Title: CA $174 Cheap Flights from Harlingen (HRL) 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 $174 Cheap Flights from Harlingen (HRL) to Chicago (ORD) [View CA $174 flight on Sat, Feb 14, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:HRL,to:ORD,departure:14/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:173.90&airProductToken=AQpoCjIIwYIBEgQzNzE4GKdcIKOxASiul4UDMJGYhQM4QkAAWAFqBUJBU0lDcghRVkFXVVNCVgoyCMGCARIEMTU3MxijsQEgrhwov5iFAzDQmYUDOEJAAVgBagVCQVNJQ3IIUVZBV1VTQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) - [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 Valley Intl. Airport (HRL) to Chicago O'Hare International Airport (ORD) - ![](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:HRL,to:ORD,departure:06/02/2026TANYT&leg2=from:ORD,to:HRL,departure:13/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](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:HRL,to:ORD,departure:06/02/2026TANYT&leg2=from:ORD,to:HRL,departure:13/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](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:HRL,to:ORD,departure:06/02/2026TANYT&leg2=from:ORD,to:HRL,departure:13/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](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:HRL,to:ORD,departure:06/02/2026TANYT&leg2=from:ORD,to:HRL,departure:13/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](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\* - ![](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\* - ![](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 Harlingen (HRL) to Chicago (ORD) Prices were available within the past 7 days and start at CA $174 for one-way flights and CA $460 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Feb 11 - Sat, Feb 14 HRL Harlingen ORD Chicago CA $460 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:HRL,to:ORD,departure:11/02/2026TANYT&leg2=from:ORD,to:HRL,departure:14/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:459.60&airProductToken=AQpGCiEIwYIBEgQ0MjM1GKdcIKOxASjM9YQDMLL2hAM4UUAAWAEKIQjBggESBDE1NzMYo7EBIK4cKO32hAMw-PeEAzhRQAFYAQpFCiAIwYIBEgM5OTQYrhwgo7EBKPSQhQMwj5KFAzhRQABYAQohCMGCARIENDMxNxijsQEgp1woxpKFAzCsk4UDOFFAAVgBEgoIARABGAEqAkFBGAEiBAgBEAEoCCgEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Feb 10 - Sat, Feb 14 HRL Harlingen ORD Chicago CA $460 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:HRL,to:ORD,departure:10/02/2026TANYT&leg2=from:ORD,to:HRL,departure:14/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:459.60&airProductToken=AQpECiAI1YIBEgQ0ODcwGKdcIIg4KN3phAMwtOqEAzhLQABYAQogCNWCARIEMTc1MhiIOCCuHCiI64QDMKrshAM4S0ABWAEKQwofCNWCARIDNzE0GK4cIIg4KIiWhQMwv5eFAzhLQABYAQogCNWCARIENDkxORiIOCCnXCiZmIUDMO-YhQM4S0ABWAESCggBEAEYASoCVUEYASIECAEQASgEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Feb 9 - Wed, Feb 11 HRL Harlingen ORD Chicago CA $473 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:HRL,to:ORD,departure:09/02/2026TANYT&leg2=from:ORD,to:HRL,departure:11/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:472.40&airProductToken=AQpmCjEI1YIBEgQ0ODcwGKdcIIg4KL3ehAMwlN-EAzhLQABYAWoFMl9lY29yCEtBQTJQRkROCjEI1YIBEgQxNzUyGIg4IK4cKOjfhAMwiuGEAzhLQABYAWoFMl9lY29yCEtBQTJQRkROCmYKMQjVggESBDE2MzMYrhwgiDgo_vCEAzC98oQDOEtAAFgBagUyX2Vjb3IIS0FLMkFaRFMKMQjVggESBDQzNDQYiDggp1wo2POEAzCu9IQDOEtAAFgBagUyX2Vjb3IIS0FLMkFaRFMSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Feb 9 - Wed, Feb 11 HRL Harlingen ORD Chicago CA $483 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:HRL,to:ORD,departure:09/02/2026TANYT&leg2=from:ORD,to:HRL,departure:11/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:482.70&airProductToken=AQpoCjIIwYIBEgQ0MjM1GKdcIKOxASiM34QDMPLfhAM4QkAAWAFqBUJBU0lDcghTVUFaWk5CWAoyCMGCARIEMTU3MxijsQEgrhworeCEAzC44YQDOEJAAVgBagVCQVNJQ3IIU1VBWlpOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Feb 12 - Fri, Feb 13 HRL Harlingen ORD Chicago CA $486 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:HRL,to:ORD,departure:12/02/2026TANYT&leg2=from:ORD,to:HRL,departure:13/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:485.40&airProductToken=AQpFCiEIwYIBEgQzNTc1GKdcIKOxASi-gYUDMKaChQM4UUAAWAEKIAjBggESAzg3NxijsQEgrhwozoKFAzDfg4UDOFFAAVgBCkUKIAjBggESAzk5NBiuHCCjsQEo1IWFAzDvhoUDOFFAAFgBCiEIwYIBEgQ0MzE3GKOxASCnXCimh4UDMIyIhQM4UUABWAESCggBEAEYASoCQUEYASIECAEQASgIKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Feb 7 - Sat, Feb 14 HRL Harlingen ORD Chicago CA $501 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:HRL,to:ORD,departure:07/02/2026TANYT&leg2=from:ORD,to:HRL,departure:14/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:500.40&airProductToken=AQpGCiEIwYIBEgQzODE4GKdcIKOxASjSwoQDMLLDhAM4TkAAWAEKIQjBggESBDEwMDYYo7EBIK4cKOfDhAMw9sSEAzhOQAFYAQpFCiAIwYIBEgM5OTQYrhwgo7EBKPSQhQMwj5KFAzhRQABYAQohCMGCARIENDMxNxijsQEgp1woxpKFAzCsk4UDOFFAAVgBEgoIARABGAEqAkFBGAEiBAgBEAEoCCgEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Feb 9 - Wed, Feb 11 HRL Harlingen ORD Chicago CA $505 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:HRL,to:ORD,departure:09/02/2026TANYT&leg2=from:ORD,to:HRL,departure:11/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:504.70&airProductToken=AQplCjEI1YIBEgQ0OTgwGKdcIIg4KILchAMw2dyEAzhLQABYAWoFMl9lY29yCEtBQTJQRkROCjAI1YIBEgM3ODcYiDggrhwopN6EAzDO34QDOEtAAFgBagUyX2Vjb3IIS0FBMlBGRE4KZgoxCNWCARIEMjYzOBiuHCCIOCjj8YQDMJzzhAM4S0AAWAFqBTJfZWNvcghLQUsyQVpEUwoxCNWCARIENDM0NBiIOCCnXCjY84QDMK70hAM4S0AAWAFqBTJfZWNvcghLQUsyQVpEUxIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Feb 7 - Fri, Feb 13 HRL Harlingen ORD Chicago CA $513 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:HRL,to:ORD,departure:07/02/2026TANYT&leg2=from:ORD,to:HRL,departure:13/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:512.20&airProductToken=AQpGCiEIwYIBEgQzODE4GKdcIKOxASjSwoQDMLLDhAM4TkAAWAEKIQjBggESBDEwMDYYo7EBIK4cKOfDhAMw9sSEAzhOQAFYAQpFCiAIwYIBEgM5OTQYrhwgo7EBKNSFhQMw74aFAzhRQABYAQohCMGCARIENDMxNxijsQEgp1wopoeFAzCMiIUDOFFAAVgBEgoIARABGAEqAkFBGAEiBAgBEAEoCCgEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Feb 9 - Wed, Feb 11 HRL Harlingen ORD Chicago CA $520 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:HRL,to:ORD,departure:09/02/2026TANYT&leg2=from:ORD,to:HRL,departure:11/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:519.80&airProductToken=AQpmCjEI1YIBEgQ0ODcwGKdcIIg4KL3ehAMwlN-EAzhLQABYAWoFMl9lY29yCEtBQTJQRkROCjEI1YIBEgQxMjkzGIg4IK4cKMbghAMw5OGEAzhLQABYAWoFMl9lY29yCEtBQTJQRkROCmYKMQjVggESBDEzNzMYrhwgiDgovPOEAzD49IQDOEtAAFgBagUyX2Vjb3IIS0FLMkFaRFMKMQjVggESBDQzNjIYiDggp1wow_WEAzCZ9oQDOEtAAFgBagUyX2Vjb3IIS0FLMkFaRFMSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Feb 6 - Sun, Feb 8 HRL Harlingen ORD Chicago CA $541 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:HRL,to:ORD,departure:06/02/2026TANYT&leg2=from:ORD,to:HRL,departure:08/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:540.20&airProductToken=AQpECiAIxJgBEgQxNzAxGKdcIMx8KPO7hAMwtL2EAzhFQABYAQogCMSYARIEMzkzOBjMfCCuHCjpvYQDMNK-hAM4RUABWAEKRAogCMSYARIEMzg1NBiuHCDMfCj_zYQDMOfOhAM4RUAAWAEKIAjEmAESBDE3MDEYzHwgp1wortCEAzD30YQDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ## Find the cheapest month to fly from Harlingen (HRL) to Chicago (ORD) ### September is typically the cheapest month to fly From CA $264 - CA $604 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:HRL,to:ORD,departure:06/02/2026TANYT&leg2=from:ORD,to:HRL,departure:11/02/2026TANYT&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 $501 ](https://www.expedia.ca/Flights-Search?leg1=from:HRL,to:ORD,departure:06/02/2026TANYT&leg2=from:ORD,to:HRL,departure:11/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) __Flight from Harlingen to Chicago (HRL - ORD) route information__ | Origin airport | Valley Intl. | | ------------------- | ------------ | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $460 | | Distance | 1953 km | ## Harlingen to Chicago Flights **The easy way to book your flights from Harlingen to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Harlingen 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 Harlingen to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Valley Intl., HRL to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Harlingen to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Harlingen currently is just CA $460 rising to CA $541\. Here are more money-saving tips: - Fly in February 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 Harlingen** 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 Valley Intl. Airport (HRL) to ORD? ### Do I need to pay a cancellation fee if I cancel my flight from Valley Intl. Airport to ORD? ### How do I find cheap flights from Valley Intl. Airport to O'Hare Airport that have flexible change policies? ### How many hours is the flight from Valley Intl. Airport (HRL) to O'Hare Airport? ### How far is the flight from Valley Intl. Airport to O'Hare Airport? ### Which airlines fly direct from Valley Intl. Airport to O'Hare Intl. Airport (ORD)? ### Are Valley Intl. Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute? ## 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) - 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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.