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Cheap flights from Vancouver to Chicago Midway Airport from C$ 131

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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
1 Jan — 8 Jan1
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 2 December 2025.

Tue 16/123:40 p.m.YVR - MDW
2 stops15h 06mMultiple Airlines
Sun 11/112:41 p.m.MDW - YVR
1 stop24h 31mMultiple Airlines
Deal found 2/12C$ 380
Wed 17/127:36 p.m.YVR - MDW
2 stops11h 43mDelta
Mon 12/11:49 p.m.MDW - YVR
2 stops12h 10mDelta
Deal found 2/12C$ 519
Tue 16/127:36 p.m.YVR - MDW
2 stops11h 43mDelta
Mon 12/11:49 p.m.MDW - YVR
2 stops12h 10mDelta
Deal found 1/12C$ 554
Wed 17/127:36 p.m.YVR - MDW
2 stops11h 43mDelta
Fri 9/11:49 p.m.MDW - YVR
2 stops12h 10mDelta
Deal found 2/12C$ 580
Sat 6/127:35 p.m.YVR - MDW
2 stops11h 44mDelta
Sat 13/129:59 a.m.MDW - YVR
2 stops14h 45mDelta
Deal found 2/12C$ 657
Mon 29/122:15 p.m.YVR - MDW
1 stop17h 50mMultiple Airlines
Mon 5/14:15 p.m.MDW - YVR
3 stops23h 29mMultiple Airlines
Deal found 30/11C$ 762
Thu 18/127:36 p.m.YVR - MDW
2 stops11h 43mDelta
Thu 8/11:28 p.m.MDW - YVR
2 stops12h 31mDelta
Deal found 2/12C$ 810
Sun 21/129:10 a.m.YVR - MDW
1 stop12h 11mMultiple Airlines
Sun 4/110:50 p.m.MDW - YVR
2 stops42h 03mMultiple Airlines
Deal found 30/11C$ 817
Mon 29/1212:20 p.m.YVR - MDW
2 stops19h 45mPorter Airlines
Mon 5/111:05 a.m.MDW - YVR
1 stop14h 54mPorter Airlines
Deal found 30/11C$ 826

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 2 December 2025.

Round-trip from

C$ 359

One-way from

C$ 131

Popular in

December

Cheapest in

October

Average price

C$ 614
5/2-8/2
  • 5/2-8/2
  • 3 total stops
  • 39h 58m total
  • Vancouver to Chicago
Search Deals
9/1
  • 9/1
  • 2 total stops
  • 26h 12m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 100 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 December 2025
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 2 December 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

Sat 10/1

9:10 a.m.-11:45 a.m.

1 stop24h 35m

Chicago Midway

Mon 12/1

9:15 a.m.-10:20 p.m.

2 stops15h 05m

C$ 362

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 31/1

4:45 p.m.-11:45 a.m.

2 stops17h 00m

Chicago Midway

Sun 8/2

5:01 p.m.-11:12 a.m.

1 stop20h 11m

C$ 379

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 16/12

3:40 p.m.-8:46 a.m.

2 stops15h 06m

Chicago Midway

Sun 11/1

12:41 p.m.-11:12 a.m.

1 stop24h 31m

C$ 380

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 22/1

7:37 p.m.-5:29 p.m.

2 stops19h 52m

Chicago Midway

Mon 26/1

1:49 p.m.-10:47 a.m.

2 stops22h 58m

C$ 438

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 1/2

11:00 p.m.-11:45 a.m.

1 stop10h 45m

Chicago Midway

Thu 5/2

6:20 a.m.-10:40 p.m.

2 stops18h 20m

C$ 473

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 24/1

7:37 p.m.-9:53 a.m.

2 stops12h 16m

Chicago Midway

Wed 28/1

9:50 a.m.-6:44 p.m.

2 stops10h 54m

C$ 488

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/3

6:20 a.m.-5:37 p.m.

2 stops9h 17m

Chicago Midway

Tue 10/3

9:32 a.m.-6:46 p.m.

2 stops11h 14m

C$ 488

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 7/1

6:20 a.m.-10:07 p.m.

2 stops13h 47m

Chicago Midway

Fri 9/1

9:32 a.m.-8:54 p.m.

2 stops13h 22m

C$ 524

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 23/1

7:37 p.m.-8:52 a.m.

2 stops11h 15m

Chicago Midway

Fri 30/1

9:33 a.m.-8:54 p.m.

2 stops13h 21m

C$ 549

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 16/12

7:36 p.m.-9:19 a.m.

2 stops11h 43m

Chicago Midway

Mon 12/1

1:49 p.m.-11:59 p.m.

2 stops12h 10m

C$ 554

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/11

Showing 1-10 of 21 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 19h 52m. 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.

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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