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Cheap flights from Vancouver Intl Airport to Chicago Midway Airport from C$ 236

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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
27 Feb — 6 Mar1
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 28 January 2026.

Wed 25/212:30 p.m.
YVR
-
MDW
2 stops33h 11m
Multiple Airlines
Mon 2/33:29 p.m.
MDW
-
YVR
1 stop10h 30m
Multiple Airlines
Deal found 27/1C$ 327
Thu 26/28:00 a.m.
YVR
-
MDW
2 stops32h 30m
Multiple Airlines
Mon 2/33:29 p.m.
MDW
-
YVR
1 stop10h 30m
Multiple Airlines
Deal found 27/1C$ 334
Fri 20/29:10 a.m.
YVR
-
MDW
1 stop8h 50m
Multiple Airlines
Mon 2/33:29 p.m.
MDW
-
YVR
1 stop10h 30m
Multiple Airlines
Deal found 27/1C$ 361
Fri 20/29:10 a.m.
YVR
-
MDW
1 stop8h 50m
Multiple Airlines
Fri 27/27:32 p.m.
MDW
-
YVR
1 stop25h 57m
Multiple Airlines
Deal found 27/1C$ 384
Mon 23/24:15 p.m.
YVR
-
MDW
1 stop15h 55m
Multiple Airlines
Mon 2/33:29 p.m.
MDW
-
YVR
1 stop10h 30m
Multiple Airlines
Deal found 25/1C$ 418
Sun 8/34:35 p.m.
YVR
-
MDW
1 stop28h 10m
Multiple Airlines
Wed 11/311:00 a.m.
MDW
-
YVR
2 stops11h 43m
Multiple Airlines
Deal found 27/1C$ 426
Fri 20/29:10 a.m.
YVR
-
MDW
1 stop8h 50m
Multiple Airlines
Thu 26/26:25 a.m.
MDW
-
YVR
2 stops15h 04m
Multiple Airlines
Deal found 27/1C$ 431
Thu 12/312:05 p.m.
YVR
-
MDW
1 stop8h 40m
Multiple Airlines
Wed 18/311:25 a.m.
MDW
-
YVR
2 stops14h 34m
Multiple Airlines
Deal found 26/1C$ 437
Fri 27/29:10 a.m.
YVR
-
MDW
1 stop12h 31m
Multiple Airlines
Mon 2/33:29 p.m.
MDW
-
YVR
1 stop10h 30m
Multiple Airlines
Deal found 26/1C$ 444

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 28 January 2026.

Round-trip from

C$ 327

One-way from

C$ 236

Popular in

December

Cheapest in

October

Average price

C$ 458
25/2-2/3
  • 25/2-2/3
  • 3 total stops
  • 43h 41m total
  • Vancouver to Chicago
Search Deals
9/2
  • 9/2
  • 3 total stops
  • 34h 07m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 19% potential increase in price (C$ 151 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 28 January 2026.
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

Wed 25/2

12:30 p.m.-11:41 p.m.

2 stops33h 11m

Chicago Midway

Mon 2/3

3:29 p.m.-11:59 p.m.

1 stop10h 30m

C$ 327

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 26/2

8:00 a.m.-6:30 p.m.

2 stops32h 30m

Chicago Midway

Mon 2/3

3:29 p.m.-11:59 p.m.

1 stop10h 30m

C$ 334

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 20/2

9:10 a.m.-8:00 p.m.

1 stop8h 50m

Chicago Midway

Mon 2/3

3:29 p.m.-11:59 p.m.

1 stop10h 30m

C$ 361

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 23/2

2:25 p.m.-10:10 a.m.

2 stops17h 45m

Chicago Midway

Mon 2/3

3:29 p.m.-11:59 p.m.

1 stop10h 30m

C$ 420

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 25/2

12:55 p.m.-10:10 a.m.

1 stop19h 15m

Chicago Midway

Wed 4/3

11:00 a.m.-11:25 p.m.

1 stop14h 25m

C$ 492

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 23/2

8:55 a.m.-11:44 p.m.

1 stop12h 49m

Chicago Midway

Tue 24/2

11:05 a.m.-10:20 a.m.

1 stop25h 15m

C$ 597

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 21/4

7:30 p.m.-12:43 p.m.

2 stops15h 13m

Chicago Midway

Tue 28/4

9:27 a.m.-11:01 p.m.

2 stops15h 34m

C$ 599

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 21/4

7:30 p.m.-12:43 p.m.

2 stops15h 13m

Chicago Midway

Sat 25/4

9:27 a.m.-9:10 p.m.

2 stops13h 43m

C$ 608

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 2/3

7:37 p.m.-12:46 p.m.

2 stops15h 09m

Chicago Midway

Wed 4/3

1:29 p.m.-11:59 p.m.

2 stops12h 30m

C$ 610

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 23/4

7:30 p.m.-8:51 a.m.

2 stops11h 21m

Chicago Midway

Sat 25/4

9:27 a.m.-9:10 p.m.

2 stops13h 43m

C$ 627

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/1

Showing 1-10 of 19 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.

  • 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.

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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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.

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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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