQAFYAWoCRVJyA1NJUBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAE) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,318 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1317.90&airProductToken=AQpeCikIuZYBEgMyMTAYyHwgwZMBKK77_AIwjPz8AjhTQABYAWoCRVJyA1NJUAoxCMGCARIEMzc5ORjBkwEgrhwow_z8AjD7_fwCOEdAAVgBagRNQUlOcghHVUJKWlNNMwqPAQovCMGCARIDOTcwGK4cIO9ZKJ_K_QIwk8v9AjhOQABYAWoETUFJTnIITjdBSlpTTTMKMQjBggESBDI2MTUY71kgwZMBKODL_QIwssz9AjhOQAFYAWoETUFJTnIITjdBSlpTTTMKKQi5lgESAzIxMxjBkwEgyHwou839AjCbzv0COFNAAVgBagJFUnIDU0lQEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwAQ) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,345 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1344.70&airProductToken=AQpdCikIuZYBEgMyMTIYyHwgwZMBKMP8_AIwmP38AjhTQABYAWoCRVJyA1NJUAowCMGCARIDODMyGMGTASCuHCii_vwCMNr__AI4UUABWAFqBE1BSU5yCFFVQUpYU00zCo4BCi8IwYIBEgQzNjYxGK4cIEMo6cr9AjDfy_0COExAAFgBagRNQUlOcghMVkRKWk5NMQowCMGCARIEMTI0MhhDIMGTASiBzP0CMNrM_QI4TEABWAFqBE1BSU5yCExWREpaTk0xCikIuZYBEgMyMTMYwZMBIMh8KLvN_QIwm879AjhTQAFYAWoCRVJyA1NJUBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAE) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Nov 13 - Thu, Nov 20 ISP Islip ORD Chicago CA $1,346 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ISP,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:ISP,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1346.00&airProductToken=AQpeCikIuZYBEgMyMTAYyHwgwZMBKK77_AIwjPz8AjhTQABYAWoCRVJyA1NJUAoxCMGCARIEMzc5ORjBkwEgrhwow_z8AjD7_fwCOEdAAVgBagRNQUlOcghHVUJKWlNNMwpeCjEIwYIBEgQ0NjA2GK4cIMGTASijyv0CMLbL_QI4R0AAWAFqBE1BSU5yCEdVQUpaU00zCikIuZYBEgMyMTMYwZMBIMh8KLvN_QIwm879AjhTQAFYAWoCRVJyA1NJUBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAE) ## Find the cheapest month to fly from Islip (ISP) to Chicago (ORD) ### February is typically the cheapest month to fly From CA $153 - CA $1,098 per traveller. ## Frequently asked questions ### How much is a flight from MacArthur Airport (ISP) to ORD? > Within the past 7 days on Expedia, for flights departing within the next year, the lowest price quoted for a round-trip journey from MacArthur Airport (ISP) to O'Hare Intl. Airport (ORD) was CA $1,148. Cheap fares don't wait forever, so book yours today. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from MacArthur Airport (ISP) to ORD? > Each air carrier has its own set of terms and conditions. If you do decide to cancel, follow the simple instructions on our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from MacArthur Airport to O'Hare Intl. Airport (ORD) that have flexible change policies? > Many airlines will allow you to move your flight at no extra charge. All you pay is the difference in the ticket price. When looking for MacArthur Airport to ORD flights, you'll find a "No change fees" box for you to select. ### How many hours is the flight from ISP to ORD? > The flight time between ISP and ORD is 5 hours and 49 minutes. If you're travelling with kids, it's always a good idea to pack some healthy snacks in your carry-on baggage. ### How far is the flight from ISP to O'Hare Intl. Airport (ORD)? > With a flight distance of 1,250 kilometres, it's only a short hop from MacArthur Airport (ISP) to O'Hare Airport. It might be a quick flight, but it's still worth packing something to keep you entertained on board. ### Which airlines fly direct from MacArthur Airport (ISP) to O'Hare Intl. Airport (ORD)? > You won't find any airlines operating directly between ISP and O'Hare Airport, so be ready to make at least one stop on your journey. A layover can be a good way to break up a trip! ### Are MacArthur Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute? > Booking your trip from MacArthur Airport to ORD last minute could be your ticket to an awesome deal. However, it could end up costing you a whole lot more! If you'd rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains up to a year in advance. If your preferred air carrier hasn't released tickets yet, check back frequently as deals are updated all the time on Expedia. ## Travel information | Origin airport | MacArthur | | --- | --- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $1,148 | | Distance | 1233 km | ## Book with confidence ### Ronkonkoma to Chicago Flights **The easy way to book your flights from Islip to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Islip whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 13 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.   Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Islip to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from MacArthur, ISP to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Islip to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Islip currently is just CA $1,148 rising to CA $1,346.   Here are more money-saving tips:  - Fly in November when flight prices are normally at their lowest  - Book about a month to 6 weeks before you travel for the best prices to Chicago   - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times  - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!  **Reasons to choose Expedia for your flight to Chicago from Islip**  Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today. ## Explore a world of travel with Expedia - Flights - [Flights from Calgary to Rosemont](https://www.expedia.ca/lp/flights/178245/7581/calgary-to-rosemont) - [Flights from Denver to Northwest Chicago](https://www.expedia.ca/lp/flights/178254/6350697/denver-to-northwest-chicago) - [Flights from Los Angeles to Evanston](https://www.expedia.ca/lp/flights/178280/8049/los-angeles-to-evanston) - [Flights from Mexico City to Northwest Chicago](https://www.expedia.ca/lp/flights/178285/6350697/mexico-city-to-northwest-chicago) - [Flights from New York to Evanston](https://www.expedia.ca/lp/flights/178293/8049/new-york-to-evanston) - [Flights from Ottawa to Evanston](https://www.expedia.ca/lp/flights/178296/8049/ottawa-to-evanston) - [Flights from Philadelphia to Rosemont](https://www.expedia.ca/lp/flights/178297/7581/philadelphia-to-rosemont) - [Flights from Portland to Rosemont](https://www.expedia.ca/lp/flights/178299/7581/portland-to-rosemont) - [Flights from San Francisco to Evanston](https://www.expedia.ca/lp/flights/178305/8049/san-francisco-to-evanston) - [Flights from Seattle to Rosemont](https://www.expedia.ca/lp/flights/178307/7581/seattle-to-rosemont) - [Flights from Washington to Evanston](https://www.expedia.ca/lp/flights/178318/8049/washington-to-evanston) - [Flights from Lincoln to Rush Street](https://www.expedia.ca/lp/flights/602964/6175183/lincoln-to-rush-street) - [Flights from Winnipeg to Rosemont](https://www.expedia.ca/lp/flights/6141041/7581/winnipeg-to-rosemont) - [Flights from Ashland (AHM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ahm/chi/ashland-to-chicago) - [Flights from Ann Arbor (ARB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/arb/mdw/ann-arbor-to-chicago) - [Flights from Aspen (ASE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ase/mdw/aspen-to-chicago) - [Flights from Atlanta (ATL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/atl/mdw/atlanta-to-chicago) - [Flights from Aurora (AUZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/auz/mdw/aurora-to-chicago) - [Flights from Hartford (BDL) to Chicago (CHI)](https://www.expedia.ca/lp/flights/bdl/chi/hartford-to-chicago) - [Flights from León (BJX) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bjx/mdw/leon-to-chicago) - [Flights from Bellingham (BLI) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bli/mdw/bellingham-to-chicago) - [Flights from Belleville (BLV) to Chicago (CHI)](https://www.expedia.ca/lp/flights/blv/chi/belleville-to-chicago) - [Flights from Boston (BOS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bos/mdw/boston-to-chicago) - [Flights from Burlington (BTV) to Chicago (CHI)](https://www.expedia.ca/lp/flights/btv/chi/burlington-to-chicago) - [Flights from Burlington (BTV) to Chicago (MDW)](https://www.expedia.ca/lp/flights/btv/mdw/burlington-to-chicago) - [Flights from Buffalo (BUF) to Chicago (CHI)](https://www.expedia.ca/lp/flights/buf/chi/buffalo-to-chicago) - [Flights from Buffalo (BUF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/buf/mdw/buffalo-to-chicago) - [Flights from Baltimore (BWI) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bwi/mdw/baltimore-to-chicago) - [Flights from Blaine (BWS) to Chicago (CHI)](https://www.expedia.ca/lp/flights/bws/chi/blaine-to-chicago) - [Flights from Belize City (BZE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bze/mdw/belize-city-to-chicago) - [Flights from Charleston (CHS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/chs/mdw/charleston-to-chicago) - [Flights from Cleveland (CLE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/cle/mdw/cleveland-to-chicago) - [Flights from Danville (DAN) to Chicago (CHI)](https://www.expedia.ca/lp/flights/dan/chi/danville-to-chicago) - [Flights from Delhi (DEL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/del/mdw/delhi-to-chicago) - [Flights from Des Moines (DSM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dsm/mdw/des-moines-to-chicago) - [Flights from Detroit (DTW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dtw/mdw/detroit-to-chicago) - [Flights from Detroit (DTW) to Chicago (PWK)](https://www.expedia.ca/lp/flights/dtw/pwk/detroit-to-chicago) - [Flights from Exeter (EXT) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ext/chi/exeter-to-chicago) - [Flights from Fishers Island (FID) to Chicago (MDW)](https://www.expedia.ca/lp/flights/fid/mdw/fishers-island-to-chicago) - [Flights from Flint (FNT) to Waukegan (UGN)](https://www.expedia.ca/lp/flights/fnt/ugn/flint-to-waukegan) - [Flights from Green Bay (GRB) to Waukegan (UGN)](https://www.expedia.ca/lp/flights/grb/ugn/green-bay-to-waukegan) - [Flights from Grand Rapids (GRR) to Chicago (PWK)](https://www.expedia.ca/lp/flights/grr/pwk/grand-rapids-to-chicago) - [Flights from Gary (GYY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/gyy/chi/gary-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/iag/chi/niagara-falls-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/iag/mdw/niagara-falls-to-chicago) - [Flights from Wilmington (ILM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ilm/chi/wilmington-to-chicago) - [Flights from Indianapolis (IND) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ind/chi/indianapolis-to-chicago) - [Flights from Nakhon Phanom (KOP) to Chicago (MDW)](https://www.expedia.ca/lp/flights/kop/mdw/nakhon-phanom-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/las/mdw/las-vegas-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (CHI)](https://www.expedia.ca/lp/flights/lax/chi/los-angeles-to-chicago) - [Flights from Montego Bay (MBJ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mbj/mdw/montego-bay-to-chicago) - [Flights from Orlando (MCO) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mco/mdw/orlando-to-chicago) - [Flights from Michigan City (MGC) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mgc/mdw/michigan-city-to-chicago) - [Flights from Muscle Shoals (MSL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/msl/mdw/muscle-shoals-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (CHI)](https://www.expedia.ca/lp/flights/msp/chi/minneapolis-to-chicago) - [Flights from New York (NYC) to Chicago (CHI)](https://www.expedia.ca/lp/flights/nyc/chi/new-york-to-chicago) - [Flights from Omaha (OMA) to Chicago (MDW)](https://www.expedia.ca/lp/flights/oma/mdw/omaha-to-chicago) - [Flights from Chicago (ORD) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ord/chi/chicago-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/phl/mdw/philadelphia-to-chicago) - [Flights from Pueblo (PUB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/pub/mdw/pueblo-to-chicago) - [Flights from Punta Cana (PUJ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/puj/chi/punta-cana-to-chicago) - [Flights from Roanoke (ROA) to Chicago (MDW)](https://www.expedia.ca/lp/flights/roa/mdw/roanoke-to-chicago) - [Flights from Selinsgrove (SEG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/seg/mdw/selinsgrove-to-chicago) - [Flights from Sacramento (SMF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/smf/mdw/sacramento-to-chicago) - [Flights from St. Louis (STL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/stl/mdw/st-louis-to-chicago) - [Flights from Newburgh (SWF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/swf/mdw/newburgh-to-chicago) - [Flights from Sydney (SYD) to Chicago (MDW)](https://www.expedia.ca/lp/flights/syd/mdw/sydney-to-chicago) - [Flights from Syracuse (SYR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/syr/mdw/syracuse-to-chicago) - [Flights from Fort Leonard Wood (TBN) to Chicago (MDW)](https://www.expedia.ca/lp/flights/tbn/mdw/fort-leonard-wood-to-chicago) - [Flights from Ua Pou (UAP) to Chicago (CHI)](https://www.expedia.ca/lp/flights/uap/chi/ua-pou-to-chicago) - [Flights from Fort Frances (YAG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yag/chi/fort-frances-to-chicago) - [Flights from Brandon (YBR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ybr/mdw/brandon-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ycd/chi/nanaimo-to-chicago) - [Flights from St. Catharines (YCM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ycm/chi/st-catharines-to-chicago) - [Flights from Edmonton (YEA) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yea/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yeg/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yeg/mdw/edmonton-to-chicago) - [Flights from Flin Flon (YFO) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yfo/chi/flin-flon-to-chicago) - [Flights from Hamilton (YHM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yhm/mdw/hamilton-to-chicago) - [Flights from Kamloops (YKA) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yka/chi/kamloops-to-chicago) - [Flights from Kelowna (YLW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ylw/mdw/kelowna-to-chicago) - [Flights from Montreal (YMQ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ymq/chi/montreal-to-chicago) - [Flights from Ottawa (YOW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago) - [Flights from Peterborough (YPQ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ypq/mdw/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqb/mdw/quebec-to-chicago) - [Flights from Regina (YQR) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yqr/chi/regina-to-chicago) - [Flights from Regina (YQR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqr/mdw/regina-to-chicago) - [Flights from Gander (YQX) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yqx/chi/gander-to-chicago) - [Flights from Sudbury (YSB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago) - [Flights from Timmins (YTS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago) - [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Montreal (YUL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (PWK)](https://www.expedia.ca/lp/flights/ywg/pwk/winnipeg-to-chicago) - [Flights from Whitehorse (YXY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yxy/chi/whitehorse-to-chicago) - [Flights from Calgary (YYC) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-to-chicago) - [Flights from Victoria (YYJ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yyj/chi/victoria-to-chicago) - [Flights from St. John's (YYT) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yyt/chi/st-johns-to-chicago) - [Flights from Toronto (YYZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (PWK)](https://www.expedia.ca/lp/flights/yyz/pwk/toronto-to-chicago) \*Available to Expedia members.