Title: CA $229 Cheap Flights from Montego Bay (MBJ) 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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $229 Cheap Flights from Montego Bay (MBJ) to Chicago (ORD) [View CA $229 flight on Sat, Oct 18, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:MBJ,to:ORD,departure:18/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:228.08&airProductToken=AQpZCioIzpYBEgMyNzAYrEgg5Voohdn6AjDv2foCOFBAAFgBagJSUHIFUEE3TlIKKwjOlgESBDEyMjUY5Vogrhwowtr6AjCK3PoCOFBAAVgBagJSUHIFUEE3TlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) - [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 Sir Donald Sangster Intl. Airport (MBJ) to Chicago O'Hare International Airport (ORD) - ![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:mbj,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:mbj,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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:mbj,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:mbj,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:mbj,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:mbj,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:mbj,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:mbj,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![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:mbj,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:mbj,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Copa](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_CM.svg) Copa [](https://www.expedia.ca/Flights-Search?leg1=from:mbj,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:mbj,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"CM"}}]) - ![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:mbj,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:mbj,departure:30/10/2025TANYT&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 Montego Bay (MBJ) to Chicago (ORD) Prices were available within the past 7 days and start at CA $229 for one-way flights and CA $368 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) Sat, Oct 25 - Sun, Oct 26 MBJ Montego Bay ORD Chicago CA $368 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:25/10/2025TANYT&leg2=from:ORD,to:MBJ,departure:26/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:367.96&airProductToken=AQpWCioIzpYBEgMyNzAYrEgg5Voo5af7AjDPqPsCOFBAAFgBagJSUHIFUEE3TlIKKAjOlgESATIY5Vogrhwo2qv7AjCdrfsCOFBAAVgBagJSUHIFUEE3TlIKWQorCM6WARIEMTIyNhiuHCDlWijLtvsCMIW4-wI4UEAAWAFqAlJQcgVQQTdOUgoqCM6WARIDODMzGOVaIKxIKPy8-wIw4L37AjhQQAFYAWoCUlByBVBBN05SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Oct 24 - Sun, Oct 26 MBJ Montego Bay ORD Chicago CA $389 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:24/10/2025TANYT&leg2=from:ORD,to:MBJ,departure:26/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:388.91&airProductToken=AQpWCioIzpYBEgMyNzAYrEgg5VooxZz7AjCvnfsCOFBAAFgBagJSUHIFUEE3TlIKKAjOlgESATIY5VogrhwouqD7AjD9ofsCOFBAAVgBagJSUHIFUEE3TlIKVgooCM6WARIBMRiuHCDlWijdr_sCMJKx-wI4UEAAWAFqAlJQcgVQQTdOUgoqCM6WARIDODMzGOVaIKxIKNyx-wIwwLL7AjhQQAFYAWoCUlByBVBBN05SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Oct 25 - Sun, Oct 26 MBJ Montego Bay ORD Chicago CA $394 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:25/10/2025TANYT&leg2=from:ORD,to:MBJ,departure:26/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:393.10&airProductToken=AQpZCioIzpYBEgMyNzAYrEgg5Voo5af7AjDPqPsCOFBAAFgBagJSUHIFUEE3TlIKKwjOlgESBDEyMjUY5Vogrhwooqn7AjDqqvsCOFBAAVgBagJSUHIFUEE3TlIKVgooCM6WARIBMRiuHCDlWijdr_sCMJKx-wI4UEAAWAFqAlJQcgVQQTdOUgoqCM6WARIDODMzGOVaIKxIKNyx-wIwwLL7AjhQQAFYAWoCUlByBVBBN05SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Oct 24 - Sun, Oct 26 MBJ Montego Bay ORD Chicago CA $454 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:24/10/2025TANYT&leg2=from:ORD,to:MBJ,departure:26/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:453.06&airProductToken=AQpoCjIIwYIBEgQxMjMwGKxIIKOxASj4nPsCMPKe-wI4QkAAWAFqBUJBU0lDcghPTlU0QVhCWgoyCMGCARIEMjM0NhijsQEgrhwo6KD7AjD6ofsCOEJAAVgBagVCQVNJQ3IIT05VNEFYQloKaAoyCMGCARIEMTc4NBiuHCDimgEo2rD7AjDZsfsCOEJAAFgBagVCQVNJQ3IIT05VNEFYQloKMgjBggESBDI3MzIY4poBIKxIKI2z-wIwxrT7AjhCQAFYAWoFQkFTSUNyCE9OVTRBWEJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Oct 24 - Sun, Oct 26 MBJ Montego Bay ORD Chicago CA $454 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:24/10/2025TANYT&leg2=from:ORD,to:MBJ,departure:26/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:453.06&airProductToken=AQpuCjUIxJgBEgQxODAwGKxIIOBcKOGd-wIwm5_7AjhFQABYAWoJTUFJTkJBU0lDcghWTlhKMFNCWgo1CMSYARIEMTE5ORjgXCCuHCiUofsCMIqi-wI4RUABWAFqCU1BSU5CQVNJQ3IIVk5YSjBTQloKbgo1CMSYARIEMTI2NBiuHCDgXCjsr_sCMN-w-wI4RUAAWAFqCU1BSU5CQVNJQ3IIVk5YSjBTQloKNQjEmAESBDMyMzUY4FwgrEgooLL7AjDMs_sCOEVAAVgBaglNQUlOQkFTSUNyCFZOWEowU0JaEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Nov 20 - Mon, Dec 8 MBJ Montego Bay ORD Chicago CA $454 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:20/11/2025TANYT&leg2=from:ORD,to:MBJ,departure:08/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:453.50&airProductToken=AQpECiAIxJgBEgQxOTg3GKxIIOBcKIPP_QIwt9D9AjhFQABYAQogCMSYARIEMTE5ORjgXCCuHCir0f0CMKrS_QI4RUABWAEKRAogCMSYARIEMTE3OBiuHCDgXCiRlv8CMIaX_wI4RUAAWAEKIAjEmAESBDE5MjMY4FwgrEgoxZf_AjDtmP8COEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Oct 25 - Sun, Oct 26 MBJ Montego Bay ORD Chicago CA $464 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:25/10/2025TANYT&leg2=from:ORD,to:MBJ,departure:26/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:463.18&airProductToken=AQpWCioIzpYBEgMyNzAYrEgg5Voo5af7AjDPqPsCOFBAAFgBagJSUHIFUEE3TlIKKAjOlgESATIY5Vogrhwo2qv7AjCdrfsCOFBAAVgBagJSUHIFUEE3TlIKhgEKKwjOlgESBDI0MTEYrhwgzHAomrb7AjDGt_sCOFBAAFgBagJSUHIFUEE3TlIKKwjOlgESBDIyMDUYzHAg5Voo_rr7AjC5u_sCOFBAAVgBagJSUHIFUEE3TlIKKgjOlgESAzgzMxjlWiCsSCj8vPsCMOC9-wI4UEABWAFqAlJQcgVQQTdOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Oct 24 - Sun, Oct 26 MBJ Montego Bay ORD Chicago CA $475 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:24/10/2025TANYT&leg2=from:ORD,to:MBJ,departure:26/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:474.06&airProductToken=AQqYAQoxCMGCARIDODc1GKxIIOKaASjwnfsCMLOf-wI4QkAAWAFqBUJBU0lDcghPTlU0QVhCWgoxCMGCARIEMTg1NRjimgEgQyiCoPsCMNig-wI4QkABWAFqBUJBU0lDcghPTlU0QVhCWgowCMGCARIEMjkwMxhDIK4cKIWh-wIwgqL7AjhCQAFYAWoFQkFTSUNyCE9OVTRBWEJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Fri, Oct 24 - Sun, Oct 26 MBJ Montego Bay ORD Chicago CA $495 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:24/10/2025TANYT&leg2=from:ORD,to:MBJ,departure:26/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:494.70&airProductToken=AQpnCjEIwYYBEgM5ODMYrEggmM4BKMac-wIwwJ77AjhHQABYAWoFQkFTSUNyCEdMWUVUMUJBCjIIwYYBEgQ1MTQzGJjOASCuHCjspfsCMN-m-wI4R0ABWAFqBUJBU0lDcghHTFlFVDFCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Nov 4 - Tue, Nov 18 MBJ Montego Bay ORD Chicago CA $521 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MBJ,to:ORD,departure:04/11/2025TANYT&leg2=from:ORD,to:MBJ,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:520.80&airProductToken=AQpBCh4IwmwSAzU4MBisSCCpUSj_lfwCMOCX_AI4TEAAWAEKHwjCbBIEMjEwNRipUSCuHCjAm_wCMOyc_AI4TEABWAEKQQofCMJsEgQyMTA2GK4cIKlRKOyz_QIw87T9AjhMQABYAQoeCMJsEgM0NzkYqVEgrEgo1Lb9AjDIuP0COExAAVgBEgoIARABGAEqAkI2GAEiBAgBEAEoBDAB) ## Find the cheapest month to fly from Montego Bay (MBJ) to Chicago (ORD) ### September is typically the cheapest month to fly From CA $316 - CA $668 per traveller. Flight from Montego Bay to Chicago (MBJ - ORD) route information | Origin airport | Sir Donald Sangster Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $368 | | Distance | 2760 km | | Average flight time | 5 hours 33 mins | ## Montego Bay to Chicago Flights **The easy way to book your flights from Montego Bay to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Montego Bay 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 American 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 Montego Bay to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Sir Donald Sangster Intl., MBJ to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Montego Bay to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Montego Bay currently is just CA $368 rising to CA $521.   Here are more money-saving tips:  - Fly in October 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 Montego Bay**  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 MBJ to O'Hare Airport? > If you're planning on travelling between MBJ and O'Hare Airport, round-trip journeys start from CA $368. This figure is based on fares quoted within the last 7 days on Expedia for flights departing within the next year, so don't hang about. 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 MBJ to O'Hare Airport? > When it comes to cancellation fees, each airline has its own set of terms and conditions. If you decide to cancel your escape, head to our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Intl. Airport (ORD) that have flexible change policies? > Flights from MBJ to O'Hare Airport with flexible change policies are available from several carriers. Simply use our "No change fees" filter while searching. 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 Sir Donald Sangster Intl. Airport (MBJ) to O'Hare Airport? > Lasting around 6 hours and 20 minutes, the flight between Sangster Intl. Airport and O'Hare Intl. Airport (ORD) is a great opportunity to do some last-minute trip planning. Why not use the time to fine tune your itinerary for Chicago? ### How far is the flight from Sangster Intl. Airport to O'Hare Airport? > Expect to be soaring through the sky for a while, as the flight distance from Sangster Intl. Airport to ORD is 2,800 kilometres. Set up a playlist of your favourite podcasts before you leave home to keep yourself entertained during the trip. ### Which airlines fly direct from Sangster Intl. Airport to O'Hare Airport? > Many adventurers choose to fly with United Airlines (UA) from Sir Donald Sangster Intl. Airport (MBJ) to ORD. It offers 30 monthly flights, so you can easily find a flight time that's right for you. American Airlines (AA) is also worth a look. It operates 26 flights every month. Between these two airlines, you'll be able to find a good deal from Montego Bay to Chicago. ### Are MBJ to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? > It is possible to find amazing last-minute deals from Sangster Intl. Airport to O'Hare Intl. Airport (ORD), but it can also be hit-or-miss. As many airlines release prices up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to book when you spot a bargain. Expedia compares carrier prices and updates flight deals frequently, so you can rest easy knowing you're always seeing the latest offers. ## 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.