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Cheap flights from Whistler to Chicago Midway Airport from C$ 158

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 26/11. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
3 Dec — 10 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 November 2025.

Sun 7/1211:00 p.m.YVR - MDW
1 stop21h 12mMultiple Airlines
Thu 11/127:23 p.m.MDW - YVR
2 stops22h 22mMultiple Airlines
Deal found 2/11C$ 287
Sun 7/1211:00 p.m.YVR - MDW
1 stop8h 52mMultiple Airlines
Fri 12/126:15 a.m.MDW - YVR
2 stops18h 30mMultiple Airlines
Deal found 2/11C$ 338
Fri 14/1111:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Tue 18/111:56 p.m.MDW - YVR
2 stops26h 49mMultiple Airlines
Deal found 2/11C$ 378
Fri 21/1111:00 p.m.YVR - MDW
1 stop13h 40mMultiple Airlines
Tue 25/116:05 a.m.MDW - YVR
2 stops18h 40mMultiple Airlines
Deal found 2/11C$ 440
Sun 23/1111:00 p.m.YVR - MDW
1 stop21h 43mMultiple Airlines
Fri 28/116:05 a.m.MDW - YVR
1 stop31h 07mMultiple Airlines
Deal found 1/11C$ 447
Fri 21/1111:00 p.m.YVR - MDW
1 stop13h 40mMultiple Airlines
Wed 26/116:05 a.m.MDW - YVR
2 stops18h 40mMultiple Airlines
Deal found 2/11C$ 518
Fri 21/1111:00 p.m.YVR - MDW
1 stop13h 40mMultiple Airlines
Thu 27/116:05 a.m.MDW - YVR
2 stops20h 10mMultiple Airlines
Deal found 2/11C$ 528
Fri 21/1111:00 p.m.YVR - MDW
1 stop13h 40mMultiple Airlines
Fri 28/116:05 a.m.MDW - YVR
2 stops20h 10mMultiple Airlines
Deal found 2/11C$ 544
Mon 10/117:45 p.m.YVR - MDW
2 stops13h 53mMultiple Airlines
Tue 18/1111:00 a.m.MDW - YVR
1 stop15h 44mMultiple Airlines
Deal found 2/11C$ 580
Mon 10/117:36 p.m.YVR - MDW
2 stops11h 18mDelta
Tue 18/119:34 a.m.MDW - YVR
2 stops13h 36mDelta
Deal found 2/11C$ 597
Fri 21/1111:00 p.m.YVR - MDW
1 stop21h 43mMultiple Airlines
Mon 24/1111:00 a.m.MDW - YVR
2 stops12h 20mMultiple Airlines
Deal found 1/11C$ 608

Cheap 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 November 2025.

Round-trip from

C$ 287

One-way from

C$ 158

Popular in

November

Cheapest in

September

Average price

C$ 595
7/12-11/12
  • 7/12-11/12
  • 3 total stops
  • 43h 34m total
  • Whistler to Chicago
Search Deals
26/11
  • 26/11
  • 1 total stop
  • 21h 43m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 3 November 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

Sun 7/12

11:00 p.m.-10:12 p.m.

1 stop21h 12m

Chicago Midway

Thu 11/12

7:23 p.m.-3:45 p.m.

2 stops22h 22m

C$ 287

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 14/11

11:00 p.m.-6:39 p.m.

1 stop17h 39m

Chicago Midway

Tue 18/11

1:56 p.m.-2:45 p.m.

2 stops26h 49m

C$ 378

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 14/1

11:00 p.m.-7:23 p.m.

1 stop18h 23m

Chicago Midway

Sat 24/1

6:00 a.m.-2:45 p.m.

2 stops34h 45m

C$ 399

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 7/12

11:00 p.m.-9:52 a.m.

1 stop8h 52m

Chicago Midway

Fri 12/12

6:15 a.m.-4:31 p.m.

1 stop12h 16m

C$ 401

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 21/11

11:00 p.m.-2:40 p.m.

1 stop13h 40m

Chicago Midway

Fri 28/11

6:05 a.m.-12:15 a.m.

2 stops20h 10m

C$ 544

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 14/11

12:07 p.m.-11:40 p.m.

2 stops9h 33m

Chicago Midway

Tue 18/11

1:15 p.m.-9:10 p.m.

2 stops9h 55m

C$ 597

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 14/1

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

2 stops11h 17m

Chicago Midway

Sat 24/1

9:34 a.m.-8:54 p.m.

2 stops13h 20m

C$ 597

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 17/11

7:36 p.m.-9:01 a.m.

2 stops11h 25m

Chicago Midway

Wed 26/11

1:15 p.m.-10:37 p.m.

2 stops11h 22m

C$ 597

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 21/11

12:07 p.m.-11:40 p.m.

2 stops9h 33m

Chicago Midway

Tue 25/11

9:34 a.m.-9:10 p.m.

2 stops13h 36m

C$ 597

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 19/11

6:15 a.m.-6:18 p.m.

2 stops10h 03m

Chicago Midway

Wed 26/11

1:15 p.m.-10:37 p.m.

2 stops11h 22m

C$ 597

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 22 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
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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.

  • 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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