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Cheap flights from Vancouver to Chicago Midway Airport from C$ 156

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 25/2. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
7 Feb — 14 Feb1
1 adult
1 adult, Economy, 0 bags

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 8 January 2026.

Round-trip from

C$ 336

One-way from

C$ 156

Popular in

December

Cheapest in

October

Average price

C$ 456
23/3-30/3
  • 23/3-30/3
  • 3 total stops
  • 35h 38m total
  • Vancouver to Chicago
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25/2
  • 25/2
  • 2 total stops
  • 29h 56m total
  • Vancouver to Chicago
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Highest demand for flights based on searches. 18% potential increase in price (C$ 148 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 27 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 8 January 2026.

Thu 22/17:37 p.m.YVR - MDW
2 stops11h 15mDelta
Wed 28/19:50 a.m.MDW - YVR
2 stops13h 04mDelta
Deal found 6/1C$ 343
Tue 14/47:08 a.m.YVR - MDW
2 stops8h 46mDelta
Sat 18/42:12 p.m.MDW - YVR
2 stops10h 19mDelta
Deal found 5/1C$ 344
Mon 2/37:25 a.m.YVR - MDW
2 stops23h 29mDelta
Wed 4/39:34 a.m.MDW - YVR
2 stops13h 26mDelta
Deal found 6/1C$ 354
Thu 29/17:45 p.m.YVR - MDW
2 stops24h 34mMultiple Airlines
Sun 1/25:01 p.m.MDW - YVR
1 stop20h 11mMultiple Airlines
Deal found 7/1C$ 368
Wed 4/211:00 p.m.YVR - MDW
1 stop10h 45mMultiple Airlines
Sun 8/27:30 a.m.MDW - YVR
1 stop18h 29mMultiple Airlines
Deal found 6/1C$ 379
Thu 5/36:20 a.m.YVR - MDW
2 stops9h 17mDelta
Tue 10/39:35 a.m.MDW - YVR
2 stops13h 19mDelta
Deal found 7/1C$ 382
Fri 6/27:37 p.m.YVR - MDW
2 stops11h 15mDelta
Mon 9/21:26 p.m.MDW - YVR
2 stops12h 33mDelta
Deal found 7/1C$ 386
Thu 19/212:05 p.m.YVR - MDW
1 stop9h 36mMultiple Airlines
Sun 22/24:15 p.m.MDW - YVR
2 stops31h 17mMultiple Airlines
Deal found 7/1C$ 391
Fri 6/27:37 p.m.YVR - MDW
2 stops11h 15mDelta
Sun 8/21:26 p.m.MDW - YVR
2 stops12h 33mDelta
Deal found 7/1C$ 393
Sat 7/312:05 p.m.YVR - MDW
1 stop8h 36mMultiple Airlines
Sun 8/32:16 p.m.MDW - YVR
1 stop11h 43mMultiple Airlines
Deal found 6/1C$ 402

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 8 January 2026.
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

Wed 4/2

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

2 stops11h 15m

Chicago Midway

Wed 11/2

1:26 p.m.-11:59 p.m.

2 stops12h 33m

C$ 343

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 2/3

7:37 p.m.-8:54 a.m.

2 stops11h 17m

Chicago Midway

Wed 4/3

9:34 a.m.-9:00 p.m.

2 stops13h 26m

C$ 343

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 3/2

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

2 stops11h 15m

Chicago Midway

Tue 10/2

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

2 stops13h 21m

C$ 343

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

9:30 a.m.-8:54 p.m.

2 stops13h 24m

C$ 343

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 22/1

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

2 stops11h 15m

Chicago Midway

Wed 28/1

9:50 a.m.-8:54 p.m.

2 stops13h 04m

C$ 343

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/2

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

2 stops11h 15m

Chicago Midway

Sun 8/2

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

2 stops13h 21m

C$ 343

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 14/4

7:08 a.m.-5:54 p.m.

2 stops8h 46m

Chicago Midway

Sat 18/4

2:12 p.m.-10:31 p.m.

2 stops10h 19m

C$ 344

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 24/4

7:30 p.m.-8:46 a.m.

2 stops11h 16m

Chicago Midway

Tue 28/4

2:12 p.m.-11:01 p.m.

2 stops10h 49m

C$ 354

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 29/1

7:45 p.m.-10:19 p.m.

2 stops24h 34m

Chicago Midway

Sun 1/2

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

1 stop20h 11m

C$ 368

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 30/1

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

2 stops11h 15m

Chicago Midway

Sun 1/2

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

2 stops13h 21m

C$ 382

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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 11h 15m. 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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