Title: Cheap Flights from Winnipeg (YWG) to Chicago (DPA) - Expedia.ca ![#hindutemple #historicalplace #landmark](https://images.trvl-media.com/place/6895/091d1018-c6de-4386-9dfa-5856e92f7e85.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Khryz Garcia ![](https://images.trvl-media.com/place/6895/091d1018-c6de-4386-9dfa-5856e92f7e85.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights from Winnipeg (YWG) to Chicago (DPA) - [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 (DPA-Dupage) - ![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:dpa,departure:03/10/2025TANYT&leg2=from:dpa,to:ywg,departure:10/10/2025TANYT&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:dpa,departure:03/10/2025TANYT&leg2=from:dpa,to:ywg,departure:10/10/2025TANYT&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:dpa,departure:03/10/2025TANYT&leg2=from:dpa,to:ywg,departure:10/10/2025TANYT&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:dpa,departure:03/10/2025TANYT&leg2=from:dpa,to:ywg,departure:10/10/2025TANYT&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:dpa,departure:03/10/2025TANYT&leg2=from:dpa,to:ywg,departure:10/10/2025TANYT&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:dpa,departure:03/10/2025TANYT&leg2=from:dpa,to:ywg,departure:10/10/2025TANYT&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:dpa,departure:03/10/2025TANYT&leg2=from:dpa,to:ywg,departure:10/10/2025TANYT&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) Flight from Winnipeg to Chicago (YWG - DPA) route information | Origin airport | Winnipeg James Armstrong Richardson Intl. | | --- | --- | | Destination airport | Dupage | | Distance | 1119 km | ## Winnipeg to West 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 Dupage, 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 Dupage, DPA**  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. So book your flight to Chicago with Expedia today. ## Frequently asked questions ### How much is a flight from YWG to DuPage Airport? > Within the past 7 days on Expedia, for flights departing within the next year, the lowest price quoted for a round-trip journey from YWG to DPA was . Cheap fares don't hang around, so make sure you book yours today. 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 DuPage Airport? > Every air carrier has its own set of terms and conditions. If you do decide to cancel, follow the easy instructions on our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from Winnipeg Airport to Dupage Airport (DPA) that have flexible change policies? > Flights from YWG to Dupage Airport (DPA) offering flexible change policies are available with many carriers. Simply use our "No change fees" filter when searching. You'll only need to pay the difference in ticket price, with no additional fees to worry about. ### How far is the flight from Winnipeg Airport to DuPage Airport? > It's only 1,150 kilometres between YWG and DPA. It's quite possible that you'll spend more time travelling to and from the airport than you will actually flying! ### Which airlines fly direct from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to DuPage Airport? > Direct flights aren't available, so you'll need to make at least one stop between Winnipeg James Armstrong Richardson Intl. Airport (YWG) and Dupage Airport (DPA). Use the layover time to stretch your legs and enjoy some personal space. ### Are YWG to DPA flight tickets cheaper when they're purchased at the last minute? > Flight prices always go up and down, so it's no sure thing. While last-minute deals between Winnipeg Airport and DPA are of course possible, it also makes sense to keep a close eye on prices well before you fly. In fact, some air carriers publish their prices up to 12 months ahead of the departure date. Expedia is continuously updating the biggest bargains around, so keep checking and be ready to grab your seat when the fares dip. ## Explore a world of travel with Expedia - Flights ### Flights - [Flights from Denver to Northwest Chicago](https://www.expedia.ca/lp/flights/178254/6350697/denver-to-northwest-chicago) - [Flights from Mexico City to Northwest Chicago](https://www.expedia.ca/lp/flights/178285/6350697/mexico-city-to-northwest-chicago) - [Flights from Ahmedabad (AMD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/amd/ord/ahmedabad-to-chicago) - [Flights from Amsterdam (AMS) to Aurora (AUZ)](https://www.expedia.ca/lp/flights/ams/auz/amsterdam-to-aurora) - [Flights from Atlanta (ATL) to Aurora (AUZ)](https://www.expedia.ca/lp/flights/atl/auz/atlanta-to-aurora) - [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 Bangor (BGR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bgr/ord/bangor-to-chicago) - [Flights from Bangkok (BKK) to Aurora (AUZ)](https://www.expedia.ca/lp/flights/bkk/auz/bangkok-to-aurora) - [Flights from Bellingham (BLI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bli/ord/bellingham-to-chicago) - [Flights from Belleville (BLV) to Aurora (AUZ)](https://www.expedia.ca/lp/flights/blv/auz/belleville-to-aurora) - [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 Baltimore (BWI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bwi/ord/baltimore-to-chicago) - [Flights from Sault Ste. 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