Title: CA $184 Cheap Flights from San José (SJO) 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 $184 Cheap Flights from San José (SJO) to Chicago (ORD) [View CA $184 flight on Sat, Feb 28, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:SJO,to:ORD,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:183.71&airProductToken=AQpaCisIzpYBEgMzMzgYsnIg5Voos7KGAzDms4YDOFdAAFgBagJSUHIGV0EyMU5SCisIzpYBEgM1ODEY5VogrhwosbSGAzCBtoYDOFdAAVgBagJSUHIGV0EyMU5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) - [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 Juan Santamaria Intl. Airport (SJO) to Chicago O'Hare International Airport (ORD) - ![Avianca](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AV.svg) Avianca [](https://www.expedia.ca/Flights-Search?leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,departure:06/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AV"}}]) - ![Aeromexico](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AM.svg) Aeromexico [](https://www.expedia.ca/Flights-Search?leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,departure:06/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AM"}}]) - ![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:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,departure:06/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,departure:06/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,departure:06/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,departure:06/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,departure:06/02/2026TANYT&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 José (SJO) to Chicago (ORD) Prices were available within the past 7 days and start at CA $184 for one-way flights and CA $428 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Jan 30 - Sun, Feb 1 SJO San José ORD Chicago CA $428 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,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:427.86&airProductToken=AQpUCigIzpYBEgMzMzgYsnIg5VookuyDAzDG7YMDOEdAAFgBagJSUHIDR05SCigIzpYBEgM1ODEY5Vogrhwose-DAzD68IMDOEdAAVgBagJSUHIDR05SCloKKwjOlgESAzIxMxiuHCDlWiiDhoQDMMeHhAM4R0AAWAFqAlJQcgZHQTE0TlIKKwjOlgESAzMzNRjlWiCyciiCjIQDMK6NhAM4R0ABWAFqAlJQcgZHQTE0TlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Jan 30 - Sun, Feb 1 SJO San José ORD Chicago CA $459 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,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:458.08&airProductToken=AQpUCigIzpYBEgMzMzgYsnIg5VookuyDAzDG7YMDOEdAAFgBagJSUHIDR05SCigIzpYBEgM1ODEY5Vogrhwose-DAzD68IMDOEdAAVgBagJSUHIDR05SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Jan 30 - Sun, Feb 1 SJO San José ORD Chicago CA $465 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,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:464.78&airProductToken=AQpUCigIzpYBEgMzMzgYsnIg5VookuyDAzDG7YMDOEdAAFgBagJSUHIDR05SCigIzpYBEgM1ODEY5Vogrhwose-DAzD68IMDOEdAAVgBagJSUHIDR05SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![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 SJO San José ORD Chicago CA $473 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,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:472.44&airProductToken=AQoyCjAIwYIBEgMzMTQYsnIgrhwolemDAzDe64MDOEJAAFgBagVCQVNJQ3IIT05VNE5YQloKMgowCMGCARIDMzM1GK4cILJyKMKEhAMw7oaEAzhCQABYAWoFQkFTSUNyCE9OVTROWEJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![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 SJO San José ORD Chicago CA $481 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,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:480.24&airProductToken=AQplCjAIwYIBEgMzNDYYsnIgjAIo0OiDAzCF6oMDOEJAAFgBagVCQVNJQ3IIT05VNE5YQloKMQjBggESBDEyMTkYjAIgrhwo1--DAzCm8YMDOEJAAVgBagVCQVNJQ3IIT05VNE5YQloKMgowCMGCARIDMzM1GK4cILJyKMKEhAMw7oaEAzhCQABYAWoFQkFTSUNyCE9OVTROWEJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Jan 30 - Sun, Feb 1 SJO San José ORD Chicago CA $511 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,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:510.39&airProductToken=AQpUCigIzpYBEgMzMzgYsnIg5VookuyDAzDG7YMDOEdAAFgBagJSUHIDR05SCigIzpYBEgM1ODEY5Vogrhwose-DAzD68IMDOEdAAVgBagJSUHIDR05SCogBCisIzpYBEgMyMTMYrhwg5Voog4aEAzDHh4QDOFdAAFgBagJSUHIGV0EyMU5SCisIzpYBEgM1NTAY5VogzHAom4qEAzDbioQDOFdAAVgBagJSUHIGV0EyMU5SCiwIzpYBEgQxMzA5GMxwILJyKL2LhAMwgY2EAzhXQAFYAWoCUlByBldBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Mon, Mar 23 - Thu, Mar 26 SJO San José ORD Chicago CA $525 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJO,to:ORD,departure:23/03/2026TANYT&leg2=from:ORD,to:SJO,departure:26/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:524.92&airProductToken=AQpSCigIzpYBEgMzMzgYsnIg5Voo0LSIAzCKtogDOEdAAFgBagJSUHIDR05SCiYIzpYBEgExGOVaIK4cKNe3iAMwobmIAzhHQAFYAWoCUlByA0dOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Fri, Jan 30 - Sun, Feb 1 SJO San José ORD Chicago CA $551 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,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:550.61&airProductToken=AQpnCjEIwYYBEgM5NTYYsnIgmM4BKOvpgwMwpuyDAzhHQABYAWoFQkFTSUNyCEdBWUVUMUJBCjIIwYYBEgQ4OTA5GJjOASCuHCie7YMDMJTugwM4R0ABWAFqBUJBU0lDcghHQVlFVDFCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Volaris Costa Rica](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/Q6.gif) Mon, Mar 23 - Thu, Mar 26 SJO San José ORD Chicago CA $584 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJO,to:ORD,departure:23/03/2026TANYT&leg2=from:ORD,to:SJO,departure:26/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:583.40&airProductToken=AQpgCi4I0WwSBDQwNTgYsnIg5lgorraIAzCFuIgDOEFAAFgBagRaZXJvcgdBTFNTSUkyCi4I2WgSBDE3MDQY5lggrhwohb2IAzDzvogDOEFAAVgBagRaZXJvcgdBTFNTSUkyEgoIARABGAEqAlk0GAEiBAgBEAEoAigDKAQwDQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Mon, Mar 23 - Thu, Mar 26 SJO San José ORD Chicago CA $1,122 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJO,to:ORD,departure:23/03/2026TANYT&leg2=from:ORD,to:SJO,departure:26/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1121.35&airProductToken=AQqNAQotCMJsEgQyMDM4GLJyIOVaKIOziAMws7SIAzhMQABYAWoCRE5yCFZDMEFVRUwxCi0IwmwSAzQ3MBjlWiDBkwEoqreIAzDxuIgDOExAAVgBagJETnIIVkMwQVVFTDEKLQjCbBIDMzExGMGTASCuHCjrvIgDMKm-iAM4TEABWAFqAkROcghVSTNRQkVMMQqNAQotCMJsEgMzMTIYrhwgwZMBKJzViAMwrNaIAzhMQABYAWoCRE5yCFdDMEFVRUwxCi0IwmwSAzQ2ORjBkwEg5VoozteIAzCi2YgDOExAAVgBagJETnIIV0MwQVVFTDEKLQjCbBIEMjAzORjlWiCyciiU3ogDMMHfiAM4TEABWAFqAkROcghaSTBBUkVMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE) ## Find the cheapest month to fly from San José (SJO) to Chicago (ORD) ### October is typically the cheapest month to fly From CA $237 - CA $564 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:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,departure:01/02/2026TANYT&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 $428 ](https://www.expedia.ca/Flights-Search?leg1=from:SJO,to:ORD,departure:30/01/2026TANYT&leg2=from:ORD,to:SJO,departure:01/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Frequently asked questions ### How much is a flight from Juan Santamaria Intl. Airport to ORD? ### Do I need to pay a cancellation fee if I cancel my flight from SJO to O'Hare Airport? ### How do I find cheap flights from Juan Santamaria Intl. Airport to O'Hare Intl. Airport (ORD) that have flexible change policies? ### How many hours is the flight from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD)? ### How far is the flight from Juan Santamaria Intl. Airport (SJO) to ORD? ### Which airlines fly direct from Juan Santamaria Intl. Airport to ORD? ### Are Juan Santamaria Intl. Airport (SJO) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? ## Travel information | Origin airport | Juan Santamaría Intl. | | ------------------- | --------------------- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $428 | | Distance | 3553 km | | Average flight time | 6 hours 9 mins | ## Book with confidence # San José to Chicago Flights **The easy way to book your flights from San José to Chicago** With Expedia, it’s simple to find and book flights to Chicago from San José 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 José to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Juan Santamaría Intl., SJO to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from San José to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from San José currently is just CA $428 rising to CA $1,122\. 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 José** 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. 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[Flights from Detroit (DTW) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/dtw/pwk/detroit-to-chicago) - [Flights from Exeter (EXT) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ext/chi/exeter-to-chicago) - [Flights from Fishers Island (FID) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/fid/mdw/fishers-island-to-chicago) - [Flights from Flint (FNT) to Waukegan (UGN) ](https://www.expedia.ca/lp/flights/fnt/ugn/flint-to-waukegan) - [Flights from Green Bay (GRB) to Waukegan (UGN) ](https://www.expedia.ca/lp/flights/grb/ugn/green-bay-to-waukegan) - [Flights from Grand Rapids (GRR) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/grr/pwk/grand-rapids-to-chicago) - [Flights from Gary (GYY) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/gyy/chi/gary-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/iag/chi/niagara-falls-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/iag/mdw/niagara-falls-to-chicago) - [Flights from Wilmington (ILM) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ilm/chi/wilmington-to-chicago) - [Flights from Indianapolis (IND) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ind/chi/indianapolis-to-chicago) - [Flights from Nakhon Phanom (KOP) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/kop/mdw/nakhon-phanom-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/las/mdw/las-vegas-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/lax/chi/los-angeles-to-chicago) - [Flights from Montego Bay (MBJ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mbj/mdw/montego-bay-to-chicago) - [Flights from Orlando (MCO) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mco/mdw/orlando-to-chicago) - [Flights from Michigan City (MGC) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mgc/mdw/michigan-city-to-chicago) - [Flights from Muscle Shoals (MSL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/msl/mdw/muscle-shoals-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/msp/chi/minneapolis-to-chicago) - [Flights from New York (NYC) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/nyc/chi/new-york-to-chicago) - [Flights from Omaha (OMA) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/oma/mdw/omaha-to-chicago) - [Flights from Chicago (ORD) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ord/chi/chicago-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/phl/mdw/philadelphia-to-chicago) - [Flights from Pueblo (PUB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/pub/mdw/pueblo-to-chicago) - [Flights from Punta Cana (PUJ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/puj/chi/punta-cana-to-chicago) - [Flights from Roanoke (ROA) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/roa/mdw/roanoke-to-chicago) - [Flights from Selinsgrove (SEG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/seg/mdw/selinsgrove-to-chicago) - [Flights from Sacramento (SMF) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/smf/mdw/sacramento-to-chicago) - [Flights from St. Louis (STL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/stl/mdw/st-louis-to-chicago) - [Flights from Newburgh (SWF) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/swf/mdw/newburgh-to-chicago) - [Flights from Sydney (SYD) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/syd/mdw/sydney-to-chicago) - [Flights from Syracuse (SYR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/syr/mdw/syracuse-to-chicago) - [Flights from Fort Leonard Wood (TBN) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/tbn/mdw/fort-leonard-wood-to-chicago) - [Flights from Ua Pou (UAP) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/uap/chi/ua-pou-to-chicago) - [Flights from Fort Frances (YAG) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yag/chi/fort-frances-to-chicago) - [Flights from Brandon (YBR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ybr/mdw/brandon-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ycd/chi/nanaimo-to-chicago) - [Flights from St. Catharines (YCM) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ycm/chi/st-catharines-to-chicago) - [Flights from Edmonton (YEA) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yea/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yeg/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yeg/mdw/edmonton-to-chicago) - [Flights from Flin Flon (YFO) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yfo/chi/flin-flon-to-chicago) - [Flights from Hamilton (YHM) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yhm/mdw/hamilton-to-chicago) - [Flights from Kamloops (YKA) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yka/chi/kamloops-to-chicago) - [Flights from Kelowna (YLW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ylw/mdw/kelowna-to-chicago) - [Flights from Montreal (YMQ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ymq/chi/montreal-to-chicago) - [Flights from Ottawa (YOW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago) - [Flights from Peterborough (YPQ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ypq/mdw/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqb/mdw/quebec-to-chicago) - [Flights from Regina (YQR) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yqr/chi/regina-to-chicago) - [Flights from Regina (YQR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqr/mdw/regina-to-chicago) - [Flights from Gander (YQX) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yqx/chi/gander-to-chicago) - [Flights from Sudbury (YSB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago) - [Flights from Timmins (YTS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago) - [Flights from Toronto (YTZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Montreal (YUL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/ywg/pwk/winnipeg-to-chicago) - [Flights from Whitehorse (YXY) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yxy/chi/whitehorse-to-chicago) - [Flights from Calgary (YYC) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-to-chicago) - [Flights from Victoria (YYJ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yyj/chi/victoria-to-chicago) - [Flights from St. John's (YYT) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yyt/chi/st-johns-to-chicago) - [Flights from Toronto (YYZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/yyz/pwk/toronto-to-chicago) \*Available to Expedia members.