Title: CA $59 Cheap Flights from Orlando (MCO) 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 $59 Cheap Flights from Orlando (MCO) to Chicago (ORD) [View CA $59 flight on Fri, Nov 7, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:MCO,to:ORD,departure:07/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:58.99&airProductToken=AQotCisIzpYBEgM2MjMYzHAgrhwomL78AjDSv_wCOFdAAFgBagJSUHIGV0EyMU5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) - [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 Orlando International Airport (MCO) to Chicago O'Hare International Airport (ORD) - ![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:mco,to:ord,departure:01/11/2025TANYT&leg2=from:ord,to:mco,departure:08/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![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:mco,to:ord,departure:01/11/2025TANYT&leg2=from:ord,to:mco,departure:08/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:mco,to:ord,departure:01/11/2025TANYT&leg2=from:ord,to:mco,departure:08/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![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:mco,to:ord,departure:01/11/2025TANYT&leg2=from:ord,to:mco,departure:08/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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:mco,to:ord,departure:01/11/2025TANYT&leg2=from:ord,to:mco,departure:08/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:mco,to:ord,departure:01/11/2025TANYT&leg2=from:ord,to:mco,departure:08/11/2025TANYT&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:mco,to:ord,departure:01/11/2025TANYT&leg2=from:ord,to:mco,departure:08/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) ![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 Orlando (MCO) to Chicago (ORD) Prices were available within the past 7 days and start at CA $59 for one-way flights and CA $118 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) Thu, Dec 4 - Sun, Dec 7 MCO Orlando ORD Chicago CA $118 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORD,departure:04/12/2025TANYT&leg2=from:ORD,to:MCO,departure:07/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:117.62&airProductToken=AQotCisIzpYBEgMzMDEYzHAgrhwon-r-AjDZ6_4COFdAAFgBagJSUHIGV0EyMU5SCi0KKwjOlgESAzg5NhiuHCDMcCiBjP8CMK2N_wI4V0AAWAFqAlJQcgZXQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Thu, Oct 30 - Mon, Nov 3 MCO Orlando ORD Chicago CA $122 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORD,departure:30/10/2025TANYT&leg2=from:ORD,to:MCO,departure:03/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:121.63&airProductToken=AQotCisIzpYBEgMzNDEYzHAgrhwoguP7AjC55PsCOFVAAFgBagJTRHIGVUExNE5SCi0KKwjOlgESAzYyMBiuHCDMcCiAi_wCMKKM_AI4VUAAWAFqAlNEcgZVQTE0TlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Dec 12 - Sun, Dec 14 MCO Orlando ORD Chicago CA $132 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORD,departure:12/12/2025TANYT&leg2=from:ORD,to:MCO,departure:14/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:131.91&airProductToken=AQotCisIzpYBEgMzMDEYzHAgrhwo6MP_AjCgxf8COFdAAFgBagJSUHIGV0EyMU5SCi0KKwjOlgESAzMwMBiuHCDMcCi72P8CMOfZ_wI4R0AAWAFqAlJQcgZHQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Nov 15 - Sun, Nov 16 MCO Orlando ORD Chicago CA $139 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORD,departure:15/11/2025TANYT&leg2=from:ORD,to:MCO,departure:16/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:138.63&airProductToken=AQpaCiwIzpYBEgQxODIzGMxwIOVaKNKX_QIwnpj9AjhXQABYAWoCUlByBldBMjFOUgoqCM6WARICMTkY5Vogrhwo25j9AjCjmv0COFdAAVgBagJSUHIGV0EyMU5SCi0KKwjOlgESAzYyMBiuHCDMcCignf0CMMKe_QI4V0AAWAFqAlJQcgZXQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Dec 12 - Sun, Dec 14 MCO Orlando ORD Chicago CA $146 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORD,departure:12/12/2025TANYT&leg2=from:ORD,to:MCO,departure:14/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:145.94&airProductToken=AQotCisIzpYBEgM4OTcYzHAgrhwoj8f_AjDHyP8COEdAAFgBagJSUHIGR0EyMU5SCi0KKwjOlgESAzMwMBiuHCDMcCi72P8CMOfZ_wI4R0AAWAFqAlJQcgZHQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Nov 8 - Sat, Nov 15 MCO Orlando ORD Chicago CA $153 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:MCO,departure:15/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:152.64&airProductToken=AQotCisIzpYBEgM2MjMYzHAgrhwouMn8AjDyyvwCOEdAAFgBagJSUHIGR0EyMU5SClwKLAjOlgESBDIwNDkYrhwg5Voo9JP9AjCwlf0COFdAAFgBagJSUHIGV0EyMU5SCiwIzpYBEgQxODI0GOVaIMxwKJiY_QIw3Jj9AjhXQAFYAWoCUlByBldBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Dec 5 - Sat, Dec 6 MCO Orlando ORD Chicago CA $170 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORD,departure:05/12/2025TANYT&leg2=from:ORD,to:MCO,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:169.41&airProductToken=AQozCjEIwYIBEgQyNzkyGMxwIK4cKJvz_gIw3fT-AjhCQABYAWoFQkFTSUNyCE9XQUxJTkJYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Dec 5 - Sat, Dec 6 MCO Orlando ORD Chicago CA $275 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORD,departure:05/12/2025TANYT&leg2=from:ORD,to:MCO,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:274.30&airProductToken=AQpuCjUIxJgBEgQxMTUwGMxwIOBcKMv3_gIwsvj-AjhFQABYAWoJTUFJTkJBU0lDcghWQVdOSzhCRwo1CMSYARIEMTE5ORjgXCCuHCiL-v4CMIr7_gI4RUABWAFqCU1BSU5CQVNJQ3IIVkFXTks4QkcKbgo1CMSYARIEMTQ1NhiuHCDgXCikgf8CMJ2C_wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFXTks4QkcKNQjEmAESBDIwMzUY4FwgzHAok4P_AjDyg_8COEVAAVgBaglNQUlOQkFTSUNyCFZBV05LOEJHEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, Dec 5 - Sat, Dec 6 MCO Orlando ORD Chicago CA $317 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORD,departure:05/12/2025TANYT&leg2=from:ORD,to:MCO,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:316.20&airProductToken=AQpeCi0IwmwSBDI3ODQYzHAgqVEo5fX-AjCF9_4COExAAFgBagJETnIIUEMyQVVFTDEKLQjCbBIEMjEwNRipUSCuHCjc-P4CMIj6_gI4TEABWAFqAkROcghQQzJBVUVMMQpfCi0IwmwSAzMxMhiuHCDBkwEotYD_AjDFgf8COExAAFgBagJETnIIUEMyQVVFTDEKLgjCbBIEMTE1MRjBkwEgzHAo3oP_AjCmhf8COExAAVgBagJETnIIUEMyQVVFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Jan 6 - Tue, Jan 20 MCO Orlando ORD Chicago CA $317 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:MCO,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:316.90&airProductToken=AQozCjEI1YIBEgQyODU4GMxwIK4cKMPggQMwgOKBAzhHQABYAWoFMl9lY29yCEdBQTVBV0ROCjMKMQjVggESBDIxNjUYrhwgzHAo6PyCAzCS_oIDOEdAAFgBagUyX2Vjb3IIR0FBNUFXRE4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ## Find the cheapest month to fly from Orlando (MCO) to Chicago (ORD) ### February is typically the cheapest month to fly From CA $97 - CA $348 per traveller. ## Frequently asked questions ### How much is a flight from Orlando Intl. Airport to O'Hare Intl. Airport (ORD)? > The lowest price advertised for a round-trip journey from Orlando Intl. Airport to O'Hare Airport is CA $118. But you better get a move on. This price is based on fares available within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Orlando Intl. Airport (MCO) to O'Hare Airport? > Each air carrier has its own terms and conditions. If you do decide to cancel, follow the simple instructions on our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from MCO to O'Hare Intl. Airport (ORD) that have flexible change policies? > Plenty of airlines offer the option to move your flight without a change fee. All you pay is the difference in the ticket price. When looking for MCO to O'Hare Intl. Airport (ORD) flights, you'll find a "No change fees" filter for you to tick. ### How many hours is the flight from MCO to O'Hare Airport? > It takes approximately 3 hours and 5 minutes to journey from Orlando Intl. Airport to ORD. But with some music and a good book, the time will go by quicker. ### How far is the flight from Orlando Intl. Airport (MCO) to O'Hare Airport? > The flight distance from Orlando Intl. Airport to O'Hare Airport is 1,600 kilometres. Bring along a snack, a drink and an interesting book to read. Keep yourself entertained and the hours will zip by. ### Which airlines fly direct from MCO to O'Hare Airport? > Getting from Orlando Intl. Airport (MCO) to O'Hare Airport is easy when you have a good range of airlines to choose from. Here are some of the best: > > > > - United Airlines - (UA) with 204 monthly flights > - American Airlines - (AA) with 108 monthly flights > - Spirit Airlines - (NK) with 52 monthly flights > - Frontier Airlines - (F9) with 26 monthly flights ### Are Orlando Intl. Airport (MCO) to ORD flight tickets cheaper when they're purchased at the last minute? > Flight prices are always on the move, so not always. While last-minute deals between MCO and O'Hare Airport are of course possible, it also makes sense to keep a close eye on prices well before you fly. In fact, some air carriers announce their prices up to a year ahead of the departure date. Expedia is continuously updating the biggest airfare bargains around, so keep checking back and be ready to grab your seat when prices drop. ## Travel information | Origin airport | Orlando Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | American Airlines, Delta, JetBlue Airways, Spirit Airlines, United | | Roundtrip price | CA $118 | | Distance | 1610 km | | Average flight time | 2 hours 1 min | ## Book with confidence ### Orlando to Chicago Flights **The easy way to book your flights from Orlando to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Orlando 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 Orlando to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Orlando Intl., MCO to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Orlando to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Orlando currently is just CA $118 rising to CA $317.   Here are more money-saving tips:  - Fly in December 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 Orlando**  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.