Title: CA $263 Cheap Flights from Montego Bay (MBJ) 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) # CA $263 Cheap Flights from Montego Bay (MBJ) to Chicago (ORD) [View CA $263 flight on Thu, Dec 25, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:MBJ,to:ORD,departure:25/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:262.17&airProductToken=AQpVCigIzpYBEgMyNzAYrEgg5VoovdaAAzCp14ADOFBAAFgBagJSUHIDUE5SCikIzpYBEgQxOTg2GOVaIK4cKN7agAMwptyAAzhQQAFYAWoCUlByA1BOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) - [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 Sir Donald Sangster Intl. Airport (MBJ) to Chicago O'Hare International Airport (ORD) - ![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:MBJ,to:ORD,departure:27/12/2025TANYT&leg2=from:ORD,to:MBJ,departure:03/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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:MBJ,to:ORD,departure:27/12/2025TANYT&leg2=from:ORD,to:MBJ,departure:03/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![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:MBJ,to:ORD,departure:27/12/2025TANYT&leg2=from:ORD,to:MBJ,departure:03/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:MBJ,to:ORD,departure:27/12/2025TANYT&leg2=from:ORD,to:MBJ,departure:03/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![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:MBJ,to:ORD,departure:27/12/2025TANYT&leg2=from:ORD,to:MBJ,departure:03/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![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:MBJ,to:ORD,departure:27/12/2025TANYT&leg2=from:ORD,to:MBJ,departure:03/01/2026TANYT&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:MBJ,to:ORD,departure:27/12/2025TANYT&leg2=from:ORD,to:MBJ,departure:03/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![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 Montego Bay (MBJ) to Chicago (ORD) Prices were available within the past 7 days and start at CA $263 for one-way flights and CA $483 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Apr 7 - Tue, Apr 14 MBJ Montego Bay ORD Chicago CA $483 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:07/04/2026TANYT&leg2=from:ORD,to:MBJ,departure:14/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:482.18&airProductToken=AQqbAQoxCMGCARIEMjYxMxisSCCMAiia3okDMIPfiQM4QkAAWAFqBUJBU0lDcghPTlUyQVhCWgoyCMGCARIEMzI5MxiMAiCjsQEopOCJAzDv4YkDOEJAAVgBagVCQVNJQ3IIT05VMkFYQloKMgjBggESBDExMjAYo7EBIK4cKNDliQMw4-aJAzhCQAFYAWoFQkFTSUNyCE9OVTJBWEJaCmYKMQjBggESBDE2NTIYrhwg71kogamKAzD6qYoDOEJAAFgBagVCQVNJQ3IIT05VMkFYQloKMQjBggESBDExNTkY71kgrEgopqqKAzCHrIoDOEJAAVgBagVCQVNJQ3IIT05VMkFYQloSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Jan 8 - Sun, Jan 18 MBJ Montego Bay ORD Chicago CA $483 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:08/01/2026TANYT&leg2=from:ORD,to:MBJ,departure:18/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:482.20&airProductToken=AQpECiAIxJgBEgQxODkzGKxIIMx8KLH1gQMw3_eBAzhFQABYAQogCMSYARIEMTU0NBjMfCCuHCjn_IEDMND9gQM4RUABWAEKRAogCMSYARIEMTI2NBiuHCDgXCiy4YIDMLTiggM4RUAAWAEKIAjEmAESBDE5OTcY4FwgrEgog-OCAzCy5IIDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Jan 8 - Thu, Jan 22 MBJ Montego Bay ORD Chicago CA $525 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:08/01/2026TANYT&leg2=from:ORD,to:MBJ,departure:22/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:524.20&airProductToken=AQpECiAIxJgBEgQxODkzGKxIIMx8KLH1gQMw3_eBAzhFQABYAQogCMSYARIEMTU0NBjMfCCuHCjn_IEDMND9gQM4RUABWAEKRAogCMSYARIEMjg3ORiuHCDgXCiXlYMDMJmWgwM4RUAAWAEKIAjEmAESBDE4MDEY4FwgrEgou5qDAzDtm4MDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Apr 7 - Tue, Apr 14 MBJ Montego Bay ORD Chicago CA $539 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:07/04/2026TANYT&leg2=from:ORD,to:MBJ,departure:14/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:538.18&airProductToken=AQqbAQoxCMGCARIEMjYxMxisSCCMAiia3okDMIPfiQM4QkAAWAFqBUJBU0lDcghPTlUyQVhCWgoyCMGCARIEMzI5MxiMAiCjsQEopOCJAzDv4YkDOEJAAVgBagVCQVNJQ3IIT05VMkFYQloKMgjBggESBDExMjAYo7EBIK4cKNDliQMw4-aJAzhCQAFYAWoFQkFTSUNyCE9OVTJBWEJaCmgKMgjBggESBDI4NDIYrhwg4poBKKKoigMwn6mKAzhCQABYAWoFQkFTSUNyCFFOVTJBWEJaCjIIwYIBEgQxNjE2GOKaASCsSCjMqYoDMIWrigM4QkABWAFqBUJBU0lDcghRTlUyQVhCWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Apr 7 - Tue, Apr 14 MBJ Montego Bay ORD Chicago CA $547 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:07/04/2026TANYT&leg2=from:ORD,to:MBJ,departure:14/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:546.18&airProductToken=AQqYAQowCMGCARIEMjYxMxisSCCMAiia3okDMIPfiQM4T0AAWAFqBE1BSU5yCE9OVTJBWE0xCjEIwYIBEgQzMjkzGIwCIKOxASik4IkDMO_hiQM4T0ABWAFqBE1BSU5yCE9OVTJBWE0xCjEIwYIBEgQxMTIwGKOxASCuHCjQ5YkDMOPmiQM4T0ABWAFqBE1BSU5yCE9OVTJBWE0xCmQKMAjBggESBDE2NTIYrhwg71kogamKAzD6qYoDOE9AAFgBagRNQUlOcghPTlUyQVhNMQowCMGCARIEMTE1ORjvWSCsSCimqooDMIesigM4T0ABWAFqBE1BSU5yCE9OVTJBWE0xEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Apr 7 - Tue, Apr 14 MBJ Montego Bay ORD Chicago CA $550 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:07/04/2026TANYT&leg2=from:ORD,to:MBJ,departure:14/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:549.30&airProductToken=AQqaAQowCMGCARIDODQyGKxIIIwCKO_eiQMw3d-JAzhCQABYAWoFQkFTSUNyCE9OVTJBWEJaCjIIwYIBEgQxOTUwGIwCIKOxASja4IkDMKLiiQM4QkABWAFqBUJBU0lDcghPTlUyQVhCWgoyCMGCARIEMjg5NhijsQEgrhwor-aJAzDH54kDOEJAAVgBagVCQVNJQ3IIT05VMkFYQloSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Apr 7 - Tue, Apr 14 MBJ Montego Bay ORD Chicago CA $558 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:07/04/2026TANYT&leg2=from:ORD,to:MBJ,departure:14/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:557.28&airProductToken=AQpaCisIzpYBEgMyNzAYrEgg5Voo3NyJAzDF3YkDOEdAAFgBagJSUHIGR0EyMU5SCisIzpYBEgMyMTIY5Vogrhwomd6JAzDl34kDOEdAAVgBagJSUHIGR0EyMU5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Apr 7 - Tue, Apr 14 MBJ Montego Bay ORD Chicago CA $566 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:07/04/2026TANYT&leg2=from:ORD,to:MBJ,departure:14/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:565.08&airProductToken=AQpaCisIzpYBEgMyNzAYrEgg5Voo3NyJAzDF3YkDOEdAAFgBagJSUHIGR0EyMU5SCisIzpYBEgMyMTIY5Vogrhwomd6JAzDl34kDOEdAAVgBagJSUHIGR0EyMU5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Apr 7 - Tue, Apr 14 MBJ Montego Bay ORD Chicago CA $619 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:07/04/2026TANYT&leg2=from:ORD,to:MBJ,departure:14/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:618.98&airProductToken=AQpdCiwIwmwSAzE4MBisSCCpUSji34kDMMvhiQM4TEAAWAFqAkROcghQSTJBQkVMMQotCMJsEgQxMzA1GKlRIK4cKILriQMwueyJAzhMQAFYAWoCRE5yCFVJMkFCRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Jan 7 - Fri, Jan 16 MBJ Montego Bay ORD Chicago CA $787 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:07/01/2026TANYT&leg2=from:ORD,to:MBJ,departure:16/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:786.88&airProductToken=AQpECiAIwYYBEgM5ODMYrEggmM4BKPbogQMw9eqBAzhMQABYAQogCMGGARIDNTA1GJjOASCuHCjB84EDMLX0gQM4TEABWAEKRQohCMGGARIENDk5NBiuHCCYzgEo_NCCAzDt0YIDOEdAAFgBCiAIwYYBEgM5ODIYmM4BIKxIKPvWggMw-tiCAzhHQAFYARIKCAEQARgBKgJBQxgBIgQIARABKAgoBDAB) ## Find the cheapest month to fly from Montego Bay (MBJ) to Chicago (ORD) ### October is typically the cheapest month to fly From CA $316 - CA $696 per traveller. __Flight from Montego Bay to Chicago (MBJ - ORD) route information__ | Origin airport | Sir Donald Sangster Intl. | | ------------------- | ------------------------- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $482 | | Distance | 2760 km | | Average flight time | 4 hours 47 mins | ## Montego Bay to Chicago Flights **The easy way to book your flights from Montego Bay to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Montego Bay 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 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 Montego Bay to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Sir Donald Sangster Intl., MBJ to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Montego Bay to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Montego Bay currently is just CA $483 rising to CA $787\. Here are more money-saving tips: - Fly in April 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 Montego Bay** 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. ## Frequently asked questions ### How much is a flight from MBJ to O'Hare Airport? ### Do I need to pay a cancellation fee if I cancel my flight from MBJ to O'Hare Airport? ### How do I find cheap flights from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD) that have flexible change policies? ### How many hours is the flight from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Airport? ### How far is the flight from Sangster Intl. Airport to O'Hare Airport? ### Which airlines fly direct from Sangster Intl. Airport to O'Hare Airport? ### Are MBJ to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? ## Explore a world of travel with Expedia - Flights ### 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) - 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[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.