Title: CA $138 Cheap Flights from Dallas (DAL) 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 $138 Cheap Flights from Dallas (DAL) to Chicago (ORD) [View CA $138 flight on Sat, Dec 13, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:DAL,to:ORD,departure:13/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:137.10&airProductToken=AQpuCjUIxJgBEgQxMTE1GINYIOBcKIrP_wIwiND_AjhFQABYAWoJTUFJTkJBU0lDcghWQVdOSDNCRwo1CMSYARIEMjg3ORjgXCCuHCjI0f8CMMvS_wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFXTkgzQkcSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) - [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 Love Field Airport (DAL) to Chicago O'Hare International Airport (ORD) - ![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:dal,to:ord,departure:28/10/2025TANYT&leg2=from:ord,to:dal,departure:04/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:dal,to:ord,departure:28/10/2025TANYT&leg2=from:ord,to:dal,departure:04/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) ![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 Dallas (DAL) to Chicago (ORD) Prices were available within the past 7 days and start at CA $138 for one-way flights and CA $275 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Nov 15 - Mon, Nov 17 DAL Dallas ORD Chicago CA $275 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DAL,to:ORD,departure:15/11/2025TANYT&leg2=from:ORD,to:DAL,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:274.30&airProductToken=AQpuCjUIxJgBEgQyNTEzGINYIOBcKOaS_QIw4JP9AjhFQABYAWoJTUFJTkJBU0lDcghWQVdOSDNCRwo1CMSYARIEMTQ3NxjgXCCuHCiLlf0CMIaW_QI4RUABWAFqCU1BSU5CQVNJQ3IIVkFXTkgzQkcKbgo1CMSYARIEMjczOBiuHCDgXCjcrf0CMNiu_QI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0I0QkMKNQjEmAESBDExMDQY4Fwgg1gotq_9AjDAsP0COEVAAVgBaglNQUlOQkFTSUNyCFZBVlNCNEJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Nov 8 - Sat, Nov 15 DAL Dallas ORD Chicago CA $277 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DAL,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:DAL,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:276.40&airProductToken=AQpuCjUIxJgBEgQyNzgwGINYIOBcKOfI_AIw6sn8AjhFQABYAWoJTUFJTkJBU0lDcghWQVZOSDNCRwo1CMSYARIEMTE5ORjgXCCuHCiwyvwCMKbL_AI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWTkgzQkcKbgo1CMSYARIEMTI2NBiuHCDgXCirkf0CMKqS_QI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFXTkgzQkcKNQjEmAESBDExMTUY4Fwgg1go3JL9AjDnk_0COEVAAVgBaglNQUlOQkFTSUNyCFZBV05IM0JHEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 12 - Sat, Nov 15 DAL Dallas ORD Chicago CA $339 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DAL,to:ORD,departure:12/11/2025TANYT&leg2=from:ORD,to:DAL,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:338.80&airProductToken=AQptCjQIxJgBEgM1MTIYg1gg4Fwox_T8AjDB9fwCOEVAAFgBaglNQUlOQkFTSUNyCFhBV05BNkJHCjUIxJgBEgQxMTM5GOBcIK4cKNb2_AIwzvf8AjhFQAFYAWoJTUFJTkJBU0lDcghYQVdOQTZCRwpuCjUIxJgBEgQxNDc3GK4cIOBcKMKW_QIwvpf9AjhFQABYAWoJTUFJTkJBU0lDcghWQVdOSDNCRwo1CMSYARIEMTEwNBjgXCCDWCjymP0CMPyZ_QI4RUABWAFqCU1BSU5CQVNJQ3IIVkFXTkgzQkcSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Nov 8 - Sat, Nov 15 DAL Dallas ORD Chicago CA $347 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DAL,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:DAL,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:346.30&airProductToken=AQpuCjUIxJgBEgQxMTE1GINYIOBcKMTF_AIwwMb8AjhFQABYAWoJTUFJTkJBU0lDcghYQVZPQTBCRwo1CMSYARIEMjczOBjgXCCuHCiHx_wCMITI_AI4RUABWAFqCU1BSU5CQVNJQ3IIWEFWT0EwQkcKbgo1CMSYARIEMTE0NxiuHCDgXCiNlP0CMIqV_QI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFXTkgzQkcKNQjEmAESBDI3ODAY4Fwgg1gojpb9AjCWl_0COEVAAVgBaglNQUlOQkFTSUNyCFZBV05IM0JHEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Nov 4 - Wed, Nov 5 DAL Dallas ORD Chicago CA $373 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DAL,to:ORD,departure:04/11/2025TANYT&leg2=from:ORD,to:DAL,departure:05/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:372.10&airProductToken=AQpuCjUIxJgBEgQyNTEzGINYIOBcKOiW_AIw45f8AjhWQABYAWoJTUFJTkNMQVNDcghWQVZTQzJNRQo1CMSYARIEMTQ3NxjgXCCuHCiXmfwCMJGa_AI4VkABWAFqCU1BSU5DTEFTQ3IIVkFWU0MyTUUKbgo1CMSYARIEMTQ3NxiuHCDgXCj3pfwCMPSm_AI4VkAAWAFqCU1BSU5DTEFTQ3IIVkFWU0I0TUUKNQjEmAESBDExMDQY4Fwgg1gov6j8AjDDqfwCOFZAAVgBaglNQUlOQ0xBU0NyCFZBVlNCNE1FEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Dec 31 - Sun, Jan 4 DAL Dallas ORD Chicago CA $380 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DAL,to:ORD,departure:31/12/2025TANYT&leg2=from:ORD,to:DAL,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:379.60&airProductToken=AQptCjQIxJgBEgM1MTYYg1gg4FwolZeBAzCVmIEDOEVAAFgBaglNQUlOQkFTSUNyCFhBVlRBNUJDCjUIxJgBEgQxMTQ3GOBcIK4cKIaZgQMwhZqBAzhFQAFYAWoJTUFJTkJBU0lDcghYQVZUQTVCQwpuCjUIxJgBEgQxMjY0GK4cIOBcKPLDgQMw9cSBAzhFQABYAWoJTUFJTkJBU0lDcghWQVdOQTBCQwo1CMSYARIEMTExNRjgXCCDWCjExYEDMNTGgQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFXTkEwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Dec 6 - Sat, Dec 13 DAL Dallas ORD Chicago CA $418 Roundtrip found 8 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DAL,to:ORD,departure:06/12/2025TANYT&leg2=from:ORD,to:DAL,departure:13/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:417.20&airProductToken=AQpuCjUIxJgBEgQxMTE1GINYIOBcKKqA_wIwqIH_AjhFQABYAWoJTUFJTkJBU0lDcghYQVZUQTVCQwo1CMSYARIEMjczOBjgXCCuHCj9gf8CMPiC_wI4RUABWAFqCU1BSU5CQVNJQ3IIWEFWVEE1QkMKbgo1CMSYARIEMTE3OBiuHCDgXCixzv8CMKbP_wI4RUAAWAFqCU1BSU5CQVNJQ3IIWEFWVEE1QkMKNQjEmAESBDI3ODAY4Fwgg1goktH_AjCZ0v8COEVAAVgBaglNQUlOQkFTSUNyCFhBVlRBNUJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Dec 31 - Sun, Jan 4 DAL Dallas ORD Chicago CA $436 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DAL,to:ORD,departure:31/12/2025TANYT&leg2=from:ORD,to:DAL,departure:04/01/2026TANYT&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=AQptCjQIxJgBEgM1MTYYg1gg4FwolZeBAzCVmIEDOEVAAFgBaglNQUlOQkFTSUNyCFhBVlRBNUJDCjUIxJgBEgQxMTQ3GOBcIK4cKIaZgQMwhZqBAzhFQAFYAWoJTUFJTkJBU0lDcghYQVZUQTVCQwpuCjUIxJgBEgQyNzM4GK4cIOBcKMHJgQMwvsqBAzhFQABYAWoJTUFJTkJBU0lDcghYQVZOQTBCQwo1CMSYARIEMTEwNBjgXCCDWCjnyoEDMPHLgQM4RUABWAFqCU1BSU5CQVNJQ3IIWEFWTkEwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Nov 17 - Tue, Nov 18 DAL Dallas ORD Chicago CA $471 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DAL,to:ORD,departure:17/11/2025TANYT&leg2=from:ORD,to:DAL,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:471.00&airProductToken=AQpuCjUIxJgBEgQxMTE1GINYIOBcKJmr_QIwkaz9AjhFQABYAWoJTUFJTkJBU0lDcghVQVZPQTBCUQo1CMSYARIEMjg3ORjgXCCuHCiSrf0CMJSu_QI4RUABWAFqCU1BSU5CQVNJQ3IIVUFWT0EwQlEKbQo1CMSYARIEMTE3OBiuHCDgXCiXtf0CMI-2_QI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0MyQkMKNAjEmAESAzUxMhjgXCCDWCjQtv0CMNi3_QI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0MyQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Dec 6 - Sat, Dec 13 DAL Dallas ORD Chicago CA $473 Roundtrip found 8 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DAL,to:ORD,departure:06/12/2025TANYT&leg2=from:ORD,to:DAL,departure:13/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:472.10&airProductToken=AQptCjQIxJgBEgM1MTYYg1gg4Fwo9f3-AjD1_v4COEVAAFgBaglNQUlOQkFTSUNyCFZBV05IM0JHCjUIxJgBEgQxNDU2GOBcIK4cKOD__gIw3oD_AjhFQAFYAWoJTUFJTkJBU0lDcghWQVdOSDNCRwpuCjUIxJgBEgQxMTQ3GK4cIOBcKJLP_wIwjtD_AjhFQABYAWoJTUFJTkJBU0lDcghVQVdPQTBCRwo1CMSYARIEMjc4MBjgXCCDWCiS0f8CMJnS_wI4RUABWAFqCU1BSU5CQVNJQ3IIVUFXT0EwQkcSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from Dallas (DAL) to Chicago (ORD) ### August is typically the cheapest month to fly From CA $147 - CA $468 per traveller. Flight from Dallas to Chicago (DAL - ORD) route information | Origin airport | Love Field | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | Delta | | Roundtrip price | CA $274 | | Distance | 1277 km | | Average flight time | 2 hours 25 mins | ## Dallas to Chicago Flights **The easy way to book your flights from Dallas to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Dallas 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 Dallas to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Love Field, DAL to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Dallas to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Dallas currently is just CA $275 rising to CA $473.   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 Dallas**  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 DAL to O'Hare Intl. Airport (ORD)? > Start packing your suitcase, because round-trip journeys between DAL and O'Hare Intl. Airport (ORD) start from CA $275. That's based on airfares available within the last 7 days on Expedia for flights departing within the next year. Prices can move quickly, so book today to nab the best deal. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Dallas Love Field to ORD? > Most flights can be conveniently cancelled online, but whether you incur a fee varies between airlines. If you do have to cancel your vacation, follow the instructions in the [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from Love Field Airport (DAL) to O'Hare Airport that have flexible change policies? > Use our "No change fees" filter to find flexible ticketing options for your flight from Love Field Airport (DAL) to O'Hare Intl. Airport (ORD). This allows you to lock in a great price in advance and still have the freedom to make changes without any additional fees. Fare adjustments may apply if your new flight is more expensive. ### How many hours is the flight from Love Field Airport (DAL) to O'Hare Airport? > With the average flight time between Love Field Airport (DAL) and ORD an easy 5 hours and 19 minutes, you'll be wandering around Chicago in no time. ### How far is the flight from DAL to O'Hare Airport? > That new movie you've been wanting to see will just have to wait — the flight distance between Dallas Love Field and O'Hare Airport is only 1,300 kilometres. The captain will be telling you to put your seat upright for touchdown before you know it. ### Which airlines fly direct from Dallas Love Field to O'Hare Airport? > Southwest Airlines (WN) will fly you from Love Field Airport (DAL) to ORD comfortably and reliably. Take your pick of 73 flights each month along this route. ### Are DAL to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute? > It is possible to score an amazing last-minute deal from Dallas Love Field to O'Hare Intl. Airport (ORD), but it's also possible to miss out altogether! As many airlines release seats up to a year in advance, it's worth keeping an eye on fares early and being ready to pounce when you spot a bargain. Expedia compares air carrier prices and updates flight deals often, so you can be certain you're always getting 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.