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CA $271 Cheap Flights from Vancouver (YVR) to Chicago (MDW)

View CA $271 flight on Wed, Sep 2, 2026Opens in a new window

Popular airlines from Vancouver International Airport (YVR) to Chicago Midway Airport (MDW)

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Cheap flights from Vancouver (YVR) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $271 for one-way flights and CA $478 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Sep 30 - Wed, Oct 28
YVR
Vancouver
MDW
Chicago
CA $478 Roundtrip, found 9 hours ago
CA $478
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Sep 30 from Vancouver to Chicago, returning Wed, Oct 28, priced at CA $478 found 9 hours ago
Delta
Tue, Oct 27 - Wed, Oct 28
YVR
Vancouver
MDW
Chicago
CA $487 Roundtrip, found 4 days ago
CA $487
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Oct 27 from Vancouver to Chicago, returning Wed, Oct 28, priced at CA $487 found 4 days ago
Delta
Sat, Nov 7 - Wed, Nov 11
YVR
Vancouver
MDW
Chicago
CA $496 Roundtrip, found 21 hours ago
CA $496
Roundtrip
found 21 hours ago
Select Delta flight, departing Sat, Nov 7 from Vancouver to Chicago, returning Wed, Nov 11, priced at CA $496 found 21 hours ago
Delta
Sat, Oct 3 - Thu, Oct 22
YVR
Vancouver
MDW
Chicago
CA $502 Roundtrip, found 6 days ago
CA $502
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Oct 3 from Vancouver to Chicago, returning Thu, Oct 22, priced at CA $502 found 6 days ago
Delta
Tue, Oct 27 - Thu, Oct 29
YVR
Vancouver
MDW
Chicago
CA $505 Roundtrip, found 4 days ago
CA $505
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Oct 27 from Vancouver to Chicago, returning Thu, Oct 29, priced at CA $505 found 4 days ago
Delta
Fri, Oct 23 - Fri, Oct 30
YVR
Vancouver
MDW
Chicago
CA $514 Roundtrip, found 7 hours ago
CA $514
Roundtrip
found 7 hours ago
Select Delta flight, departing Fri, Oct 23 from Vancouver to Chicago, returning Fri, Oct 30, priced at CA $514 found 7 hours ago
Delta
Sat, Oct 31 - Fri, Nov 6
YVR
Vancouver
MDW
Chicago
CA $514 Roundtrip, found 2 days ago
CA $514
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Oct 31 from Vancouver to Chicago, returning Fri, Nov 6, priced at CA $514 found 2 days ago
Delta
Tue, Oct 6 - Sat, Oct 17
YVR
Vancouver
MDW
Chicago
CA $515 Roundtrip, found 6 days ago
CA $515
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Oct 6 from Vancouver to Chicago, returning Sat, Oct 17, priced at CA $515 found 6 days ago
Delta
Thu, Oct 29 - Fri, Oct 30
YVR
Vancouver
MDW
Chicago
CA $523 Roundtrip, found 4 days ago
CA $523
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Oct 29 from Vancouver to Chicago, returning Fri, Oct 30, priced at CA $523 found 4 days ago
Porter Airlines
Thu, Sep 10 - Mon, Sep 14
YVR
Vancouver
MDW
Chicago
CA $997 Roundtrip, found 10 hours ago
CA $997
Roundtrip
found 10 hours ago
Select Porter Airlines flight, departing Thu, Sep 10 from Vancouver to Chicago, returning Mon, Sep 14, priced at CA $997 found 10 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $681
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $681

Frequently asked questions

How much does a flight from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from CA $271 and cheap return flights from CA $478 YVR to MDW with Expedia. Return flights often range between CA$1018 and CA$4074. 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 YVR to MDW ticket fares go up or down.
What is the cheapest month to fly from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from YVR to MDW 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 Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter YVR to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.)?
Porter Airlines is one of the cheapest airlines offering connecting return flights from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.), with prices starting from around CA$1292 for flights that can be booked for departure within the next year. These flights typically include a layover in Pearson Intl. (YYZ). 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 Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway 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 Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway 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 Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 23 connecting flights per day from Vancouver International (YVR) to Midway International (MDW). Some common connection points include Pearson International (YYZ), Seattle - Tacoma International (SEA), and Calgary International (YYC).
What is the earliest flight from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs around 12:55 AM. This service is offered by United and Delta, and it's a seasonal service active in July. An early departure like this can be great if you want to maximize 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 Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Vancouver International Airport (YVR) to Midway International Airport (MDW) on a Monday, with around 25 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include United, WestJet, and Air Canada. Flight schedules are fairly consistent throughout the week, with only slight variations on other days.
What are the most popular departure times for flights from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.) are in the afternoon, from 3pm to 6pm. Many major carriers, including WestJet, United and Air Canada, offer flights during this window. This timing works well for many travellers as it allows for a productive morning before heading to the airport, and you'll arrive in Chicago in the evening.
How long does it take to fly from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are no nonstop flights from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.). The distance between these two airports is approximately 2853 kilometres. If you're looking for a flight with one stop, you can expect the journey to take around 9 hours. Flights with two or more stops typically take longer, averaging about 12 hours 18 minutes. Keep in mind that actual travel times can vary based on your specific routing, layover durations, and factors like wind patterns.
Can you fly business or first class from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can fly business class or first class between YVR and MDW. First class cabins are available on Delta.
How do I earn miles on a Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway 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 Chicago, IL (MDW) from Vancouver, BC (YVR)?
If you're planning to travel to Chicago from Vancouver Intl. (YVR), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like Seattle - Tacoma Intl. (SEA), Calgary Intl. (YYC), or San Francisco Intl. (SFO) before reaching Chicago. 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 Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway 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 Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway 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 Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Vancouver, BC (YVR-Vancouver Intl.) to Chicago, IL (MDW-Midway 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
Vancouver Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Porter Airlines, WestJet
Roundtrip price
CA $478
Distance
2836 km

Book with confidence

Vancouver to Chicago Flights

The easy way to book your flights from Vancouver to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Vancouver 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 Midway 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 Vancouver to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Vancouver Intl., YVR to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Vancouver to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Vancouver currently is just CA $478 rising to CA $997.  

Here are more money-saving tips: 

  • Fly in September 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 Vancouver 

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.

Vancouver to Chicago Flights

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