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Cheap flights from Whistler to Chicago Midway Airport from C$ 311

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 30/8. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
19 Jul — 26 Jul1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Whistler to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Whistler to Midway
Explore the most affordable flight options available from Whistler to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 19 June 2026.

Thu 24/96:00 a.m.
YVR
-
MDW
1 stop10h 11m
Delta
Wed 30/91:47 p.m.
MDW
-
YVR
2 stops11h 21m
Delta
Deal found 16/6C$ 569
Sat 10/105:15 p.m.
YVR
-
MDW
2 stops13h 34m
Delta
Tue 13/1012:30 p.m.
MDW
-
YVR
2 stops8h 40m
Delta
Deal found 17/6C$ 606
Thu 10/97:30 p.m.
YVR
-
MDW
2 stops11h 18m
Delta
Mon 14/91:14 p.m.
MDW
-
YVR
2 stops9h 12m
Delta
Deal found 15/6C$ 609
Sat 19/95:30 p.m.
YVR
-
MDW
2 stops17h 04m
Delta
Wed 30/91:47 p.m.
MDW
-
YVR
2 stops12h 28m
Delta
Deal found 17/6C$ 628
Sat 10/106:15 a.m.
YVR
-
MDW
1 stop8h 35m
Delta
Sun 18/1012:30 p.m.
MDW
-
YVR
1 stop10h 02m
Delta
Deal found 16/6C$ 648
Thu 20/86:00 a.m.
YVR
-
MDW
1 stop10h 01m
Delta
Mon 24/81:51 p.m.
MDW
-
YVR
1 stop8h 41m
Delta
Deal found 14/6C$ 654
Mon 13/76:00 a.m.
YVR
-
MDW
1 stop10h 18m
Delta
Mon 20/71:49 p.m.
MDW
-
YVR
1 stop8h 40m
Delta
Deal found 18/6C$ 676
Fri 7/86:05 a.m.
YVR
-
MDW
1 stop10h 01m
WestJet
Sat 15/81:56 p.m.
MDW
-
YVR
1 stop8h 41m
WestJet
Deal found 17/6C$ 685

Find flight deals from Whistler to Midway

Keep the following information in mind while searching for Whistler to Midway flight deals. Data was last updated 19 June 2026.

Round-trip from

C$ 569

One-way from

C$ 311

Popular in

December

Cheapest in

September

Average price

C$ 621
Delta
  • Delta
  • 24/9-30/9
  • 3 total stops
  • 21h 32m total
  • Whistler to Chicago
Search Deals
30/8
  • 30/8
  • 3 total stops
  • 25h 25m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 110 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 June 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Whistler 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 19 June 2026.
Use the filters below to find and compare flights from Whistler 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

Sat 10/10

5:15 p.m.-8:49 a.m.

2 stops13h 34m

Chicago Midway

Tue 13/10

12:30 p.m.-7:10 p.m.

2 stops8h 40m

C$ 606

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 19/9

5:30 p.m.-12:34 p.m.

2 stops17h 04m

Chicago Midway

Wed 30/9

1:47 p.m.-12:15 a.m.

2 stops12h 28m

C$ 628

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

7:35 p.m.-8:49 a.m.

2 stops11h 14m

Chicago Midway

Sun 18/10

12:30 p.m.-8:32 p.m.

1 stop10h 02m

C$ 648

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 25/8

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

1 stop10h 01m

Chicago Midway

Sat 29/8

1:27 p.m.-10:35 p.m.

2 stops11h 08m

C$ 705

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 22/8

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

2 stops10h 33m

Chicago Midway

Mon 24/8

9:59 a.m.-5:44 p.m.

2 stops9h 45m

C$ 738
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 28/8

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

1 stop10h 01m

Chicago Midway

Mon 31/8

1:51 p.m.-8:32 p.m.

1 stop8h 41m

C$ 750
Cheapest one-way

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 9/9

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

1 stop10h 19m

C$ 312

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 24/10

7:35 p.m.-8:45 a.m.

2 stops11h 10m

C$ 312
Quickest one-way

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 22/10

6:15 a.m.-4:50 p.m.

1 stop8h 35m

C$ 312

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 6/7

6:00 a.m.-6:18 p.m.

1 stop10h 18m

C$ 313

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/6

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

Best time to book a flight from Whistler to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Whistler 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 Whistler 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 Whistler 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 Whistler to Chicago Midway Airport?

    A quick flight from Whistler to Chicago Midway Airport can take about 10h 11m. Delta provides one of the quickest options available for as low as C$ 569. The distance between Whistler and Chicago Midway Airport is about 2850 km.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Whistler 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 Whistler to Midway?

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

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

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