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Cheap flights from Vancouver Intl Airport to Chicago Midway Airport from C$ 192

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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Vancouver Intl to Midway

Enter your travel dates to find the best prices.

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 12 December 2025.

Sat 27/1210:55 p.m.YVR - MDW
1 stop14h 25mMultiple Airlines
Wed 14/16:14 p.m.MDW - YVR
2 stops19h 15mMultiple Airlines
Deal found 10/12C$ 894
Sat 27/1212:20 p.m.YVR - MDW
2 stops19h 45mPorter Airlines
Wed 14/111:00 a.m.MDW - YVR
2 stops12h 25mPorter Airlines
Deal found 10/12C$ 953
Thu 25/1212:45 p.m.YVR - MDW
1 stop20h 21mWestJet
Mon 5/11:49 p.m.MDW - YVR
1 stop23h 10mWestJet
Deal found 10/12C$ 974
Wed 31/1211:00 p.m.YVR - MDW
1 stop16h 38mMultiple Airlines
Sun 4/110:50 p.m.MDW - YVR
2 stops24h 05mMultiple Airlines
Deal found 10/12C$ 996
Wed 31/1211:00 p.m.YVR - MDW
1 stop8h 05mWestJet
Sun 4/16:08 p.m.MDW - YVR
2 stops20h 56mWestJet
Deal found 10/12C$ 1,004
Sun 28/1211:00 p.m.YVR - MDW
1 stop8h 05mWestJet
Wed 14/11:28 p.m.MDW - YVR
2 stops13h 16mWestJet
Deal found 11/12C$ 1,025
Wed 24/129:15 p.m.YVR - MDW
2 stops18h 04mWestJet
Sun 4/16:08 p.m.MDW - YVR
2 stops20h 56mWestJet
Deal found 9/12C$ 1,058
Tue 30/129:15 p.m.YVR - MDW
2 stops18h 04mWestJet
Sat 3/16:08 p.m.MDW - YVR
2 stops20h 56mWestJet
Deal found 10/12C$ 1,080

Find 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 12 December 2025.

Round-trip from

C$ 367

One-way from

C$ 192

Popular in

December

Cheapest in

October

Average price

C$ 658
25/1-1/2
  • 25/1-1/2
  • 3 total stops
  • 27h 35m total
  • Vancouver to Chicago
Search Deals
10/1
  • 10/1
  • 2 total stops
  • 21h 15m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 126 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 12 December 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

Sun 25/1

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

1 stop10h 45m

Chicago Midway

Sun 1/2

7:30 a.m.-10:20 p.m.

2 stops16h 50m

C$ 368

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 15/2

10:55 p.m.-3:20 p.m.

1 stop14h 25m

Chicago Midway

Sun 22/2

3:02 p.m.-11:59 p.m.

2 stops34h 57m

C$ 429

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 21/1

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

2 stops11h 15m

Chicago Midway

Sat 24/1

9:33 a.m.-6:44 p.m.

2 stops11h 11m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 17/1

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

2 stops13h 47m

Chicago Midway

Wed 21/1

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

2 stops10h 54m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 22/1

6:20 a.m.-8:52 a.m.

2 stops24h 32m

Chicago Midway

Mon 26/1

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

2 stops22h 58m

C$ 490

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.-6:46 p.m.

2 stops11h 16m

C$ 490

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 16/1

8:00 a.m.-11:47 p.m.

2 stops13h 47m

Chicago Midway

Fri 23/1

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

1 stop20h 11m

C$ 492

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 2/3

7:37 p.m.-8:53 a.m.

2 stops11h 16m

Chicago Midway

Thu 5/3

1:28 p.m.-9:00 p.m.

2 stops9h 32m

C$ 494

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/1

12:30 p.m.-11:45 a.m.

2 stops21h 15m

C$ 192

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 13/1

10:15 p.m.-11:47 a.m.

3 stops35h 32m

C$ 201

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 18 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 11h 15m. Delta provides one of the quickest options available for as low as C$ 487. 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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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