Find flights
When to book
FAQs

Cheap flights from Vancouver to Chicago Midway Airport from C$ 199

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
19 Feb — 26 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Vancouver to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Vancouver to Midway
Explore the most affordable flight options available from Vancouver to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 January 2026.

Sun 8/26:00 a.m.
YVR
-
MDW
1 stop26h 10m
Multiple Airlines
Tue 10/211:05 a.m.
MDW
-
YVR
2 stops12h 27m
Multiple Airlines
Deal found 18/1C$ 435
Fri 27/23:40 p.m.
YVR
-
MDW
2 stops21h 39m
Multiple Airlines
Mon 2/37:25 p.m.
MDW
-
YVR
1 stop23h 02m
Multiple Airlines
Deal found 19/1C$ 436
Wed 4/33:45 p.m.
YVR
-
MDW
2 stops30h 06m
Multiple Airlines
Wed 11/36:00 a.m.
MDW
-
YVR
1 stop31h 12m
Multiple Airlines
Deal found 18/1C$ 453
Wed 18/211:00 p.m.
YVR
-
MDW
1 stop10h 27m
Multiple Airlines
Mon 23/23:24 p.m.
MDW
-
YVR
1 stop10h 35m
Multiple Airlines
Deal found 19/1C$ 457
Sat 7/210:30 p.m.
YVR
-
MDW
1 stop14h 50m
Multiple Airlines
Tue 10/211:05 a.m.
MDW
-
YVR
2 stops12h 27m
Multiple Airlines
Deal found 18/1C$ 461
Thu 19/212:05 p.m.
YVR
-
MDW
1 stop9h 36m
Multiple Airlines
Mon 23/23:24 p.m.
MDW
-
YVR
1 stop10h 35m
Multiple Airlines
Deal found 19/1C$ 464
Sat 7/26:15 p.m.
YVR
-
MDW
2 stops19h 05m
Multiple Airlines
Sun 15/23:21 p.m.
MDW
-
YVR
1 stop10h 38m
Multiple Airlines
Deal found 18/1C$ 468
Thu 5/312:05 p.m.
YVR
-
MDW
1 stop9h 46m
Multiple Airlines
Mon 9/32:16 p.m.
MDW
-
YVR
1 stop11h 43m
Multiple Airlines
Deal found 19/1C$ 469

Find flight deals from Vancouver to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Vancouver (8CA) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 20 January 2026.

Round-trip from

C$ 435

One-way from

C$ 199

Popular in

December

Cheapest in

October

Average price

C$ 462
Porter Airlines
  • Porter Airlines
  • 8/2-10/2
  • 3 total stops
  • 38h 37m total
  • Vancouver to Chicago
Search Deals
4/3
  • 4/3
  • 2 total stops
  • 38h 41m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 155 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Vancouver to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 20 January 2026.
Use the filters below to find and compare flights from Vancouver to Chicago Midway Airport that are best for you.

Fly from

Vancouver

Fly to

Midway

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 27/2

3:40 p.m.-3:19 p.m.

2 stops21h 39m

Chicago Midway

Mon 2/3

7:25 p.m.-4:27 p.m.

1 stop23h 02m

C$ 436

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 7/2

10:30 p.m.-3:20 p.m.

1 stop14h 50m

Chicago Midway

Mon 9/2

11:05 a.m.-9:07 p.m.

1 stop12h 02m

C$ 490

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/2

7:00 a.m.-10:10 a.m.

2 stops25h 10m

Chicago Midway

Sun 8/2

7:30 a.m.-11:59 p.m.

1 stop18h 29m

C$ 518

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 18/2

7:37 p.m.-8:54 a.m.

2 stops11h 17m

Chicago Midway

Wed 25/2

1:26 p.m.-11:59 p.m.

2 stops12h 33m

C$ 540

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 17/2

7:37 p.m.-8:54 a.m.

2 stops11h 17m

Chicago Midway

Tue 24/2

9:50 a.m.-6:47 p.m.

2 stops10h 57m

C$ 540

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 2/3

7:37 p.m.-8:54 a.m.

2 stops11h 17m

Chicago Midway

Wed 4/3

9:50 a.m.-9:00 p.m.

2 stops13h 10m

C$ 550

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/3

7:37 p.m.-8:54 a.m.

2 stops11h 17m

Chicago Midway

Tue 10/3

2:05 p.m.-11:59 p.m.

2 stops11h 54m

C$ 550

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 16/2

6:00 a.m.-10:10 a.m.

2 stops26h 10m

Chicago Midway

Thu 19/2

11:05 a.m.-11:25 p.m.

1 stop14h 20m

C$ 551

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 8/2

7:37 p.m.-12:46 p.m.

2 stops15h 09m

Chicago Midway

Tue 10/2

1:51 p.m.-11:59 p.m.

2 stops12h 08m

C$ 555

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/3

7:10 a.m.-11:51 p.m.

2 stops38h 41m

C$ 199

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/1

Showing 1-10 of 16 results
1
2

Best time to book a flight from Vancouver to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Vancouver with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Vancouver to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Vancouver to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Vancouver to Chicago Midway Airport?

    Departing from Vancouver to Chicago Midway Airport will take you 11h 17m. There are 2850 km between Vancouver and Chicago Midway Airport.

  • Can I find deals for flights from Vancouver to Midway that include hotel bookings?

    Yes. In addition to deals on Vancouver to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Vancouver to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Vancouver to Midway.

  • Can I find deals for business class flights from Vancouver to Midway?

    Yes. Cheapflights offers flight deals from Vancouver to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Vancouver to Midway?

Cheapflights makes it easy to find Vancouver to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Vancouver to Midway?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Vancouver to Midway for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Vancouver to Midway with no change fees?

Need flexible booking options for your flight to Midway from Vancouver? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Vancouver to Midway become cheaper?

Not ready to book yet? You can track prices for flights from Vancouver to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.