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Cheap flights from Whistler to Chicago Midway Airport from C$ 213

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 25/2. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
5 Mar — 12 Mar1
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 3 February 2026.

Thu 12/39:10 a.m.
YVR
-
MDW
1 stop11h 35m
Multiple Airlines
Tue 17/36:00 a.m.
MDW
-
YVR
2 stops18h 40m
Multiple Airlines
Deal found 1/2C$ 571
Sat 7/312:05 p.m.
YVR
-
MDW
1 stop8h 36m
Multiple Airlines
Mon 9/39:51 p.m.
MDW
-
YVR
2 stops20h 16m
Multiple Airlines
Deal found 2/2C$ 590
Thu 5/36:20 a.m.
YVR
-
MDW
2 stops9h 17m
Delta
Tue 10/31:10 p.m.
MDW
-
YVR
2 stops12h 49m
Delta
Deal found 3/2C$ 613
Thu 12/312:05 p.m.
YVR
-
MDW
1 stop8h 40m
Multiple Airlines
Mon 16/32:16 p.m.
MDW
-
YVR
1 stop11h 43m
Multiple Airlines
Deal found 1/2C$ 623
Mon 2/37:37 p.m.
YVR
-
MDW
2 stops11h 17m
Delta
Wed 4/31:29 p.m.
MDW
-
YVR
2 stops12h 30m
Delta
Deal found 2/2C$ 638
Thu 28/56:15 a.m.
YVR
-
MDW
1 stop9h 41m
Delta
Mon 1/61:22 p.m.
MDW
-
YVR
2 stops11h 27m
Delta
Deal found 3/2C$ 646
Wed 25/211:00 p.m.
YVR
-
MDW
1 stop15h 16m
Multiple Airlines
Thu 12/311:00 a.m.
MDW
-
YVR
2 stops11h 43m
Multiple Airlines
Deal found 1/2C$ 647
Thu 5/36:20 a.m.
YVR
-
MDW
2 stops9h 17m
Delta
Mon 9/39:30 a.m.
MDW
-
YVR
2 stops13h 24m
Delta
Deal found 1/2C$ 649
Fri 1/510:55 p.m.
YVR
-
MDW
1 stop9h 01m
Delta
Tue 5/59:31 a.m.
MDW
-
YVR
2 stops11h 39m
Delta
Deal found 1/2C$ 722

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 3 February 2026.

Round-trip from

C$ 571

One-way from

C$ 213

Popular in

December

Cheapest in

October

Average price

C$ 410
12/3-17/3
  • 12/3-17/3
  • 3 total stops
  • 30h 15m total
  • Whistler to Chicago
Search Deals
25/2
  • 25/2
  • 1 total stop
  • 21h 29m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 146 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 February 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 3 February 2026.
Use the filters below to find and compare flights from Whistler to Chicago Midway Airport that are best for you.

Fly from

Whistler

Fly to

Midway

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 7/3

12:05 p.m.-10:41 p.m.

1 stop8h 36m

Chicago Midway

Mon 9/3

9:51 p.m.-4:07 p.m.

2 stops20h 16m

C$ 590

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

9:35 a.m.-8:54 p.m.

2 stops13h 19m

C$ 613

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

1:29 p.m.-11:59 p.m.

2 stops12h 30m

C$ 638

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 28/5

6:15 a.m.-5:56 p.m.

1 stop9h 41m

Chicago Midway

Mon 1/6

1:22 p.m.-10:49 p.m.

2 stops11h 27m

C$ 646

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/3

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

2 stops9h 17m

Chicago Midway

Mon 9/3

9:30 a.m.-8:54 p.m.

2 stops13h 24m

C$ 649

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 25/2

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

2 stops11h 17m

Chicago Midway

Thu 12/3

9:30 a.m.-6:43 p.m.

2 stops11h 13m

C$ 722

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 1/5

10:55 p.m.-9:56 a.m.

1 stop9h 01m

Chicago Midway

Tue 5/5

9:31 a.m.-7:10 p.m.

2 stops11h 39m

C$ 722

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 16/4

7:23 a.m.-5:58 p.m.

2 stops8h 35m

Chicago Midway

Mon 20/4

9:31 a.m.-6:43 p.m.

2 stops11h 12m

C$ 722

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 25/2

11:00 p.m.-10:29 p.m.

1 stop21h 29m

C$ 213

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 24/4

11:00 p.m.-10:19 p.m.

1 stop21h 19m

C$ 221

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/1

Showing 1-10 of 16 results
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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 9h 17m. Delta provides one of the quickest options available for as low as C$ 613. 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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