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$161+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
May 11 — May 181
Mon 5/11
Mon 5/18
1 adult, Economy
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Find cheap flights from Vancouver Intl to Midway with Cheapflights

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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 April 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/57:30 pm
YVR
-
MDW
2 stops24h 32m
Multiple Airlines
Tue 5/1210:30 am
MDW
-
YVR
1 stop16h 14m
Multiple Airlines
Deal found 4/6$396
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 5/810:55 pm
YVR
-
MDW
1 stop10h 09m
Multiple Airlines
Thu 5/1412:19 pm
MDW
-
YVR
2 stops33h 36m
Multiple Airlines
Deal found 4/7$401
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 5/1010:55 pm
YVR
-
MDW
1 stop10h 14m
Multiple Airlines
Tue 5/1210:30 am
MDW
-
YVR
1 stop16h 14m
Multiple Airlines
Deal found 4/7$406
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 5/177:30 pm
YVR
-
MDW
2 stops13h 39m
Multiple Airlines
Fri 5/2910:30 am
MDW
-
YVR
1 stop16h 14m
Multiple Airlines
Deal found 4/7$408
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 5/177:30 pm
YVR
-
MDW
2 stops13h 39m
Multiple Airlines
Tue 5/2610:30 am
MDW
-
YVR
1 stop16h 14m
Multiple Airlines
Deal found 4/7$409
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 6/16:40 pm
YVR
-
MDW
2 stops14h 32m
Multiple Airlines
Thu 6/410:25 am
MDW
-
YVR
1 stop16h 19m
Multiple Airlines
Deal found 4/7$411
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/110:55 pm
YVR
-
MDW
1 stop17h 42m
Multiple Airlines
Sun 5/32:15 pm
MDW
-
YVR
1 stop22h 30m
Multiple Airlines
Deal found 4/8$412
This Delta deal was found by Cheapflights users on 4/6. 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 10/107:35 pm
YVR
-
MDW
2 stops11h 14m
Delta
Tue 10/1312:30 pm
MDW
-
YVR
1 stop10h 02m
Delta
Deal found 4/6$414
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 5/167:30 pm
YVR
-
MDW
2 stops13h 39m
Multiple Airlines
Tue 5/2610:30 am
MDW
-
YVR
1 stop16h 14m
Multiple Airlines
Deal found 4/7$417
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 4/3012:35 pm
YVR
-
MDW
1 stop9h 08m
Multiple Airlines
Wed 5/612:04 pm
MDW
-
YVR
1 stop24h 41m
Multiple Airlines
Deal found 4/7$420
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 4/2411:00 pm
YVR
-
MDW
1 stop17h 37m
Multiple Airlines
Sat 5/27:34 pm
MDW
-
YVR
1 stop17h 11m
Multiple Airlines
Deal found 4/7$421

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 April 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$396
(Kiwi.com)

One-way from

$161
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$441
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. 14% potential increase in price ($68 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 April 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 April 11, 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

Wed 5/13

6:00 am-5:56 pm

1 stop9h 56m

Chicago Midway

Fri 5/15

9:23 am-7:10 pm

2 stops11h 47m

$472
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/28

6:00 am-6:33 pm

2 stops10h 33m

Chicago Midway

Sat 6/6

1:59 pm-8:39 pm

1 stop8h 40m

$472

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 4/24

7:30 pm-9:06 am

2 stops11h 36m

Chicago Midway

Mon 4/27

2:12 pm-11:01 pm

2 stops10h 49m

$473

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 4/21

7:30 pm-8:47 am

2 stops11h 17m

Chicago Midway

Mon 5/4

9:29 am-6:40 pm

2 stops11h 11m

$473

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 5/12

6:00 am-6:33 pm

2 stops10h 33m

Chicago Midway

Tue 5/19

1:22 pm-10:35 pm

2 stops11h 13m

$495

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 5/1

7:30 pm-8:47 am

2 stops11h 17m

Chicago Midway

Fri 5/8

1:22 pm-10:51 pm

2 stops11h 29m

$586

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/28

7:41 pm-8:42 am

2 stops11h 01m

Chicago Midway

Thu 6/4

9:23 am-5:54 pm

2 stops10h 31m

$621

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 5/1

7:00 am-9:45 am

2 stops24h 45m

Chicago Midway

Tue 5/5

10:30 am-8:50 pm

2 stops12h 20m

$638

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 5/3

7:30 pm-8:46 am

2 stops11h 16m

Chicago Midway

Fri 5/8

1:22 pm-10:51 pm

2 stops11h 29m

$644
Cheapest one-way

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 5/2

6:35 am-10:28 pm

2 stops13h 53m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/6

Showing 1-10 of 20 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 April.
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 $472, Delta can have you in Chicago Midway Airport from Vancouver Intl Airport in 9h 56m. 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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Alternative routes for Vancouver Intl to Midway

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