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Cheap flights from Whistler to Chicago from C$ 135

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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
5 Mar — 12 Mar1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Whistler to Chicago are usually found in October or September, booked 32 days in advance, depart on a Wednesday or Friday and return on a Wednesday

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 3 February 2026.

Mon 20/48:15 a.m.
YVR
-
ORD
2 stops29h 02m
Multiple Airlines
Mon 11/55:30 p.m.
ORD
-
YVR
1 stop7h 05m
Multiple Airlines
Deal found 1/2C$ 318
Thu 23/47:00 a.m.
YVR
-
ORD
1 stop10h 33m
Multiple Airlines
Sun 26/45:30 p.m.
ORD
-
YVR
1 stop7h 05m
Multiple Airlines
Deal found 31/1C$ 330
Sun 8/310:10 p.m.
YVR
-
ORD
1 stop13h 25m
Multiple Airlines
Wed 11/38:55 p.m.
ORD
-
YVR
1 stop27h 25m
Multiple Airlines
Deal found 31/1C$ 341
Fri 22/56:00 a.m.
YVR
-
ORD
1 stop8h 40m
WestJet
Mon 25/55:30 p.m.
ORD
-
YVR
1 stop18h 40m
WestJet
Deal found 2/2C$ 343
Mon 13/43:40 p.m.
YVR
-
ORD
1 stop13h 07m
Multiple Airlines
Tue 21/41:27 p.m.
ORD
-
YVR
2 stops35h 13m
Multiple Airlines
Deal found 1/2C$ 344
Mon 9/34:35 p.m.
YVR
-
ORD
1 stop21h 24m
Multiple Airlines
Tue 17/39:28 a.m.
ORD
-
YVR
2 stops15h 12m
Multiple Airlines
Deal found 31/1C$ 351
Mon 9/34:35 p.m.
YVR
-
ORD
1 stop21h 24m
Multiple Airlines
Wed 18/37:18 p.m.
ORD
-
YVR
1 stop17h 54m
Multiple Airlines
Deal found 31/1C$ 355
Mon 13/43:40 p.m.
YVR
-
ORD
1 stop13h 07m
Multiple Airlines
Wed 22/41:27 p.m.
ORD
-
YVR
2 stops33h 41m
Multiple Airlines
Deal found 1/2C$ 356
Fri 6/33:40 p.m.
YVR
-
ORD
1 stop12h 28m
Multiple Airlines
Sun 8/39:08 p.m.
ORD
-
YVR
2 stops18h 47m
Multiple Airlines
Deal found 31/1C$ 366
Thu 12/39:10 a.m.
YVR
-
MDW
1 stop11h 35m
Multiple Airlines
Tue 17/36:00 a.m.
MDW
-
YVR
2 stops18h 40m
Multiple Airlines
Deal found 1/2C$ 571
Sat 7/312:05 p.m.
YVR
-
MDW
1 stop8h 36m
Multiple Airlines
Mon 9/39:51 p.m.
MDW
-
YVR
2 stops20h 16m
Multiple Airlines
Deal found 2/2C$ 590
Thu 5/36:20 a.m.
YVR
-
MDW
2 stops9h 17m
Delta
Tue 10/31:10 p.m.
MDW
-
YVR
2 stops12h 49m
Delta
Deal found 3/2C$ 613

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 3 February 2026.

Round-trip from

C$ 318

One-way from

C$ 135

Popular in

December

Cheapest in

October

Average price

C$ 410
WestJet
  • WestJet
  • 20/4-11/5
  • 3 total stops
  • 36h 07m total
  • Whistler to Chicago
Search Deals
WestJet
  • WestJet
  • 27/4
  • 1 total stop
  • 7h 10m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 146 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 3 February 2026.
Use the filters below to find and compare flights from Whistler to Chicago that are best for you.

Fly from

Whistler

Fly to

Chicago

Route

Depart

Return

Price

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 30/4

5:05 p.m.-6:47 a.m.

1 stop11h 42m

Chicago O'Hare Intl

Mon 4/5

9:18 p.m.-4:15 p.m.

1 stop20h 57m

C$ 396

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 1/6

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

1 stop7h 10m

Chicago O'Hare Intl

Wed 10/6

5:30 p.m.-7:40 a.m.

1 stop16h 10m

C$ 412

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 29/5

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

1 stop7h 10m

Chicago O'Hare Intl

Mon 1/6

8:53 p.m.-7:25 p.m.

2 stops24h 32m

C$ 421

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 25/4

9:27 a.m.-11:58 p.m.

1 stop12h 31m

Chicago O'Hare Intl

Tue 28/4

6:00 p.m.-11:01 p.m.

1 stop7h 01m

C$ 479

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 2/3

7:37 p.m.-1:22 p.m.

1 stop15h 45m

Chicago O'Hare Intl

Wed 4/3

2:20 p.m.-6:47 p.m.

1 stop6h 27m

C$ 492

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 27/3

7:35 p.m.-1:25 p.m.

1 stop15h 50m

Chicago O'Hare Intl

Tue 31/3

7:25 a.m.-8:55 p.m.

1 stop15h 30m

C$ 493

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 14/4

7:23 a.m.-4:39 p.m.

1 stop7h 16m

Chicago O'Hare Intl

Mon 20/4

6:00 p.m.-8:37 a.m.

1 stop16h 37m

C$ 497

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 16/4

7:23 a.m.-4:39 p.m.

1 stop7h 16m

Chicago O'Hare Intl

Sat 18/4

7:15 a.m.-2:45 p.m.

1 stop9h 30m

C$ 507

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 5/3

11:40 a.m.-11:52 p.m.

1 stop10h 12m

Chicago O'Hare Intl

Tue 10/3

2:20 p.m.-6:44 p.m.

1 stop6h 24m

C$ 507

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 10/3

11:40 a.m.-12:39 a.m.

1 stop10h 59m

Chicago O'Hare Intl

Mon 16/3

2:20 p.m.-8:55 p.m.

1 stop8h 35m

C$ 511

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/2

Showing 1-10 of 37 results
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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

How far ahead should I book a flight from Whistler to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Whistler to Chicago. Price data was last updated on 30 January 2026.

To ensure you get the cheapest price possible for a flight from Whistler to Chicago, you should look to book at least 32 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Whistler to Chicago?

Currently, October is the cheapest month in which you can book a flight from Whistler to Chicago (average of C$ 149). Flying from Whistler to Chicago in January is currently the most expensive (average of C$ 402). 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.

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 3 February 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 3 February 2026.

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

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 3 February 2026.
Read reviews from past customers who have flown United Airlines,American Airlines, andWestJet 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
9,236 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,236 reviews
United Airlines
7.4
Good
9,236 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
American Airlines
7.2
Good
11,218 reviews
United Airlines
7.4
Good
9,236 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
WestJet
7.2
Good
3,255 reviews
United Airlines
7.4
Good
9,236 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
Air Canada
7.1
Good
10,684 reviews
United Airlines
7.4
Good
9,236 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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 7h 10m. WestJet provides one of the quickest options available for as low as C$ 412. Airlines will cover a distance of 2829 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$ 166 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 WestJet and Air Canada, with prices starting from C$ 170 and C$ 194, 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: Emirates (90%), Avianca (81%), Air Canada( 78%).

  • What are the cheapest flights from Whistler to Chicago?

    On average you can expect to pay C$ 1,156 for a flight from Whistler to Chicago. The cheapest flight overall is C$ 221 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 356.

  • 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.

  • What is the cheapest month to book a flight from Whistler to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Whistler to Chicago (average of C$ 149). Flying from Whistler to Chicago in January is currently the most expensive (average of C$ 402). 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.

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 5 airlines flying from Whistler to Chicago

Discover the top 5 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 3 February 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 196AverageC$ 472FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 231AverageC$ 331FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 232AverageC$ 396FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 235AverageC$ 491FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Alaska AirlinesCheapestC$ 382AverageC$ 493FlexibilityNo cancel feeOn-time75%
Search Alaska 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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