Title: CA $163 Cheap Flights from San Francisco (SFO) 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 $163 Cheap Flights from San Francisco (SFO) to Chicago (ORD) [View CA $163 flight on Wed, Jan 28, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:SFO,to:ORD,departure:28/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:162.90&airProductToken=AQpgCi4IwaYBEgQzNDczGLJxIJJoKN3VgwMwxdaDAzhYQABYAWoCU1ZyCEdIMk9YSkJOCi4IwaYBEgQxNDkzGJJoIK4cKKbYgwMwsdqDAzhYQAFYAWoCU1ZyCEdIMk9YSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) - [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 San Francisco International Airport (SFO) to Chicago O'Hare International Airport (ORD) - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:SFO,to:ORD,departure:25/12/2025TANYT&leg2=from:ORD,to:SFO,departure:01/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![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:SFO,to:ORD,departure:25/12/2025TANYT&leg2=from:ORD,to:SFO,departure:01/01/2026TANYT&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:SFO,to:ORD,departure:25/12/2025TANYT&leg2=from:ORD,to:SFO,departure:01/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:SFO,to:ORD,departure:25/12/2025TANYT&leg2=from:ORD,to:SFO,departure:01/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:SFO,to:ORD,departure:25/12/2025TANYT&leg2=from:ORD,to:SFO,departure:01/01/2026TANYT&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:SFO,to:ORD,departure:25/12/2025TANYT&leg2=from:ORD,to:SFO,departure:01/01/2026TANYT&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:SFO,to:ORD,departure:25/12/2025TANYT&leg2=from:ORD,to:SFO,departure:01/01/2026TANYT&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 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 San Francisco (SFO) to Chicago (ORD) Prices were available within the past 7 days and start at CA $163 for one-way flights and CA $331 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 13 - Tue, Jan 20 SFO San Francisco ORD Chicago CA $331 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SFO,to:ORD,departure:13/01/2026TANYT&leg2=from:ORD,to:SFO,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:330.20&airProductToken=AQpECiAIxJgBEgQxMzMxGLJxIPISKJmqggMwiquCAzhFQABYAQogCMSYARIEMjI0NxjyEiCuHCi5q4IDMPqsggM4RUABWAEKQwofCMSYARIDOTUzGK4cIMx8KLr5ggMwnPqCAzhFQABYAQogCMSYARIEMjA3NBjMfCCycSja-oIDMNv8ggM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Fri, Jan 30 - Sun, Feb 1 SFO San Francisco ORD Chicago CA $361 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SFO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SFO,departure:01/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:360.30&airProductToken=AQpfCi4IwaYBEgQxMzQyGLJxIJIBKMbtgwMwz-6DAzhYQABYAWoCU1ZyCEdIMk9BSkJOCi0IwaYBEgM1MzgYkgEgrhwoju-DAzD-8IMDOFhAAVgBagJTVnIIR0gyT0FKQk4KXgotCMGmARIDNTg3GK4cIJIBKIiAhAMwpoKEAzhYQABYAWoCU1ZyCEdIMk9BSkJOCi0IwaYBEgM2NTUYkgEgsnEo34KEAzDog4QDOFhAAVgBagJTVnIIR0gyT0FKQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Jan 30 - Sun, Feb 1 SFO San Francisco ORD Chicago CA $362 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SFO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SFO,departure:01/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:361.30&airProductToken=AQpvCjUIxJgBEgMzMzUYsnEg47QBKL7xgwMw0fODAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCQwo2CMSYARIEMTY1NBjjtAEgrhwo5_SDAzDN9YMDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJDCm4KNQjEmAESBDM4NTQYrhwgzHwon_-DAzCHgIQDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJDCjUIxJgBEgQyMDc0GMx8ILJxKNqBhAMw24OEAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Jan 17 - Sat, Jan 24 SFO San Francisco ORD Chicago CA $363 Roundtrip found 13 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SFO,to:ORD,departure:17/01/2026TANYT&leg2=from:ORD,to:SFO,departure:24/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:362.50&airProductToken=AQpfCi4IwaYBEgQxMzQyGLJxIJIBKKbbggMwr9yCAzhYQABYAWoCU1ZyCEdIMk9BVkJOCi0IwaYBEgM1MzgYkgEgrhwo7tyCAzDe3oIDOFhAAVgBagJTVnIIT0gyT0FWQk4KXgotCMGmARIDNDA3GK4cIJIBKM-pgwMw7quDAzhYQABYAWoCU1ZyCE9IMk9BVkJOCi0IwaYBEgM1MjgYkgEgsnEogq2DAzCHroMDOFhAAVgBagJTVnIIR0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Jan 30 - Sun, Feb 1 SFO San Francisco ORD Chicago CA $363 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SFO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SFO,departure:01/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:362.90&airProductToken=AQpuCjUIxJgBEgQxNDEyGLJxIJIBKMvtgwMw1u6DAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCQwo1CMSYARIEMjEwOBiSASCuHCiT74MDMIHxgwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Jan 17 - Sat, Jan 24 SFO San Francisco ORD Chicago CA $368 Roundtrip found 13 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SFO,to:ORD,departure:17/01/2026TANYT&leg2=from:ORD,to:SFO,departure:24/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:367.90&airProductToken=AQpfCi4IwaYBEgQxMzQyGLJxIJIBKKbbggMwr9yCAzhYQABYAWoCU1ZyCEdIMk9BVkJOCi0IwaYBEgM1MzgYkgEgrhwo7tyCAzDe3oIDOFhAAVgBagJTVnIIT0gyT0FWQk4KYAouCMGmARIEMTQ3MBiuHCCSaCjEpoMDMN-ogwM4WEAAWAFqAlNWcghPSDJPWkpCTgouCMGmARIEMzA3MhiSaCCycSiSqYMDMP6pgwM4WEABWAFqAlNWcghPSDJPWkpCThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Jan 30 - Sun, Feb 1 SFO San Francisco ORD Chicago CA $378 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SFO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SFO,departure:01/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:377.56&airProductToken=AQpuCjUIxJgBEgQxNDEyGLJxIJIBKMvtgwMw1u6DAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCQwo1CMSYARIEMjEwOBiSASCuHCiT74MDMIHxgwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Jan 30 - Sun, Feb 1 SFO San Francisco ORD Chicago CA $389 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SFO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SFO,departure:01/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:389.00&airProductToken=AQozCjEIwYIBEgQyNjE0GLJxIK4cKMjpgwMw0euDAzhCQABYAWoFQkFTSUNyCE5WQUtaU0JYCjMKMQjBggESBDE0NzUYrhwgsnEoxIWEAzDqh4QDOEJAAFgBagVCQVNJQ3IITlZBS1pTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Mon, Dec 29 - Mon, Jan 5 SFO San Francisco ORD Chicago CA $538 Roundtrip found 11 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SFO,to:ORD,departure:29/12/2025TANYT&leg2=from:ORD,to:SFO,departure:05/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:537.70&airProductToken=AQpGCiEIyIIBEgQ3MDA4GLJxIO-4ASjoh4EDMNeIgQM4VUAAWAEKIQjIggESBDYzNzQY77gBIK4cKMSJgQMwtouBAzhVQAFYAQpECiAIyIIBEgQ3NDY2GK4cIJJoKLLWgQMw0NiBAzhVQABYAQogCMiCARIENjU0NBiSaCCycSjX24EDMM_cgQM4VUABWAESCggBEAEYASoCSEEYASIECAEQASgEMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Jan 17 - Sat, Jan 24 SFO San Francisco ORD Chicago CA $582 Roundtrip found 13 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SFO,to:ORD,departure:17/01/2026TANYT&leg2=from:ORD,to:SFO,departure:24/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:581.80&airProductToken=AQpdCiwIwmwSAzgxNhiycSCpUSjk14IDMK7aggM4TEAAWAFqAkROcghaSTRBUkVMMQotCMJsEgQxMzA1GKlRIK4cKKHbggMw4NyCAzhMQAFYAWoCRE5yCFBJN1FCRUwxCl4KLQjCbBIEMTMwNhiuHCCpUSjspoMDMPSngwM4TEAAWAFqAkROcghQSTlRQlNMMQotCMJsEgQyNjE1GKlRILJxKMSrgwMw1q6DAzhMQAFYAWoCRE5yCFBJMlFCRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ## Find the cheapest month to fly from San Francisco (SFO) to Chicago (ORD) ### September is typically the cheapest month to fly From CA $181 - CA $512 per traveller. ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.ca/Flights-Search?leg1=from:SFO,to:ORD,departure:25/12/2025TANYT&leg2=from:ORD,to:SFO,departure:05/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. Cheapest 23 min [Flights from CA $453 ](https://www.expedia.ca/Flights-Search?leg1=from:SFO,to:ORD,departure:25/12/2025TANYT&leg2=from:ORD,to:SFO,departure:05/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) __Flight from San Francisco to Chicago (SFO - ORD) route information__ | Origin airport | San Francisco Intl. | | ------------------- | ------------------------------------------------------------------ | | Destination airport | O'Hare Intl. | | Airlines serving | Alaska Airlines, American Airlines, Delta, JetBlue Airways, United | | Roundtrip price | CA $330 | | Distance | 2947 km | | Average flight time | 6 hours 15 mins | ## San Francisco to Chicago Flights **The easy way to book your flights from San Francisco to Chicago** With Expedia, it’s simple to find and book flights to Chicago from San Francisco 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 San Francisco to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from San Francisco Intl., SFO to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from San Francisco to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from San Francisco currently is just CA $331 rising to CA $582\. Here are more money-saving tips: - Fly in January 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 San Francisco** 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 San Francisco Airport to ORD? ### Do I need to pay a cancellation fee if I cancel my flight from SFO to ORD? ### How do I find cheap flights from SFO to O'Hare Intl. Airport (ORD) that have flexible change policies? ### How many hours is the flight from San Francisco Intl. Airport (SFO) to O'Hare Intl. Airport (ORD)? ### How far is the flight from San Francisco Airport to O'Hare Intl. Airport (ORD)? ### Which airlines fly direct from San Francisco Intl. 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[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.