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Cheap flights from Whistler to Chicago Midway Airport from C$ 241

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 23/5. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
5 May — 12 May1
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 30 April 2025.

Round-trip from

C$ 412

One-way from

C$ 241

Popular in

December

Cheapest in

January

Average price

C$ 444
29/5-1/6
  • 29/5-1/6
  • 2 total stops
  • 37h 25m total
  • Whistler to Chicago
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23/5
  • 23/5
  • 1 total stop
  • 21h 02m total
  • Whistler to Chicago
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Highest demand for flights based on searches. 5% potential increase in price (C$ 42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 16 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 30 April 2025.

Thu 29/55:35 p.m.YVR - MDW
1 stop19h 25mMultiple Airlines
Sun 1/66:25 a.m.MDW - YVR
1 stop18h 00mMultiple Airlines
Deal found 28/4C$ 412
Thu 5/66:15 a.m.YVR - MDW
1 stop9h 30mDelta
Wed 11/69:21 a.m.MDW - YVR
2 stops10h 27mDelta
Deal found 28/4C$ 437
Wed 3/94:35 p.m.YVR - MDW
1 stop13h 44mPorter Airlines
Tue 9/99:15 a.m.MDW - YVR
2 stops14h 12mPorter Airlines
Deal found 28/4C$ 603
Thu 24/76:15 a.m.YVR - MDW
1 stop9h 24mWestJet
Mon 28/71:46 p.m.MDW - YVR
1 stop8h 45mWestJet
Deal found 28/4C$ 995

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 30 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

Thu 29/5

5:35 p.m.-3:00 p.m.

1 stop19h 25m

Chicago Midway

Sun 1/6

6:25 a.m.-10:25 p.m.

1 stop18h 00m

C$ 412

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/6

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

1 stop9h 30m

Chicago Midway

Wed 11/6

9:21 a.m.-5:48 p.m.

2 stops10h 27m

C$ 437

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 10/6

10:10 a.m.-4:54 p.m.

2 stops28h 44m

Chicago Midway

Fri 20/6

9:40 a.m.-9:27 p.m.

2 stops13h 47m

C$ 775

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 24/7

6:15 a.m.-5:39 p.m.

1 stop9h 24m

Chicago Midway

Mon 28/7

1:46 p.m.-8:31 p.m.

1 stop8h 45m

C$ 995

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 23/5

11:00 p.m.-10:02 p.m.

1 stop21h 02m

C$ 241

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 13/5

7:32 p.m.-8:36 a.m.

2 stops11h 04m

C$ 249

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 13/5

6:00 a.m.-9:40 a.m.

3 stops25h 40m

C$ 526

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/4

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 30 April 2025.
See what other customers who have flown with Porter Airlines, Delta and WestJet from Whistler to Chicago have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,936 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,826 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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.

  • 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.

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