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Cheap flights from Vancouver to Chicago Midway Airport from C$ 171

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 15/12. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
10 Dec — 17 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 10 November 2025.

Sun 7/129:10 a.m.YVR - MDW
1 stop27h 42mMultiple Airlines
Sun 14/126:15 a.m.MDW - YVR
1 stop30h 57mMultiple Airlines
Deal found 9/11C$ 327
Fri 5/126:15 p.m.YVR - MDW
2 stops17h 44mMultiple Airlines
Sun 7/127:27 p.m.MDW - YVR
1 stop17h 45mMultiple Airlines
Deal found 9/11C$ 345
Mon 17/116:45 p.m.YVR - MDW
2 stops14h 53mMultiple Airlines
Wed 26/113:47 p.m.MDW - YVR
1 stop21h 25mMultiple Airlines
Deal found 9/11C$ 476
Tue 2/127:35 p.m.YVR - MDW
2 stops11h 19mDelta
Tue 9/121:14 p.m.MDW - YVR
2 stops12h 45mDelta
Deal found 8/11C$ 486
Sun 14/126:15 a.m.YVR - MDW
2 stops10h 03mDelta
Tue 16/129:59 a.m.MDW - YVR
2 stops13h 05mDelta
Deal found 9/11C$ 497
Sat 6/129:10 a.m.YVR - MDW
1 stop31h 13mMultiple Airlines
Sat 20/128:15 a.m.MDW - YVR
2 stops33h 30mMultiple Airlines
Deal found 9/11C$ 514
Sun 7/1211:00 p.m.YVR - MDW
1 stop8h 52mMultiple Airlines
Fri 19/128:00 a.m.MDW - YVR
2 stops18h 15mMultiple Airlines
Deal found 9/11C$ 529
Sat 6/129:10 a.m.YVR - MDW
1 stop31h 13mMultiple Airlines
Fri 19/128:00 a.m.MDW - YVR
2 stops18h 15mMultiple Airlines
Deal found 9/11C$ 562

Cheap 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 10 November 2025.

Round-trip from

C$ 327

One-way from

C$ 171

Popular in

December

Cheapest in

October

Average price

C$ 562
7/12-14/12
  • 7/12-14/12
  • 2 total stops
  • 58h 39m total
  • Vancouver to Chicago
Search Deals
15/12
  • 15/12
  • 2 total stops
  • 33h 31m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 78 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 November 2025
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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 10 November 2025.
Use the filters below to find and compare flights from Vancouver to Chicago Midway Airport that are best for you.

Fly from

Vancouver

Fly to

Midway

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 7/12

11:00 p.m.-9:52 a.m.

1 stop8h 52m

Chicago Midway

Sun 14/12

7:27 p.m.-11:12 a.m.

1 stop17h 45m

C$ 419

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 14/12

6:15 a.m.-6:18 p.m.

2 stops10h 03m

Chicago Midway

Tue 16/12

9:59 a.m.-9:04 p.m.

2 stops13h 05m

C$ 497

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 6/12

9:10 a.m.-6:23 p.m.

1 stop31h 13m

Chicago Midway

Sat 20/12

8:15 a.m.-3:45 p.m.

2 stops33h 30m

C$ 514

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 14/3

6:00 a.m.-10:05 a.m.

1 stop26h 05m

Chicago Midway

Thu 19/3

11:00 a.m.-10:34 p.m.

1 stop13h 34m

C$ 542

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 6/12

9:10 a.m.-6:23 p.m.

1 stop31h 13m

Chicago Midway

Fri 19/12

8:00 a.m.-12:15 a.m.

2 stops18h 15m

C$ 562

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 8/12

6:15 a.m.-6:18 p.m.

2 stops10h 03m

Chicago Midway

Mon 15/12

1:14 p.m.-11:59 p.m.

2 stops12h 45m

C$ 579

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 5/12

11:00 p.m.-1:59 p.m.

1 stop12h 59m

Chicago Midway

Sun 7/12

7:27 p.m.-11:12 a.m.

1 stop17h 45m

C$ 586

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 26/11

11:00 p.m.-10:43 p.m.

1 stop21h 43m

Chicago Midway

Sun 30/11

4:15 p.m.-11:25 a.m.

2 stops21h 10m

C$ 600

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 8/12

5:00 p.m.-10:05 a.m.

1 stop15h 05m

Chicago Midway

Mon 15/12

6:15 a.m.-4:31 p.m.

1 stop12h 16m

C$ 653

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 27/3

7:35 p.m.-8:54 a.m.

2 stops11h 19m

Chicago Midway

Tue 31/3

1:00 p.m.-8:52 p.m.

2 stops9h 52m

C$ 654

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 19 results
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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 03m. 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?

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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