Title: CA $205 Cheap Flights from San Jose (SJC) 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 $205 Cheap Flights from San Jose (SJC) to Chicago (ORD) [View CA $205 flight on Fri, Nov 14, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:SJC,to:ORD,departure:14/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:204.60&airProductToken=AQqlAQo1CMSYARIENDA0MRiyEiCSASjph_0CMIqJ_QI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlEKNQjEmAESBDEyNjUYkgEg8hIo44n9AjDhiv0COEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJECjUIxJgBEgQyNDEzGPISIK4cKJSM_QIwzY39AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCRBIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) - [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 Norman Y. Mineta San Jose Intl. Airport (SJC) 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:sjc,to:ord,departure:25/10/2025TANYT&leg2=from:ord,to:sjc,departure:01/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![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:sjc,to:ord,departure:25/10/2025TANYT&leg2=from:ord,to:sjc,departure:01/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:sjc,to:ord,departure:25/10/2025TANYT&leg2=from:ord,to:sjc,departure:01/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:sjc,to:ord,departure:25/10/2025TANYT&leg2=from:ord,to:sjc,departure:01/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:sjc,to:ord,departure:25/10/2025TANYT&leg2=from:ord,to:sjc,departure:01/11/2025TANYT&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:sjc,to:ord,departure:25/10/2025TANYT&leg2=from:ord,to:sjc,departure:01/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![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:sjc,to:ord,departure:25/10/2025TANYT&leg2=from:ord,to:sjc,departure:01/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"HA"}}]) ![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 Jose (SJC) to Chicago (ORD) Prices were available within the past 7 days and start at CA $205 for one-way flights and CA $360 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Mon, Nov 24 - Wed, Dec 3 SJC San Jose ORD Chicago CA $360 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:24/11/2025TANYT&leg2=from:ORD,to:SJC,departure:03/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:359.20&airProductToken=AQpECiAIyIIBEgQ3MDU2GLISIJJoKIP8_QIw3Pz9AjhVQABYAQogCMiCARIENzQ5MxiSaCCuHCib_f0CMIz__QI4VUABWAEKRAogCMiCARIENzQ3MBiuHCCSaCi_3f4CMMrf_gI4VUAAWAEKIAjIggESBDY1NDgYkmggshIop-D-AjCI4f4COFVAAVgBEgoIARABGAEqAkhBGAEiBAgBEAEoBDAB) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Mon, Nov 24 - Sat, Dec 6 SJC San Jose ORD Chicago CA $374 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:24/11/2025TANYT&leg2=from:ORD,to:SJC,departure:06/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:373.20&airProductToken=AQpECiAIyIIBEgQ3MDU2GLISIJJoKIP8_QIw3Pz9AjhVQABYAQogCMiCARIENzQ5MxiSaCCuHCib_f0CMIz__QI4VUABWAEKRAogCMiCARIENzQ3MBiuHCCSaCif__4CMKqB_wI4VUAAWAEKIAjIggESBDY1NDgYkmggshIoh4L_AjDogv8COFVAAVgBEgoIARABGAEqAkhBGAEiBAgBEAEoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Mon, Nov 10 - Mon, Nov 17 SJC San Jose ORD Chicago CA $392 Roundtrip found 11 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:10/11/2025TANYT&leg2=from:ORD,to:SJC,departure:17/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:391.40&airProductToken=AQpgCi4IwaYBEgQzNDI5GLISIJJoKMTe_AIwnt_8AjhYQABYAWoCU1ZyCE9IMk9BVUJOCi4IwaYBEgQxNDkzGJJoIK4cKO3f_AIw5-H8AjhYQAFYAWoCU1ZyCE9IMk9BVUJOCmAKLgjBpgESBDE0NDcYrhwgkmgopqz9AjCvrv0COFhAAFgBagJTVnIIT0gyT0FVQk4KLgjBpgESBDM0NTkYkmggshIoi7D9AjDtsP0COFhAAVgBagJTVnIIT0gyT0FVQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Mon, Nov 10 - Mon, Nov 17 SJC San Jose ORD Chicago CA $413 Roundtrip found 11 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:10/11/2025TANYT&leg2=from:ORD,to:SJC,departure:17/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:412.90&airProductToken=AQpgCi4IwaYBEgQzNDU4GLISIJJoKOTa_AIwv9v8AjhYQABYAWoCU1ZyCE9IMk9BVkJOCi4IwaYBEgQxNDc4GJJoIK4cKPXd_AIw89_8AjhYQAFYAWoCU1ZyCE9IMk9BVUJOCmAKLgjBpgESBDE0NDcYrhwgkmgopqz9AjCvrv0COFhAAFgBagJTVnIIT0gyT0FVQk4KLgjBpgESBDM0NTkYkmggshIoi7D9AjDtsP0COFhAAVgBagJTVnIIT0gyT0FVQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Fri, Jan 16 - Tue, Jan 20 SJC San Jose ORD Chicago CA $422 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:16/01/2026TANYT&leg2=from:ORD,to:SJC,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:421.50&airProductToken=AQpgCi4IwaYBEgQyNDkyGLISIJJoKJ7PggMw88-CAzhYQABYAWoCU1ZyCFFIMk9BVUJOCi4IwaYBEgQxNDkzGJJoIK4cKKbRggMwsdOCAzhYQAFYAWoCU1ZyCEdIMk9BVUJOCl4KLQjBpgESAzU4NxiuHCCSASiI-YIDMKb7ggM4WEAAWAFqAlNWcghPSDdPQVZCTgotCMGmARIDNTIxGJIBILISKI78ggMwkv2CAzhYQAFYAWoCU1ZyCEdIMk9YVUJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Fri, Jan 16 - Tue, Jan 20 SJC San Jose ORD Chicago CA $433 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:16/01/2026TANYT&leg2=from:ORD,to:SJC,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:432.30&airProductToken=AQpgCi4IwaYBEgQyNDkyGLISIJJoKJ7PggMw88-CAzhYQABYAWoCU1ZyCFFIMk9BVUJOCi4IwaYBEgQxNDkzGJJoIK4cKKbRggMwsdOCAzhYQAFYAWoCU1ZyCEdIMk9BVUJOCmAKLgjBpgESBDE0NDcYrhwgkmgoxfyCAzDf_oIDOFhAAFgBagJTVnIIR0g3T0FWQk4KLgjBpgESBDIxODMYkmggshIoi4CDAzDrgIMDOFhAAVgBagJTVnIIUUgyT1hWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Hawaiian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/HA.gif) Mon, Nov 24 - Tue, Dec 2 SJC San Jose ORD Chicago CA $436 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:24/11/2025TANYT&leg2=from:ORD,to:SJC,departure:02/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:435.50&airProductToken=AQpECiAIyIIBEgQ3MDU2GLISIJJoKIP8_QIw3Pz9AjhVQABYAQogCMiCARIENzQ5MxiSaCCuHCib_f0CMIz__QI4VUABWAEKRAogCMiCARIENzQ2NhiuHCCSaCjz1_4CMP_Z_gI4VUAAWAEKIAjIggESBDY1NDcYkmggshIojt_-AjDu3_4COFVAAVgBEgoIARABGAEqAkhBGAEiBAgBEAEoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Mon, Nov 10 - Mon, Nov 17 SJC San Jose ORD Chicago CA $457 Roundtrip found 11 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:10/11/2025TANYT&leg2=from:ORD,to:SJC,departure:17/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:457.00&airProductToken=AQpgCi4IwaYBEgQzNDU4GLISIJJoKOTa_AIwv9v8AjhYQABYAWoCU1ZyCE9IMk9BVkJOCi4IwaYBEgQxNDc4GJJoIK4cKPXd_AIw89_8AjhYQAFYAWoCU1ZyCE9IMk9BVUJOCmAKLgjBpgESBDE0NzAYrhwgkmgo2Kn9AjDhq_0COFhAAFgBagJTVnIIT0gyT0FVQk4KLgjBpgESBDM0OTgYkmggshIonq79AjCAr_0COFhAAVgBagJTVnIIUUgyT0FVQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Mon, Nov 10 - Mon, Nov 17 SJC San Jose ORD Chicago CA $477 Roundtrip found 11 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:10/11/2025TANYT&leg2=from:ORD,to:SJC,departure:17/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:476.40&airProductToken=AQpeCi0IwaYBEgM3NDUYshIgkgEor978AjC_3_wCOFhAAFgBagJTVnIIT0gyT0FVQk4KLQjBpgESAzMyOBiSASCuHCj04vwCMObk_AI4WEABWAFqAlNWcghPSDJPWFVCTgpgCi4IwaYBEgQxNDQ3GK4cIJJoKKas_QIwr679AjhYQABYAWoCU1ZyCE9IMk9BVUJOCi4IwaYBEgQzNDU5GJJoILISKIuw_QIw7bD9AjhYQAFYAWoCU1ZyCE9IMk9BVUJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Mon, Nov 10 - Mon, Nov 17 SJC San Jose ORD Chicago CA $478 Roundtrip found 11 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJC,to:ORD,departure:10/11/2025TANYT&leg2=from:ORD,to:SJC,departure:17/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:477.40&airProductToken=AQpgCi4IwaYBEgQzNDk5GLISIJJoKLHc_AIwjN38AjhYQABYAWoCU1ZyCFFIMk9BVUJOCi4IwaYBEgQxNDc4GJJoIK4cKPXd_AIw89_8AjhYQAFYAWoCU1ZyCE9IMk9BVUJOCmAKLgjBpgESBDE0NzAYrhwgkmgo2Kn9AjDhq_0COFhAAFgBagJTVnIIT0gyT0FVQk4KLgjBpgESBDM0MjkYkmggshIolKz9AjD_rP0COFhAAVgBagJTVnIIUUgyT0FVQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from San Jose (SJC) to Chicago (ORD) ### February is typically the cheapest month to fly From CA $143 - CA $560 per traveller. ## Frequently asked questions ### How much is a flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Airport? > If you're planning on travelling between San Jose Intl. Airport and O'Hare Airport, round-trip flights start from CA $360. This figure is based on fares advertised within the last 7 days on Expedia for flights departing within the next year, so don't hang around. Book today and save yourself both 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 Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Airport? > We get that your situation can change unexpectedly, so we've made it as hassle-free as possible for you to cancel your flight online. Just head to the [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions. ### How do I find cheap flights from San Jose Intl. Airport to ORD that have flexible change policies? > Flights from San Jose Intl. Airport to ORD with flexible change policies are available from several airlines. Simply use our "No change fees" filter when searching. You'll only need to cover the fare difference, without any added fees to worry about. ### How many hours is the flight from San Jose Intl. Airport to ORD? > Lasting around 5 hours and 53 minutes, the flight between San Jose Intl. Airport and O'Hare Intl. Airport (ORD) is a great opportunity to do some last-minute planning. Why not use some of this time to work on your itinerary for Chicago? ### How far is the flight from San Jose Intl. Airport to O'Hare Airport? > The flight distance from San Jose to Chicago is 2,900 kilometres. Pack yourself a snack, a drink and an interesting book to read. Keep yourself entertained and the hours will fly by. ### Which airlines fly direct from Norman Y. Mineta San Jose Intl. Airport (SJC) to ORD? > A favourite with many frequent flyers, United Airlines (UA) offers 30 flights every month from San Jose Intl. Airport to O'Hare Intl. Airport (ORD). Pick the one that fits with your travel schedule and book your seat today. ### Are Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? > Late planners can sometimes find a bargain, with some of the cheapest fares from San Jose Intl. Airport to ORD arising a few weeks before the departure date. If you'd rather book ahead, Expedia compares and updates the best flight deals regularly — as early as 12 months in advance in some cases. It depends on the carrier though, as not all airlines advertise prices that far in advance. ## Travel information | Origin airport | Norman Y. Mineta San Jose Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | Alaska Airlines, American Airlines, Delta, United | | Roundtrip price | CA $359 | | Distance | 2919 km | | Average flight time | 4 hours 25 mins | ## Book with confidence ### San Jose to Chicago Flights **The easy way to book your flights from San Jose to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from San Jose 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 United Airlines 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 Jose to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Norman Y. Mineta San Jose Intl., SJC to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from San Jose to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from San Jose currently is just CA $360 rising to CA $478.   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 San Jose**  Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today. ## Explore a world of travel with Expedia - 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.