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Cheap flights from Vancouver Intl Airport to Chicago Midway Airport from C$ 147

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 14/10. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Vancouver Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Vancouver Intl (YVR) 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 11 September 2025.

Round-trip from

C$ 245

One-way from

C$ 147

Popular in

December

Cheapest in

October

Average price

C$ 417
31/10-4/11
  • 31/10-4/11
  • 3 total stops
  • 44h 28m total
  • Vancouver to Chicago
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14/10
  • 14/10
  • 2 total stops
  • 15h 08m total
  • Vancouver to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (C$ 63 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 Intl to Midway

Cheapest flights from Vancouver Intl to Midway
Explore the most affordable flight options available from Vancouver Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 11 September 2025.

Thu 23/109:30 a.m.YVR - MDW
1 stop8h 51mMultiple Airlines
Wed 29/102:06 p.m.MDW - YVR
2 stops28h 48mMultiple Airlines
Deal found 9/9C$ 238
Fri 17/109:30 a.m.YVR - MDW
1 stop12h 16mMultiple Airlines
Sun 19/106:20 a.m.MDW - YVR
2 stops17h 31mMultiple Airlines
Deal found 9/9C$ 247
Tue 7/108:30 p.m.YVR - MDW
2 stops15h 08mMultiple Airlines
Tue 14/108:05 a.m.MDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 9/9C$ 248
Thu 2/109:30 a.m.YVR - MDW
1 stop12h 11mMultiple Airlines
Sun 5/106:20 a.m.MDW - YVR
1 stop16h 28mMultiple Airlines
Deal found 9/9C$ 254
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 10/9C$ 287
Fri 17/109:30 a.m.YVR - MDW
1 stop12h 16mMultiple Airlines
Wed 22/108:05 a.m.MDW - YVR
2 stops15h 46mMultiple Airlines
Deal found 8/9C$ 298
Thu 30/107:45 p.m.YVR - MDW
2 stops24h 00mMultiple Airlines
Sun 2/119:00 a.m.MDW - YVR
1 stop9h 31mMultiple Airlines
Deal found 9/9C$ 301

Cheapflights Fare Finder

 
Customize your flight search to find flights from Vancouver Intl 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 11 September 2025.
Use the filters below to find and compare flights from Vancouver Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Vancouver Intl

Fly to

Midway

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 30/10

7:45 p.m.-9:45 p.m.

2 stops24h 00m

Chicago Midway

Sun 2/11

9:00 a.m.-4:31 p.m.

1 stop9h 31m

C$ 301

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 1/10

5:35 p.m.-9:18 a.m.

2 stops13h 43m

Chicago Midway

Thu 2/10

4:56 p.m.-8:48 p.m.

1 stop29h 52m

C$ 317

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 27/9

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

1 stop9h 40m

Chicago Midway

Sat 4/10

1:08 p.m.-8:31 p.m.

2 stops9h 23m

C$ 341

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 22/10

6:00 a.m.-5:43 p.m.

1 stop9h 43m

Chicago Midway

Sat 25/10

3:00 p.m.-11:57 p.m.

2 stops10h 57m

C$ 341

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 20/10

7:36 p.m.-8:40 a.m.

2 stops11h 04m

Chicago Midway

Thu 23/10

1:48 p.m.-8:35 p.m.

1 stop8h 47m

C$ 341

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 20/10

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

2 stops15h 08m

Chicago Midway

Thu 23/10

9:26 p.m.-8:48 p.m.

1 stop25h 22m

C$ 342

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 8/10

6:00 a.m.-5:43 p.m.

1 stop9h 43m

Chicago Midway

Wed 15/10

1:48 p.m.-8:35 p.m.

1 stop8h 47m

C$ 400

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 4/10

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

1 stop12h 11m

Chicago Midway

Wed 8/10

9:35 a.m.-8:53 p.m.

2 stops13h 18m

C$ 403

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 17/10

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

1 stop9h 48m

Chicago Midway

Wed 22/10

9:20 a.m.-5:36 p.m.

2 stops10h 16m

C$ 414

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 14/10

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

2 stops15h 08m

C$ 147

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 20 results
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Best time to book a flight from Vancouver Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Vancouver Intl 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.

Related info for your journey

Find useful and relevant information for your journey from Vancouver Intl 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 Intl Airport to Chicago Midway Airport?

    A quick flight from Vancouver Intl Airport to Chicago Midway Airport can take about 9h 40m. Delta provides one of the quickest options available for as low as C$ 341. The distance from Vancouver Intl Airport to Chicago Midway Airport is about 2850 km.

  • Can I find deals for flights from Vancouver Intl to Midway that include hotel bookings?

    Yes. In addition to deals on Vancouver Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Vancouver Intl to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Vancouver Intl to Midway.

  • Can I find deals for business class flights from Vancouver Intl to Midway?

    Yes. Cheapflights offers flight deals from Vancouver Intl 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 Intl Airport to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago Midway Airport (average of C$ 209). Flying from Vancouver Intl Airport 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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Alternative routes for Vancouver Intl to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Vancouver Intl to O'Hare Intl flights

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How does Cheapflights help users find flights from Vancouver Intl to Midway?

Cheapflights makes it easy to find Vancouver Intl 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 Intl to Midway?

Cheapflights helps you find that perfect flight to Midway from Vancouver Intl by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Vancouver Intl to Midway with no change fees?

Certainly. Search results for flights to Midway from Vancouver Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Vancouver Intl to Midway become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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