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Cheap flights from Vancouver Intl Airport to Chicago Midway Airport from C$ 157

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
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Vancouver Intl to Midway

Enter your travel dates to find the best prices.

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 28 October 2025.

Fri 5/1211:00 p.m.YVR - MDW
1 stop12h 59mMultiple Airlines
Mon 8/128:42 p.m.MDW - YVR
2 stops20h 03mMultiple Airlines
Deal found 28/10C$ 297
Sun 23/119:10 a.m.YVR - MDW
1 stop27h 38mMultiple Airlines
Thu 27/116:05 a.m.MDW - YVR
2 stops18h 40mMultiple Airlines
Deal found 27/10C$ 312
Sun 16/1111:00 p.m.YVR - MDW
2 stops13h 33mMultiple Airlines
Wed 19/111:56 p.m.MDW - YVR
1 stop23h 16mMultiple Airlines
Deal found 27/10C$ 331
Fri 26/127:32 p.m.YVR - MDW
2 stops11h 17mDelta
Mon 12/11:28 p.m.MDW - YVR
2 stops12h 35mDelta
Deal found 26/10C$ 365
Wed 24/129:15 p.m.YVR - MDW
2 stops18h 23mMultiple Airlines
Sun 11/18:26 p.m.MDW - YVR
1 stop22h 05mMultiple Airlines
Deal found 26/10C$ 389
Thu 20/115:00 p.m.YVR - MDW
1 stop20h 20mMultiple Airlines
Thu 27/116:05 a.m.MDW - YVR
2 stops18h 40mMultiple Airlines
Deal found 26/10C$ 406
Fri 31/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Sun 2/115:20 a.m.MDW - YVR
1 stop30h 52mMultiple Airlines
Deal found 26/10C$ 421
Fri 26/127:32 p.m.YVR - MDW
2 stops11h 17mDelta
Thu 15/19:50 a.m.MDW - YVR
2 stops10h 59mDelta
Deal found 26/10C$ 439
Thu 25/126:00 a.m.YVR - MDW
2 stops9h 19mDelta
Wed 14/11:28 p.m.MDW - YVR
2 stops12h 35mDelta
Deal found 26/10C$ 443
Fri 26/127:32 p.m.YVR - MDW
2 stops11h 17mDelta
Fri 16/11:28 p.m.MDW - YVR
2 stops13h 16mDelta
Deal found 26/10C$ 448
Fri 7/1111:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Tue 11/111:56 p.m.MDW - YVR
2 stops34h 49mMultiple Airlines
Deal found 26/10C$ 460
Fri 7/1111:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Wed 12/112:06 p.m.MDW - YVR
1 stop23h 06mMultiple Airlines
Deal found 26/10C$ 466

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 28 October 2025.

Round-trip from

C$ 297

One-way from

C$ 157

Popular in

November

Cheapest in

September

Average price

C$ 429
5/12-8/12
  • 5/12-8/12
  • 3 total stops
  • 33h 02m total
  • Vancouver to Chicago
Search Deals
12/12
  • 12/12
  • 2 total stops
  • 25h 07m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 629,999 searches. Data last updated 28 October 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 5/12

11:00 p.m.-1:59 p.m.

1 stop12h 59m

Chicago Midway

Mon 8/12

8:42 p.m.-2:45 p.m.

2 stops20h 03m

C$ 297

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 23/11

9:10 a.m.-2:48 p.m.

1 stop27h 38m

Chicago Midway

Thu 27/11

6:05 a.m.-10:45 p.m.

2 stops18h 40m

C$ 312

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 16/11

11:00 p.m.-2:33 p.m.

2 stops13h 33m

Chicago Midway

Wed 19/11

1:56 p.m.-11:12 a.m.

1 stop23h 16m

C$ 331

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 9/12

12:13 p.m.-11:47 p.m.

2 stops9h 34m

Chicago Midway

Tue 16/12

1:50 p.m.-11:59 p.m.

2 stops12h 09m

C$ 365

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 26/12

7:32 p.m.-8:49 a.m.

2 stops11h 17m

Chicago Midway

Wed 14/1

1:28 p.m.-12:03 a.m.

2 stops12h 35m

C$ 365

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 15/11

6:45 a.m.-6:18 p.m.

2 stops9h 33m

Chicago Midway

Tue 18/11

1:47 p.m.-10:37 p.m.

2 stops10h 50m

C$ 365

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 6/2

11:00 p.m.-11:25 p.m.

1 stop22h 25m

Chicago Midway

Fri 13/2

12:25 p.m.-4:27 p.m.

1 stop30h 02m

C$ 420

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 14/11

7:36 p.m.-9:01 a.m.

2 stops11h 25m

Chicago Midway

Mon 17/11

9:34 a.m.-6:46 p.m.

2 stops11h 12m

C$ 443

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 25/12

6:00 a.m.-5:19 p.m.

2 stops9h 19m

Chicago Midway

Tue 13/1

9:50 a.m.-8:54 p.m.

2 stops13h 04m

C$ 443

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 25/12

6:00 a.m.-5:19 p.m.

2 stops9h 19m

Chicago Midway

Mon 12/1

1:28 p.m.-12:03 a.m.

2 stops12h 35m

C$ 443

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

Showing 1-10 of 19 results
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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?

    A quick flight from Vancouver Intl Airport to Chicago Midway Airport can take about 9h 34m. Delta provides one of the quickest options available for as low as C$ 365. The distance from Vancouver Intl Airport to Chicago Midway Airport is about 2850 km.

  • 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

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Alternative routes for Vancouver Intl to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Vancouver Intl to O'Hare Intl flights

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How does Cheapflights help users find flights from Vancouver Intl to Midway?

Cheapflights makes it easy to find Vancouver Intl to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Vancouver Intl to Midway?

Cheapflights helps you find that perfect flight to Midway from Vancouver Intl by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Vancouver Intl to Midway with no change fees?

Certainly. Search results for flights to Midway from Vancouver Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Vancouver Intl to Midway become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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