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Cheap flights from Whistler to Chicago from C$ 286

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 31/10. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
3 Sep — 10 Sep1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Whistler to Chicago are usually found in September or October, booked 42 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap flight deals from Whistler to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Whistler to Chicago
Explore the most affordable flight options available from Whistler to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 4 August 2026.

Fri 28/86:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Mon 31/85:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 2/8C$ 400
Thu 10/96:00 a.m.
YVR
-
ORD
1 stop8h 40m
WestJet
Tue 22/95:30 p.m.
ORD
-
YVR
1 stop8h 45m
WestJet
Deal found 1/8C$ 403
Sun 6/96:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Sun 13/95:30 p.m.
ORD
-
YVR
1 stop8h 45m
WestJet
Deal found 2/8C$ 404
Thu 15/106:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Thu 22/105:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 31/7C$ 406
Tue 15/98:25 a.m.
YVR
-
ORD
Nonstop4h 18m
Air Canada
Tue 22/93:40 p.m.
ORD
-
YVR
Nonstop4h 35m
Air Canada
Deal found 1/8C$ 407
Fri 4/96:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Mon 14/95:30 p.m.
ORD
-
YVR
1 stop8h 45m
WestJet
Deal found 2/8C$ 408
Thu 10/97:30 a.m.
YVR
-
ORD
1 stop7h 10m
WestJet
Mon 14/95:30 p.m.
ORD
-
YVR
1 stop8h 45m
WestJet
Deal found 2/8C$ 413
Fri 25/97:30 a.m.
YVR
-
ORD
1 stop7h 10m
WestJet
Sun 27/95:30 p.m.
ORD
-
YVR
1 stop29h 10m
WestJet
Deal found 1/8C$ 431
Tue 29/96:00 a.m.
YVR
-
MDW
1 stop10h 19m
Delta
Tue 27/1010:01 a.m.
MDW
-
YVR
2 stops14h 35m
Delta
Deal found 2/8C$ 479
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$ 480
Fri 2/106:00 a.m.
YVR
-
MDW
1 stop10h 19m
Delta
Wed 28/1012:27 p.m.
MDW
-
YVR
1 stop10h 06m
Delta
Deal found 2/8C$ 497
Fri 2/106:00 a.m.
YVR
-
MDW
1 stop10h 19m
Delta
Thu 29/1012:27 p.m.
MDW
-
YVR
1 stop10h 06m
Delta
Deal found 2/8C$ 515

Find flight deals from Whistler to Chicago

Keep the following information in mind while searching for Whistler to Chicago flight deals. Data was last updated 4 August 2026.

Round-trip from

C$ 400

One-way from

C$ 286

Popular in

July

Cheapest in

September

Average price

C$ 553
WestJet
  • WestJet
  • 28/8-31/8
  • 2 total stops
  • 15h 00m total
  • Whistler to Chicago
Search Deals
Air Canada
  • Air Canada
  • 31/10
  • 1 total stop
  • 7h 48m 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 Chicago 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 4 August 2026.
Use the filters below to find and compare flights from Whistler to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 1/9

9:47 a.m.-9:30 p.m.

1 stop9h 43m

Chicago O'Hare Intl

Sun 6/9

10:00 p.m.-9:51 a.m.

1 stop13h 51m

C$ 497

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 1/9

9:47 a.m.-9:30 p.m.

1 stop9h 43m

Chicago O'Hare Intl

Tue 8/9

5:00 a.m.-9:51 a.m.

1 stop6h 51m

C$ 501

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 19/10

2:20 p.m.-11:59 p.m.

1 stop7h 39m

Chicago O'Hare Intl

Sun 1/11

8:49 a.m.-1:45 p.m.

Nonstop5h 56m

C$ 515

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 10/9

7:20 p.m.-6:56 a.m.

1 stop9h 36m

Chicago O'Hare Intl

Mon 21/9

7:48 p.m.-10:25 p.m.

Nonstop4h 37m

C$ 515

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 15/9

1:45 p.m.-8:06 p.m.

Nonstop4h 21m

Chicago O'Hare Intl

Thu 17/9

5:00 a.m.-9:51 a.m.

1 stop6h 51m

C$ 517

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 22/1

11:30 a.m.-3:38 p.m.

Nonstop3h 08m

Chicago O'Hare Intl

Tue 26/1

2:18 p.m.-11:14 p.m.

1 stop9h 56m

C$ 546

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 28/9

7:30 a.m.-4:40 p.m.

1 stop7h 10m

Chicago O'Hare Intl

Tue 29/9

5:44 p.m.-10:59 p.m.

1 stop7h 15m

C$ 574
Quickest round-trip

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 4/12

11:30 a.m.-3:38 p.m.

Nonstop3h 08m

Chicago O'Hare Intl

Fri 11/12

3:30 p.m.-8:17 p.m.

Nonstop5h 47m

C$ 578

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$ 581

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 4/12

8:34 p.m.-9:45 a.m.

2 stops12h 11m

Chicago O'Hare Intl

Fri 11/12

5:55 p.m.-12:59 a.m.

1 stop8h 04m

C$ 584

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

Showing 1-10 of 35 resultsSorted by cheapest first
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Best time to book a flight from Whistler to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

What is the cheapest time of day to fly from WH1 to CHI?

Find hourly flight availability from Whistler to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 4 August 2026.

When flying from Whistler to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Whistler to Chicago

Explore weekly flight availability from Whistler to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 4 August 2026.

The most flights from WH1 to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Whistler to Chicago?

Airfare is typical for this route at the moment.
Whistler to Chicago flights typically cost between C$ 357 and C$ 693 in August.
The cheapest round-trip price found within the last 5 days was C$ 400 on WestJet (28 Aug-31 Aug).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 4 August 2026.
Read reviews from past customers who have flown United Airlines,WestJet, andAmerican Airlines from Whistler to Chicago. 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.
United Airlines
7.4
Good
10,060 reviews
Check prices

Boarding

7.7

Food

6.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
10,060 reviews
United Airlines
7.4
Good
10,060 reviews
Check prices

Boarding

7.7

Food

6.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,426 reviews
United Airlines
7.4
Good
10,060 reviews
Check prices

Boarding

7.7

Food

6.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,845 reviews
United Airlines
7.4
Good
10,060 reviews
Check prices

Boarding

7.7

Food

6.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
11,424 reviews
United Airlines
7.4
Good
10,060 reviews
Check prices

Boarding

7.7

Food

6.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Whistler to Chicago. 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?

    A quick flight from Whistler to Chicago can take about 9h 08m. United Airlines provides one of the quickest options available for as low as C$ 581. Airlines will cover a distance of 2850 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

    C$ 170 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Air Canada and WestJet, with prices starting from C$ 171 and C$ 178, respectively.

  • What are the most reliable airlines from Whistler to Chicago?

    Before booking your flight to Chicago from Whistler, check out the most reliable airlines to get you to your destination on time: American Airlines (65%), Finnair (63%), Air Canada( 51%).

  • What are the cheapest flights from Whistler to Chicago?

    On average you can expect to pay C$ 874 for a flight from Whistler to Chicago. The cheapest flight overall is C$ 290 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 430.

  • Can I find deals for flights from Whistler to Chicago that include hotel bookings?

    Yes. In addition to deals on Whistler to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Whistler to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Whistler to Chicago.

  • Can I find deals for business class flights from Whistler to Chicago?

    Yes. Cheapflights offers flight deals from Whistler to Chicago 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.

Top 4 airlines flying from Whistler to Chicago

Discover the top 4 airlines that operate flights from Whistler to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 4 August 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 201AverageC$ 543FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 213AverageC$ 415FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 275AverageC$ 673FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 275AverageC$ 607FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

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 Chicago?

Cheapflights helps you search for flights from Whistler to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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

Cheapflights simply makes it quick and affordable to book flights from Whistler to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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

Cheapflights does show flights with no change fees to all users. To see these options for flights from Whistler to Chicago, users can toggle the no change fees filter when performing a flight search.

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

Yes! Start tracking prices for Whistler to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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