Title: CA $230 Cheap Flights from Winnipeg (YWG) to Chicago (CHI) - 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 $230 Cheap Flights from Winnipeg (YWG) to Chicago (CHI) [View CA $230 flight on Fri, Feb 13, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YWG,to:ORD,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:229.88&airProductToken=AQplCjAI16YBEgMyMjMY2DUgmBYon4aFAzCsh4UDOEVAAFgBagVCQVNJQ3IITFRWRDBaQksKMQjXpgESBDE2MTAYmBYgrhwogIiFAzDXiYUDOEVAAVgBagVCQVNJQ3IITFRWRDBaQksSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) - [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 - ![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:chi,departure:07/11/2025TANYT&leg2=from:chi,to:ywg,departure:14/11/2025TANYT&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:chi,departure:07/11/2025TANYT&leg2=from:chi,to:ywg,departure:14/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:chi,departure:07/11/2025TANYT&leg2=from:chi,to:ywg,departure:14/11/2025TANYT&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:ywg,to:chi,departure:07/11/2025TANYT&leg2=from:chi,to:ywg,departure:14/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) ![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 (CHI) Prices were available within the past 7 days and start at CA $230 for one-way flights and CA $392 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 13 - Mon, Feb 16 YWG Winnipeg ORD Chicago CA $392 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:13/02/2026TANYT&leg2=from:ORD,to:YWG,departure:16/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:391.58&airProductToken=AQplCjAI16YBEgMyMjMY2DUgmBYon4aFAzCsh4UDOEVAAFgBagVCQVNJQ3IITFRWRDBaQksKMQjXpgESBDE2MTAYmBYgrhwogIiFAzDXiYUDOEVAAVgBagVCQVNJQ3IITFRWRDBaQksKZQoxCNemARIEMTYxMRiuHCCYFijkq4UDMM-thQM4RUAAWAFqBUJBU0lDcghMVFZEMFpCSwowCNemARIDMjQ4GJgWINg1KNuuhQMw2K-FAzhFQAFYAWoFQkFTSUNyCExUVkQwWkJLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Feb 13 - Mon, Feb 16 YWG Winnipeg ORD Chicago CA $446 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:13/02/2026TANYT&leg2=from:ORD,to:YWG,departure:16/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:445.21&airProductToken=AQplCjAI16YBEgMyMjMY2DUgmBYon4aFAzCsh4UDOEVAAFgBagVCQVNJQ3IITFRWRDBaQksKMQjXpgESBDE2MTAYmBYgrhwogIiFAzDXiYUDOEVAAVgBagVCQVNJQ3IITFRWRDBaQksKZQoxCNemARIEMTYxMRiuHCCYFijkq4UDMM-thQM4RUAAWAFqBUJBU0lDcghMVFZEMFpCSwowCNemARIDMjUyGJgWINg1KNOvhQMw0LCFAzhFQAFYAWoFQkFTSUNyCExUVkQwWkJLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Mon, Jan 19 - Fri, Mar 6 YWG Winnipeg ORD Chicago CA $480 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:19/01/2026TANYT&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:479.78&airProductToken=AQplCjAI16YBEgMyMjMY2DUgmBYo_-yCAzCS7oIDOExAAFgBagVFQ09OT3IITFRWRDBaRUsKMQjXpgESBDE2MTAYmBYgrhwo4O6CAzC38IIDOExAAVgBagVFQ09OT3IITFRWRDBaRUsKZQoxCNemARIEMTYxMRiuHCCYFiik9oYDMI_4hgM4TEAAWAFqBUVDT05PcghMVFZEMFpFSwowCNemARIDMjQ4GJgWINg1KJv5hgMwmPqGAzhMQAFYAWoFRUNPTk9yCExUVkQwWkVLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sun, Nov 23 - Fri, Nov 28 YWG Winnipeg ORD Chicago CA $500 Roundtrip found 21 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:23/11/2025TANYT&leg2=from:ORD,to:YWG,departure:28/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:499.10&airProductToken=AQpDCh8I16YBEgMyNDcY2DUgmBYo1_H9AjDk8v0COEVAAFgBCiAI16YBEgQxNjEwGJgWIK4cKOD4_QIwt_r9AjhFQAFYAQpDCiAI16YBEgQxNjExGK4cIJgWKOSn_gIwz6n-AjhFQABYAQofCNemARIDMjUyGJgWINg1KNOr_gIw0az-AjhFQAFYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Thu, Dec 25 - Fri, Jan 9 YWG Winnipeg ORD Chicago CA $511 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:25/12/2025TANYT&leg2=from:ORD,to:YWG,departure:09/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:510.62&airProductToken=AQpDCh8I16YBEgMyNDcY2DUgmBYo19mAAzDk2oADOEVAAFgBCiAI16YBEgQxNjEwGJgWIK4cKODggAMwt-KAAzhFQAFYAQpDCiAI16YBEgQxNjExGK4cIJgWKKSAggMwj4KCAzhFQABYAQofCNemARIDMjQ4GJgWINg1KJuDggMwmYSCAzhFQAFYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Dec 5 - Mon, Dec 8 YWG Winnipeg ORD Chicago CA $519 Roundtrip found 14 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:05/12/2025TANYT&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:518.61&airProductToken=AQqlAQo1CMSYARIENDAwNRjYNSDMfCiR-P4CMPX4_gI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWTkEwQlEKNQjEmAESBDEwMzIYzHwg4FworPn-AjDO-v4COEVAAVgBaglNQUlOQkFTSUNyCFZBVk5BMEJRCjUIxJgBEgQxMTc4GOBcIK4cKI7-_gIwj__-AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZTWDBCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Mon, Jan 19 - Fri, Mar 6 YWG Winnipeg ORD Chicago CA $534 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:19/01/2026TANYT&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:533.41&airProductToken=AQplCjAI16YBEgMyMjMY2DUgmBYo_-yCAzCS7oIDOExAAFgBagVFQ09OT3IITFRWRDBaRUsKMQjXpgESBDE2MTAYmBYgrhwo4O6CAzC38IIDOExAAVgBagVFQ09OT3IITFRWRDBaRUsKZQoxCNemARIEMTYxMRiuHCCYFiik9oYDMI_4hgM4TEAAWAFqBUVDT05PcghMVFZEMFpFSwowCNemARIDMjUyGJgWINg1KJP6hgMwkPuGAzhMQAFYAWoFRUNPTk9yCExUVkQwWkVLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Jan 19 - Fri, Mar 6 YWG Winnipeg ORD Chicago CA $582 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:19/01/2026TANYT&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:581.12&airProductToken=AQo4CjYI1YIBEgQ1NjM5GNg1IK4cKOTwggMwh_KCAzhOQABYAWoKMV9iYXNpY2Vjb3IIS05BNUFVQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Tue, Jan 27 - Sat, Jan 31 YWG Winnipeg ORD Chicago CA $634 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:27/01/2026TANYT&leg2=from:ORD,to:YWG,departure:31/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:633.26&airProductToken=AQpFCiAIwYYBEgMyOTMY2DUguI0BKPDGgwMwtciDAzhHQABYAQohCMGGARIEMTA0OBi4jQEgrhwo_siDAzD5yoMDOEdAAVgBCkUKIQjBhgESBDEwNDkYrhwguI0BKLT4gwMwx_qDAzhHQABYAQogCMGGARIDMjk4GLiNASDYNSjE-4MDMO38gwM4R0ABWAESCggBEAEYASoCQUMYASIECAEQASgIKAQwAQ) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Mon, Mar 23 - Fri, Mar 27 YWG Winnipeg ORD Chicago CA $1,011 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YWG,to:ORD,departure:23/03/2026TANYT&leg2=from:ORD,to:YWG,departure:27/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1010.68&airProductToken=AQptCjQI0IgBEgM0MjQY2DUgmM4BKJSxiAMwrLKIAzhBQABYAWoIU1RBTkRBUkRyCEE0QzBaUlpTCjUI0IgBEgQ2MDY1GJjOASCuHCiBtIgDMPm0iAM4QUABWAFqCFNUQU5EQVJEcghBNk4xWk9aUwptCjUI0IgBEgQ2MDA3GK4cIJjOASiM34gDMOvfiAM4QUAAWAFqCFNUQU5EQVJEcghBNk4xWk9aUwo0CNCIARIDNDIzGJjOASDYNSip4YgDMM7iiAM4QUABWAFqCFNUQU5EQVJEcghBNEMwWlJaUxIKCAEQARgBKgJQRBgBIgQIARABKAIoAygEMAE) ## Find the cheapest month to fly from Winnipeg (YWG) to Chicago (CHI) ### October is typically the cheapest month to fly From CA $346 - CA $1,205 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:ORD,departure:07/11/2025TANYT&leg2=from:ORD,to:YWG,departure:20/11/2025TANYT&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 $1,099](https://www.expedia.ca/Flights-Search?leg1=from:YWG,to:ORD,departure:07/11/2025TANYT&leg2=from:ORD,to:YWG,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.ca/Flights-Search?leg1=from:YWG,to:MDW,departure:07/11/2025TANYT&leg2=from:MDW,to:YWG,departure:14/11/2025TANYT&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 $1,204](https://www.expedia.ca/Flights-Search?leg1=from:YWG,to:MDW,departure:07/11/2025TANYT&leg2=from:MDW,to:YWG,departure:14/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Frequently asked questions ### How much is a flight from YWG to Chicago, IL (CHI-All Airports)? > Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports) was CA $392. Fares this good don't wait forever, so make sure you book yours ASAP. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from YWG to Chicago, IL (CHI-All Airports)? > We get that life can throw the odd curveball, so we've made it as simple as possible for you to cancel your trip online. Just head to the [Customer Service Portal](https://www.expedia.ca/service/?langid=1033) and follow the instructions. ### How do I find cheap flights from Winnipeg Airport to Chicago, IL (CHI-All Airports) that have flexible change policies? > Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for YWG to Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select. ### How far is the flight from Winnipeg Airport to Chicago, IL (CHI-All Airports)? > With a flight distance of 1,100 kilometers, it's just a short hop from YWG to Chicago, IL (CHI-All Airports). It might be a quick flight, but it's still worth packing a book to read. ### Which airlines fly direct from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports)? > You won't find any airlines flying directly between Winnipeg James Armstrong Richardson Intl. Airport (YWG) and Chicago, IL (CHI-All Airports), so be prepared to make at least one stop on your journey. A layover can be a good way to break up a trip! ### Are Winnipeg Airport to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute? > Booking last minute from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports) can be hit-or-miss. You may be able to find a bargain, but you could also completely miss out! If you'd prefer to start your trip planning ahead of time, Expedia compares flight deals up to 12 months in advance. Just keep in mind that not all airlines publish their prices that far in advance. Our suggestion? Check back often as updates are made frequently. ## Travel information | Origin airport | Winnipeg James Armstrong Richardson Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $392 | | Distance | 1130 km | ## Book with confidence ### Winnipeg to Illinois 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 CHI-All Airports, 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 CHI-All Airports, CHI**  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 $392 rising to CA $1,011.   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. ## Explore a world of travel with Expedia - Flights - [Flights from Allentown (ABE) to Rockford (RFD)](https://www.expedia.ca/lp/flights/abe/rfd/allentown-to-rockford) - [Flights from Ahmedabad (AMD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/amd/ord/ahmedabad-to-chicago) - [Flights from Atlanta (ATL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/atl/ord/atlanta-to-chicago) - [Flights from Austin (AUS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/aus/ord/austin-to-chicago) - [Flights from Mesa (AZA) to Rockford (RFD)](https://www.expedia.ca/lp/flights/aza/rfd/mesa-to-rockford) - [Flights from Binghamton (BGM) to Rockford (RFD)](https://www.expedia.ca/lp/flights/bgm/rfd/binghamton-to-rockford) - [Flights from Bangor (BGR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bgr/ord/bangor-to-chicago) - [Flights from Bellingham (BLI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bli/ord/bellingham-to-chicago) - [Flights from Nashville (BNA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bna/ord/nashville-to-chicago) - [Flights from Mumbai (BOM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bom/ord/mumbai-to-chicago) - [Flights from Burlington (BTV) to Chicago (ORD)](https://www.expedia.ca/lp/flights/btv/ord/burlington-to-chicago) - [Flights from Buffalo (BUF) to Rockford (RFD)](https://www.expedia.ca/lp/flights/buf/rfd/buffalo-to-rockford) - [Flights from Baltimore (BWI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bwi/ord/baltimore-to-chicago) - [Flights from Charlottesville (CHO) to Rockford (RFD)](https://www.expedia.ca/lp/flights/cho/rfd/charlottesville-to-rockford) - [Flights from Sault Ste. Marie (CIU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ciu/ord/sault-ste-marie-to-chicago) - [Flights from Charlotte (CLT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/clt/ord/charlotte-to-chicago) - [Flights from Columbus (CMH) to Chicago (ORD)](https://www.expedia.ca/lp/flights/cmh/ord/columbus-to-chicago) - [Flights from Cincinnati (CVG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/cvg/ord/cincinnati-to-chicago) - [Flights from Washington (DCA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dca/ord/washington-to-chicago) - [Flights from Denver (DEN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/den/ord/denver-to-chicago) - [Flights from Duluth (DLH) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dlh/ord/duluth-to-chicago) - [Flights from Detroit (DTW) to Rockford (RFD)](https://www.expedia.ca/lp/flights/dtw/rfd/detroit-to-rockford) - [Flights from Dubai (DXB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dxb/ord/dubai-to-chicago) - [Flights from Fort Lauderdale (FLL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/fll/ord/fort-lauderdale-to-chicago) - 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[Flights from Niagara Falls (IAG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/iag/ord/niagara-falls-to-chicago) - [Flights from Indianapolis (IND) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ind/ord/indianapolis-to-chicago) - [Flights from New York (JFK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/jfk/ord/new-york-to-chicago) - [Flights from New York (JFK) to Rockford (RFD)](https://www.expedia.ca/lp/flights/jfk/rfd/new-york-to-rockford) - [Flights from Lansing (LAN) to Rockford (RFD)](https://www.expedia.ca/lp/flights/lan/rfd/lansing-to-rockford) - [Flights from Las Vegas (LAS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/las/ord/las-vegas-to-chicago) - [Flights from Larnaca (LCA) to Rockford (RFD)](https://www.expedia.ca/lp/flights/lca/rfd/larnaca-to-rockford) - [Flights from London (LHR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/lhr/ord/london-to-chicago) - [Flights from London (LHR) to Rockford (RFD)](https://www.expedia.ca/lp/flights/lhr/rfd/london-to-rockford) - [Flights from Mackinac Island (MCD) to Rockford (RFD)](https://www.expedia.ca/lp/flights/mcd/rfd/mackinac-island-to-rockford) - [Flights from Kansas City (MCI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mci/ord/kansas-city-to-chicago) - [Flights from Kansas City (MCI) to Rockford (RFD)](https://www.expedia.ca/lp/flights/mci/rfd/kansas-city-to-rockford) - [Flights from Orlando (MCO) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mco/ord/orlando-to-chicago) - [Flights from Mexico City (MEX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mex/ord/mexico-city-to-chicago) - [Flights from Miami (MIA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mia/ord/miami-to-chicago) - [Flights from Minot (MOT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mot/ord/minot-to-chicago) - [Flights from Minot (MOT) to Rockford (RFD)](https://www.expedia.ca/lp/flights/mot/rfd/minot-to-rockford) - [Flights from Muscle Shoals (MSL) to Rockford (RFD)](https://www.expedia.ca/lp/flights/msl/rfd/muscle-shoals-to-rockford) - [Flights from Madison (MSN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/msn/ord/madison-to-chicago) - [Flights from Minneapolis (MSP) to Rockford (RFD)](https://www.expedia.ca/lp/flights/msp/rfd/minneapolis-to-rockford) - [Flights from Tokyo (NRT) to Rockford (RFD)](https://www.expedia.ca/lp/flights/nrt/rfd/tokyo-to-rockford) - [Flights from Ogdensburg (OGS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ogs/ord/ogdensburg-to-chicago) - [Flights from Omaha (OMA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/oma/ord/omaha-to-chicago) - [Flights from Ontario (ONT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ont/ord/ontario-to-chicago) - [Flights from Ontario (ONT) to Rockford (RFD)](https://www.expedia.ca/lp/flights/ont/rfd/ontario-to-rockford) - [Flights from Chicago (ORD) to Rockford (RFD)](https://www.expedia.ca/lp/flights/ord/rfd/chicago-to-rockford) - [Flights from Paducah (PAH) to Rockford (RFD)](https://www.expedia.ca/lp/flights/pah/rfd/paducah-to-rockford) - [Flights from Plattsburgh (PBG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pbg/ord/plattsburgh-to-chicago) - [Flights from Portland (PDX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pdx/ord/portland-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/phl/ord/philadelphia-to-chicago) - [Flights from Pittsburgh (PIT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pit/ord/pittsburgh-to-chicago) - [Flights from Redding (RDD) to Rockford (RFD)](https://www.expedia.ca/lp/flights/rdd/rfd/redding-to-rockford) - [Flights from Rockford (RFD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/rfd/ord/rockford-to-chicago) - [Flights from Roswell (ROW) to Rockford (RFD)](https://www.expedia.ca/lp/flights/row/rfd/roswell-to-rockford) - [Flights from San Diego (SAN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/san/ord/san-diego-to-chicago) - [Flights from Louisville (SDF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/sdf/ord/louisville-to-chicago) - [Flights from Santander (SDR) to Rockford (RFD)](https://www.expedia.ca/lp/flights/sdr/rfd/santander-to-rockford) - [Flights from San Francisco (SFO) to Chicago (ORD)](https://www.expedia.ca/lp/flights/sfo/ord/san-francisco-to-chicago) - [Flights from Salt Lake City (SLC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/slc/ord/salt-lake-city-to-chicago) - [Flights from Syracuse (SYR) to Rockford (RFD)](https://www.expedia.ca/lp/flights/syr/rfd/syracuse-to-rockford) - [Flights from Sault Ste. Marie (YAM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yam/ord/sault-ste-marie-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ycd/ord/nanaimo-to-chicago) - [Flights from Edmonton (YEG) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yeg/rfd/edmonton-to-rockford) - [Flights from Fredericton (YFC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yfc/ord/fredericton-to-chicago) - [Flights from Kingston (YGK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ygk/ord/kingston-to-chicago) - [Flights from Hamilton (YHM) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yhm/rfd/hamilton-to-rockford) - [Flights from Halifax (YHZ) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yhz/rfd/halifax-to-rockford) - [Flights from Kamloops (YKA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yka/ord/kamloops-to-chicago) - [Flights from Kelowna (YLW) to Rockford (RFD)](https://www.expedia.ca/lp/flights/ylw/rfd/kelowna-to-rockford) - [Flights from Ottawa (YOW) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yow/rfd/ottawa-to-rockford) - [Flights from Peterborough (YPQ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ypq/ord/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqb/ord/quebec-to-chicago) - [Flights from Moncton (YQM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqm/ord/moncton-to-chicago) - [Flights from Sudbury (YSB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ysb/ord/sudbury-to-chicago) - [Flights from Toronto (YTO) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yto/rfd/toronto-to-rockford) - [Flights from Toronto (YTZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ytz/ord/toronto-to-chicago) - [Flights from Montreal (YUL) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yul/rfd/montreal-to-rockford) - [Flights from Vancouver (YVR) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yvr/rfd/vancouver-to-rockford) - [Flights from Winnipeg (YWG) to Rockford (RFD)](https://www.expedia.ca/lp/flights/ywg/rfd/winnipeg-to-rockford) - [Flights from Abbotsford (YXX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yxx/ord/abbotsford-to-chicago) - [Flights from North Bay (YYB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyb/ord/north-bay-to-chicago) - [Flights from Calgary (YYC) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yyc/rfd/calgary-to-rockford) - [Flights from Charlottetown (YYG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyg/ord/charlottetown-to-chicago) - [Flights from St. John's (YYT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyt/ord/st-johns-to-chicago) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Flights from Toronto (YYZ) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yyz/rfd/toronto-to-rockford) - [Flights from Sarnia (YZR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yzr/ord/sarnia-to-chicago) \*Available to Expedia members.