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Cheap flights from Vancouver to Chicago Midway Airport from C$ 314

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 25/8. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
31 Jul — 7 Aug1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Vancouver to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Vancouver to Midway
Explore the most affordable flight options available from Vancouver to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 1 July 2026.

Thu 1/105:45 p.m.
YVR
-
MDW
2 stops13h 03m
Delta
Mon 5/106:05 a.m.
MDW
-
YVR
2 stops18h 29m
Delta
Deal found 30/6C$ 584
Sat 10/106:00 a.m.
YVR
-
MDW
1 stop8h 39m
Delta
Tue 13/109:29 a.m.
MDW
-
YVR
2 stops11h 17m
Delta
Deal found 30/6C$ 651
Sun 4/106:00 a.m.
YVR
-
MDW
2 stops10h 19m
Delta
Wed 7/101:28 p.m.
MDW
-
YVR
2 stops12h 47m
Delta
Deal found 30/6C$ 670
Sat 29/86:00 a.m.
YVR
-
MDW
1 stop10h 01m
Delta
Thu 3/91:51 p.m.
MDW
-
YVR
2 stops10h 44m
Delta
Deal found 28/6C$ 682
Fri 28/89:25 a.m.
YVR
-
MDW
3 stops23h 25m
Multiple Airlines
Mon 31/89:26 p.m.
MDW
-
YVR
2 stops19h 39m
Multiple Airlines
Deal found 30/6C$ 698
Fri 18/96:05 a.m.
YVR
-
MDW
1 stop10h 19m
WestJet
Wed 23/92:05 p.m.
MDW
-
YVR
1 stop8h 26m
WestJet
Deal found 28/6C$ 711
Thu 10/910:55 p.m.
YVR
-
MDW
1 stop10h 03m
Multiple Airlines
Mon 14/97:25 a.m.
MDW
-
YVR
2 stops13h 45m
Multiple Airlines
Deal found 30/6C$ 734

Find flight deals from Vancouver to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Vancouver (8CA) 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 1 July 2026.

Round-trip from

C$ 584

One-way from

C$ 314

Popular in

December

Cheapest in

September

Average price

C$ 665
Delta
  • Delta
  • 1/10-5/10
  • 4 total stops
  • 31h 32m total
  • Vancouver to Chicago
Search Deals
25/8
  • 25/8
  • 3 total stops
  • 22h 15m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 111 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Vancouver 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 1 July 2026.
Use the filters below to find and compare flights from Vancouver 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 1/10

5:45 p.m.-8:48 a.m.

2 stops13h 03m

Chicago Midway

Mon 5/10

6:05 a.m.-10:34 p.m.

2 stops18h 29m

C$ 584

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 5/10

7:30 p.m.-8:47 a.m.

2 stops11h 17m

Chicago Midway

Fri 30/10

12:28 p.m.-6:46 p.m.

2 stops8h 18m

C$ 586

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 30/10

7:36 p.m.-8:47 a.m.

2 stops11h 11m

Chicago Midway

Mon 2/11

12:28 p.m.-11:13 p.m.

2 stops11h 45m

C$ 586

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 4/10

10:55 p.m.-9:50 a.m.

1 stop8h 55m

Chicago Midway

Wed 7/10

9:59 a.m.-7:10 p.m.

2 stops11h 11m

C$ 670

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

6:00 a.m.-4:39 p.m.

1 stop8h 39m

Chicago Midway

Tue 13/10

12:28 p.m.-11:08 p.m.

2 stops12h 40m

C$ 682
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 16/9

6:00 a.m.-6:33 p.m.

2 stops10h 33m

Chicago Midway

Sun 20/9

2:00 p.m.-8:26 p.m.

1 stop8h 26m

C$ 852

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 4/8

6:00 a.m.-6:01 p.m.

2 stops10h 01m

Chicago Midway

Tue 25/8

1:25 p.m.-10:34 p.m.

2 stops11h 09m

C$ 943

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 15/7

7:00 a.m.-2:35 p.m.

2 stops29h 35m

Chicago Midway

Wed 22/7

10:25 a.m.-9:35 p.m.

2 stops13h 10m

C$ 972
Cheapest one-way

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 8/9

3:40 p.m.-9:58 p.m.

3 stops28h 18m

C$ 321

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 8/9

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

1 stop10h 19m

C$ 324

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 15 resultsSorted by cheapest first
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Best time to book a flight from Vancouver to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Vancouver 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.

Cheapflights Insights

Everything you need to know about your flight from Vancouver to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Vancouver 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 to Chicago Midway Airport?

    Departing from Vancouver to Chicago Midway Airport will take you 13h 03m. There are 2850 km between Vancouver and Chicago Midway Airport.

  • Can I find deals for flights from Vancouver to Midway that include hotel bookings?

    Yes. In addition to deals on Vancouver to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Vancouver to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Vancouver to Midway.

  • Can I find deals for business class flights from Vancouver to Midway?

    Yes. Cheapflights offers flight deals from Vancouver 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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Why should you use Cheapflights to find cheap flight tickets from Vancouver to Midway?

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

Need flexible booking options for your flight to Midway from Vancouver? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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

Not ready to book yet? You can track prices for flights from Vancouver to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.

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