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Cheap flights from Vancouver to Chicago Midway Airport from C$ 167

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 20/10. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
15 Oct — 22 Oct1
1 adult
1 adult, Economy

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 15 September 2025.

Round-trip from

C$ 277

One-way from

C$ 167

Popular in

November

Cheapest in

September

Average price

C$ 403
29/10-5/11
  • 29/10-5/11
  • 2 total stops
  • 40h 45m total
  • Vancouver to Chicago
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20/10
  • 20/10
  • 2 total stops
  • 15h 08m total
  • Vancouver to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (C$ 55 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Vancouver to Midway

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 15 September 2025.

Wed 29/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Wed 5/112:06 p.m.MDW - YVR
1 stop23h 06mMultiple Airlines
Deal found 14/9C$ 277
Mon 20/108:30 p.m.YVR - MDW
2 stops15h 08mMultiple Airlines
Wed 22/108:05 a.m.MDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 14/9C$ 280
Thu 2/109:30 a.m.YVR - MDW
1 stop12h 11mMultiple Airlines
Mon 6/106:20 a.m.MDW - YVR
1 stop16h 28mMultiple Airlines
Deal found 13/9C$ 282
Sat 4/109:30 a.m.YVR - MDW
1 stop12h 11mMultiple Airlines
Tue 7/108:05 a.m.MDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 13/9C$ 285
Wed 29/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Mon 3/111:37 p.m.MDW - YVR
2 stops29h 17mMultiple Airlines
Deal found 13/9C$ 320
Wed 15/107:00 a.m.YVR - MDW
2 stops25h 46mMultiple Airlines
Wed 22/108:05 a.m.MDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 15/9C$ 328
Fri 31/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Mon 3/116:30 a.m.MDW - YVR
2 stops15h 15mMultiple Airlines
Deal found 14/9C$ 338
Fri 26/95:55 a.m.YVR - MDW
1 stop9h 40mDelta
Sat 4/101:43 p.m.MDW - YVR
1 stop8h 48mDelta
Deal found 14/9C$ 340
Fri 24/109:30 a.m.YVR - MDW
1 stop12h 16mMultiple Airlines
Mon 27/1010:56 p.m.MDW - YVR
1 stop19h 35mMultiple Airlines
Deal found 13/9C$ 367
Thu 25/97:44 p.m.YVR - MDW
2 stops11h 09mDelta
Tue 30/91:43 p.m.MDW - YVR
1 stop8h 48mDelta
Deal found 14/9C$ 378
Fri 31/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Sun 2/119:00 a.m.MDW - YVR
1 stop9h 31mMultiple Airlines
Deal found 14/9C$ 390

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 15 September 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

Thu 2/10

9:30 a.m.-11:41 p.m.

1 stop12h 11m

Chicago Midway

Mon 6/10

5:33 p.m.-1:36 p.m.

2 stops22h 03m

C$ 284

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 4/10

9:30 a.m.-11:41 p.m.

1 stop12h 11m

Chicago Midway

Tue 7/10

8:05 a.m.-8:48 p.m.

1 stop14h 43m

C$ 285

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 26/9

5:55 a.m.-5:35 p.m.

1 stop9h 40m

Chicago Midway

Mon 29/9

1:43 p.m.-8:31 p.m.

1 stop8h 48m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 28/10

7:25 a.m.-5:43 p.m.

2 stops8h 18m

Chicago Midway

Tue 4/11

1:08 p.m.-11:57 p.m.

2 stops12h 49m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 18/10

5:55 a.m.-5:43 p.m.

1 stop9h 48m

Chicago Midway

Tue 28/10

1:48 p.m.-11:57 p.m.

2 stops12h 09m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 26/9

5:55 a.m.-5:35 p.m.

1 stop9h 40m

Chicago Midway

Sat 4/10

1:43 p.m.-8:31 p.m.

1 stop8h 48m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 18/10

5:55 a.m.-5:43 p.m.

1 stop9h 48m

Chicago Midway

Sat 25/10

1:06 p.m.-8:54 p.m.

2 stops9h 48m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 26/9

5:55 a.m.-5:35 p.m.

1 stop9h 40m

Chicago Midway

Tue 30/9

1:43 p.m.-8:31 p.m.

1 stop8h 48m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 20/10

8:30 p.m.-1:38 p.m.

2 stops15h 08m

C$ 167

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 7/10

9:30 a.m.-1:38 p.m.

1 stop26h 08m

C$ 176

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/9

Showing 1-10 of 17 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 9h 40m. 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.

  • What is the cheapest month to book a flight from Vancouver to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Vancouver to Chicago Midway Airport (average of C$ 209). Flying from Vancouver to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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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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