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Cheap flights from Whistler to Chicago Midway Airport from C$ 268

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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
22 Apr — 29 Apr1
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 23 March 2026.

Thu 16/47:23 a.m.
YVR
-
MDW
2 stops8h 35m
Delta
Wed 22/41:24 p.m.
MDW
-
YVR
2 stops11h 37m
Delta
Deal found 21/3C$ 584
Fri 1/57:30 p.m.
YVR
-
MDW
2 stops11h 17m
Delta
Sat 9/51:22 p.m.
MDW
-
YVR
2 stops11h 10m
Delta
Deal found 22/3C$ 586
Fri 1/57:30 p.m.
YVR
-
MDW
2 stops15h 13m
Delta
Tue 5/510:41 a.m.
MDW
-
YVR
2 stops13h 50m
Delta
Deal found 20/3C$ 604
Fri 17/47:30 p.m.
YVR
-
MDW
2 stops11h 36m
Delta
Sat 25/41:24 p.m.
MDW
-
YVR
2 stops11h 07m
Delta
Deal found 21/3C$ 606
Tue 19/57:41 p.m.
YVR
-
MDW
2 stops11h 01m
Delta
Sat 30/51:59 p.m.
MDW
-
YVR
1 stop8h 40m
Delta
Deal found 18/3C$ 616
Fri 22/56:00 a.m.
YVR
-
MDW
1 stop9h 56m
Delta
Sat 30/51:59 p.m.
MDW
-
YVR
1 stop8h 40m
Delta
Deal found 18/3C$ 627
Mon 4/57:30 p.m.
YVR
-
MDW
2 stops11h 17m
Delta
Mon 11/51:59 p.m.
MDW
-
YVR
1 stop8h 40m
Delta
Deal found 20/3C$ 630
Tue 19/57:41 p.m.
YVR
-
MDW
2 stops11h 01m
Delta
Thu 28/59:22 a.m.
MDW
-
YVR
2 stops13h 17m
Delta
Deal found 18/3C$ 643
Fri 22/55:23 p.m.
YVR
-
MDW
2 stops13h 19m
Delta
Thu 28/59:22 a.m.
MDW
-
YVR
2 stops13h 17m
Delta
Deal found 18/3C$ 654
Sat 10/107:35 p.m.
YVR
-
MDW
2 stops11h 14m
Delta
Wed 14/102:00 p.m.
MDW
-
YVR
1 stop8h 32m
Delta
Deal found 18/3C$ 657

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 23 March 2026.

Round-trip from

C$ 584

One-way from

C$ 268

Popular in

December

Cheapest in

October

Average price

C$ 675
Delta
  • Delta
  • 16/4-22/4
  • 4 total stops
  • 20h 12m total
  • Whistler to Chicago
Search Deals
2/5
  • 2/5
  • 1 total stop
  • 10h 44m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 138 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 23 March 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

Thu 16/4

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

2 stops8h 35m

Chicago Midway

Wed 22/4

1:24 p.m.-11:01 p.m.

2 stops11h 37m

C$ 584

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 1/5

7:30 p.m.-12:43 p.m.

2 stops15h 13m

Chicago Midway

Tue 5/5

10:41 a.m.-10:31 p.m.

2 stops13h 50m

C$ 604

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 4/5

7:30 p.m.-8:47 a.m.

2 stops11h 17m

Chicago Midway

Mon 11/5

1:59 p.m.-8:39 p.m.

1 stop8h 40m

C$ 630

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 22/4

7:30 p.m.-8:47 a.m.

2 stops11h 17m

Chicago Midway

Sat 25/4

1:24 p.m.-10:31 p.m.

2 stops11h 07m

C$ 846

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 21/5

6:00 a.m.-5:56 p.m.

1 stop9h 56m

Chicago Midway

Mon 25/5

1:22 p.m.-10:35 p.m.

2 stops11h 13m

C$ 947

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 2/4

6:20 a.m.-5:54 p.m.

2 stops9h 34m

Chicago Midway

Tue 21/4

1:24 p.m.-11:01 p.m.

2 stops11h 37m

C$ 964

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 29/7

6:15 a.m.-6:05 p.m.

1 stop9h 50m

Chicago Midway

Tue 4/8

2:00 p.m.-10:25 p.m.

2 stops10h 25m

C$ 1,006
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 31/7

6:15 a.m.-6:05 p.m.

1 stop9h 50m

Chicago Midway

Mon 3/8

2:00 p.m.-8:22 p.m.

1 stop8h 22m

C$ 1,006

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 19/5

6:45 a.m.-5:56 p.m.

2 stops9h 11m

Chicago Midway

Sun 24/5

1:22 p.m.-10:51 p.m.

2 stops11h 29m

C$ 1,036
Cheapest one-way

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 10/6

6:00 a.m.-6:31 p.m.

2 stops10h 31m

C$ 324

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/3

Showing 1-10 of 19 resultsSorted by cheapest first
1
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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 8h 35m. Delta provides one of the quickest options available for as low as C$ 584. 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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