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Cheap flights from Whistler to Chicago Midway Airport from C$ 223

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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 398

One-way from

C$ 223

Popular in

December

Cheapest in

April

Average price

C$ 499
5/8-12/8
  • 5/8-12/8
  • 3 total stops
  • 23h 23m total
  • Whistler to Chicago
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8/9
  • 8/9
  • 2 total stops
  • 24h 28m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 51 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).
Search Deals
Average for round-trip flights in June 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 12 June 2025.

Tue 5/88:30 p.m.YVR - MDW
2 stops12h 10mMultiple Airlines
Tue 12/811:39 a.m.MDW - YVR
1 stop11h 13mMultiple Airlines
Deal found 11/6C$ 398
Thu 24/76:15 a.m.YVR - MDW
1 stop9h 24mDelta
Tue 29/71:46 p.m.MDW - YVR
1 stop8h 45mDelta
Deal found 11/6C$ 435
Fri 20/68:40 a.m.YVR - MDW
2 stops22h 05mPorter Airlines
Thu 26/69:40 a.m.MDW - YVR
2 stops13h 21mPorter Airlines
Deal found 10/6C$ 662
Thu 24/79:30 a.m.YVR - MDW
1 stop10h 12mWestJet
Sun 27/712:43 p.m.MDW - YVR
1 stop10h 09mWestJet
Deal found 11/6C$ 946

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 12 June 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

Tue 5/8

8:30 p.m.-10:40 a.m.

2 stops12h 10m

Chicago Midway

Tue 12/8

11:39 a.m.-8:52 p.m.

1 stop11h 13m

C$ 398

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 24/7

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

1 stop9h 24m

Chicago Midway

Wed 30/7

9:25 a.m.-8:31 p.m.

2 stops13h 06m

C$ 435

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 24/7

10:15 a.m.-8:45 a.m.

2 stops20h 30m

Chicago Midway

Thu 31/7

9:40 a.m.-9:01 p.m.

2 stops13h 21m

C$ 715

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 24/7

11:00 p.m.-9:45 a.m.

1 stop8h 45m

Chicago Midway

Sun 27/7

12:43 p.m.-9:50 p.m.

2 stops11h 07m

C$ 946

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 8/9

8:30 p.m.-10:58 p.m.

2 stops24h 28m

C$ 223

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/7

6:15 a.m.-6:41 p.m.

2 stops10h 26m

C$ 249

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 19/7

8:40 a.m.-8:45 a.m.

2 stops22h 05m

C$ 304

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 4/8

11:00 p.m.-9:45 a.m.

1 stop8h 45m

C$ 505

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

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 12 June 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
288 reviews
Check prices

Entertainment

7.0

Crew

8.7

Overall

8.0

Comfort

8.1

Boarding

8.2

Food

7.6

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Entertainment

7.0

Crew

8.7

Overall

8.0

Comfort

8.1

Boarding

8.2

Food

7.6

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,950 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Entertainment

7.0

Crew

8.7

Overall

8.0

Comfort

8.1

Boarding

8.2

Food

7.6

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Entertainment

7.0

Crew

8.7

Overall

8.0

Comfort

8.1

Boarding

8.2

Food

7.6

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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$ 249. 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.

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