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Cheap flights from Vancouver to Chicago Midway Airport from C$ 172

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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
25 Dec — 1 Jan1
1 adult
1 adult, Economy, 0 bags

Find 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 25 November 2025.

Sun 7/1211:00 p.m.YVR - MDW
1 stop31h 46mMultiple Airlines
Wed 10/122:49 p.m.MDW - YVR
2 stops11h 21mMultiple Airlines
Deal found 24/11C$ 477
Sun 14/1210:55 p.m.YVR - MDW
1 stop14h 25mMultiple Airlines
Tue 16/122:49 p.m.MDW - YVR
2 stops33h 31mMultiple Airlines
Deal found 25/11C$ 529
Thu 4/1212:13 p.m.YVR - MDW
2 stops9h 34mDelta
Wed 10/121:50 p.m.MDW - YVR
2 stops12h 09mDelta
Deal found 23/11C$ 597
Sun 14/127:36 p.m.YVR - MDW
2 stops11h 18mDelta
Tue 16/121:50 p.m.MDW - YVR
2 stops10h 54mDelta
Deal found 25/11C$ 655
Fri 5/1211:00 p.m.YVR - MDW
1 stop12h 59mMultiple Airlines
Sun 7/127:27 p.m.MDW - YVR
1 stop17h 45mMultiple Airlines
Deal found 24/11C$ 681
Thu 27/116:45 a.m.YVR - MDW
2 stops14h 55mDelta
Tue 2/121:50 p.m.MDW - YVR
2 stops10h 54mDelta
Deal found 24/11C$ 703
Thu 4/1210:55 p.m.YVR - MDW
1 stop14h 25mMultiple Airlines
Wed 10/122:49 p.m.MDW - YVR
2 stops11h 21mMultiple Airlines
Deal found 23/11C$ 768
Tue 23/125:45 p.m.YVR - MDW
2 stops26h 13mMultiple Airlines
Wed 31/126:12 a.m.MDW - YVR
1 stop31h 00mMultiple Airlines
Deal found 23/11C$ 782
Thu 4/126:00 a.m.YVR - MDW
2 stops13h 53mMultiple Airlines
Sun 7/127:27 p.m.MDW - YVR
1 stop17h 45mMultiple Airlines
Deal found 24/11C$ 818
Fri 19/1211:00 p.m.YVR - MDW
1 stop12h 21mMultiple Airlines
Sun 4/110:50 p.m.MDW - YVR
2 stops21h 55mMultiple Airlines
Deal found 25/11C$ 859
Thu 18/127:36 p.m.YVR - MDW
2 stops11h 43mDelta
Wed 7/11:28 p.m.MDW - YVR
2 stops12h 31mDelta
Deal found 24/11C$ 880

Cheap 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 25 November 2025.

Round-trip from

C$ 433

One-way from

C$ 172

Popular in

December

Cheapest in

October

Average price

C$ 598
5/3-10/3
  • 5/3-10/3
  • 3 total stops
  • 33h 45m total
  • Vancouver to Chicago
Search Deals
9/1
  • 9/1
  • 2 total stops
  • 26h 12m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 93 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 November 2025
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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 25 November 2025.
Use the filters below to find and compare flights from Vancouver to Chicago Midway Airport that are best for you.

Fly from

Vancouver

Fly to

Midway

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/3

5:00 p.m.-10:05 a.m.

1 stop15h 05m

Chicago Midway

Tue 10/3

6:00 a.m.-10:40 p.m.

2 stops18h 40m

C$ 433

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 26/1

7:37 p.m.-9:53 a.m.

2 stops12h 16m

Chicago Midway

Sat 31/1

10:46 a.m.-8:54 p.m.

2 stops12h 08m

C$ 498

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 14/12

10:55 p.m.-3:20 p.m.

1 stop14h 25m

Chicago Midway

Tue 16/12

2:49 p.m.-10:20 p.m.

2 stops33h 31m

C$ 529

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 28/3

10:30 p.m.-3:20 p.m.

1 stop14h 50m

Chicago Midway

Wed 1/4

11:00 a.m.-8:43 p.m.

2 stops11h 43m

C$ 530

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/3

7:37 p.m.-8:53 a.m.

2 stops11h 16m

Chicago Midway

Tue 10/3

2:03 p.m.-11:51 p.m.

2 stops11h 48m

C$ 552

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 5/12

7:35 p.m.-9:19 a.m.

2 stops11h 44m

Chicago Midway

Mon 8/12

1:14 p.m.-9:04 p.m.

2 stops9h 50m

C$ 703

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/3

12:20 p.m.-10:05 a.m.

2 stops19h 45m

Chicago Midway

Tue 10/3

11:00 a.m.-9:20 p.m.

2 stops12h 20m

C$ 727

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 8/1

7:37 p.m.-8:52 a.m.

2 stops11h 15m

Chicago Midway

Thu 15/1

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

2 stops13h 04m

C$ 765

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 23/12

5:45 p.m.-9:58 p.m.

2 stops26h 13m

Chicago Midway

Wed 31/12

6:12 a.m.-11:12 a.m.

1 stop31h 00m

C$ 782

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 27/3

9:15 p.m.-9:55 a.m.

2 stops10h 40m

Chicago Midway

Tue 31/3

9:30 a.m.-9:08 p.m.

2 stops13h 38m

C$ 792

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/11

Showing 1-10 of 19 results
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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 12h 16m. 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.

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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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