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$139+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
Apr 8 — Apr 151
Wed 4/8
Wed 4/15
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 March 9, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/5. 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 4/194:35 pm
YVR
-
MDW
2 stops27h 46m
Multiple Airlines
Sun 4/266:00 am
MDW
-
YVR
1 stop30h 45m
Multiple Airlines
Deal found 3/5$306
This Delta deal was found by Cheapflights users on 3/4. 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 3/317:35 pm
YVR
-
MDW
2 stops14h 54m
Delta
Wed 4/86:34 pm
MDW
-
YVR
2 stops26h 11m
Delta
Deal found 3/4$344
This Delta deal was found by Cheapflights users on 3/9. 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.
Wed 4/157:30 pm
YVR
-
MDW
2 stops11h 17m
Delta
Tue 4/219:27 am
MDW
-
YVR
2 stops11h 13m
Delta
Deal found 3/9$368
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 5/29:30 am
YVR
-
MDW
1 stop10h 44m
Multiple Airlines
Thu 5/76:15 am
MDW
-
YVR
1 stop15h 40m
Multiple Airlines
Deal found 3/9$371
This Delta deal was found by Cheapflights users on 3/8. 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 4/167:30 pm
YVR
-
MDW
2 stops11h 17m
Delta
Tue 4/219:27 am
MDW
-
YVR
2 stops11h 13m
Delta
Deal found 3/8$376
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 3/304:35 pm
YVR
-
MDW
2 stops20h 58m
Multiple Airlines
Tue 4/711:00 am
MDW
-
YVR
1 stop15h 38m
Multiple Airlines
Deal found 3/4$386
This Delta deal was found by Cheapflights users on 3/4. 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.
Sat 5/236:00 am
YVR
-
MDW
1 stop9h 56m
Delta
Tue 5/261:59 pm
MDW
-
YVR
1 stop8h 40m
Delta
Deal found 3/4$413
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 4/282:35 pm
YVR
-
MDW
2 stops17h 40m
Multiple Airlines
Wed 5/610:25 am
MDW
-
YVR
1 stop15h 00m
Multiple Airlines
Deal found 3/4$422
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 4/14:15 pm
YVR
-
MDW
1 stop16h 00m
Multiple Airlines
Tue 4/711:00 am
MDW
-
YVR
1 stop15h 38m
Multiple Airlines
Deal found 3/4$430
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 3/2810:30 pm
YVR
-
MDW
1 stop14h 50m
Multiple Airlines
Tue 4/711:00 am
MDW
-
YVR
1 stop15h 38m
Multiple Airlines
Deal found 3/5$436
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 4/204:15 pm
YVR
-
MDW
1 stop16h 00m
Multiple Airlines
Mon 4/2711:00 am
MDW
-
YVR
1 stop11h 59m
Multiple Airlines
Deal found 3/4$441

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 March 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$306
(Kiwi.com)

One-way from

$139
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$462
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. 16% potential increase in price ($77 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 9, 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 4/16

7:30 pm-8:47 am

2 stops11h 17m

Chicago Midway

Tue 4/21

9:27 am-6:40 pm

2 stops11h 13m

$376
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 5/23

6:00 am-5:56 pm

1 stop9h 56m

Chicago Midway

Tue 5/26

1:59 pm-8:39 pm

1 stop8h 40m

$413

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 5/1

7:30 pm-8:47 am

2 stops11h 17m

Chicago Midway

Tue 5/5

9:29 am-7:10 pm

2 stops11h 41m

$468

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/15

7:30 pm-8:47 am

2 stops11h 17m

Chicago Midway

Sat 4/18

1:24 pm-9:10 pm

2 stops9h 46m

$535

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 4/16

7:30 pm-8:47 am

2 stops11h 17m

Chicago Midway

Sat 4/18

1:24 pm-10:31 pm

2 stops11h 07m

$544

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/28

7:41 pm-8:42 am

2 stops11h 01m

Chicago Midway

Mon 6/1

1:59 pm-10:49 pm

2 stops10h 50m

$559

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 3/30

12:10 am-12:29 pm

2 stops10h 19m

Chicago Midway

Mon 4/6

4:05 pm-10:20 am

1 stop20h 15m

$597

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 4/6

7:35 pm-8:53 am

2 stops11h 18m

Chicago Midway

Mon 4/13

9:29 am-6:43 pm

2 stops11h 14m

$652

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 5/29

6:00 am-5:56 pm

1 stop9h 56m

Chicago Midway

Sun 5/31

9:23 am-8:39 pm

1 stop13h 16m

$655
Cheapest one-way

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 4/14

7:30 pm-5:58 pm

2 stops20h 28m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/5

Showing 1-10 of 18 resultsSorted by cheapest first
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 March.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 FlightHub the most. FlightHub 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 $376, 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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