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Cheap flights from Vancouver Intl Airport to Chicago Midway Airport from C$ 282

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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
31 May — 7 Jun1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Vancouver Intl to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Vancouver Intl to Midway
Explore the most affordable flight options available from Vancouver Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 1 May 2026.

Sat 23/56:00 a.m.
YVR
-
MDW
1 stop9h 56m
Delta
Thu 11/61:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 26/4C$ 559
Wed 3/66:00 a.m.
YVR
-
MDW
1 stop9h 56m
Delta
Tue 9/61:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 30/4C$ 569
Fri 10/76:00 a.m.
YVR
-
MDW
1 stop10h 18m
Delta
Tue 14/79:49 a.m.
MDW
-
YVR
2 stops9h 54m
Delta
Deal found 29/4C$ 576
Sat 10/105:15 p.m.
YVR
-
MDW
2 stops13h 34m
Delta
Tue 13/1012:30 p.m.
MDW
-
YVR
1 stop10h 02m
Delta
Deal found 28/4C$ 589
Mon 25/510:55 p.m.
YVR
-
MDW
1 stop21h 07m
Multiple Airlines
Mon 1/610:15 a.m.
MDW
-
YVR
1 stop25h 35m
Multiple Airlines
Deal found 27/4C$ 600
Tue 15/96:15 a.m.
YVR
-
MDW
1 stop9h 50m
Delta
Wed 23/92:00 p.m.
MDW
-
YVR
1 stop8h 22m
Delta
Deal found 27/4C$ 622
Thu 21/56:00 a.m.
YVR
-
MDW
2 stops10h 33m
Delta
Sat 30/51:22 p.m.
MDW
-
YVR
2 stops11h 13m
Delta
Deal found 28/4C$ 623
Mon 22/66:00 a.m.
YVR
-
MDW
1 stop10h 18m
Delta
Sun 5/71:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 30/4C$ 638
Mon 8/66:40 p.m.
YVR
-
MDW
2 stops14h 32m
Multiple Airlines
Tue 16/610:15 a.m.
MDW
-
YVR
1 stop16h 29m
Multiple Airlines
Deal found 30/4C$ 644

Find flight deals from Vancouver Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Vancouver Intl (YVR) 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 1 May 2026.

Round-trip from

C$ 559

One-way from

C$ 282

Popular in

December

Cheapest in

October

Average price

C$ 528
Delta
  • Delta
  • 23/5-11/6
  • 2 total stops
  • 18h 38m total
  • Vancouver to Chicago
Search Deals
11/5
  • 11/5
  • 2 total stops
  • 13h 39m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 125 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Vancouver Intl 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 1 May 2026.
Use the filters below to find and compare flights from Vancouver Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

6:15 a.m.-4:50 p.m.

1 stop8h 35m

Chicago Midway

Tue 13/10

12:30 p.m.-8:32 p.m.

1 stop10h 02m

C$ 589

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 1/6

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

1 stop9h 56m

Chicago Midway

Tue 9/6

1:49 p.m.-8:31 p.m.

1 stop8h 42m

C$ 640

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 5/6

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

1 stop9h 56m

Chicago Midway

Tue 9/6

9:17 a.m.-5:47 p.m.

2 stops10h 30m

C$ 682

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 14/6

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

2 stops9h 33m

Chicago Midway

Fri 19/6

1:49 p.m.-10:35 p.m.

2 stops10h 46m

C$ 694

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 8/6

7:36 p.m.-8:37 a.m.

2 stops11h 01m

Chicago Midway

Tue 16/6

9:54 a.m.-5:47 p.m.

2 stops9h 53m

C$ 723

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 22/6

7:36 p.m.-8:37 a.m.

2 stops11h 01m

Chicago Midway

Sun 5/7

1:49 p.m.-8:31 p.m.

1 stop8h 42m

C$ 727
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 24/9

6:15 a.m.-6:05 p.m.

1 stop9h 50m

Chicago Midway

Mon 28/9

2:00 p.m.-8:22 p.m.

1 stop8h 22m

C$ 731

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 19/6

6:00 a.m.-6:18 p.m.

1 stop10h 18m

Chicago Midway

Sun 28/6

9:54 a.m.-5:50 p.m.

2 stops9h 56m

C$ 767

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 13/5

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

1 stop9h 56m

Chicago Midway

Fri 15/5

1:22 p.m.-12:15 a.m.

2 stops12h 53m

C$ 922
Cheapest one-way

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 27/5

6:20 a.m.-6:33 p.m.

2 stops10h 13m

C$ 296

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

Showing 1-10 of 16 resultsSorted by cheapest first
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Best time to book a flight from Vancouver Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Vancouver Intl 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.

Related info for your journey

Find useful and relevant information for your journey from Vancouver Intl 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 Intl Airport to Chicago Midway Airport?

    A quick flight from Vancouver Intl Airport to Chicago Midway Airport can take about 8h 35m. Delta provides one of the quickest options available for as low as C$ 589. The distance from Vancouver Intl Airport to Chicago Midway Airport is about 2850 km.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Vancouver Intl 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

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Alternative routes for Vancouver Intl to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Vancouver Intl to O'Hare Intl flights

Fly with Cheapflights

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

Cheapflights makes it easy to find Vancouver Intl 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 Intl to Midway?

Cheapflights helps you find that perfect flight to Midway from Vancouver Intl by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

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

Certainly. Search results for flights to Midway from Vancouver Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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