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Cheap flights from Whistler to Chicago Midway Airport from C$ 160

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 31/1. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
17 Jan — 24 Jan1
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 18 December 2025.

Wed 24/126:45 p.m.YVR - MDW
2 stops20h 34mWestJet
Sun 4/19:50 a.m.MDW - YVR
2 stops32h 10mWestJet
Deal found 16/12C$ 1,042
Sun 21/1212:45 p.m.YVR - MDW
1 stop20h 21mWestJet
Wed 31/125:59 p.m.MDW - YVR
1 stop19h 29mWestJet
Deal found 16/12C$ 1,112
Fri 26/1210:30 p.m.YVR - MDW
2 stops16h 56mWestJet
Sun 4/16:08 p.m.MDW - YVR
2 stops20h 56mWestJet
Deal found 17/12C$ 1,145
Fri 26/125:00 p.m.YVR - MDW
1 stop15h 05mMultiple Airlines
Sun 4/110:50 p.m.MDW - YVR
2 stops19h 41mMultiple Airlines
Deal found 17/12C$ 1,153
Mon 29/121:45 p.m.YVR - MDW
2 stops18h 20mMultiple Airlines
Fri 2/14:15 p.m.MDW - YVR
1 stop20h 05mMultiple Airlines
Deal found 16/12C$ 1,168
Wed 31/1211:00 p.m.YVR - MDW
1 stop8h 05mWestJet
Sat 3/16:08 p.m.MDW - YVR
2 stops20h 56mWestJet
Deal found 16/12C$ 1,174

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 18 December 2025.

Round-trip from

C$ 391

One-way from

C$ 160

Popular in

December

Cheapest in

October

Average price

C$ 682
20/2-23/2
  • 20/2-23/2
  • 2 total stops
  • 21h 55m total
  • Whistler to Chicago
Search Deals
31/1
  • 31/1
  • 2 total stops
  • 25h 28m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 136 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 18 December 2025.
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

Wed 21/1

7:37 p.m.-8:52 a.m.

2 stops11h 15m

Chicago Midway

Tue 27/1

9:50 a.m.-8:54 p.m.

2 stops13h 04m

C$ 488

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 20/1

7:37 p.m.-8:52 a.m.

2 stops11h 15m

Chicago Midway

Wed 28/1

9:50 a.m.-8:54 p.m.

2 stops13h 04m

C$ 488

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 24/1

3:30 p.m.-8:52 a.m.

2 stops15h 22m

Chicago Midway

Wed 28/1

9:50 a.m.-6:44 p.m.

2 stops10h 54m

C$ 488

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 20/1

7:37 p.m.-8:52 a.m.

2 stops11h 15m

Chicago Midway

Tue 27/1

9:50 a.m.-8:54 p.m.

2 stops13h 04m

C$ 488

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 22/1

7:37 p.m.-8:52 a.m.

2 stops11h 15m

Chicago Midway

Thu 29/1

9:33 a.m.-8:54 p.m.

2 stops13h 21m

C$ 493

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 29/1

3:30 p.m.-8:52 a.m.

2 stops15h 22m

Chicago Midway

Sun 1/2

9:53 a.m.-6:44 p.m.

2 stops10h 51m

C$ 493

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 22/1

11:40 a.m.-8:52 a.m.

2 stops19h 12m

Chicago Midway

Mon 26/1

1:49 p.m.-10:47 a.m.

2 stops22h 58m

C$ 497

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

12:47 p.m.-11:51 p.m.

2 stops13h 04m

C$ 497

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 17/2

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

2 stops9h 17m

Chicago Midway

Wed 25/2

1:26 p.m.-11:59 p.m.

2 stops12h 33m

C$ 499

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 17/2

7:37 p.m.-8:53 a.m.

2 stops11h 16m

Chicago Midway

Tue 24/2

1:26 p.m.-9:00 p.m.

2 stops9h 34m

C$ 499

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/12

Showing 1-10 of 18 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 11h 15m. Delta provides one of the quickest options available for as low as C$ 488. 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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