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$163+ Cheap flights from Vancouver Intl (YVR) to Midway (MDW)

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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:40 pm
YVR
-
MDW
2 stops21h 39m
Multiple Airlines
Sun 3/13:21 pm
MDW
-
YVR
1 stop10h 38m
Multiple Airlines
Deal found 1/20$303
This Kiwi.com deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:40 pm
YVR
-
MDW
2 stops21h 39m
Multiple Airlines
Mon 3/27:25 pm
MDW
-
YVR
1 stop23h 02m
Multiple Airlines
Deal found 1/19$314
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:05 pm
YVR
-
MDW
1 stop9h 46m
Multiple Airlines
Sun 3/82:16 pm
MDW
-
YVR
1 stop11h 43m
Multiple Airlines
Deal found 1/20$326
This Kiwi.com deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:00 pm
YVR
-
MDW
1 stop10h 27m
Multiple Airlines
Mon 2/233:24 pm
MDW
-
YVR
1 stop10h 35m
Multiple Airlines
Deal found 1/19$329
This Kiwi.com deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:05 pm
YVR
-
MDW
1 stop9h 36m
Multiple Airlines
Mon 2/233:24 pm
MDW
-
YVR
1 stop10h 35m
Multiple Airlines
Deal found 1/19$334
This Kiwi.com deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:05 pm
YVR
-
MDW
1 stop9h 46m
Multiple Airlines
Mon 3/92:16 pm
MDW
-
YVR
1 stop11h 43m
Multiple Airlines
Deal found 1/19$338
This Kiwi.com deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:00 pm
YVR
-
MDW
1 stop10h 27m
Multiple Airlines
Tue 2/2411:05 am
MDW
-
YVR
2 stops12h 27m
Multiple Airlines
Deal found 1/19$343
This Kiwi.com deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:00 pm
YVR
-
MDW
1 stop10h 27m
Multiple Airlines
Wed 2/2511:05 am
MDW
-
YVR
2 stops12h 27m
Multiple Airlines
Deal found 1/19$351
This Kiwi.com deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/166:00 am
YVR
-
MDW
2 stops26h 10m
Multiple Airlines
Mon 2/237:25 pm
MDW
-
YVR
1 stop30h 34m
Multiple Airlines
Deal found 1/19$355

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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$251
(Kiwi.com)

One-way from

$163
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$333
Provider with most accurate pricing for Vancouver Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Vancouver Intl-Chicago Midway flights.
Search Deals
From Vancouver Intl to Chicago Midway
Search Deals
One-way flight from Vancouver Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($80 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 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 2,558,603 searches. Data last updated January 21, 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

Fri 2/27

3:40 pm-3:19 pm

2 stops21h 39m

Chicago Midway

Sun 3/1

3:21 pm-11:59 pm

1 stop10h 38m

$303

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/5

12:05 pm-11:51 pm

1 stop9h 46m

Chicago Midway

Sun 3/8

2:16 pm-11:59 pm

1 stop11h 43m

$343

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 2/19

12:05 pm-11:41 pm

1 stop9h 36m

Chicago Midway

Mon 2/23

11:05 am-9:32 pm

2 stops12h 27m

$361

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 2/18

7:37 pm-8:54 am

2 stops11h 17m

Chicago Midway

Wed 2/25

1:26 pm-11:59 pm

2 stops12h 33m

$389

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/5

7:37 pm-8:54 am

2 stops11h 17m

Chicago Midway

Tue 3/10

1:10 pm-11:59 pm

2 stops12h 49m

$390

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 3/2

7:37 pm-8:54 am

2 stops11h 17m

Chicago Midway

Wed 3/4

9:50 am-9:00 pm

2 stops13h 10m

$396

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 2/8

7:37 pm-12:46 pm

2 stops15h 09m

Chicago Midway

Tue 2/10

1:51 pm-11:59 pm

2 stops12h 08m

$400

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/5

7:37 pm-8:54 am

2 stops11h 17m

Chicago Midway

Mon 3/9

9:30 am-8:54 pm

2 stops13h 24m

$403

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 2/16

6:00 am-10:10 am

2 stops26h 10m

Chicago Midway

Fri 2/20

3:21 pm-11:59 pm

1 stop10h 38m

$408

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 3/6

4:35 pm-10:41 pm

1 stop28h 06m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 18 results
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Compare providers for flights from Vancouver Intl to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Vancouver Intl to Midway in January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Vancouver Intl Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Vancouver Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Vancouver Intl Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Vancouver Intl Airport-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Vancouver Intl Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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?

    For as low as $389, Delta can have you in Chicago Midway Airport from Vancouver Intl Airport in 11h 17m. The distance from Vancouver Intl Airport to Chicago Midway Airport is about 1771 mi.

  • 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Vancouver Intl to Midway

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