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$121+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$200
(Kiwi.com)

One-way from

$121
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$291
From Vancouver Intl to Chicago Midway
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One-way flight from Vancouver Intl to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/2911:00 pmYVR - MDW
1 stop17h 39mMultiple Airlines
Wed 11/52:06 pmMDW - YVR
1 stop23h 06mMultiple Airlines
Deal found 9/14$200
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/208:30 pmYVR - MDW
2 stops15h 08mMultiple Airlines
Wed 10/228:05 amMDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 9/14$202
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/29:30 amYVR - MDW
1 stop12h 11mMultiple Airlines
Mon 10/66:20 amMDW - YVR
1 stop16h 28mMultiple Airlines
Deal found 9/13$204
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sat 10/49:30 amYVR - MDW
1 stop12h 11mMultiple Airlines
Tue 10/78:05 amMDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 9/13$206
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/2911:00 pmYVR - MDW
1 stop17h 39mMultiple Airlines
Mon 11/31:37 pmMDW - YVR
2 stops29h 17mMultiple Airlines
Deal found 9/13$231
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/157:00 amYVR - MDW
2 stops25h 46mMultiple Airlines
Wed 10/228:05 amMDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 9/15$237
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/3111:00 pmYVR - MDW
1 stop17h 39mMultiple Airlines
Mon 11/36:30 amMDW - YVR
2 stops15h 15mMultiple Airlines
Deal found 9/14$244
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/265:55 amYVR - MDW
1 stop9h 40mDelta
Mon 9/291:43 pmMDW - YVR
1 stop8h 48mDelta
Deal found 9/15$246
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/249:30 amYVR - MDW
1 stop12h 16mMultiple Airlines
Mon 10/2710:56 pmMDW - YVR
1 stop19h 35mMultiple Airlines
Deal found 9/13$265
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:44 pmYVR - MDW
2 stops11h 09mDelta
Tue 9/301:43 pmMDW - YVR
1 stop8h 48mDelta
Deal found 9/14$273
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/3111:00 pmYVR - MDW
1 stop17h 39mMultiple Airlines
Sun 11/29:00 amMDW - YVR
1 stop9h 31mMultiple Airlines
Deal found 9/14$282

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 September 15, 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 10/2

9:30 am-11:41 pm

1 stop12h 11m

Chicago Midway

Mon 10/6

5:33 pm-1:36 pm

2 stops22h 03m

$205

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 9/26

5:55 am-5:35 pm

1 stop9h 40m

Chicago Midway

Mon 9/29

1:43 pm-8:31 pm

1 stop8h 48m

$246

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 10/28

7:25 am-5:43 pm

2 stops8h 18m

Chicago Midway

Tue 11/4

1:08 pm-11:57 pm

2 stops12h 49m

$246

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/18

5:55 am-5:43 pm

1 stop9h 48m

Chicago Midway

Tue 10/28

1:48 pm-11:57 pm

2 stops12h 09m

$246

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 9/27

5:55 am-5:35 pm

1 stop9h 40m

Chicago Midway

Sat 10/4

1:43 pm-8:31 pm

1 stop8h 48m

$246

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 9/26

5:55 am-5:35 pm

1 stop9h 40m

Chicago Midway

Sat 10/4

1:43 pm-8:31 pm

1 stop8h 48m

$246

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/18

5:55 am-5:43 pm

1 stop9h 48m

Chicago Midway

Sat 10/25

1:06 pm-8:54 pm

2 stops9h 48m

$246

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 9/26

5:55 am-5:35 pm

1 stop9h 40m

Chicago Midway

Tue 9/30

1:43 pm-8:31 pm

1 stop8h 48m

$246

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 10/20

8:30 pm-1:38 pm

2 stops15h 08m

$121

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 10/7

9:30 am-1:38 pm

1 stop26h 08m

$127

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 17 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?

    For as low as $246, Delta can have you in Chicago Midway Airport from Vancouver Intl Airport in 9h 40m. 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.

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

    Currently, April is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago Midway Airport (average of $160). Flying from Vancouver Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

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

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