Title: Cheap Flights from Winnipeg (YWG) to Chicago (PWK) - 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) # Cheap Flights from Winnipeg (YWG) to Chicago (PWK) - [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, IL (PWK-Chicago Executive) - ![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:pwk,departure:20/11/2025TANYT&leg2=from:pwk,to:ywg,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![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:pwk,departure:20/11/2025TANYT&leg2=from:pwk,to:ywg,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![Flair Airlines](https://a.travel-assets.com/air/airlines/f8_sq.svg) Flair Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:ywg,to:pwk,departure:20/11/2025TANYT&leg2=from:pwk,to:ywg,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F8"}}]) - ![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:ywg,to:pwk,departure:20/11/2025TANYT&leg2=from:pwk,to:ywg,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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:pwk,departure:20/11/2025TANYT&leg2=from:pwk,to:ywg,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:pwk,departure:20/11/2025TANYT&leg2=from:pwk,to:ywg,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Porter Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_PD.svg) Porter Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:ywg,to:pwk,departure:20/11/2025TANYT&leg2=from:pwk,to:ywg,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) - ![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) ## 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:20/11/2025TANYT&leg2=from:ORD,to:YWG,departure:26/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. 23 min [Flights from CA $737](https://www.expedia.ca/Flights-Search?leg1=from:YWG,to:ORD,departure:20/11/2025TANYT&leg2=from:ORD,to:YWG,departure:26/11/2025TANYT&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:20/11/2025TANYT&leg2=from:MDW,to:YWG,departure:26/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. CheapestClosest 16 min [Flights from CA $632](https://www.expedia.ca/Flights-Search?leg1=from:YWG,to:MDW,departure:20/11/2025TANYT&leg2=from:MDW,to:YWG,departure:26/11/2025TANYT&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 Winnipeg Airport to Chicago Executive Airport? > Start packing your suitcase, because round-trip journeys from YWG to PWK start from . That's based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can move quickly, so book today to score the best deal. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago Executive Airport (PWK)? > The majority of flights can be conveniently cancelled online, but whether you are charged a fee depends on your airline. If you do have to cancel your trip, follow the instructions in the [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago Executive Airport (PWK) that have flexible change policies? > Flights from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to PWK with flexible change policies are available with many airlines. Simply use our "No change fees" filter while searching. You'll only need to pay the cost difference between flights, with no added fees to worry about. ### How far is the flight from YWG to Chicago Executive Airport (PWK)? > A flight distance of just 1,150 kilometres separates Winnipeg and Wheeling. Once you're up in the air, 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 PWK? > You won't find any airlines flying directly between Winnipeg Airport and Chicago Executive Airport, 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 Executive Airport (PWK) flight tickets cheaper when they're purchased at the last minute? > Flight prices are always on the move, so there are no guarantees. While last-minute deals between YWG and PWK are of course possible, it's also a good idea to monitor prices well before you fly. In fact, some carriers release their prices up to a year before the departure date. Expedia is constantly updating the best bargains around, so keep checking and be ready to lock in your seat when the price dips. ## Travel information | Origin airport | Winnipeg James Armstrong Richardson Intl. | | --- | --- | | Destination airport | Chicago Executive | | Distance | 1117 km | ## Book with confidence ### 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 airlines that cover this route. There are nonstop flights to Chicago Executive, 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 Chicago Executive, PWK**  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 rising to .   Here are more money-saving tips:  - Fly in 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. 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