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Cheap flights from Whistler to Chicago Midway Airport from C$ 153

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 31/10. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
16 Oct — 23 Oct1
1 adult
1 adult, Economy

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 16 September 2025.

Round-trip from

C$ 276

One-way from

C$ 153

Popular in

November

Cheapest in

September

Average price

C$ 402
29/10-5/11
  • 29/10-5/11
  • 2 total stops
  • 40h 45m total
  • Whistler to Chicago
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31/10
  • 31/10
  • 1 total stop
  • 17h 39m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 55 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 September 2025
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Find flight deals from Whistler to Midway

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 16 September 2025.

Wed 29/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Wed 5/112:06 p.m.MDW - YVR
1 stop23h 06mMultiple Airlines
Deal found 14/9C$ 276
Mon 20/108:30 p.m.YVR - MDW
2 stops15h 08mMultiple Airlines
Wed 22/108:05 a.m.MDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 14/9C$ 279
Fri 3/108:30 p.m.YVR - MDW
2 stops25h 11mMultiple Airlines
Mon 6/106:20 a.m.MDW - YVR
1 stop16h 28mMultiple Airlines
Deal found 15/9C$ 290
Sun 14/1211:00 p.m.YVR - MDW
1 stop22h 05mMultiple Airlines
Tue 16/128:00 a.m.MDW - YVR
2 stops16h 45mMultiple Airlines
Deal found 15/9C$ 296
Fri 31/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Fri 7/116:15 a.m.MDW - YVR
1 stop30h 57mMultiple Airlines
Deal found 16/9C$ 316
Wed 29/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Mon 3/111:37 p.m.MDW - YVR
2 stops29h 17mMultiple Airlines
Deal found 13/9C$ 319
Fri 24/109:30 a.m.YVR - MDW
1 stop12h 16mMultiple Airlines
Sun 26/109:26 p.m.MDW - YVR
1 stop15h 46mMultiple Airlines
Deal found 16/9C$ 320
Wed 15/107:00 a.m.YVR - MDW
2 stops25h 46mMultiple Airlines
Wed 22/108:05 a.m.MDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 15/9C$ 327
Fri 31/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Mon 3/116:30 a.m.MDW - YVR
2 stops15h 15mMultiple Airlines
Deal found 14/9C$ 337
Fri 26/95:55 a.m.YVR - MDW
1 stop9h 40mDelta
Tue 30/91:43 p.m.MDW - YVR
1 stop8h 48mDelta
Deal found 15/9C$ 340
Fri 26/95:55 a.m.YVR - MDW
1 stop9h 40mDelta
Mon 29/91:43 p.m.MDW - YVR
1 stop8h 48mDelta
Deal found 16/9C$ 351

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 16 September 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 29/10

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

1 stop17h 39m

Chicago Midway

Mon 3/11

1:37 p.m.-4:54 p.m.

2 stops29h 17m

C$ 319

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 24/10

9:30 a.m.-11:46 p.m.

1 stop12h 16m

Chicago Midway

Sun 26/10

9:26 p.m.-11:12 a.m.

1 stop15h 46m

C$ 320

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 26/9

5:55 a.m.-5:35 p.m.

1 stop9h 40m

Chicago Midway

Mon 29/9

1:43 p.m.-8:31 p.m.

1 stop8h 48m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 18/10

5:55 a.m.-5:43 p.m.

1 stop9h 48m

Chicago Midway

Tue 28/10

1:48 p.m.-11:57 p.m.

2 stops12h 09m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 27/9

5:55 a.m.-5:35 p.m.

1 stop9h 40m

Chicago Midway

Sat 4/10

1:43 p.m.-8:31 p.m.

1 stop8h 48m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 26/9

5:55 a.m.-5:35 p.m.

1 stop9h 40m

Chicago Midway

Sat 4/10

1:43 p.m.-8:31 p.m.

1 stop8h 48m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 18/10

5:55 a.m.-5:43 p.m.

1 stop9h 48m

Chicago Midway

Sat 25/10

1:06 p.m.-8:54 p.m.

2 stops9h 48m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 26/9

5:55 a.m.-5:35 p.m.

1 stop9h 40m

Chicago Midway

Tue 30/9

1:43 p.m.-8:31 p.m.

1 stop8h 48m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 29/10

6:45 a.m.-5:43 p.m.

2 stops8h 58m

Chicago Midway

Wed 5/11

1:08 p.m.-11:57 p.m.

2 stops12h 49m

C$ 340

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 3/10

8:30 p.m.-11:41 p.m.

2 stops25h 11m

C$ 177

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

Showing 1-10 of 17 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 9h 40m. Delta provides one of the quickest options available for as low as C$ 340. 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.

  • What is the cheapest month to book a flight from Whistler to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Whistler to Chicago Midway Airport (average of C$ 207). Flying from Whistler to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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