Find flights
When to book
FAQs

Cheap flights from Vancouver to Chicago Midway Airport from C$ 157

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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
13 Nov — 20 Nov1
1 adult
1 adult, Economy

Find 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 14 October 2025.

Sun 9/1111:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Fri 14/111:37 p.m.MDW - YVR
1 stop23h 35mMultiple Airlines
Deal found 13/10C$ 327
Sat 25/107:36 p.m.YVR - MDW
2 stops11h 19mDelta
Wed 29/109:35 a.m.MDW - YVR
2 stops11h 11mDelta
Deal found 13/10C$ 343
Tue 11/1112:07 p.m.YVR - MDW
2 stops9h 33mDelta
Fri 14/111:15 p.m.MDW - YVR
2 stops9h 55mDelta
Deal found 11/10C$ 381
Wed 19/1111:00 p.m.YVR - MDW
1 stop10h 52mDelta
Sat 22/111:26 p.m.MDW - YVR
2 stops12h 33mDelta
Deal found 11/10C$ 417
Fri 31/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Sun 2/115:30 a.m.MDW - YVR
2 stops19h 13mMultiple Airlines
Deal found 13/10C$ 447
Tue 11/117:00 a.m.YVR - MDW
2 stops14h 55mMultiple Airlines
Fri 14/111:37 p.m.MDW - YVR
1 stop23h 35mMultiple Airlines
Deal found 11/10C$ 466
Fri 28/115:00 p.m.YVR - MDW
2 stops18h 07mMultiple Airlines
Fri 5/128:42 p.m.MDW - YVR
1 stop16h 30mMultiple Airlines
Deal found 14/10C$ 485
Mon 27/109:10 a.m.YVR - MDW
1 stop10h 36mMultiple Airlines
Thu 30/108:30 a.m.MDW - YVR
1 stop10h 01mMultiple Airlines
Deal found 13/10C$ 506
Sat 8/117:36 p.m.YVR - MDW
2 stops11h 25mDelta
Thu 13/111:15 p.m.MDW - YVR
2 stops12h 44mDelta
Deal found 12/10C$ 507
Fri 7/1111:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Thu 13/116:30 a.m.MDW - YVR
2 stops19h 13mMultiple Airlines
Deal found 13/10C$ 523
Thu 30/106:45 p.m.YVR - MDW
2 stops25h 00mMultiple Airlines
Sun 2/119:00 a.m.MDW - YVR
1 stop9h 31mMultiple Airlines
Deal found 12/10C$ 535

Cheap 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 14 October 2025.

Round-trip from

C$ 327

One-way from

C$ 157

Popular in

November

Cheapest in

September

Average price

C$ 438
9/11-14/11
  • 9/11-14/11
  • 2 total stops
  • 41h 14m total
  • Vancouver to Chicago
Search Deals
2/11
  • 2/11
  • 1 total stop
  • 21h 11m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 75 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 14 October 2025.
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

Sun 9/11

11:00 p.m.-6:39 p.m.

1 stop17h 39m

Chicago Midway

Fri 14/11

1:37 p.m.-11:12 a.m.

1 stop23h 35m

C$ 327

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 13/12

12:13 p.m.-11:49 p.m.

2 stops9h 36m

Chicago Midway

Mon 15/12

1:50 p.m.-11:59 p.m.

2 stops12h 09m

C$ 343

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 25/10

6:00 a.m.-5:43 p.m.

1 stop9h 43m

Chicago Midway

Wed 29/10

9:35 a.m.-6:46 p.m.

2 stops11h 11m

C$ 343

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 19/11

6:45 a.m.-6:18 p.m.

2 stops9h 33m

Chicago Midway

Sat 22/11

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

2 stops12h 33m

C$ 343

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 11/11

12:07 p.m.-11:40 p.m.

2 stops9h 33m

Chicago Midway

Fri 14/11

1:15 p.m.-9:10 p.m.

2 stops9h 55m

C$ 381

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 13/11

7:36 p.m.-9:01 a.m.

2 stops11h 25m

Chicago Midway

Mon 17/11

12:47 p.m.-10:37 p.m.

2 stops11h 50m

C$ 381

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 3/3

7:35 p.m.-12:35 p.m.

2 stops15h 00m

Chicago Midway

Mon 9/3

9:20 a.m.-6:43 p.m.

2 stops11h 23m

C$ 417

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 28/11

6:45 a.m.-6:18 p.m.

2 stops9h 33m

Chicago Midway

Fri 5/12

1:14 p.m.-9:04 p.m.

2 stops9h 50m

C$ 461

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 11/11

7:00 a.m.-11:55 p.m.

2 stops14h 55m

Chicago Midway

Fri 14/11

1:37 p.m.-11:12 a.m.

1 stop23h 35m

C$ 466

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 28/11

5:00 p.m.-1:07 p.m.

2 stops18h 07m

Chicago Midway

Fri 5/12

8:42 p.m.-11:12 a.m.

1 stop16h 30m

C$ 485

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 20 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 9h 36m. 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.