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Cheap flights from Whistler to Chicago Midway Airport from C$ 252

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 30/9. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
5 Aug — 12 Aug1
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 31 July 2025.

Round-trip from

C$ 401

One-way from

C$ 252

Popular in

July

Cheapest in

April

Average price

C$ 632
3/10-8/10
  • 3/10-8/10
  • 2 total stops
  • 26h 38m total
  • Whistler to Chicago
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30/9
  • 30/9
  • 2 total stops
  • 17h 28m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).
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Average for round-trip flights in July 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 31 July 2025.

Fri 3/109:30 a.m.YVR - MDW
1 stop11h 50mMultiple Airlines
Wed 8/108:00 a.m.MDW - YVR
1 stop14h 48mMultiple Airlines
Deal found 29/7C$ 401
Fri 29/86:15 a.m.YVR - MDW
1 stop9h 22mDelta
Wed 3/91:43 p.m.MDW - YVR
1 stop8h 50mDelta
Deal found 29/7C$ 426
Wed 26/117:00 a.m.YVR - MDW
2 stops25h 05mPorter Airlines
Sun 30/114:15 p.m.MDW - YVR
2 stops21h 00mPorter Airlines
Deal found 31/7C$ 768
Wed 1/1010:35 p.m.YVR - MDW
2 stops21h 01mWestJet
Sun 30/119:20 a.m.MDW - YVR
2 stops49h 44mWestJet
Deal found 30/7C$ 792

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 31 July 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 3/10

9:30 a.m.-11:20 p.m.

1 stop11h 50m

Chicago Midway

Wed 8/10

8:00 a.m.-8:48 p.m.

1 stop14h 48m

C$ 401

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 29/8

6:15 a.m.-5:37 p.m.

1 stop9h 22m

Chicago Midway

Wed 3/9

1:43 p.m.-10:58 p.m.

2 stops11h 15m

C$ 426

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 26/11

7:00 a.m.-10:05 a.m.

2 stops25h 05m

Chicago Midway

Sun 30/11

4:15 p.m.-11:15 a.m.

2 stops21h 00m

C$ 768

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 1/10

10:35 p.m.-9:36 p.m.

2 stops21h 01m

Chicago Midway

Sun 30/11

9:20 a.m.-9:04 a.m.

2 stops49h 44m

C$ 792

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 30/9

8:30 p.m.-3:58 p.m.

2 stops17h 28m

C$ 252

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 28/11

12:10 p.m.-10:05 a.m.

2 stops19h 55m

C$ 262

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 27/8

6:15 a.m.-5:37 p.m.

1 stop9h 22m

C$ 271

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 23/10

9:00 a.m.-10:14 p.m.

2 stops11h 14m

C$ 353

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/7

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.

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 31 July 2025.
Read reviews from past customers who have flown Porter Airlines,Delta, andWestJet from Whistler to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews
Check prices

Crew

8.7

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Crew

8.7

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,981 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Crew

8.7

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,978 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Crew

8.7

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 Porter Airlines, with whom users have recently found tickets for as low as C$ 262. However, be on the lookout for offers from Delta 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, June is the cheapest month in which you can book a flight from Whistler to Chicago Midway Airport (average of C$ 233). 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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