Find flights
When to book
FAQs

Cheap flights from Whistler to Chicago Midway Airport from C$ 289

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 24/10. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — MDW
2 Sep — 9 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Whistler to Midway

Enter your travel dates to find the best prices.

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 3 August 2026.

Tue 29/96:00 a.m.
YVR
-
MDW
1 stop10h 19m
Delta
Wed 28/1012:27 p.m.
MDW
-
YVR
1 stop10h 06m
Delta
Deal found 2/8C$ 478
Tue 15/96:00 a.m.
YVR
-
MDW
1 stop10h 19m
Delta
Tue 22/92:00 p.m.
MDW
-
YVR
1 stop8h 26m
Delta
Deal found 1/8C$ 479
Fri 2/105:45 p.m.
YVR
-
MDW
2 stops13h 03m
Delta
Wed 28/1012:27 p.m.
MDW
-
YVR
2 stops12h 32m
Delta
Deal found 2/8C$ 496
Fri 2/105:45 p.m.
YVR
-
MDW
2 stops13h 03m
Delta
Thu 29/109:29 a.m.
MDW
-
YVR
2 stops15h 30m
Delta
Deal found 2/8C$ 514
Fri 28/87:35 p.m.
YVR
-
MDW
2 stops11h 04m
Delta
Fri 30/1012:27 p.m.
MDW
-
YVR
2 stops8h 19m
Delta
Deal found 3/8C$ 518
Wed 30/96:05 a.m.
YVR
-
MDW
1 stop10h 19m
WestJet
Wed 28/1012:32 p.m.
MDW
-
YVR
1 stop10h 06m
WestJet
Deal found 2/8C$ 525
Sat 5/96:00 a.m.
YVR
-
MDW
1 stop7h 57m
Delta
Sat 12/99:59 a.m.
MDW
-
YVR
2 stops10h 41m
Delta
Deal found 29/7C$ 528
Mon 9/118:34 p.m.
YVR
-
MDW
2 stops11h 08m
Delta
Sun 15/1112:30 p.m.
MDW
-
YVR
2 stops13h 29m
Delta
Deal found 29/7C$ 530
Fri 23/106:05 a.m.
YVR
-
MDW
1 stop8h 47m
WestJet
Fri 30/1012:32 p.m.
MDW
-
YVR
1 stop10h 06m
WestJet
Deal found 3/8C$ 542
Thu 10/96:00 a.m.
YVR
-
MDW
1 stop10h 19m
Delta
Wed 16/92:00 p.m.
MDW
-
YVR
1 stop8h 26m
Delta
Deal found 29/7C$ 562
Mon 19/107:36 p.m.
YVR
-
MDW
2 stops11h 08m
Delta
Wed 21/1012:27 p.m.
MDW
-
YVR
1 stop10h 06m
Delta
Deal found 29/7C$ 566

Find flight deals from Whistler to Midway

Keep the following information in mind while searching for Whistler to Midway flight deals. Data was last updated 3 August 2026.

Round-trip from

C$ 479

One-way from

C$ 289

Popular in

July

Cheapest in

September

Average price

C$ 552
Delta
  • Delta
  • 15/9-22/9
  • 2 total stops
  • 18h 45m total
  • Whistler to Chicago
Search Deals
Delta
  • Delta
  • 24/10
  • 2 total stops
  • 11h 08m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 79 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals

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 3 August 2026.
Use the filters below to find and compare flights from Whistler to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 10/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Wed 16/9

2:00 p.m.-8:26 p.m.

1 stop8h 26m

C$ 573

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 19/10

10:55 p.m.-10:03 a.m.

1 stop9h 08m

Chicago Midway

Wed 21/10

12:27 p.m.-8:33 p.m.

1 stop10h 06m

C$ 580

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 4/12

7:15 a.m.-3:39 p.m.

2 stops7h 24m

Chicago Midway

Fri 11/12

12:30 p.m.-12:59 a.m.

2 stops13h 29m

C$ 583
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/11

7:00 a.m.-3:47 p.m.

1 stop7h 47m

Chicago Midway

Sat 7/11

1:27 p.m.-11:13 p.m.

2 stops10h 46m

C$ 614

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 24/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Wed 30/9

2:00 p.m.-10:59 p.m.

2 stops10h 59m

C$ 898
Cheapest one-way

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 24/10

7:36 p.m.-9:17 a.m.

2 stops11h 41m

C$ 289

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 31/10

6:00 a.m.-4:47 p.m.

1 stop8h 47m

C$ 289

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 26/10

7:36 p.m.-8:44 a.m.

2 stops11h 08m

C$ 289

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 26/1

7:35 p.m.-7:45 a.m.

2 stops11h 10m

C$ 298

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 27/10

9:00 a.m.-10:58 a.m.

3 stops23h 58m

C$ 335

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

Showing 1-10 of 12 resultsSorted by cheapest first
1
2

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 10h 19m. Delta provides one of the quickest options available for as low as C$ 573. 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Whistler to Midway?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Midway from Whistler today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Whistler to Midway?

Cheapflights helps you find that perfect flight to Midway from Whistler by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Whistler to Midway with no change fees?

Yes, we can. To see specific flights from Whistler to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Whistler to Midway become cheaper?

Not ready to book yet? You can track prices for flights from Whistler to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.