Title: CA $122 Cheap Flights from Oakland (OAK) 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 $122 Cheap Flights from Oakland (OAK) to Chicago (ORD) [View CA $122 flight on Thu, Oct 2, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:OAK,to:ORD,departure:02/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:121.10&airProductToken=AQpeCi0IzpYBEgQyMTg2GI5QIIuQASiqo_kCMIik-QI4UEAAWAFqAlJQcgZQQTIxTlIKLQjOlgESBDIwNzAYi5ABIK4cKN6n-QIwvKn5AjhQQAFYAWoCUlByBlBBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) - [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 Oakland Intl. Airport (OAK) 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:oak,to:ord,departure:02/10/2025TANYT&leg2=from:ord,to:oak,departure:09/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![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:oak,to:ord,departure:02/10/2025TANYT&leg2=from:ord,to:oak,departure:09/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![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:oak,to:ord,departure:02/10/2025TANYT&leg2=from:ord,to:oak,departure:09/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:oak,to:ord,departure:02/10/2025TANYT&leg2=from:ord,to:oak,departure:09/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![Hawaiian Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_HA.svg) Hawaiian Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:oak,to:ord,departure:02/10/2025TANYT&leg2=from:ord,to:oak,departure:09/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"HA"}}]) - ## Plan, book, fly with confidence - ### Be in the know Get alerts if flight prices drop or rise\* - ### Book smarter Save up to 30% on select hotels after you book a flight\* - ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Oakland (OAK) to Chicago (ORD) Prices were available within the past 7 days and start at CA $122 for one-way flights and CA $466 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) Wed, Nov 19 - Fri, Nov 21 OAK Oakland ORD Chicago CA $466 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:OAK,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:OAK,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:465.70&airProductToken=AQpfCi4IwaYBEgQxMzU5GI5QIJIBKNnD_QIw2cT9AjhYQABYAWoCU1ZyCE9IMk9BSkJOCi0IwaYBEgM1MzgYkgEgrhwop8X9AjCgx_0COFhAAVgBagJTVnIIT0gyT0FKQk4KXwotCMGmARIDNTg3GK4cIJIBKIjW_QIwp9j9AjhYQABYAWoCU1ZyCFFIMk9BSkJOCi4IwaYBEgQxMzI4GJIBII5QKNPY_QIw2tn9AjhYQAFYAWoCU1ZyCFFIMk9BSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 19 - Fri, Nov 21 OAK Oakland ORD Chicago CA $470 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:OAK,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:OAK,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:469.39&airProductToken=AQpuCjUIxJgBEgQ0MTM0GI5QIPISKMzC_QIww8P9AjhFQABYAWoJTUFJTkJBU0lDcghWQVZOQTBCQwo1CMSYARIEMjQxMxjyEiCuHCi0xP0CMO3F_QI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWTkEwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Nov 19 - Fri, Nov 21 OAK Oakland ORD Chicago CA $536 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:OAK,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:OAK,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:535.60&airProductToken=AQpeCi0IwaYBEgM3MTcYjlAgkgEo5r_9AjDnwP0COFhAAFgBagJTVnIIT0gyT0FKQk4KLQjBpgESAzQyORiSASCuHCjHwf0CMMbD_QI4WEABWAFqAlNWcghPSDJPQUpCTgpeCi0IwaYBEgM0MDcYrhwgkgEoy9n9AjDn2_0COFhAAFgBagJTVnIITkgyT0FKQk4KLQjBpgESAzcwNhiSASCOUCi53f0CML_e_QI4WEABWAFqAlNWcghOSDJPQUpCThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 19 - Fri, Nov 21 OAK Oakland ORD Chicago CA $540 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:OAK,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:OAK,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:539.94&airProductToken=AQpuCjUIxJgBEgQ0MTM0GI5QIPISKMzC_QIww8P9AjhFQABYAWoJTUFJTkJBU0lDcghWQVZOQTBCQwo1CMSYARIEMjQxMxjyEiCuHCi0xP0CMO3F_QI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWTkEwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Nov 19 - Fri, Nov 21 OAK Oakland ORD Chicago CA $541 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:OAK,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:OAK,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:540.90&airProductToken=AQpfCi4IwaYBEgQyMjAzGI5QIJIBKPnB_QIw98L9AjhYQABYAWoCU1ZyCFFIMk9ESkJOCi0IwaYBEgM0MTAYkgEgrhwog8T9AjD8xf0COFhAAVgBagJTVnIIUUgyT0RKQk4KYAouCMGmARIEMTQ2NBiuHCCSASiQ1f0CMKXX_QI4WEAAWAFqAlNWcghRSDJPQUpCTgouCMGmARIEMTMyOBiSASCOUCjT2P0CMNrZ_QI4WEABWAFqAlNWcghRSDJPQUpCThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 19 - Fri, Nov 21 OAK Oakland ORD Chicago CA $549 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:OAK,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:OAK,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:548.50&airProductToken=AQpuCjUIxJgBEgQ0MTM0GI5QIPISKMzC_QIww8P9AjhFQABYAWoJTUFJTkJBU0lDcghWQVZOQTBCQwo1CMSYARIEMjQxMxjyEiCuHCi0xP0CMO3F_QI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWTkEwQkMKbgo1CMSYARIEMjIzMRiuHCDyEijt1f0CMMjX_QI4RUAAWAFqCU1BSU5CQVNJQ3IITEFWT0EwQkMKNQjEmAESBDQxMzQY8hIgjlAo6df9AjDk2P0COEVAAVgBaglNQUlOQkFTSUNyCExBVk9BMEJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Nov 19 - Fri, Nov 21 OAK Oakland ORD Chicago CA $553 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:OAK,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:OAK,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:552.96&airProductToken=AQpfCi4IwaYBEgQxMzU5GI5QIJIBKNnD_QIw2cT9AjhYQABYAWoCU1ZyCE9IMk9BSkJOCi0IwaYBEgM1MzgYkgEgrhwop8X9AjCgx_0COFhAAVgBagJTVnIIT0gyT0FKQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Nov 19 - Fri, Nov 21 OAK Oakland ORD Chicago CA $613 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:OAK,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:OAK,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:613.00&airProductToken=AQpfCi4IwaYBEgQyMjAzGI5QIJIBKPnB_QIw98L9AjhYQABYAWoCU1ZyCFFIMk9ESkJOCi0IwaYBEgM0MTAYkgEgrhwog8T9AjD8xf0COFhAAVgBagJTVnIIUUgyT0RKQk4KXgotCMGmARIDNDA3GK4cIJIBKMvZ_QIw59v9AjhYQABYAWoCU1ZyCE5IMk9BSkJOCi0IwaYBEgM3MDYYkgEgjlAoud39AjC_3v0COFhAAVgBagJTVnIITkgyT0FKQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Nov 19 - Fri, Nov 21 OAK Oakland ORD Chicago CA $625 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:OAK,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:OAK,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:624.80&airProductToken=AQpfCi4IwaYBEgQxMzU5GI5QIJIBKNnD_QIw2cT9AjhYQABYAWoCU1ZyCE9IMk9BSkJOCi0IwaYBEgM1MzgYkgEgrhwop8X9AjCgx_0COFhAAVgBagJTVnIIT0gyT0FKQk4KYQouCMGmARIDMzI1GK4cIO-4ASj62P0CMJLb_QI4WEAAWAFqAlNWcghTSDdPQUpCTgovCMGmARIEMjI4MxjvuAEgjlAovdv9AjCn3P0COFhAAVgBagJTVnIIU0g3T0FKQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Nov 19 - Fri, Nov 21 OAK Oakland ORD Chicago CA $630 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:OAK,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:OAK,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:629.97&airProductToken=AQpfCi4IwaYBEgQyMjAzGI5QIJIBKPnB_QIw98L9AjhYQABYAWoCU1ZyCFFIMk9ESkJOCi0IwaYBEgM0MTAYkgEgrhwog8T9AjD8xf0COFhAAVgBagJTVnIIUUgyT0RKQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from Oakland (OAK) to Chicago (ORD) ### January is typically the cheapest month to fly From CA $147 - CA $459 per traveller. Flight from Oakland to Chicago (OAK - ORD) route information | Origin airport | Oakland Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | Alaska Airlines, Delta | | Roundtrip price | CA $466 | | Distance | 2929 km | ## Oakland to Chicago Flights **The easy way to book your flights from Oakland to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Oakland 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 Oakland to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Oakland Intl., OAK to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Oakland to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Oakland currently is just CA $466 rising to CA $630.   Here are more money-saving tips:  - Fly in November when flight prices are normally at their lowest  - Book about a month to 6 weeks before you travel for the best prices to Chicago   - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times  - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!  **Reasons to choose Expedia for your flight to Chicago from Oakland**  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 OAK to O'Hare Airport? > If you're travelling between Oakland Intl. Airport and O'Hare Airport, round-trip journeys start from CA $466. This figure is based on fares available within the last 7 days on Expedia for flights departing within the next year, so don't wait around. Book today and save yourself money and time. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Oakland Intl. Airport (OAK) to O'Hare Airport? > Each air carrier has its own terms and conditions. If you do decide to cancel, follow the instructions on our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from OAK to O'Hare Airport that have flexible change policies? > Flights from OAK to O'Hare Intl. Airport (ORD) with flexible change policies are available from several airlines. Simply use our "No change fees" filter during your search. You'll only need to cover the cost difference between flights, without any additional fees to worry about. ### How many hours is the flight from Oakland Intl. Airport to O'Hare Airport? > You may like to bring your own entertainment (like some downloaded podcasts), as it takes an average of 6 hours and 26 minutes to reach O'Hare Intl. Airport (ORD) from OAK. A good pair of noise-cancelling headphones will be handy too. ### How far is the flight from Oakland Intl. Airport to O'Hare Intl. Airport (ORD)? > The flying distance from Oakland Intl. Airport (OAK) to O'Hare Airport is 3,000 kilometres. Sneak in a nap or read a good book and the trip will zip on by. ### Which airlines fly direct from Oakland Intl. Airport to ORD? > If you want to travel straight from OAK to ORD, you'll need to book a flight with one or more stops. Unfortunately, there are no airlines that fly directly between these airports. ### Are OAK to ORD flight tickets cheaper when they're purchased at the last minute? > Tickets from Oakland Intl. Airport (OAK) to O'Hare Airport are available up to 12 months prior to departure on Expedia. And although you may occasionally pick up a fantastic last-minute deal, it's not something you should count on. Also, booking your flights well in advance means you'll have more options — and you can avoid getting stuck in the dreaded middle seat! We frequently update our fares to bring you the biggest bargains, so check back often for all the latest specials. ## 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) - [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.