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Cheap flights from Whistler to Chicago Midway Airport from C$ 224

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 20/5. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
6 Apr — 13 Apr1
1 adult

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 1 April 2025.

Round-trip from

C$ 363

One-way from

C$ 224

Popular in

December

Cheapest in

January

Average price

C$ 548
9/5-13/5
  • 9/5-13/5
  • 2 total stops
  • 21h 51m total
  • Whistler to Chicago
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20/5
  • 20/5
  • 1 total stop
  • 10h 26m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 14 potential savings vs. average RT price).
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Average for round-trip flights in April 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 1 April 2025.

Fri 9/511:00 p.m.YVR - MDW
1 stop8h 33mMultiple Airlines
Tue 13/59:34 a.m.MDW - YVR
1 stop13h 18mMultiple Airlines
Deal found 31/3C$ 363
Tue 20/56:30 a.m.YVR - MDW
2 stops9h 15mDelta
Wed 28/59:20 a.m.MDW - YVR
2 stops10h 22mDelta
Deal found 31/3C$ 451
Sat 17/57:00 a.m.YVR - MDW
2 stops31h 54mPorter Airlines
Tue 27/59:40 a.m.MDW - YVR
2 stops13h 15mPorter Airlines
Deal found 31/3C$ 726
Mon 28/410:35 p.m.YVR - MDW
2 stops21h 47mWestJet
Mon 5/57:00 p.m.MDW - YVR
2 stops23h 14mWestJet
Deal found 31/3C$ 774

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 1 April 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

Fri 9/5

11:00 p.m.-9:33 a.m.

1 stop8h 33m

Chicago Midway

Tue 13/5

9:34 a.m.-8:52 p.m.

1 stop13h 18m

C$ 363

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 20/5

6:30 a.m.-5:45 p.m.

2 stops9h 15m

Chicago Midway

Wed 28/5

9:20 a.m.-5:42 p.m.

2 stops10h 22m

C$ 451

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 17/5

7:00 a.m.-4:54 p.m.

2 stops31h 54m

Chicago Midway

Wed 28/5

9:40 a.m.-8:55 p.m.

2 stops13h 15m

C$ 726

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 28/4

10:35 p.m.-10:22 p.m.

2 stops21h 47m

Chicago Midway

Mon 5/5

7:00 p.m.-4:14 p.m.

2 stops23h 14m

C$ 774

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 20/5

11:00 p.m.-11:26 a.m.

1 stop10h 26m

C$ 224

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 25/5

6:15 a.m.-5:45 p.m.

1 stop9h 30m

C$ 253

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 14/7

10:10 p.m.-4:24 p.m.

1 stop16h 14m

C$ 395

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 4/8

11:00 p.m.-9:51 a.m.

1 stop8h 51m

C$ 491

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

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

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 1 April 2025.
Delta
8.0
Very good
7,898 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,898 reviews
Delta
8.0
Very good
7,898 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Porter Airlines
7.9
Good
278 reviews
Delta
8.0
Very good
7,898 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,789 reviews
Delta
8.0
Very good
7,898 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • What are the cheapest airlines to fly from Whistler to Chicago Midway Airport one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as C$ 253. However, be on the lookout for offers from Porter Airlines and WestJet, as they are both options that can get you from Whistler to Chicago Midway Airport for a low price.

  • 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, January is the cheapest month in which you can book a flight from Whistler to Chicago Midway Airport (average of C$ 243). 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.

See more FAQs

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