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CA $304 Cheap Flights from Chicago (MDW) to Winnipeg (YWG)

View CA $304 flight on Tue, Dec 8, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)

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Cheap flights from Chicago (MDW) to Winnipeg (YWG)

Prices were available within the past 7 days and start at CA $304 for one-way flights and CA $903 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Dec 3 - Tue, Dec 8
MDW
Chicago
YWG
Winnipeg
CA $903 Roundtrip, found 3 days ago
CA $903
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 3 from Chicago to Winnipeg, returning Tue, Dec 8, priced at CA $903 found 3 days ago
Delta
Thu, Dec 3 - Tue, Dec 8
MDW
Chicago
YWG
Winnipeg
CA $915 Roundtrip, found 3 days ago
CA $915
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 3 from Chicago to Winnipeg, returning Tue, Dec 8, priced at CA $915 found 3 days ago
Delta
Thu, Dec 3 - Tue, Dec 8
MDW
Chicago
YWG
Winnipeg
CA $918 Roundtrip, found 3 days ago
CA $918
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 3 from Chicago to Winnipeg, returning Tue, Dec 8, priced at CA $918 found 3 days ago
Delta
Thu, Dec 3 - Tue, Dec 8
MDW
Chicago
YWG
Winnipeg
CA $954 Roundtrip, found 3 days ago
CA $954
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 3 from Chicago to Winnipeg, returning Tue, Dec 8, priced at CA $954 found 3 days ago
Delta
Thu, Dec 3 - Tue, Dec 8
MDW
Chicago
YWG
Winnipeg
CA $965 Roundtrip, found 3 days ago
CA $965
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 3 from Chicago to Winnipeg, returning Tue, Dec 8, priced at CA $965 found 3 days ago
Delta
Thu, Dec 3 - Tue, Dec 8
MDW
Chicago
YWG
Winnipeg
CA $986 Roundtrip, found 3 days ago
CA $986
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 3 from Chicago to Winnipeg, returning Tue, Dec 8, priced at CA $986 found 3 days ago
Delta
Thu, Dec 3 - Tue, Dec 8
MDW
Chicago
YWG
Winnipeg
CA $1,006 Roundtrip, found 3 days ago
CA $1,006
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 3 from Chicago to Winnipeg, returning Tue, Dec 8, priced at CA $1,006 found 3 days ago
Delta
Mon, Nov 30 - Tue, Dec 1
MDW
Chicago
YWG
Winnipeg
CA $1,014 Roundtrip, found 3 days ago
CA $1,014
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Nov 30 from Chicago to Winnipeg, returning Tue, Dec 1, priced at CA $1,014 found 3 days ago
WestJet
Thu, Dec 3 - Tue, Dec 8
MDW
Chicago
YWG
Winnipeg
CA $1,045 Roundtrip, found 3 days ago
CA $1,045
Roundtrip
found 3 days ago
Select WestJet flight, departing Thu, Dec 3 from Chicago to Winnipeg, returning Tue, Dec 8, priced at CA $1,045 found 3 days ago
Delta
Thu, Dec 3 - Tue, Dec 8
MDW
Chicago
YWG
Winnipeg
CA $1,048 Roundtrip, found 3 days ago
CA $1,048
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 3 from Chicago to Winnipeg, returning Tue, Dec 8, priced at CA $1,048 found 3 days ago

Frequently asked questions

How much does a flight from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) cost?
You can find cheap one-way flights from CA $304 and cheap return flights from CA $903 MDW to YWG with Expedia. One-way flights typically cost between CA$624 and CA$1426. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when MDW to YWG ticket fares go up or down.
What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
The cheapest months to fly from MDW to YWG are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
Enter MDW to YWG and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
Delta is one of the cheapest airlines offering connecting return flights from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.), with prices starting from around CA$890 for flights that can be booked for departure within the next year, with a layover in Minneapolis - St. Paul Intl. (MSP). These prices are per adult, for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
There are approximately 8 connecting flights per day from Chicago Midway International Airport (MDW) to Winnipeg James Armstrong Richardson International Airport (YWG). Some common connection points include Hartsfield-Jackson Atlanta International Airport (ATL), Detroit Metropolitan Wayne County (DTW), and Minneapolis - St. Paul International Airport (MSP).
What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
The earliest flight from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) typically departs around 6:00 AM. This service is offered by Delta. This is a seasonal service active only in April. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
You'll typically find the most flights from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) on a Friday, with around 11 flights available. This gives you a good selection for your travel plans. Delta is a major airline on this route.
What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
The most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) are in the morning, from 9am to 12pm. Delta offers flights during this window. Many travelers prefer this timing as it allows for an early start to their journey, getting them to their destination with plenty of time left in the day.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
There are no nonstop flights from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.). The distance between these two airports is approximately 1,163 kilometres. If you're looking for a flight, you'll typically find one-stop options that take around 4 hours 18 minutes. Flights with two or more stops usually take longer, averaging about 10 hours 30 minutes. Keep in mind that actual travel times can vary depending on factors like layover duration, routing, and weather conditions.
Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
You can fly first class between MDW and YWG. First class cabins are available on Delta.
How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Winnipeg, MB (YWG) from Chicago, IL (MDW)?
If you're planning to travel to Winnipeg from Midway Intl. (MDW), you can fly directly into Winnipeg James Armstrong Richardson Intl. (YWG). Some flights may connect through major hubs like Minneapolis - St. Paul Intl. (MSP), Detroit Metropolitan Wayne County (DTW), or Hartsfield-Jackson Atlanta Intl. (ATL) before reaching Winnipeg. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) flight and hotel package?
Securing a Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
If you booked your Chicago, IL (MDW-Midway Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Midway Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Airlines serving
Delta, WestJet
Roundtrip price
CA $903
Distance
1154 km

Book with confidence

Chicago to Winnipeg Flights

The easy way to book your flights from Chicago to Winnipeg 

With Expedia, it’s simple to find and book flights to Winnipeg from Chicago 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 Winnipeg James Armstrong Richardson 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 Chicago to Winnipeg today, tomorrow, or this week.  

 

Save dollars with cheap flights from Midway Intl., MDW to Winnipeg James Armstrong Richardson Intl., YWG 

Sort your search results by price to find great deals on your flight from Chicago to Winnipeg—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Winnipeg from Chicago currently is just CA $903 rising to CA $1,048.  

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 Winnipeg  
  • 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 Winnipeg from Chicago 

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 Winnipeg with Expedia today.

Chicago to Winnipeg Flights

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