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Cheap flights from Vancouver to Chicago Midway Airport from C$ 154

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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
4 Dec — 11 Dec1
1 adult
1 adult, Economy, 0 bags

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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 4 November 2025.

Sun 7/1211:00 p.m.YVR - MDW
1 stop21h 12mMultiple Airlines
Thu 11/127:23 p.m.MDW - YVR
2 stops22h 22mMultiple Airlines
Deal found 2/11C$ 288
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 3/11C$ 302
Sun 7/1211:00 p.m.YVR - MDW
1 stop8h 52mMultiple Airlines
Fri 12/126:15 a.m.MDW - YVR
2 stops18h 30mMultiple Airlines
Deal found 2/11C$ 338
Fri 5/129:15 p.m.YVR - MDW
2 stops14h 44mMultiple Airlines
Mon 15/126:15 a.m.MDW - YVR
1 stop12h 16mMultiple Airlines
Deal found 3/11C$ 365
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 3/11C$ 366
Fri 14/1111:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Tue 18/111:56 p.m.MDW - YVR
2 stops26h 49mMultiple Airlines
Deal found 2/11C$ 379
Fri 21/1111:00 p.m.YVR - MDW
1 stop13h 40mMultiple Airlines
Tue 25/116:05 a.m.MDW - YVR
2 stops18h 40mMultiple Airlines
Deal found 2/11C$ 441
Thu 13/115:30 a.m.YVR - MDW
2 stops16h 25mMultiple Airlines
Wed 19/111:56 p.m.MDW - YVR
1 stop23h 16mMultiple Airlines
Deal found 4/11C$ 442

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 4 November 2025.

Round-trip from

C$ 288

One-way from

C$ 154

Popular in

November

Cheapest in

September

Average price

C$ 597
7/12-11/12
  • 7/12-11/12
  • 3 total stops
  • 43h 34m total
  • Vancouver to Chicago
Search Deals
3/12
  • 3/12
  • 1 total stop
  • 17h 08m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 15 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 4 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

Fri 5/12

9:15 p.m.-1:59 p.m.

2 stops14h 44m

Chicago Midway

Mon 15/12

6:15 a.m.-4:31 p.m.

1 stop12h 16m

C$ 365

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 14/11

11:00 p.m.-6:39 p.m.

1 stop17h 39m

Chicago Midway

Tue 18/11

1:56 p.m.-2:45 p.m.

2 stops26h 49m

C$ 379

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 14/1

11:00 p.m.-7:23 p.m.

1 stop18h 23m

Chicago Midway

Sat 24/1

6:00 a.m.-2:45 p.m.

2 stops34h 45m

C$ 400

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 7/12

11:00 p.m.-9:52 a.m.

1 stop8h 52m

Chicago Midway

Fri 12/12

6:15 a.m.-4:31 p.m.

1 stop12h 16m

C$ 401

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 24/12

11:24 a.m.-8:49 a.m.

2 stops19h 25m

Chicago Midway

Tue 13/1

9:50 a.m.-12:03 a.m.

2 stops16h 13m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 3/12

7:35 p.m.-8:54 a.m.

2 stops11h 19m

Chicago Midway

Wed 10/12

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

2 stops9h 50m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 23/12

7:32 p.m.-11:06 a.m.

2 stops13h 34m

Chicago Midway

Tue 13/1

1:49 p.m.-12:03 a.m.

2 stops12h 14m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 23/12

7:32 p.m.-11:06 a.m.

2 stops13h 34m

Chicago Midway

Wed 7/1

9:34 a.m.-6:44 p.m.

2 stops11h 10m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 24/12

11:24 a.m.-8:49 a.m.

2 stops19h 25m

Chicago Midway

Wed 7/1

9:34 a.m.-12:03 a.m.

2 stops16h 29m

C$ 487

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 2/12

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

2 stops11h 44m

Chicago Midway

Tue 9/12

1:14 p.m.-11:59 p.m.

2 stops12h 45m

C$ 487

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 21 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
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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.

  • 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.

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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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