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Cheap flights from Whistler to Chicago Midway Airport from C$ 266

YVR — MDW
20 Oct — 27 Oct1
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

Sat 24/106:00 a.m. -
1 stop8h 47m
Tue 27/1012:27 p.m. -
2 stops12h 32m
Deal found 18/9C$ 468
Sun 4/1010:55 p.m. -
1 stop22h 48m
Wed 7/106:25 a.m. -
2 stops14h 45m
Deal found 15/9C$ 559
Sat 24/106:07 a.m. -
1 stop8h 47m
Thu 29/1012:34 p.m. -
1 stop10h 06m
Deal found 19/9C$ 562
Sat 10/107:36 p.m. -
2 stops11h 08m
Tue 13/1012:27 p.m. -
1 stop10h 06m
Deal found 18/9C$ 580
Wed 21/106:00 a.m. -
1 stop8h 47m
Tue 27/1012:27 p.m. -
2 stops8h 19m
Deal found 16/9C$ 587
Sat 31/106:00 a.m. -
1 stop8h 47m
Sat 7/1112:27 p.m. -
1 stop11h 06m
Deal found 16/9C$ 629
Mon 5/107:35 p.m. -
2 stops11h 09m
Wed 7/101:27 p.m. -
2 stops11h 32m
Deal found 20/9C$ 660

Find flight deals from Whistler to Midway

Round-trip from

C$ 468

One-way from

C$ 266

Popular in

December

Cheapest in

September

Average price

C$ 520
Delta
  • Delta
  • 24/10-27/10
  • 3 total stops
  • 21h 19m total
  • Whistler to Chicago
Search Deals
Delta
  • Delta
  • 24/10-31/12
  • 1 total stop
  • 8h 47m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
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Cheapflights Fare Finder

 
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 Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Sat 24/10

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

2 stops10h 00m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 266
Quickest round-trip

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Mon 2/11

7:00 a.m.-3:47 p.m.

1 stop7h 47m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 266

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Sun 22/11

8:45 p.m.-7:50 a.m.

2 stops10h 05m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 266

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Mon 12/10

10:55 p.m.-11:43 p.m.

1 stop22h 48m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 277

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 25/11

8:45 p.m.-9:25 a.m.

2 stops11h 40m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 294

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Tue 13/10

7:36 p.m.-9:32 a.m.

2 stops11h 56m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 295

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Mon 12/10

7:36 p.m.-8:44 a.m.

2 stops11h 08m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 295

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Sat 24/10

6:00 a.m.-4:47 p.m.

1 stop8h 47m

Chicago Midway

Tue 27/10

12:27 p.m.-8:33 p.m.

1 stop10h 06m

C$ 470

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Sun 22/11

8:45 p.m.-7:50 a.m.

2 stops10h 05m

Chicago Midway

Wed 25/11

12:30 p.m.-12:42 a.m.

2 stops13h 12m

C$ 524

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Sat 21/11

8:45 p.m.-7:50 a.m.

2 stops10h 05m

Chicago Midway

Wed 25/11

12:30 p.m.-12:56 a.m.

2 stops13h 26m

C$ 524

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/9

Showing 1-10 of 17 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

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

  • How long is the flight from Whistler to Chicago Midway Airport?

    A quick flight from Whistler to Chicago Midway Airport can take about 8h 47m. Delta provides one of the quickest options available for as low as C$ 470. 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.

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