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$115+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
Dec 14 — Dec 211
Sun 12/14
Sun 12/21
1 adult, Economy
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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 November 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sun 12/711:00 pmYVR - MDW
1 stop31h 46mMultiple Airlines
Sun 12/146:15 amMDW - YVR
1 stop30h 57mMultiple Airlines
Deal found 11/11$204
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sun 12/711:00 pmYVR - MDW
1 stop8h 52mMultiple Airlines
Fri 12/128:42 pmMDW - YVR
1 stop16h 30mMultiple Airlines
Deal found 11/11$217
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/59:15 pmYVR - MDW
2 stops14h 44mMultiple Airlines
Fri 12/128:42 pmMDW - YVR
1 stop16h 30mMultiple Airlines
Deal found 11/11$221
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sun 11/2311:00 pmYVR - MDW
1 stop21h 43mMultiple Airlines
Wed 11/266:05 amMDW - YVR
1 stop31h 07mMultiple Airlines
Deal found 11/11$224
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sun 11/2311:00 pmYVR - MDW
1 stop21h 43mMultiple Airlines
Tue 11/256:05 amMDW - YVR
2 stops18h 40mMultiple Airlines
Deal found 11/11$239
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 11/226:15 pmYVR - MDW
2 stops26h 18mMultiple Airlines
Fri 12/58:42 pmMDW - YVR
1 stop16h 30mMultiple Airlines
Deal found 11/11$254
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/83:40 pmYVR - MDW
2 stops15h 06mMultiple Airlines
Fri 12/128:42 pmMDW - YVR
1 stop16h 30mMultiple Airlines
Deal found 11/12$281
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 11/2710:55 pmYVR - MDW
1 stop14h 25mMultiple Airlines
Thu 12/47:23 pmMDW - YVR
2 stops29h 22mMultiple Airlines
Deal found 11/11$337
This Kiwi.com deal was found by Cheapflights users on 11/14. 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.
Thu 12/410:55 pmYVR - MDW
1 stop14h 25mMultiple Airlines
Mon 12/88:42 pmMDW - YVR
2 stops22h 12mMultiple Airlines
Deal found 11/14$342
This Delta deal was found by Cheapflights users on 11/11. 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.
Tue 12/27:35 pmYVR - MDW
2 stops11h 44mDelta
Wed 12/109:59 amMDW - YVR
2 stops10h 45mDelta
Deal found 11/11$348
This Delta deal was found by Cheapflights users on 11/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:36 pmYVR - MDW
2 stops11h 18mDelta
Tue 12/169:59 amMDW - YVR
2 stops13h 05mDelta
Deal found 11/13$349

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 November 14, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$204
(Kiwi.com)

One-way from

$115
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$400
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. 10% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 14, 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 1/15

3:45 pm-11:47 am

2 stops18h 02m

Chicago Midway

Mon 1/19

12:57 pm-4:31 pm

1 stop29h 34m

$292

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 11/27

10:55 pm-3:20 pm

1 stop14h 25m

Chicago Midway

Thu 12/4

7:23 pm-10:45 pm

2 stops29h 22m

$337

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 12/4

10:55 pm-3:20 pm

1 stop14h 25m

Chicago Midway

Mon 12/8

8:42 pm-4:54 pm

2 stops22h 12m

$342

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 12/13

7:36 pm-9:19 am

2 stops11h 43m

Chicago Midway

Tue 12/16

9:59 am-9:04 pm

2 stops13h 05m

$348

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 12/2

7:35 pm-9:19 am

2 stops11h 44m

Chicago Midway

Sat 12/13

1:50 pm-11:59 pm

2 stops12h 09m

$348

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 12/9

7:36 pm-9:19 am

2 stops11h 43m

Chicago Midway

Tue 12/16

9:59 am-9:04 pm

2 stops13h 05m

$348

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 12/2

7:35 pm-9:19 am

2 stops11h 44m

Chicago Midway

Tue 12/9

1:50 pm-11:59 pm

2 stops12h 09m

$348

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 12/3

7:35 pm-8:54 am

2 stops11h 19m

Chicago Midway

Sat 12/13

1:50 pm-11:59 pm

2 stops12h 09m

$348

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 12/10

3:31 pm-9:19 am

2 stops15h 48m

Chicago Midway

Tue 12/16

9:59 am-9:04 pm

2 stops13h 05m

$348

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 12/3

7:35 pm-8:54 am

2 stops11h 19m

Chicago Midway

Tue 12/9

1:50 pm-11:59 pm

2 stops12h 09m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 20 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Vancouver Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $348, Delta can have you in Chicago Midway Airport from Vancouver Intl Airport in 11h 43m. 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
Hammond
Porter
Benton Harbor
Merrillville

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