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$127+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
Dec 17 — Dec 241
Wed 12/17
Wed 12/24
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 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/17. 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 11/269:15 pmYVR - MDW
2 stops23h 28mMultiple Airlines
Fri 12/128:42 pmMDW - YVR
1 stop16h 30mMultiple Airlines
Deal found 11/17$244
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/1110:10 pmYVR - MDW
2 stops22h 02mMultiple Airlines
Sun 12/147:27 pmMDW - YVR
1 stop17h 45mMultiple Airlines
Deal found 11/17$307
This Kiwi.com deal was found by Cheapflights users on 11/16. 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
Mon 12/84:15 pmMDW - YVR
1 stop18h 49mMultiple Airlines
Deal found 11/16$319
This Kiwi.com deal was found by Cheapflights users on 11/17. 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
Mon 12/156:15 amMDW - YVR
1 stop12h 16mMultiple Airlines
Deal found 11/17$332
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.
Wed 12/35:00 pmYVR - MDW
1 stop15h 05mMultiple Airlines
Mon 12/88:42 pmMDW - YVR
2 stops22h 12mMultiple Airlines
Deal found 11/14$345
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.
Wed 12/1011:00 pmYVR - MDW
1 stop17h 08mMultiple Airlines
Wed 12/172:49 pmMDW - YVR
2 stops33h 31mMultiple Airlines
Deal found 11/14$352
This Delta deal was found by Cheapflights users on 11/16. 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 stops12h 09mDelta
Deal found 11/16$354
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$364
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 12/35:00 pmYVR - MDW
1 stop15h 05mMultiple Airlines
Sun 12/76:15 amMDW - YVR
2 stops17h 40mMultiple Airlines
Deal found 11/15$365
This Delta 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 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
Sat 12/69:59 amMDW - YVR
2 stops10h 45mDelta
Deal found 11/14$386

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 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$276
(Kiwi.com)

One-way from

$127
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$419
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. 11% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 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 17, 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

Fri 2/13

11:00 pm-11:25 pm

1 stop22h 25m

Chicago Midway

Wed 2/18

11:00 am-11:25 pm

1 stop14h 25m

$281

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 2/12

5:30 pm-1:04 pm

2 stops17h 34m

Chicago Midway

Thu 2/19

11:00 am-11:25 pm

1 stop14h 25m

$304

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 12/11

10:10 pm-10:12 pm

2 stops22h 02m

Chicago Midway

Sun 12/14

7:27 pm-11:12 am

1 stop17h 45m

$307

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 12/5

9:15 pm-1:59 pm

2 stops14h 44m

Chicago Midway

Mon 12/8

4:15 pm-9:04 am

1 stop18h 49m

$319

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 1/24

7:37 pm-9:53 am

2 stops12h 16m

Chicago Midway

Tue 1/27

9:50 am-8:54 pm

2 stops13h 04m

$347

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 12/14

7:36 pm-8:54 am

2 stops11h 18m

Chicago Midway

Tue 12/16

1:50 pm-11:59 pm

2 stops12h 09m

$354

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 1/9

6:20 am-10:07 pm

2 stops13h 47m

Chicago Midway

Mon 1/12

1:49 pm-11:59 pm

2 stops12h 10m

$361

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

$364

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 12/3

5:00 pm-10:05 am

1 stop15h 05m

Chicago Midway

Sun 12/7

6:15 am-9:55 pm

2 stops17h 40m

$365

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 12/10

11:00 pm-6:08 pm

1 stop17h 08m

Chicago Midway

Wed 12/17

2:49 pm-11:12 am

1 stop22h 23m

$374

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 18 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 $347, Delta can have you in Chicago Midway Airport from Vancouver Intl Airport in 12h 16m. 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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