Title: CA $265 Cheap Flights from George Town (GCM) to Chicago (CHI) - 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) # CA $265 Cheap Flights from George Town (GCM) to Chicago (CHI) [View CA $265 flight on Thu, Dec 11, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:GCM,to:ORD,departure:11/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:264.80&airProductToken=AQpaCioIzpYBEgIyMhjGYCDlWijcuf8CMLu6_wI4V0AAWAFqAlJQcgZXQTIxTlIKLAjOlgESBDE5ODYY5Vogrhwoj73_AjDbvv8COFdAAVgBagJSUHIGV0EyMU5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) - [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 Owen Roberts Intl. Airport (GCM) to Chicago - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:gcm,to:chi,departure:08/11/2025TANYT&leg2=from:chi,to:gcm,departure:15/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:gcm,to:chi,departure:08/11/2025TANYT&leg2=from:chi,to:gcm,departure:15/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:gcm,to:chi,departure:08/11/2025TANYT&leg2=from:chi,to:gcm,departure:15/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:gcm,to:chi,departure:08/11/2025TANYT&leg2=from:chi,to:gcm,departure:15/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Air Canada](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada [](https://www.expedia.ca/Flights-Search?leg1=from:gcm,to:chi,departure:08/11/2025TANYT&leg2=from:chi,to:gcm,departure:15/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![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:gcm,to:chi,departure:08/11/2025TANYT&leg2=from:chi,to:gcm,departure:15/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:gcm,to:chi,departure:08/11/2025TANYT&leg2=from:chi,to:gcm,departure:15/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) ![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 George Town (GCM) to Chicago (CHI) Prices were available within the past 7 days and start at CA $265 for one-way flights and CA $519 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Fri, Oct 31 - Sat, Nov 1 GCM Grand Cayman ORD Chicago CA $519 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:GCM,to:ORD,departure:31/10/2025TANYT&leg2=from:ORD,to:GCM,departure:01/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:518.58&airProductToken=AQpFCiAIwYYBEgM5NzMYxmAgmM4BKLrr-wIwr-37AjhHQABYAQohCMGGARIENDk2MRiYzgEgrhwo_O77AjD57_sCOEdAAVgBCkQKIAjBhgESAzUxMBiuHCCYzgEoq_r7AjCO-_sCOEdAAFgBCiAIwYYBEgM5NzIYmM4BIMZgKPv_-wIw9YH8AjhHQAFYARIKCAEQARgBKgJBQxgBIgQIARABKAgoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Oct 30 - Fri, Oct 31 GCM Grand Cayman ORD Chicago CA $568 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:GCM,to:ORD,departure:30/10/2025TANYT&leg2=from:ORD,to:GCM,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:567.40&airProductToken=AQpECiAIxJgBEgQxODcwGMZgIOBcKL3g-wIw5uH7AjhFQABYAQogCMSYARIEMTE5ORjgXCCuHCjU5PsCMMrl-wI4RUABWAEKQwogCMSYARIEMTI2NBiuHCDgXCiM6PsCMP_o-wI4RUAAWAEKHwjEmAESAzYwMBjgXCDGYCjp6fsCMInr-wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Oct 31 - Mon, Nov 3 GCM Grand Cayman ORD Chicago CA $568 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:GCM,to:ORD,departure:31/10/2025TANYT&leg2=from:ORD,to:GCM,departure:03/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:567.41&airProductToken=AQpmCjEIwYIBEgQxMTA2GMZgIIwCKMXp-wIwpOr7AjhCQABYAWoFQkFTSUNyCE9OTjdOWEJaCjEIwYIBEgQxMTU5GIwCIK4cKLLs-wIw_e37AjhCQAFYAWoFQkFTSUNyCE9OTjdOWEJaCmcKMgjBggESBDE2MzIYrhwg4poBKJSK_AIwjov8AjhCQABYAWoFQkFTSUNyCE9OTjdOWEJaCjEIwYIBEgMzMDEY4poBIMZgKMiL_AIw-Iz8AjhCQAFYAWoFQkFTSUNyCE9OTjdOWEJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Oct 28 - Wed, Nov 5 GCM Grand Cayman ORD Chicago CA $599 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:GCM,to:ORD,departure:28/10/2025TANYT&leg2=from:ORD,to:GCM,departure:05/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:598.40&airProductToken=AQpFCiAIwYIBEgMzMDEYxmAg4poBKNXJ-wIwicv7AjhPQABYAQohCMGCARIEMTE5ORjimgEgrhwo6Mv7AjDqzPsCOE9AAVgBCkMKHwjBggESAzg2NhiuHCCMAiijp_wCMOGo_AI4T0AAWAEKIAjBggESBDEzMDAYjAIgxmAo-q38AjDprvwCOE9AAVgBEgoIARABGAEqAkFBGAEiBAgBEAEoCCgEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sun, Nov 2 - Wed, Nov 5 GCM Grand Cayman ORD Chicago CA $606 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:GCM,to:ORD,departure:02/11/2025TANYT&leg2=from:ORD,to:GCM,departure:05/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:605.40&airProductToken=AQplCh8IwYIBEgMzNjcYxmAgjAIotIP8AjCRhPwCOE9AAFgBCiAIwYIBEgQyMjM2GIwCIO9ZKKWG_AIwyof8AjhPQAFYAQogCMGCARIEMTY1MhjvWSCuHCj2ifwCMJCL_AI4T0ABWAEKQwofCMGCARIDODY2GK4cIIwCKKOn_AIw4aj8AjhPQABYAQogCMGCARIEMTMwMBiMAiDGYCj6rfwCMOmu_AI4T0ABWAESCggBEAEYASoCQUEYASIECAEQASgIKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Oct 31 - Mon, Nov 3 GCM Grand Cayman ORD Chicago CA $624 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:GCM,to:ORD,departure:31/10/2025TANYT&leg2=from:ORD,to:GCM,departure:03/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:623.41&airProductToken=AQpkCjAIwYIBEgM0NzcYxmAgjAIopuv7AjCA7PsCOEJAAFgBagVCQVNJQ3IIT05ON05YQloKMAjBggESAzQ4MxiMAiCuHCik7_sCMOrw-wI4QkABWAFqBUJBU0lDcghPTk43TlhCWgpmCjEIwYIBEgQyOTg0GK4cIIwCKJSK_AIwzov8AjhCQABYAWoFQkFTSUNyCFFOTjdOWEJaCjEIwYIBEgQxMzAwGIwCIMZgKKKM_AIwkI38AjhCQAFYAWoFQkFTSUNyCFFOTjdOWEJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Oct 28 - Fri, Oct 31 GCM Grand Cayman ORD Chicago CA $651 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:GCM,to:ORD,departure:28/10/2025TANYT&leg2=from:ORD,to:GCM,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:650.40&airProductToken=AQpFCiAIwYIBEgMzMDEYxmAg4poBKNXJ-wIwicv7AjhPQABYAQohCMGCARIEMTE5ORjimgEgrhwo6Mv7AjDqzPsCOE9AAVgBCkIKHwjBggESAzc5MRiuHCCMAiiL7PsCMMbt-wI4T0AAWAEKHwjBggESAzk5MBiMAiDGYCj17fsCMNTu-wI4T0ABWAESCggBEAEYASoCQUEYASIECAEQASgIKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Oct 28 - Tue, Nov 4 GCM Grand Cayman ORD Chicago CA $669 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:GCM,to:ORD,departure:28/10/2025TANYT&leg2=from:ORD,to:GCM,departure:04/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:668.40&airProductToken=AQpFCiAIwYIBEgMzMDEYxmAg4poBKNXJ-wIwicv7AjhPQABYAQohCMGCARIEMTE5ORjimgEgrhwo6Mv7AjDqzPsCOE9AAVgBCkUKIQjBggESBDE2MzIYrhwg4poBKLSV_AIwrpb8AjhRQABYAQogCMGCARIDMzAxGOKaASDGYCjolvwCMJiY_AI4UUABWAESCggBEAEYASoCQUEYASIECAEQASgIKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Fri, Oct 31 - Mon, Nov 3 GCM Grand Cayman ORD Chicago CA $812 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:GCM,to:ORD,departure:31/10/2025TANYT&leg2=from:ORD,to:GCM,departure:03/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:811.40&airProductToken=AQpmCjEI1YIBEgQxODU0GMZgIIg4KLnt-wIw-u77AjhLQABYAWoFMl9lY29yCEtOWDdCOURTCjEI1YIBEgQxMjkzGIg4IK4cKOPv-wIw-_D7AjhLQABYAWoFMl9lY29yCEtOWDdCOURTCmUKMQjVggESBDEyMzEYrhwgiDgolov8AjDMjPwCOEtAAFgBagUyX2Vjb3IIS05YN0I5RFMKMAjVggESAzc1MxiIOCDGYCjfjfwCMIqP_AI4S0AAWAFqBTJfZWNvcghLTlg3QjlEUxIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, Oct 31 - Mon, Nov 3 GCM Grand Cayman ORD Chicago CA $966 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:GCM,to:ORD,departure:31/10/2025TANYT&leg2=from:ORD,to:GCM,departure:03/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:965.41&airProductToken=AQpdCiwIwmwSAzc2NhjGYCCpUSjB7PsCMKLu-wI4TEAAWAFqAkROcghTSTBBVUVMMQotCMJsEgQyMTA1GKlRIK4cKJX5-wIwwfr7AjhMQAFYAWoCRE5yCFBJN1FCRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) Flight from George Town to Chicago (GCM - ORD) route information | Origin airport | Owen Roberts Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $519 | | Distance | 2581 km | ## George Town to Illinois Flights **The easy way to book your flights from George Town to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from George Town whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to CHI-All Airports, 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 George Town to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Owen Roberts Intl., GCM to CHI-All Airports, CHI**  Sort your search results by price to find great deals on your flight from George Town to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from George Town currently is just CA $519 rising to CA $966.   Here are more money-saving tips:  - Fly in October 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 George Town**  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 \*Available to Expedia members.