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Cheap flights from Whistler to Chicago Midway Airport from C$ 286

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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
6 Jun — 13 Jun1
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 7 May 2026.

Wed 17/66:15 a.m.
YVR
-
MDW
2 stops10h 16m
Delta
Wed 24/61:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 2/5C$ 550
Mon 22/66:00 a.m.
YVR
-
MDW
1 stop10h 18m
Delta
Sun 5/71:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 3/5C$ 555
Sat 6/66:00 a.m.
YVR
-
MDW
1 stop9h 56m
Delta
Sat 13/61:49 p.m.
MDW
-
YVR
2 stops10h 46m
Delta
Deal found 7/5C$ 615
Sat 10/106:15 a.m.
YVR
-
MDW
1 stop8h 35m
Delta
Tue 13/1012:30 p.m.
MDW
-
YVR
1 stop10h 02m
Delta
Deal found 4/5C$ 632
Fri 19/66:00 a.m.
YVR
-
MDW
1 stop10h 18m
Delta
Mon 29/61:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 5/5C$ 633
Tue 9/66:00 a.m.
YVR
-
MDW
1 stop10h 18m
Delta
Thu 11/61:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 4/5C$ 634
Tue 2/67:41 p.m.
YVR
-
MDW
2 stops11h 01m
Delta
Tue 9/61:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 4/5C$ 666
Fri 22/510:55 p.m.
YVR
-
MDW
1 stop21h 07m
Multiple Airlines
Fri 5/610:15 a.m.
MDW
-
YVR
2 stops13h 04m
Multiple Airlines
Deal found 2/5C$ 671
Thu 11/65:30 p.m.
YVR
-
MDW
1 stop14h 05m
Multiple Airlines
Wed 17/610:15 a.m.
MDW
-
YVR
2 stops12h 44m
Multiple Airlines
Deal found 3/5C$ 674
Wed 24/66:00 a.m.
YVR
-
MDW
1 stop10h 18m
Delta
Sun 5/71:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 5/5C$ 686
Wed 7/106:15 a.m.
YVR
-
MDW
1 stop8h 35m
Delta
Wed 14/1012:30 p.m.
MDW
-
YVR
1 stop10h 02m
Delta
Deal found 2/5C$ 687

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 7 May 2026.

Round-trip from

C$ 550

One-way from

C$ 286

Popular in

December

Cheapest in

October

Average price

C$ 521
Delta
  • Delta
  • 17/6-24/6
  • 3 total stops
  • 18h 58m total
  • Whistler to Chicago
Search Deals
1/6
  • 1/6
  • 2 total stops
  • 14h 32m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 122 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 7 May 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

Wed 17/6

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

1 stop10h 18m

Chicago Midway

Wed 24/6

1:49 p.m.-8:31 p.m.

1 stop8h 42m

C$ 550

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 6/6

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

1 stop9h 56m

Chicago Midway

Sat 13/6

1:49 p.m.-10:35 p.m.

2 stops10h 46m

C$ 615

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

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

1 stop8h 35m

Chicago Midway

Thu 15/10

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

1 stop10h 02m

C$ 632

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 19/6

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

1 stop10h 18m

Chicago Midway

Mon 29/6

1:49 p.m.-8:31 p.m.

1 stop8h 42m

C$ 633

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 12/6

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

2 stops10h 16m

Chicago Midway

Tue 16/6

1:49 p.m.-8:31 p.m.

1 stop8h 42m

C$ 674

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 7/10

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

1 stop8h 35m

Chicago Midway

Tue 13/10

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

1 stop10h 02m

C$ 687

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 8/10

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

1 stop8h 35m

Chicago Midway

Sat 10/10

12:30 p.m.-10:24 p.m.

2 stops11h 54m

C$ 687

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 8/10

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

1 stop8h 35m

Chicago Midway

Wed 14/10

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

1 stop10h 02m

C$ 687

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 22/5

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

1 stop9h 56m

Chicago Midway

Mon 25/5

1:22 p.m.-9:09 p.m.

2 stops9h 47m

C$ 705
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

10:55 p.m.-9:52 a.m.

1 stop8h 57m

Chicago Midway

Wed 14/10

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

2 stops8h 40m

C$ 716

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

Showing 1-10 of 20 resultsSorted by cheapest first
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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 10h 18m. Delta provides one of the quickest options available for as low as C$ 550. 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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