Title: CA $232 Cheap Flights from Vancouver (YVR) 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 $232 Cheap Flights from Vancouver (YVR) to Chicago (ORD) [View CA $232 flight on Tue, Jun 2, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YVR,to:ORD,departure:02/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:231.28&airProductToken=AQpmCjEI16YBEgMxMDIYuI0BIJgWKOzQjgMwxtGOAzhFQABYAWoFQkFTSUNyCExUVkQwWkJLCjEI16YBEgQxNjEwGJgWIK4cKKfTjgMw99SOAzhFQAFYAWoFQkFTSUNyCExUVkQwWkJLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) - [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 Vancouver International Airport (YVR) 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:YVR,to:ORD,departure:24/12/2025TANYT&leg2=from:ORD,to:YVR,departure:31/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![Porter Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_PD.svg) Porter Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:YVR,to:ORD,departure:24/12/2025TANYT&leg2=from:ORD,to:YVR,departure:31/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) - ![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:YVR,to:ORD,departure:24/12/2025TANYT&leg2=from:ORD,to:YVR,departure:31/12/2025TANYT&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:YVR,to:ORD,departure:24/12/2025TANYT&leg2=from:ORD,to:YVR,departure:31/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![WestJet](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WS.svg) WestJet [](https://www.expedia.ca/Flights-Search?leg1=from:YVR,to:ORD,departure:24/12/2025TANYT&leg2=from:ORD,to:YVR,departure:31/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![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:YVR,to:ORD,departure:24/12/2025TANYT&leg2=from:ORD,to:YVR,departure:31/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![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:YVR,to:ORD,departure:24/12/2025TANYT&leg2=from:ORD,to:YVR,departure:31/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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 Vancouver (YVR) to Chicago (ORD) Prices were available within the past 7 days and start at CA $232 for one-way flights and CA $355 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Mon, Feb 2 - Tue, Feb 10 YVR Vancouver ORD Chicago CA $355 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:02/02/2026TANYT&leg2=from:ORD,to:YVR,departure:10/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:354.42&airProductToken=AQpECiEIwaYBEgQyMzY5GLiNASCSASjXkYQDMJeShAM4WEAAWAEKHwjBpgESAzI2NRiSASCuHCjel4QDMNaZhAM4WEABWAEKRAofCMGmARIDNDA3GK4cIJIBKO_ohAMwjuuEAzhYQABYAQohCMGmARIEMjA0MRiSASC4jQEo6-uEAzCn7IQDOFhAAVgBEgoIARABGAEqAkFTGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 20 - Tue, Jan 27 YVR Vancouver ORD Chicago CA $360 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:YVR,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:359.03&airProductToken=AQpvCjYIxJgBEgQzNzY0GLiNASCSASjC_YIDMIj-ggM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQlEKNQjEmAESBDIxMDgYkgEgrhwo0_6CAzDBgIMDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNDMkJDCm8KNQjEmAESBDIwNDEYrhwgkgEoyseDAzDnyYMDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNDMkJDCjYIxJgBEgQzNjgyGJIBILiNASihzYMDMOTNgwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 20 - Tue, Jan 27 YVR Vancouver ORD Chicago CA $366 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:YVR,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:365.81&airProductToken=AQpvCjYIxJgBEgQzNzY0GLiNASCSASjC_YIDMIj-ggM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQlEKNQjEmAESBDIxMDgYkgEgrhwo0_6CAzDBgIMDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNDMkJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Jan 20 - Tue, Jan 27 YVR Vancouver ORD Chicago CA $369 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:YVR,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:368.25&airProductToken=AQpgCi8IwaYBEgQzMDA4GLiNASCSASiI-YIDMNP5ggM4WEAAWAFqAlNWcghHSDJUWFZCTgotCMGmARIDMjY1GJIBIK4cKJ76ggMwlvyCAzhYQAFYAWoCU1ZyCEdIMk9EVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Jan 13 - Fri, Jan 23 YVR Vancouver ORD Chicago CA $382 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:13/01/2026TANYT&leg2=from:ORD,to:YVR,departure:23/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:381.05&airProductToken=AQpECiEIwaYBEgQyMDQyGLiNASCSASibq4IDMNqrggM4WEAAWAEKHwjBpgESAzQxMBiSASCuHCjUrIIDMM6uggM4WEABWAEKRAofCMGmARIDNDA5GK4cIJIBKMafgwMw6KGDAzhYQABYAQohCMGmARIEMzMxORiSASC4jQEozKiDAzCOqYMDOFhAAVgBEgoIARABGAEqAkFTGAEiBAgBEAEoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Mon, Feb 2 - Thu, Feb 5 YVR Vancouver ORD Chicago CA $386 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:02/02/2026TANYT&leg2=from:ORD,to:YVR,departure:05/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:385.54&airProductToken=AQpECiEIwaYBEgQyMzY5GLiNASCSASjXkYQDMJeShAM4WEAAWAEKHwjBpgESAzI2NRiSASCuHCjel4QDMNaZhAM4WEABWAEKRAofCMGmARIDNDA5GK4cIJIBKOaxhAMwiLSEAzhYQABYAQohCMGmARIEMzAwNRiSASC4jQEoibWEAzDKtYQDOFhAAVgBEgoIARABGAEqAkFTGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Jan 24 - Wed, Jan 28 YVR Vancouver ORD Chicago CA $387 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:24/01/2026TANYT&leg2=from:ORD,to:YVR,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:386.64&airProductToken=AQpvCjYIxJgBEgQzNzY0GLiNASCSASjCqoMDMIirgwM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQlEKNQjEmAESBDIxMDgYkgEgrhwo06uDAzDBrYMDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBNUJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Tue, Jun 2 - Sat, Jun 6 YVR Vancouver ORD Chicago CA $409 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:02/06/2026TANYT&leg2=from:ORD,to:YVR,departure:06/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:408.15&airProductToken=AQpmCjEI16YBEgMxMDYYuI0BIJgWKILSjgMw3NKOAzhFQABYAWoFQkFTSUNyCExUVkQwWkJLCjEI16YBEgQxNjEwGJgWIK4cKKfTjgMw99SOAzhFQAFYAWoFQkFTSUNyCExUVkQwWkJLCmYKMQjXpgESBDE2MTEYrhwgmBYopoKPAzCLhI8DOEVAAFgBagVCQVNJQ3IITFRWRDBaQksKMQjXpgESAzEzNxiYFiC4jQEoz4WPAzCuho8DOEVAAVgBagVCQVNJQ3IITFRWRDBaQksSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Jan 12 - Wed, Jan 21 YVR Vancouver ORD Chicago CA $431 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:12/01/2026TANYT&leg2=from:ORD,to:YVR,departure:21/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:430.72&airProductToken=AQqcAQozCMGCARIEMTQxNRi4jQEgo7EBKNiiggMw2KSCAzhCQABYAWoFQkFTSUNyCE9XQUNaU0JWCjIIwYIBEgQxNDg0GKOxASChAyivpYIDMJqmggM4QkABWAFqBUJBU0lDcghPV0FDWlNCVgoxCMGCARIENjI1ORihAyCuHCj3qYIDMPiqggM4QkABWAFqBUJBU0lDcghPVkFJWVNCWAqeAQoyCMGCARIENDU3MBiuHCCAlQEo7omDAzCsi4MDOEJAAFgBagVCQVNJQ3IIT1ZBSUtTQlgKMwjBggESBDE2NTgYgJUBIKOxASjVjoMDMJ6PgwM4QkABWAFqBUJBU0lDcghPVUFDWlNCVgozCMGCARIEMTQxNRijsQEguI0BKL-QgwMwzpKDAzhCQAFYAWoFQkFTSUNyCE9VQUNaU0JWEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Fri, Jan 23 - Sun, Feb 1 YVR Vancouver ORD Chicago CA $514 Roundtrip found 11 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:23/01/2026TANYT&leg2=from:ORD,to:YVR,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:513.07&airProductToken=AQo0CjIIwYYBEgQxMDQ4GLiNASCuHCj-m4MDMPmdgwM4R0AAWAFqBUJBU0lDcghHTkEyQTlCQQo0CjIIwYYBEgQxMDQ5GK4cILiNASjPg4QDMOKFhAM4R0AAWAFqBUJBU0lDcghHTkEyQTlCQRIKCAIQARgCKgJBQxgBIgQIARABKAIoAygEMA0) ## Find the cheapest month to fly from Vancouver (YVR) to Chicago (ORD) ### September is typically the cheapest month to fly From CA $200 - CA $588 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:YVR,to:MDW,departure:24/12/2025TANYT&leg2=from:MDW,to:YVR,departure:28/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. Closest 16 min [Flights from CA $1,816 ](https://www.expedia.ca/Flights-Search?leg1=from:YVR,to:MDW,departure:24/12/2025TANYT&leg2=from:MDW,to:YVR,departure:28/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) __Flight from Vancouver to Chicago (YVR - ORD) route information__ | Origin airport | Vancouver Intl. | | ------------------- | -------------------------------------------------------------------------------------------------------- | | Destination airport | O'Hare Intl. | | Airlines serving | Air Canada, Alaska Airlines, American Airlines, Delta, JetBlue Airways, Porter Airlines, United, WestJet | | Roundtrip price | CA $336 | | Distance | 2814 km | | Average flight time | 6 hours 12 mins | ## Vancouver to Chicago Flights **The easy way to book your flights from Vancouver to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Vancouver 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 Vancouver to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Vancouver Intl., YVR to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Vancouver to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Vancouver currently is just CA $355 rising to CA $514\. Here are more money-saving tips: - Fly in February 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 Vancouver** 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 Vancouver Intl. Airport to ORD? ### Do I need to pay a cancellation fee if I cancel my flight from Vancouver Intl. Airport to ORD? ### How do I find cheap flights from YVR to ORD that have flexible change policies? ### How many hours is the flight from Vancouver Intl. Airport (YVR) to O'Hare Airport? ### How far is the flight from Vancouver Intl. Airport to O'Hare Intl. Airport (ORD)? ### Which airlines fly direct from Vancouver Intl. Airport to O'Hare Airport? ### Are Vancouver Intl. Airport (YVR) to O'Hare Intl. 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[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.