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Cheap flights from Vancouver to Chicago Midway Airport from C$ 153

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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
27 Jan — 3 Feb1
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 28 December 2025.

Tue 30/127:32 p.m.YVR - MDW
2 stops11h 17mDelta
Wed 7/11:28 p.m.MDW - YVR
2 stops12h 31mDelta
Deal found 26/12C$ 719
Tue 30/127:32 p.m.YVR - MDW
2 stops11h 17mDelta
Tue 6/11:28 p.m.MDW - YVR
2 stops12h 31mDelta
Deal found 26/12C$ 778
Sun 28/127:32 p.m.YVR - MDW
2 stops11h 17mDelta
Tue 30/1211:48 a.m.MDW - YVR
2 stops13h 11mDelta
Deal found 27/12C$ 951
Wed 31/1212:45 p.m.YVR - MDW
1 stop20h 21mWestJet
Mon 5/111:21 a.m.MDW - YVR
2 stops31h 33mWestJet
Deal found 26/12C$ 1,110
Wed 31/1211:00 p.m.YVR - MDW
1 stop8h 05mWestJet
Sun 4/19:50 a.m.MDW - YVR
2 stops32h 10mWestJet
Deal found 26/12C$ 1,118
Tue 30/127:32 p.m.YVR - MDW
2 stops11h 17mDelta
Sat 3/19:29 a.m.MDW - YVR
2 stops11h 10mDelta
Deal found 26/12C$ 1,276
Wed 31/127:00 a.m.YVR - MDW
2 stops28h 01mMultiple Airlines
Sun 4/13:01 p.m.MDW - YVR
1 stop27h 30mMultiple Airlines
Deal found 27/12C$ 1,278

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 28 December 2025.

Round-trip from

C$ 425

One-way from

C$ 153

Popular in

December

Cheapest in

October

Average price

C$ 675
16/1-18/1
  • 16/1-18/1
  • 3 total stops
  • 36h 23m total
  • Vancouver to Chicago
Search Deals
2/3
  • 2/3
  • 1 total stop
  • 12h 44m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 132 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 28 December 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

Fri 16/1

11:00 p.m.-10:13 p.m.

1 stop21h 13m

Chicago Midway

Sun 18/1

11:05 a.m.-12:15 a.m.

2 stops15h 10m

C$ 425

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 17/1

3:30 p.m.-8:52 a.m.

2 stops15h 22m

Chicago Midway

Thu 22/1

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

2 stops13h 04m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 17/1

6:20 a.m.-8:52 a.m.

2 stops24h 32m

Chicago Midway

Tue 20/1

9:50 a.m.-11:59 p.m.

2 stops16h 09m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 29/1

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

2 stops11h 15m

Chicago Midway

Sun 1/2

9:33 a.m.-11:59 p.m.

2 stops16h 26m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 2/3

7:37 p.m.-8:54 a.m.

2 stops11h 17m

Chicago Midway

Wed 4/3

1:49 p.m.-10:49 a.m.

2 stops23h 00m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/3

6:20 a.m.-5:37 p.m.

2 stops9h 17m

Chicago Midway

Tue 10/3

2:05 p.m.-11:51 p.m.

2 stops11h 46m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 13/1

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

2 stops11h 15m

Chicago Midway

Tue 20/1

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

2 stops13h 04m

C$ 513

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 29/1

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

2 stops11h 15m

Chicago Midway

Mon 2/2

1:26 p.m.-11:59 p.m.

2 stops12h 33m

C$ 513

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 7/2

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

2 stops11h 15m

Chicago Midway

Tue 24/2

1:26 p.m.-9:00 p.m.

2 stops9h 34m

C$ 517

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 23/4

7:30 p.m.-8:46 a.m.

2 stops11h 16m

Chicago Midway

Mon 27/4

2:12 p.m.-11:01 p.m.

2 stops10h 49m

C$ 537

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/12

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 15h 22m. 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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