Title: CA $236 Cheap Flights from Kelowna (YLW) 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 $236 Cheap Flights from Kelowna (YLW) to Chicago (ORD) [View CA $236 flight on Fri, Dec 12, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YLW,to:ORD,departure:12/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:235.03&airProductToken=AQpmCjEI16YBEgMxODAY-LIBIJgWKIDC_wIwyML_AjhFQABYAWoFQkFTSUNyCExUVkQwWkJLCjEI16YBEgQxNjEwGJgWIK4cKKDD_wIw98T_AjhFQAFYAWoFQkFTSUNyCExUVkQwWkJLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) - [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 Kelowna Intl. Airport (YLW) 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:ylw,to:ord,departure:12/11/2025TANYT&leg2=from:ord,to:ylw,departure:19/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:ylw,to:ord,departure:12/11/2025TANYT&leg2=from:ord,to:ylw,departure:19/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![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:ylw,to:ord,departure:12/11/2025TANYT&leg2=from:ord,to:ylw,departure:19/11/2025TANYT&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:ylw,to:ord,departure:12/11/2025TANYT&leg2=from:ord,to:ylw,departure:19/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:ylw,to:ord,departure:12/11/2025TANYT&leg2=from:ord,to:ylw,departure:19/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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:ylw,to:ord,departure:12/11/2025TANYT&leg2=from:ord,to:ylw,departure:19/11/2025TANYT&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 Kelowna (YLW) to Chicago (ORD) Prices were available within the past 7 days and start at CA $236 for one-way flights and CA $413 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, Dec 12 - Mon, Dec 15 YLW Kelowna ORD Chicago CA $413 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:ORD,departure:12/12/2025TANYT&leg2=from:ORD,to:YLW,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:412.37&airProductToken=AQpmCjEI16YBEgMxODAY-LIBIJgWKIDC_wIwyML_AjhFQABYAWoFQkFTSUNyCExUVkQwWkJLCjEI16YBEgQxNjEwGJgWIK4cKKDD_wIw98T_AjhFQAFYAWoFQkFTSUNyCExUVkQwWkJLCmYKMQjXpgESBDE2MTEYrhwgmBYohOf_AjDv6P8COEVAAFgBagVCQVNJQ3IITFRWRDBaQksKMQjXpgESAzE4NRiYFiD4sgEo0-n_AjCe6v8COEVAAVgBagVCQVNJQ3IITFRWRDBaQksSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Mar 25 - Tue, Apr 7 YLW Kelowna ORD Chicago CA $413 Roundtrip found 9 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:ORD,departure:25/03/2026TANYT&leg2=from:ORD,to:YLW,departure:07/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:412.44&airProductToken=AQpHCiIIwYYBEgQ4MjY1GPiyASC4jQEo4MiIAzCjyYgDOEdAAFgBCiEIwYYBEgQxMDQ4GLiNASCuHCieyogDMJnMiAM4R0ABWAEKRwohCMGGARIEMTA0ORiuHCC4jQEo9N6JAzCD4YkDOEdAAFgBCiIIwYYBEgQ4Mjg0GLiNASD4sgEo6OKJAzCh44kDOEdAAVgBEgoIARABGAEqAkFDGAEiBAgBEAEoCCgEMAE) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Mon, Jan 12 - Mon, Feb 2 YLW Kelowna ORD Chicago CA $413 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:ORD,departure:12/01/2026TANYT&leg2=from:ORD,to:YLW,departure:02/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:412.51&airProductToken=AQpECiAI16YBEgMxODAY-LIBIJgWKOCeggMwqJ-CAzhFQABYAQogCNemARIEMTYxMBiYFiCuHCiAoIIDMNehggM4RUABWAEKRAogCNemARIEMTYxMRiuHCCYFiikjoQDMI-QhAM4RUAAWAEKIAjXpgESAzE4NRiYFiD4sgEo85CEAzC8kYQDOEVAAVgBEgoIARABGAEqAldTGAEiBAgBEAEoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Feb 18 - Sat, Mar 7 YLW Kelowna ORD Chicago CA $421 Roundtrip found 9 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:ORD,departure:18/02/2026TANYT&leg2=from:ORD,to:YLW,departure:07/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:420.27&airProductToken=AQpECiEIwaYBEgQzNDA4GPiyASCSASjSwIUDMJfBhQM4WEAAWAEKHwjBpgESAzQxMBiSASCuHCiBwoUDMPbDhQM4WEABWAEKaAogCMGmARIDMzI1GK4cIO-4ASi1gYcDMMeDhwM4WEAAWAEKIQjBpgESBDIyNDEY77gBIJIBKPqDhwMwr4SHAzhYQAFYAQohCMGmARIEMzM5MhiSASD4sgEohoWHAzDQhYcDOFhAAVgBEgoIARABGAEqAkFTGAEiBAgBEAEoBDAB) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, Jan 17 - Tue, Jan 20 YLW Kelowna ORD Chicago CA $431 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:ORD,departure:17/01/2026TANYT&leg2=from:ORD,to:YLW,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:430.46&airProductToken=AQqdAQozCMGGARIEODI4MRj4sgEguI0BKIfdggMwxt2CAzhHQABYAWoFQkFTSUNyCEdOQTVBMkJBCjIIwYYBEgMxMjYYuI0BIJjOASia34IDMKfhggM4R0ABWAFqBUJBU0lDcghHTkE1QTJCQQoyCMGGARIEODkwMRiYzgEgrhwom-KCAzCR44IDOEdAAVgBagVCQVNJQ3IIR05BNUEyQkEKaAoxCMGGARIDNTA4GK4cIJjOASjj_IIDMMb9ggM4R0AAWAFqBUJBU0lDcghHTkE1QTJCQQozCMGGARIEMTkxMxiYzgEg-LIBKLX-ggMw3ICDAzhHQAFYAWoFQkFTSUNyCEdOQTVBMkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwAQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Feb 11 - Mon, Feb 23 YLW Kelowna ORD Chicago CA $431 Roundtrip found 8 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:ORD,departure:11/02/2026TANYT&leg2=from:ORD,to:YLW,departure:23/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:430.52&airProductToken=AQpHCiIIwYYBEgQxOTEyGPiyASCYzgEo2PiEAzDg-oQDOEdAAFgBCiEIwYYBEgQ4OTAxGJjOASCuHCi7-4QDMLH8hAM4R0ABWAEKRgogCMGGARIDNTA4GK4cIJjOASij-4UDMIb8hQM4R0AAWAEKIgjBhgESBDE5MTMYmM4BIPiyASj1_IUDMJz_hQM4R0ABWAESCggBEAEYASoCQUMYASIECAEQASgIKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Fri, Feb 27 - Tue, Mar 10 YLW Kelowna ORD Chicago CA $435 Roundtrip found 9 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:ORD,departure:27/02/2026TANYT&leg2=from:ORD,to:YLW,departure:10/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:434.79&airProductToken=AQpECiEIwaYBEgQzNDA4GPiyASCSASjypYYDMLemhgM4WEAAWAEKHwjBpgESAzQxMBiSASCuHCihp4YDMJaphgM4WEABWAEKRAofCMGmARIDNTg3GK4cIJIBKJmghwMwvKKHAzhYQABYAQohCMGmARIEMzM5MhiSASD4sgEo5qaHAzCwp4cDOFhAAVgBEgoIARABGAEqAkFTGAEiBAgBEAEoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sun, Jan 18 - Tue, Jan 27 YLW Kelowna ORD Chicago CA $442 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:ORD,departure:18/01/2026TANYT&leg2=from:ORD,to:YLW,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:441.63&airProductToken=AQpECiEIwaYBEgQzMzQ0GPiyASCSASjA44IDMJvkggM4WEAAWAEKHwjBpgESAzUzOBiSASCuHCiO6IIDMIPqggM4WEABWAEKRAofCMGmARIDNDA3GK4cIJIBKK_LgwMwzs2DAzhYQABYAQohCMGmARIEMzM5MhiSASD4sgEoq86DAzD6zoMDOFhAAVgBEgoIARABGAEqAkFTGAEiBAgBEAEoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, Jan 17 - Tue, Jan 20 YLW Kelowna ORD Chicago CA $486 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:ORD,departure:17/01/2026TANYT&leg2=from:ORD,to:YLW,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:485.88&airProductToken=AQpnCjII1YIBEgQ4MDM0GPiyASCYFijN2IIDMJLZggM4R0AAWAFqBTJfZWNvcghHTkE1QTJURwoxCNWCARIEMTY1NRiYFiCuHCj52YIDMMzbggM4R0AAWAFqBTJfZWNvcghHTkE1QTJURwqbAQowCNWCARIDNzkxGK4cIINpKMz4ggMw9fmCAzhHQABYAWoFMl9lY29yCEdOQTVBMlRHCjII1YIBEgQyNDMyGINpILiNASim-4IDMOb8ggM4R0AAWAFqBTJfZWNvcghHTkE1QTJURwozCNWCARIEODM2Nxi4jQEg-LIBKIj-ggMwwv6CAzhHQABYAWoFMl9lY29yCEdOQTVBMlRHEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Feb 13 - Sat, Feb 28 YLW Kelowna ORD Chicago CA $501 Roundtrip found 8 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:ORD,departure:13/02/2026TANYT&leg2=from:ORD,to:YLW,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:500.65&airProductToken=AQpFCiEIxJgBEgQ2OTU5GPiyASCYFijghoUDMKeHhQM4VkAAWAEKIAjEmAESBDcwNjMYmBYgrhwogIiFAzDXiYUDOFZAAVgBCkUKIAjEmAESBDIwNDEYrhwgkgEoyq-GAzDnsYYDOFZAAFgBCiEIxJgBEgQ2OTI0GJIBIPiyASjLsoYDMJazhgM4VkABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ## Find the cheapest month to fly from Kelowna (YLW) to Chicago (ORD) ### September is typically the cheapest month to fly From CA $265 - CA $716 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:YLW,to:ORD,departure:12/11/2025TANYT&leg2=from:ORD,to:YLW,departure:01/12/2025TANYT&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 $1,070](https://www.expedia.ca/Flights-Search?leg1=from:YLW,to:ORD,departure:12/11/2025TANYT&leg2=from:ORD,to:YLW,departure:01/12/2025TANYT&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 Kelowna Intl. Airport to O'Hare Airport? > The lowest price advertised for a round-trip journey between Kelowna Intl. Airport (YLW) and ORD is CA $413. But you better get a move on. This price is based on fares available within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Kelowna Intl. Airport to ORD? > Most flights can be cancelled online, but whether or not you incur a fee varies between airlines. If you do have to cancel your getaway, follow the instructions in the [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from Kelowna Intl. Airport (YLW) to O'Hare Airport that have flexible change policies? > Use our "No change fees" filter to find flexible travel options for your flight from Kelowna Intl. Airport to O'Hare Intl. Airport (ORD). This allows you to secure a great price ahead of time and still have the freedom to reschedule without any additional fees. Fare adjustments may apply if your new flight is more expensive. ### How many hours is the flight from Kelowna Intl. Airport to O'Hare Airport? > You may like to bring your own on-board entertainment, as it takes about 6 hours and 2 minutes to touch down in O'Hare Intl. Airport (ORD) from Kelowna Intl. Airport. A set of noise-cancelling earphones will be useful too. ### How far is the flight from Kelowna Intl. Airport (YLW) to ORD? > Around 2,600 kilometres separates Kelowna and Chicago, so pack some in-flight entertainment to help you while away a couple of hours. That juicy novel you've yet to start will be perfect. ### Which airlines fly direct from YLW to O'Hare Intl. Airport (ORD)? > Unfortunately, there aren't any airlines that fly directly between Kelowna Intl. Airport (YLW) and O'Hare Intl. Airport (ORD). You'll need to book a flight with one or more stops. ### Are Kelowna Intl. Airport (YLW) to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute? > Booking last minute from YLW to ORD can be hit-or-miss. It is possible to score a bargain, but then again, you could miss out altogether! If you'd prefer to start your trip planning early on, Expedia compares flight deals up to 12 months in advance. Just remember that not all airlines list their prices that far in advance. Our advice? Check back often as updates are made frequently. ## Travel information | Origin airport | Kelowna Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | Air Canada, Alaska Airlines, American Airlines, Delta, United, WestJet | | Roundtrip price | CA $412 | | Distance | 2551 km | ## Book with confidence ### Kelowna to Chicago Flights **The easy way to book your flights from Kelowna to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Kelowna 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 Kelowna to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Kelowna Intl., YLW to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Kelowna to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Kelowna currently is just CA $413 rising to CA $501.   Here are more money-saving tips:  - Fly in December 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 Kelowna**  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 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.