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Cheap flights from Vancouver Intl Airport to Chicago Midway Airport from C$ 292

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 25/8. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
27 Aug — 3 Sep1
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 28 July 2026.

Tue 15/96:00 a.m.
YVR
-
MDW
1 stop10h 19m
Delta
Tue 29/99:59 a.m.
MDW
-
YVR
2 stops10h 41m
Delta
Deal found 27/7C$ 467
Sat 5/127:15 a.m.
YVR
-
MDW
2 stops7h 24m
Delta
Wed 9/1210:22 a.m.
MDW
-
YVR
2 stops15h 37m
Delta
Deal found 26/7C$ 484
Mon 5/107:30 p.m.
YVR
-
MDW
2 stops11h 17m
Delta
Wed 7/1012:28 p.m.
MDW
-
YVR
2 stops12h 40m
Delta
Deal found 24/7C$ 485
Sat 17/106:00 a.m.
YVR
-
MDW
1 stop8h 47m
Delta
Mon 26/1012:27 p.m.
MDW
-
YVR
1 stop10h 06m
Delta
Deal found 26/7C$ 502
Tue 8/96:00 a.m.
YVR
-
MDW
2 stops10h 19m
Delta
Tue 15/92:00 p.m.
MDW
-
YVR
2 stops10h 34m
Delta
Deal found 25/7C$ 551
Sat 10/106:45 a.m.
YVR
-
MDW
2 stops9h 20m
Delta
Tue 13/109:29 a.m.
MDW
-
YVR
2 stops11h 17m
Delta
Deal found 24/7C$ 570

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 28 July 2026.

Round-trip from

C$ 467

One-way from

C$ 292

Popular in

July

Cheapest in

September

Average price

C$ 723
Delta
  • Delta
  • 15/9-29/9
  • 3 total stops
  • 21h 00m total
  • Vancouver to Chicago
Search Deals
25/8
  • 25/8
  • 3 total stops
  • 22h 15m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 80 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 July 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 28 July 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

Mon 5/10

7:30 p.m.-8:47 a.m.

2 stops11h 17m

Chicago Midway

Wed 7/10

12:28 p.m.-11:08 p.m.

2 stops12h 40m

C$ 485

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 15/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Tue 29/9

2:00 p.m.-10:59 p.m.

2 stops10h 59m

C$ 516

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

6:45 a.m.-6:05 p.m.

2 stops9h 20m

Chicago Midway

Tue 13/10

9:29 a.m.-6:46 p.m.

2 stops11h 17m

C$ 570
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 9/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Wed 16/9

2:00 p.m.-8:26 p.m.

1 stop8h 26m

C$ 633

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 27/8

6:00 a.m.-6:01 p.m.

1 stop10h 01m

Chicago Midway

Tue 1/9

9:59 a.m.-5:44 p.m.

2 stops9h 45m

C$ 702
Cheapest one-way
Quickest one-way

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 24/10

10:55 p.m.-10:03 a.m.

1 stop9h 08m

C$ 324

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 18/9

10:35 p.m.-12:39 p.m.

2 stops12h 04m

C$ 336

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 23/9

5:45 p.m.-8:48 a.m.

2 stops13h 03m

C$ 344

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 4/8

7:35 p.m.-8:39 a.m.

2 stops11h 04m

C$ 346

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 25/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

C$ 368

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/7

Showing 1-10 of 15 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 11h 17m. Delta provides one of the quickest options available for as low as C$ 485. 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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