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Cheap flights from Vancouver to Chicago Midway Airport from C$ 319

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 20/6. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
4 Jul — 11 Jul1
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 4 June 2026.

Fri 19/66:00 a.m.
YVR
-
MDW
1 stop10h 18m
Delta
Mon 22/61:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 1/6C$ 577
Thu 24/96:00 a.m.
YVR
-
MDW
1 stop10h 11m
Delta
Wed 30/91:47 p.m.
MDW
-
YVR
1 stop8h 39m
Delta
Deal found 2/6C$ 584
Tue 18/86:00 a.m.
YVR
-
MDW
1 stop10h 01m
Delta
Sat 22/81:51 p.m.
MDW
-
YVR
1 stop8h 41m
Delta
Deal found 30/5C$ 595
Thu 17/97:30 p.m.
YVR
-
MDW
2 stops11h 20m
Delta
Thu 24/91:47 p.m.
MDW
-
YVR
1 stop8h 39m
Delta
Deal found 3/6C$ 605
Thu 8/106:15 a.m.
YVR
-
MDW
1 stop8h 35m
Delta
Wed 14/109:30 a.m.
MDW
-
YVR
2 stops13h 02m
Delta
Deal found 31/5C$ 635
Tue 15/97:30 p.m.
YVR
-
MDW
2 stops11h 20m
Delta
Sat 19/91:47 p.m.
MDW
-
YVR
2 stops11h 21m
Delta
Deal found 1/6C$ 638
Thu 3/96:00 a.m.
YVR
-
MDW
1 stop10h 01m
Delta
Sun 6/99:59 a.m.
MDW
-
YVR
2 stops9h 45m
Delta
Deal found 1/6C$ 639
Tue 18/86:00 a.m.
YVR
-
MDW
1 stop10h 01m
Delta
Sun 23/81:51 p.m.
MDW
-
YVR
1 stop8h 41m
Delta
Deal found 4/6C$ 641
Thu 6/86:00 a.m.
YVR
-
MDW
1 stop10h 01m
Delta
Sun 16/81:51 p.m.
MDW
-
YVR
1 stop8h 41m
Delta
Deal found 1/6C$ 645
Sun 18/106:15 a.m.
YVR
-
MDW
1 stop8h 35m
Delta
Fri 23/1012:30 p.m.
MDW
-
YVR
1 stop10h 02m
Delta
Deal found 1/6C$ 666

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 4 June 2026.

Round-trip from

C$ 577

One-way from

C$ 319

Popular in

December

Cheapest in

October

Average price

C$ 603
Delta
  • Delta
  • 19/6-22/6
  • 2 total stops
  • 19h 00m total
  • Vancouver to Chicago
Search Deals
Delta
  • Delta
  • 20/6
  • 2 total stops
  • 14h 17m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 109 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 4 June 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

Cheapest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 18/8

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

1 stop10h 01m

Chicago Midway

Sat 22/8

1:51 p.m.-8:32 p.m.

1 stop8h 41m

C$ 595

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/9

6:45 a.m.-6:01 p.m.

2 stops9h 16m

Chicago Midway

Sun 6/9

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

2 stops9h 45m

C$ 639

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 15/9

7:30 p.m.-8:50 a.m.

2 stops11h 20m

Chicago Midway

Sat 19/9

1:47 p.m.-11:08 p.m.

2 stops11h 21m

C$ 648

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 6/8

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

2 stops11h 04m

Chicago Midway

Sun 16/8

1:51 p.m.-8:32 p.m.

1 stop8h 41m

C$ 677

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 1/7

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

2 stops11h 01m

Chicago Midway

Tue 7/7

1:49 p.m.-8:29 p.m.

1 stop8h 40m

C$ 714
Quickest 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.-7:10 p.m.

2 stops8h 40m

C$ 720

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 8/10

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

1 stop8h 35m

Chicago Midway

Mon 12/10

9:55 a.m.-7:10 p.m.

2 stops11h 15m

C$ 727

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 13/8

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

1 stop10h 01m

Chicago Midway

Sat 15/8

1:51 p.m.-8:32 p.m.

1 stop8h 41m

C$ 732

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 28/8

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

1 stop10h 01m

Chicago Midway

Mon 31/8

1:51 p.m.-8:32 p.m.

1 stop8h 41m

C$ 761

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 15/7

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

1 stop10h 18m

Chicago Midway

Wed 22/7

1:49 p.m.-8:29 p.m.

1 stop8h 40m

C$ 832

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 19 resultsSorted by cheapest first
1
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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 10h 01m. 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

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

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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.

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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.

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