$142 Cheap Flights from Vancouver (YVR) to Chicago (MDW)

View $142 flight on Wed, Sep 17, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Vancouver to Chicago (YVR-MDW)

Prices were available within the past 7 days and start at $142 for one-way flights and $290 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Aug 26 - Sat, Sep 13
YVR
Vancouver
MDW
Chicago
$290 Roundtrip, found 13 hours ago
$290
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Aug 26 from Vancouver to Chicago, returning Sat, Sep 13, priced at $290 found 13 hours ago
Delta
Sun, Sep 28 - Sat, Oct 11
YVR
Vancouver
MDW
Chicago
$335 Roundtrip, found 13 hours ago
$335
Roundtrip
found 13 hours ago
Select Delta flight, departing Sun, Sep 28 from Vancouver to Chicago, returning Sat, Oct 11, priced at $335 found 13 hours ago
Delta
Fri, Sep 19 - Mon, Oct 6
YVR
Vancouver
MDW
Chicago
$347 Roundtrip, found 13 hours ago
$347
Roundtrip
found 13 hours ago
Select Delta flight, departing Fri, Sep 19 from Vancouver to Chicago, returning Mon, Oct 6, priced at $347 found 13 hours ago
Delta
Fri, Aug 29 - Tue, Sep 2
YVR
Vancouver
MDW
Chicago
$348 Roundtrip, found 2 days ago
$348
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Aug 29 from Vancouver to Chicago, returning Tue, Sep 2, priced at $348 found 2 days ago
Delta
Sat, Sep 20 - Sat, Sep 27
YVR
Vancouver
MDW
Chicago
$350 Roundtrip, found 2 days ago
$350
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 20 from Vancouver to Chicago, returning Sat, Sep 27, priced at $350 found 2 days ago
Delta
Fri, Aug 29 - Tue, Sep 2
YVR
Vancouver
MDW
Chicago
$358 Roundtrip, found 2 days ago
$358
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Aug 29 from Vancouver to Chicago, returning Tue, Sep 2, priced at $358 found 2 days ago
Delta
Fri, Sep 19 - Wed, Sep 24
YVR
Vancouver
MDW
Chicago
$364 Roundtrip, found 5 days ago
$364
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Sep 19 from Vancouver to Chicago, returning Wed, Sep 24, priced at $364 found 5 days ago
Delta
Tue, Aug 26 - Mon, Sep 15
YVR
Vancouver
MDW
Chicago
$367 Roundtrip, found 13 hours ago
$367
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Aug 26 from Vancouver to Chicago, returning Mon, Sep 15, priced at $367 found 13 hours ago
Delta
Thu, Aug 14 - Tue, Aug 26
YVR
Vancouver
MDW
Chicago
$377 Roundtrip, found 13 hours ago
$377
Roundtrip
found 13 hours ago
Select Delta flight, departing Thu, Aug 14 from Vancouver to Chicago, returning Tue, Aug 26, priced at $377 found 13 hours ago
WestJet
Thu, Jun 11 - Sun, Jun 21
YVR
Vancouver
MDW
Chicago
$788 Roundtrip, found 3 hours ago
$788
Roundtrip
found 3 hours ago
Select WestJet flight, departing Thu, Jun 11 from Vancouver to Chicago, returning Sun, Jun 21, priced at $788 found 3 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 center is 23 minutes. Flights from $496
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $496
Flights from Vancouver (YVR) to Chicago (MDW)
Origin airport
Vancouver Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$289
Distance
1772 mi

Vancouver to Chicago Flights

The cheapest times to fly from Vancouver to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Vancouver to Chicago are during the month of August. You can find some of the cheapest flights from Vancouver to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Vancouver to Chicago

Sunday is one of the best days to book for cheap flights from Vancouver to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Vancouver to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Vancouver to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $142 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Vancouver to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Vancouver to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from YVR to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from YVR to MDW?
The cheapest flights from YVR to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from YVR to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from YVR to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW)?
There are no daily direct flights departing from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from YVR to MDW?
Generally you'll find the widest variety of flight choices on a Friday. Tuesdays are often the quietest.* However, this can vary based on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW)?
Book a flight from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the likelihood of delays. Later departures are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Vancouver Intl. Airport (YVR)?
Compare your flight options from Vancouver Intl. Airport (YVR) to O'Hare Intl. Airport (ORD). This is the only Chicago airport you can jet into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from YVR to MDW are usually more expensive. For the best rates, start looking for flights ahead of time. That being said, if you're flexible with your travel dates, you may find a cheap fare right before your trip.
Is it cheaper to book a YVR to MDW flight and hotel package?
Booking a YVR to MDW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Pick from our wide range of accommodations and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW)?
If you booked your YVR to MDW flight in the last 24 hours, you may be able to cancel or modify it without 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, visit our Customer Service portal if you want more information.

Explore a world of travel with Expedia

*Available to One Key members.