Find flights
When to book
FAQs

Cheap flights from Vancouver to Chicago Midway Airport from C$ 190

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 27/4. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
4 Apr — 11 Apr1
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 5 March 2026.

Sun 26/410:55 p.m.
YVR
-
MDW
1 stop18h 36m
Multiple Airlines
Thu 30/46:00 a.m.
MDW
-
YVR
2 stops15h 10m
Multiple Airlines
Deal found 4/3C$ 381
Fri 17/410:30 p.m.
YVR
-
MDW
1 stop11h 40m
Multiple Airlines
Sat 25/47:34 p.m.
MDW
-
YVR
2 stops20h 01m
Multiple Airlines
Deal found 28/2C$ 441
Wed 25/311:00 p.m.
YVR
-
MDW
1 stop18h 47m
Multiple Airlines
Wed 1/42:56 p.m.
MDW
-
YVR
1 stop22h 16m
Multiple Airlines
Deal found 4/3C$ 458
Tue 24/312:05 p.m.
YVR
-
MDW
2 stops28h 08m
Multiple Airlines
Wed 1/42:56 p.m.
MDW
-
YVR
1 stop22h 16m
Multiple Airlines
Deal found 4/3C$ 467
Tue 31/37:35 p.m.
YVR
-
MDW
2 stops14h 54m
Delta
Wed 8/46:34 p.m.
MDW
-
YVR
2 stops26h 11m
Delta
Deal found 4/3C$ 470
Mon 4/58:25 p.m.
YVR
-
MDW
2 stops21h 06m
Multiple Airlines
Fri 8/56:15 a.m.
MDW
-
YVR
1 stop15h 40m
Multiple Airlines
Deal found 1/3C$ 481
Thu 26/312:05 p.m.
YVR
-
MDW
1 stop8h 40m
Multiple Airlines
Wed 1/42:56 p.m.
MDW
-
YVR
1 stop22h 16m
Multiple Airlines
Deal found 4/3C$ 502
Fri 27/39:10 a.m.
YVR
-
MDW
1 stop12h 29m
Multiple Airlines
Wed 1/42:56 p.m.
MDW
-
YVR
1 stop22h 16m
Multiple Airlines
Deal found 4/3C$ 517
Sat 4/45:00 p.m.
YVR
-
MDW
1 stop15h 15m
Multiple Airlines
Tue 7/411:00 a.m.
MDW
-
YVR
1 stop15h 38m
Multiple Airlines
Deal found 4/3C$ 521
Sat 4/45:00 p.m.
YVR
-
MDW
1 stop15h 15m
Multiple Airlines
Wed 8/411:00 a.m.
MDW
-
YVR
1 stop12h 03m
Multiple Airlines
Deal found 4/3C$ 522
Mon 30/34:35 p.m.
YVR
-
MDW
2 stops20h 58m
Multiple Airlines
Tue 7/411:00 a.m.
MDW
-
YVR
1 stop15h 38m
Multiple Airlines
Deal found 4/3C$ 523

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 5 March 2026.

Round-trip from

C$ 381

One-way from

C$ 190

Popular in

December

Cheapest in

October

Average price

C$ 523
26/4-30/4
  • 26/4-30/4
  • 3 total stops
  • 33h 46m total
  • Vancouver to Chicago
Search Deals
27/4
  • 27/4
  • 1 total stop
  • 18h 36m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 19% potential increase in price (C$ 166 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 5 March 2026.
Use the filters below to find and compare flights from Vancouver to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 31/3

7:35 p.m.-12:29 p.m.

2 stops14h 54m

Chicago Midway

Wed 8/4

6:34 p.m.-6:45 p.m.

2 stops26h 11m

C$ 470

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 28/4

2:35 p.m.-10:15 a.m.

2 stops17h 40m

Chicago Midway

Wed 6/5

10:25 a.m.-11:25 p.m.

1 stop15h 00m

C$ 577

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 28/5

7:41 p.m.-8:42 a.m.

2 stops11h 01m

Chicago Midway

Mon 1/6

1:59 p.m.-10:49 p.m.

2 stops10h 50m

C$ 577

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 20/4

4:15 p.m.-10:15 a.m.

1 stop16h 00m

Chicago Midway

Mon 27/4

11:00 a.m.-9:11 p.m.

2 stops12h 11m

C$ 588

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 17/4

7:30 p.m.-9:06 a.m.

2 stops11h 36m

Chicago Midway

Fri 24/4

9:29 a.m.-6:43 p.m.

2 stops11h 14m

C$ 637

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 1/5

10:55 p.m.-10:14 a.m.

1 stop9h 19m

Chicago Midway

Sun 3/5

1:24 p.m.-11:01 p.m.

2 stops11h 37m

C$ 764

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 24/3

6:20 a.m.-5:54 p.m.

2 stops9h 34m

Chicago Midway

Mon 30/3

6:34 p.m.-10:57 a.m.

2 stops18h 23m

C$ 775

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 15/4

7:00 a.m.-10:15 a.m.

2 stops25h 15m

Chicago Midway

Wed 22/4

11:00 a.m.-9:11 p.m.

2 stops12h 11m

C$ 860

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 12/5

7:41 p.m.-8:43 a.m.

2 stops11h 02m

C$ 303

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 14/5

6:00 a.m.-5:56 p.m.

1 stop9h 56m

C$ 303

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 18 resultsSorted by cheapest first
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 14h 54m. 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.