Title: CA $219 Cheap Flights from Winnipeg (YWG) 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 $219 Cheap Flights from Winnipeg (YWG) to Chicago (ORD) [View CA $219 flight on Sun, Oct 26, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YWG,to:ORD,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:218.38&airProductToken=AQplCjAI16YBEgMyMjMY2DUgmBYoo7D7AjC2sfsCOEVAAFgBagVCQVNJQ3IITFRWRDBaQksKMQjXpgESBDE2MTAYmBYgrhwohLL7AjDbs_sCOEVAAVgBagVCQVNJQ3IITFRWRDBaQksSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) - [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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago O'Hare International Airport (ORD) - ![WestJet](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WS.svg) WestJet [](https://www.expedia.ca/Flights-Search?leg1=from:ywg,to:ord,departure:12/10/2025TANYT&leg2=from:ord,to:ywg,departure:19/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![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:ywg,to:ord,departure:12/10/2025TANYT&leg2=from:ord,to:ywg,departure:19/10/2025TANYT&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:ywg,to:ord,departure:12/10/2025TANYT&leg2=from:ord,to:ywg,departure:19/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:ywg,to:ord,departure:12/10/2025TANYT&leg2=from:ord,to:ywg,departure:19/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) ![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 Winnipeg (YWG) to Chicago (ORD) Prices were available within the past 7 days and start at CA $219 for one-way flights and CA $369 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Feb 27 - Fri, Mar 6 YWG Winnipeg ORD Chicago CA $369 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:27/02/2026TANYT&leg2=from:ORD,to:YWG,departure:06/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:368.86&airProductToken=AQpDCh8I16YBEgMyMjMY2DUgmBYo36OGAzDspIYDOEVAAFgBCiAI16YBEgQxNjEwGJgWIK4cKMClhgMwl6eGAzhFQAFYAQpDCiAI16YBEgQxNjExGK4cIJgWKKT2hgMwj_iGAzhFQABYAQofCNemARIDMjQ4GJgWINg1KJv5hgMwmPqGAzhFQAFYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Dec 12 - Mon, Dec 15 YWG Winnipeg ORD Chicago CA $370 Roundtrip found 1 hour ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:12/12/2025TANYT&leg2=from:ORD,to:YWG,departure:15/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:369.54&airProductToken=AQplCjAI16YBEgMyMjMY2DUgmBYov8H_AjDSwv8COEVAAFgBagVCQVNJQ3IITFRWRDBaQksKMQjXpgESBDE2MTAYmBYgrhwooMP_AjD3xP8COEVAAVgBagVCQVNJQ3IITFRWRDBaQksKZQoxCNemARIEMTYxMRiuHCCYFiiE5_8CMO_o_wI4RUAAWAFqBUJBU0lDcghMVFZEMFpCSwowCNemARIDMjQ4GJgWINg1KPvp_wIw-er_AjhFQAFYAWoFQkFTSUNyCExUVkQwWkJLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Thu, Nov 27 - Mon, Dec 1 YWG Winnipeg ORD Chicago CA $423 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:27/11/2025TANYT&leg2=from:ORD,to:YWG,departure:01/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:422.50&airProductToken=AQpDCh8I16YBEgMyNTEY2DUgmBYo1J_-AjDhoP4COEVAAFgBCiAI16YBEgQxNjEwGJgWIK4cKOCl_gIwt6f-AjhFQAFYAQpDCiAI16YBEgQxNjExGK4cIJgWKMTJ_gIwr8v-AjhFQABYAQofCNemARIDMjQ4GJgWINg1KLvM_gIwuc3-AjhFQAFYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Nov 28 - Mon, Dec 8 YWG Winnipeg ORD Chicago CA $423 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:28/11/2025TANYT&leg2=from:ORD,to:YWG,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:422.53&airProductToken=AQplCjAI16YBEgMyMjMY2DUgmBYo_6P-AjCSpf4COEVAAFgBagVCQVNJQ3IITFRWRDBaQksKMQjXpgESBDE2MTAYmBYgrhwo4KX-AjC3p_4COEVAAVgBagVCQVNJQ3IITFRWRDBaQksKZQoxCNemARIEMTYxMRiuHCCYFiikmP8CMI-a_wI4RUAAWAFqBUJBU0lDcghMVFZEMFpCSwowCNemARIDMjUyGJgWINg1KJOc_wIwkZ3_AjhFQAFYAWoFQkFTSUNyCExUVkQwWkJLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sat, Oct 25 - Fri, Oct 31 YWG Winnipeg ORD Chicago CA $428 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:25/10/2025TANYT&leg2=from:ORD,to:YWG,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:427.28&airProductToken=AQplCjAI16YBEgMyNjEY2DUgmBYoiqb7AjCQp_sCOEVAAFgBagVCQVNJQ3IITFRVRDBaQksKMQjXpgESBDE1ODgYmBYgrhwop6j7AjD3qfsCOEVAAVgBagVCQVNJQ3IITFRVRDBaQksKZQoxCNemARIEMTYxMRiuHCCYFiio7PsCMJPu-wI4RUAAWAFqBUJBU0lDcghMVFZEMFpCSwowCNemARIDMjQ4GJgWINg1KJ_v-wIwnfD7AjhFQAFYAWoFQkFTSUNyCExUVkQwWkJLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Thu, Oct 23 - Fri, Oct 31 YWG Winnipeg ORD Chicago CA $429 Roundtrip found 21 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:23/10/2025TANYT&leg2=from:ORD,to:YWG,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:428.26&airProductToken=AQpDCh8I16YBEgMyNjEY2DUgmBYoyo_7AjDQkPsCOEVAAFgBCiAI16YBEgQxNTg4GJgWIK4cKOeR-wIwt5P7AjhFQAFYAQpDCiAI16YBEgQxNjExGK4cIJgWKKjs-wIwk-77AjhFQABYAQofCNemARIDMjQ4GJgWINg1KJ_v-wIwnfD7AjhFQAFYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Dec 12 - Mon, Dec 29 YWG Winnipeg ORD Chicago CA $434 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:12/12/2025TANYT&leg2=from:ORD,to:YWG,departure:29/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:433.96&airProductToken=AQpDCh8I16YBEgMyMjMY2DUgmBYov8H_AjDSwv8COEVAAFgBCiAI16YBEgQxNjEwGJgWIK4cKKDD_wIw98T_AjhFQAFYAQpDCiAI16YBEgQxNjExGK4cIJgWKMSEgQMwr4aBAzhFQABYAQofCNemARIDMjQ4GJgWINg1KLuHgQMwuYiBAzhFQAFYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sun, Oct 19 - Thu, Oct 23 YWG Winnipeg ORD Chicago CA $498 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:19/10/2025TANYT&leg2=from:ORD,to:YWG,departure:23/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:497.28&airProductToken=AQo4CjYI1YIBEgQ1NjM5GNg1IK4cKKjl-gIwv-b6AjhOQABYAWoKMV9iYXNpY2Vjb3IIR05BMkEyQk4KOAo2CNWCARIENTg2OBiuHCDYNSj2lPsCMJWW-wI4TkAAWAFqCjFfYmFzaWNlY29yCEdOQTJBMkJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Dec 3 - Mon, Dec 8 YWG Winnipeg ORD Chicago CA $500 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:03/12/2025TANYT&leg2=from:ORD,to:YWG,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:499.77&airProductToken=AQqlAQo1CMSYARIEMzg3MRjYNSDMfCim3_4CMIbg_gI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFXTkEwQlEKNQjEmAESBDEwMzIYzHwg4Fwo7OL-AjCN5P4COEVAAVgBaglNQUlOQkFTSUNyCFZBV05BMEJRCjUIxJgBEgQxMTc4GOBcIK4cKNPn_gIw1ej-AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZTWDRCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Oct 15 - Thu, Oct 23 YWG Winnipeg ORD Chicago CA $506 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:15/10/2025TANYT&leg2=from:ORD,to:YWG,departure:23/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:505.70&airProductToken=AQpmCjEIwYYBEgMyNTYY2DUgmM4BKPiz-gIwibX6AjhHQABYAWoFQkFTSUNyCEdOQTJBMkJBCjEIwYYBEgM1MDUYmM4BIK4cKPS2-gIw5rf6AjhHQAFYAWoFQkFTSUNyCEdOQTJBMkJBCmQKMAjBhgESAzUyMBiuHCCYXSjUj_sCMNqQ-wI4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQowCMGGARIDMzczGJhdINg1KJyR-wIw0JL7AjhHQAFYAWoFQkFTSUNyCEdOQTJBMkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwDQ) ## Find the cheapest month to fly from Winnipeg (YWG) to Chicago (ORD) ### June is typically the cheapest month to fly From CA $333 - CA $729 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:YWG,to:MDW,departure:12/10/2025TANYT&leg2=from:MDW,to:YWG,departure:16/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. Closest 16 min [Flights from CA $939](https://www.expedia.ca/Flights-Search?leg1=from:YWG,to:MDW,departure:12/10/2025TANYT&leg2=from:MDW,to:YWG,departure:16/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Flight from Winnipeg to Chicago (YWG - ORD) route information | Origin airport | Winnipeg James Armstrong Richardson Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | Air Canada, Delta, United, WestJet | | Roundtrip price | CA $369 | | Distance | 1130 km | | Average flight time | 2 hours 31 mins | ## Winnipeg to Chicago Flights **The easy way to book your flights from Winnipeg to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Winnipeg 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 Winnipeg to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Winnipeg James Armstrong Richardson Intl., YWG to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Winnipeg to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Winnipeg currently is just CA $369 rising to CA $506.   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 Winnipeg**  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 YWG to O'Hare Airport? > If you're travelling from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Airport, round-trip flights start from CA $369. This figure is based on fares advertised within the last 7 days on Expedia for flights departing within the next year, so don't hang around. 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 Winnipeg Airport to ORD? > We get that circumstances change unexpectedly, so we've made it as hassle-free as possible for you to cancel your flight online. Just visit the [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions. ### How do I find cheap flights from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to ORD that have flexible change policies? > Flights from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD) with flexible change policies are available from several carriers. Simply use our "No change fees" filter when searching. You'll only need to cover the cost difference between flights, with no additional fees to worry about. ### How many hours is the flight from YWG to ORD? > It takes around 5 hours and 12 minutes to fly from Winnipeg Airport to ORD. But with your favourite playlist and a good book, the time will go by quicker. ### How far is the flight from YWG to ORD? > A flight distance of just 1,150 kilometres separates Winnipeg and Chicago. Once you're up in the skies, you won't have time to do much more than browse the magazine in your seat-back pocket. ### Which airlines fly direct from Winnipeg Airport to O'Hare Airport? > A popular choice with many travellers, United Airlines (UA) offers 30 flights monthly from YWG to ORD. Pick the one that fits in with your travel plans and book your ticket today. ### Are YWG to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? > Booking your trip from YWG to ORD last minute could be your ticket to an awesome deal. However, it could end up costing you a whole lot more! If you'd prefer to err on the side of caution, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to 12 months in advance. If your preferred air carrier hasn't released tickets yet, check back frequently as deals are updated on Expedia all the time. ## 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.