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$122+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Find cheap flights from Vancouver Intl to Midway with Cheapflights

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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 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/24. 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
Wed 12/102:49 pmMDW - YVR
2 stops11h 21mMultiple Airlines
Deal found 11/24$338
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/1410:55 pmYVR - MDW
1 stop14h 25mMultiple Airlines
Tue 12/162:49 pmMDW - YVR
2 stops33h 31mMultiple Airlines
Deal found 11/25$375
This Delta deal was found by Cheapflights users on 11/23. 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 12/412:13 pmYVR - MDW
2 stops9h 34mDelta
Wed 12/101:50 pmMDW - YVR
2 stops12h 09mDelta
Deal found 11/23$423
This Delta deal was found by Cheapflights users on 11/25. 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 12/161:50 pmMDW - YVR
2 stops10h 54mDelta
Deal found 11/25$464
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/511:00 pmYVR - MDW
1 stop12h 59mMultiple Airlines
Sun 12/77:27 pmMDW - YVR
1 stop17h 45mMultiple Airlines
Deal found 11/24$483
This Delta deal was found by Cheapflights users on 11/24. 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 11/276:45 amYVR - MDW
2 stops14h 55mDelta
Tue 12/21:50 pmMDW - YVR
2 stops10h 54mDelta
Deal found 11/24$498
This Kiwi.com deal was found by Cheapflights users on 11/23. 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
Wed 12/102:49 pmMDW - YVR
2 stops11h 21mMultiple Airlines
Deal found 11/23$544
This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
Tue 12/235:45 pmYVR - MDW
2 stops26h 13mMultiple Airlines
Wed 12/316:12 amMDW - YVR
1 stop31h 00mMultiple Airlines
Deal found 11/23$554
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/46:00 amYVR - MDW
2 stops13h 53mMultiple Airlines
Sun 12/77:27 pmMDW - YVR
1 stop17h 45mMultiple Airlines
Deal found 11/24$580
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/2611:00 pmYVR - MDW
1 stop12h 21mMultiple Airlines
Sun 1/410:50 pmMDW - YVR
2 stops21h 55mMultiple Airlines
Deal found 11/25$605
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/1911:00 pmYVR - MDW
1 stop12h 21mMultiple Airlines
Sun 1/410:50 pmMDW - YVR
2 stops21h 55mMultiple Airlines
Deal found 11/25$609

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 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$307
(Kiwi.com)

One-way from

$122
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$424
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. 12% potential increase in price ($47 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 26, 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 3/5

5:00 pm-10:05 am

1 stop15h 05m

Chicago Midway

Tue 3/10

6:00 am-10:40 pm

2 stops18h 40m

$307

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 4/12

11:00 pm-11:33 am

1 stop10h 33m

Chicago Midway

Sun 4/19

11:00 am-10:38 pm

2 stops13h 38m

$319

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/15

5:00 pm-10:05 am

1 stop15h 05m

Chicago Midway

Sun 4/19

11:00 am-9:08 pm

1 stop12h 08m

$335

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 4/11

12:10 am-3:20 pm

1 stop13h 10m

Chicago Midway

Wed 4/15

4:15 pm-11:50 am

1 stop21h 35m

$344

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 1/26

7:37 pm-9:53 am

2 stops12h 16m

Chicago Midway

Sat 1/31

10:46 am-8:54 pm

2 stops12h 08m

$353

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 12/14

10:55 pm-3:20 pm

1 stop14h 25m

Chicago Midway

Tue 12/16

2:49 pm-10:20 pm

2 stops33h 31m

$375

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 3/28

10:30 pm-3:20 pm

1 stop14h 50m

Chicago Midway

Wed 4/1

11:00 am-8:43 pm

2 stops11h 43m

$376

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/5

7:37 pm-8:53 am

2 stops11h 16m

Chicago Midway

Tue 3/10

2:03 pm-11:51 pm

2 stops11h 48m

$391

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 4/21

7:50 pm-3:20 pm

2 stops17h 30m

$150

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 3/11

11:00 pm-11:33 am

1 stop10h 33m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 17 results
1
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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 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.

  • 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.

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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