S$404 Cheap Flights from Vancouver to Chicago

View S$404 flight on Fri, 28 Nov, 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 S$404 for one-way flights and S$848 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 26 Nov - Fri, 28 Nov
YVR
Vancouver
MDW
Chicago
S$848 Return, found 5 hours ago
S$848
Return
found 5 hours ago
Select Delta flight, departing Wed, 26 Nov from Vancouver to Chicago, returning Fri, 28 Nov, priced at S$848 found 5 hours ago
Delta
Wed, 26 Nov - Fri, 28 Nov
YVR
Vancouver
MDW
Chicago
S$877 Return, found 5 hours ago
S$877
Return
found 5 hours ago
Select Delta flight, departing Wed, 26 Nov from Vancouver to Chicago, returning Fri, 28 Nov, priced at S$877 found 5 hours ago
Delta
Fri, 28 Nov - Mon, 1 Dec
YVR
Vancouver
MDW
Chicago
S$926 Return, found 5 hours ago
S$926
Return
found 5 hours ago
Select Delta flight, departing Fri, 28 Nov from Vancouver to Chicago, returning Mon, 1 Dec, priced at S$926 found 5 hours ago
Delta
Wed, 26 Nov - Fri, 28 Nov
YVR
Vancouver
MDW
Chicago
S$955 Return, found 5 hours ago
S$955
Return
found 5 hours ago
Select Delta flight, departing Wed, 26 Nov from Vancouver to Chicago, returning Fri, 28 Nov, priced at S$955 found 5 hours ago
Delta
Wed, 26 Nov - Fri, 28 Nov
YVR
Vancouver
MDW
Chicago
S$964 Return, found 5 hours ago
S$964
Return
found 5 hours ago
Select Delta flight, departing Wed, 26 Nov from Vancouver to Chicago, returning Fri, 28 Nov, priced at S$964 found 5 hours ago
Delta
Fri, 28 Nov - Mon, 1 Dec
YVR
Vancouver
MDW
Chicago
S$994 Return, found 5 hours ago
S$994
Return
found 5 hours ago
Select Delta flight, departing Fri, 28 Nov from Vancouver to Chicago, returning Mon, 1 Dec, priced at S$994 found 5 hours ago
Delta
Fri, 28 Nov - Mon, 1 Dec
YVR
Vancouver
MDW
Chicago
S$1,014 Return, found 5 hours ago
S$1,014
Return
found 5 hours ago
Select Delta flight, departing Fri, 28 Nov from Vancouver to Chicago, returning Mon, 1 Dec, priced at S$1,014 found 5 hours ago
Delta
Fri, 28 Nov - Mon, 1 Dec
YVR
Vancouver
MDW
Chicago
S$1,023 Return, found 5 hours ago
S$1,023
Return
found 5 hours ago
Select Delta flight, departing Fri, 28 Nov from Vancouver to Chicago, returning Mon, 1 Dec, priced at S$1,023 found 5 hours ago
Delta
Fri, 28 Nov - Mon, 1 Dec
YVR
Vancouver
MDW
Chicago
S$1,042 Return, found 5 hours ago
S$1,042
Return
found 5 hours ago
Select Delta flight, departing Fri, 28 Nov from Vancouver to Chicago, returning Mon, 1 Dec, priced at S$1,042 found 5 hours ago
Alaska Airlines
Wed, 26 Nov - Fri, 28 Nov
YVR
Vancouver
MDW
Chicago
S$1,287 Return, found 5 hours ago
S$1,287
Return
found 5 hours ago
Select Alaska Airlines flight, departing Wed, 26 Nov from Vancouver to Chicago, returning Fri, 28 Nov, priced at S$1,287 found 5 hours ago

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Vancouver to Chicago route information
Origin airport
Vancouver Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Return price
S$847
Distance
2836 km

Perfect flights from Vancouver to Chicago

Your Journey from Vancouver to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Vancouver to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, WestJet, Alaska Airlines, United. Our selection of flights from Vancouver Intl. to Midway Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Vancouver to Chicago Flights

Experience the joy of finding cheap flights from Vancouver Intl. to Midway Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$404 and roundtrip prices from S$848*.
 

Pre-Flight Essentials

Ensure a smooth journey from Vancouver to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Vancouver to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Vancouver to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Vancouver to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Vancouver to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from Vancouver Intl. Airport (YVR) to Midway Airport?
If you're travelling from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW), round-trip flights start from S$848. This price is based on fares advertised within the last 7 days on Expedia for flights departing within the next year, so don't delay. Book now and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Vancouver Intl. Airport (YVR) to MDW?
We understand that your situation can change unexpectedly, so we've made it as easy as possible for you to cancel your trip online. Just visit the Customer Service Portal and follow the instructions.
How do I find cheap flights from YVR to Midway Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Vancouver Intl. Airport to Chicago Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from YVR to MDW?
The flight distance between Vancouver Intl. Airport and Midway Airport is 2,900 kilometres. Pack yourself a drink, a snack and a laptop filled with movies. Keep yourself entertained and the time will fly by.
Which airlines fly direct from Vancouver Intl. Airport (YVR) to Chicago Airport?
If you want to travel straight from Vancouver Intl. Airport (YVR) to Chicago Airport, you'll have to book a flight with one or more stops. Unfortunately, there aren't any airlines that fly directly between these airports.
Are Vancouver Intl. Airport to Midway Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Vancouver Intl. Airport (YVR) to Chicago Airport last minute could be your ticket to a cheap deal. However, it could end up costing a great deal more! If you'd prefer to err on the side of caution, book well ahead of your departure date. In fact, Expedia has some of the best bargains as far ahead as 12 months in advance. If your preferred air carrier hasn't released tickets yet, check back regularly as deals are updated on Expedia all the time.

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Vancouver to O'Hare Intl.
S$548.20
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