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

View $142 flight on Wed, Oct 8, 2025Opens in a new window

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

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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 $240 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Oct 4 - Sat, Oct 11
YVR
Vancouver
MDW
Chicago
$240 Roundtrip, found 5 days ago
$240
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Oct 4 from Vancouver to Chicago, returning Sat, Oct 11, priced at $240 found 5 days ago
Delta
Sat, Oct 4 - Sat, Oct 11
YVR
Vancouver
MDW
Chicago
$298 Roundtrip, found 5 days ago
$298
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Oct 4 from Vancouver to Chicago, returning Sat, Oct 11, priced at $298 found 5 days ago
Delta
Mon, Oct 6 - Tue, Oct 7
YVR
Vancouver
MDW
Chicago
$414 Roundtrip, found 4 days ago
$414
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Oct 6 from Vancouver to Chicago, returning Tue, Oct 7, priced at $414 found 4 days ago
Delta
Wed, Oct 8 - Sun, Oct 12
YVR
Vancouver
MDW
Chicago
$427 Roundtrip, found 2 hours ago
$427
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Oct 8 from Vancouver to Chicago, returning Sun, Oct 12, priced at $427 found 2 hours ago
Delta
Thu, Oct 16 - Tue, Oct 21
YVR
Vancouver
MDW
Chicago
$429 Roundtrip, found 3 days ago
$429
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Oct 16 from Vancouver to Chicago, returning Tue, Oct 21, priced at $429 found 3 days ago
Delta
Fri, Oct 3 - Mon, Oct 6
YVR
Vancouver
MDW
Chicago
$445 Roundtrip, found 6 days ago
$445
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Oct 3 from Vancouver to Chicago, returning Mon, Oct 6, priced at $445 found 6 days ago
Delta
Mon, Sep 29 - Mon, Oct 6
YVR
Vancouver
MDW
Chicago
$448 Roundtrip, found 1 day ago
$448
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 29 from Vancouver to Chicago, returning Mon, Oct 6, priced at $448 found 1 day ago
Delta
Wed, Oct 8 - Sat, Oct 11
YVR
Vancouver
MDW
Chicago
$478 Roundtrip, found 4 days ago
$478
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Oct 8 from Vancouver to Chicago, returning Sat, Oct 11, priced at $478 found 4 days ago
Delta
Sun, Oct 12 - Tue, Oct 14
YVR
Vancouver
MDW
Chicago
$484 Roundtrip, found 11 hours ago
$484
Roundtrip
found 11 hours ago
Select Delta flight, departing Sun, Oct 12 from Vancouver to Chicago, returning Tue, Oct 14, priced at $484 found 11 hours ago
WestJet
Tue, Nov 25 - Thu, Nov 27
YVR
Vancouver
MDW
Chicago
$586 Roundtrip, found 4 days ago
$586
Roundtrip
found 4 days ago
Select WestJet flight, departing Tue, Nov 25 from Vancouver to Chicago, returning Thu, Nov 27, priced at $586 found 4 days 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. Average driving time to city center is 23 minutes. Flights from $553
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $553
Flights from Vancouver (YVR) to Chicago (MDW)
Origin airport
Vancouver Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$240
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 October. 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?
Get a cheap one-way flight from $142 or cheap return flight from $240 from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW)?
The cheapest month to fly from YVR to MDW is October, when there's less demand. Off-peak months are generally when you'll find lower airfares between these airports.
What is the cheapest airline that flies from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll fly you from YVR to MDW. Then, sort your results by "Price (lowest to highest)" to snag 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.

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*Available to One Key members.