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Cheap flights from Vancouver to Chicago Midway Airport from C$ 286

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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
4 Jun — 11 Jun1
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 May 2026.

Wed 17/66:15 a.m.
YVR
-
MDW
2 stops10h 16m
Delta
Wed 24/61:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 2/5C$ 550
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 3/5C$ 555
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$ 567
Sat 10/106:15 a.m.
YVR
-
MDW
1 stop8h 35m
Delta
Tue 13/1012:30 p.m.
MDW
-
YVR
1 stop10h 02m
Delta
Deal found 1/5C$ 597
Tue 9/66:00 a.m.
YVR
-
MDW
1 stop10h 18m
Delta
Thu 11/61:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 4/5C$ 634
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$ 642

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 May 2026.

Round-trip from

C$ 550

One-way from

C$ 286

Popular in

December

Cheapest in

October

Average price

C$ 521
Delta
  • Delta
  • 17/6-24/6
  • 3 total stops
  • 18h 58m total
  • Vancouver to Chicago
Search Deals
1/6
  • 1/6
  • 2 total stops
  • 14h 32m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 122 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 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 May 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

Wed 17/6

6:15 a.m.-6:31 p.m.

2 stops10h 16m

Chicago Midway

Wed 24/6

1:26 p.m.-8:31 p.m.

2 stops9h 05m

C$ 641

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

5:15 p.m.-8:49 a.m.

2 stops13h 34m

Chicago Midway

Tue 13/10

9:30 a.m.-8:32 p.m.

2 stops13h 02m

C$ 652

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 25/6

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

1 stop10h 18m

Chicago Midway

Sun 5/7

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

1 stop8h 42m

C$ 686

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 25/6

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

1 stop10h 18m

Chicago Midway

Tue 7/7

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

1 stop8h 40m

C$ 686

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 7/10

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$ 687

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 22/5

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

1 stop9h 56m

Chicago Midway

Mon 25/5

1:22 p.m.-9:09 p.m.

2 stops9h 47m

C$ 705

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$ 725

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 8/6

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

2 stops11h 01m

Chicago Midway

Mon 15/6

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

1 stop8h 42m

C$ 737

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 8/10

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

1 stop8h 35m

Chicago Midway

Sun 11/10

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

1 stop10h 02m

C$ 740
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 11/6

7:23 a.m.-6:31 p.m.

2 stops9h 08m

Chicago Midway

Mon 15/6

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

1 stop8h 42m

C$ 747

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/4

Showing 1-10 of 18 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 16m. 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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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.

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