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Cheap flights from Whistler to Chicago from C$ 137

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 30/10. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
15 Oct — 22 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Whistler to Chicago are usually found in September or October, booked 32 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from Whistler to Chicago

Keep the following information in mind while searching for Whistler to Chicago flight deals. Data was last updated 15 September 2025.

Round-trip from

C$ 206

One-way from

C$ 137

Popular in

November

Cheapest in

September

Average price

C$ 402
WestJet
  • WestJet
  • 17/10-18/10
  • 2 total stops
  • 14h 49m total
  • Whistler to Chicago
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WestJet
  • WestJet
  • 30/10
  • 2 total stops
  • 22h 00m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Find flight deals from Whistler to Chicago

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 15 September 2025.

Sun 12/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Sun 19/105:30 p.m.ORD - YVR
1 stop8h 41mWestJet
Deal found 13/9C$ 206
Fri 24/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Mon 27/102:20 p.m.ORD - YVR
1 stop7h 25mWestJet
Deal found 15/9C$ 213
Sun 12/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Fri 17/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Deal found 14/9C$ 217
Fri 17/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Mon 27/102:20 p.m.ORD - YVR
1 stop7h 25mWestJet
Deal found 14/9C$ 221
Thu 16/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Thu 23/105:30 p.m.ORD - YVR
1 stop8h 41mWestJet
Deal found 15/9C$ 222
Tue 28/108:30 a.m.YVR - ORD
Nonstop4h 11mAir Canada
Tue 4/113:40 p.m.ORD - YVR
Nonstop4h 35mAir Canada
Deal found 13/9C$ 224
Sun 12/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Fri 24/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Deal found 15/9C$ 228
Wed 29/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Wed 5/112:06 p.m.MDW - YVR
1 stop23h 06mMultiple Airlines
Deal found 14/9C$ 276
Mon 20/108:30 p.m.YVR - MDW
2 stops15h 08mMultiple Airlines
Wed 22/108:05 a.m.MDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 14/9C$ 279
Thu 2/109:30 a.m.YVR - MDW
1 stop12h 11mMultiple Airlines
Mon 6/106:20 a.m.MDW - YVR
1 stop16h 28mMultiple Airlines
Deal found 13/9C$ 282
Sat 4/109:30 a.m.YVR - MDW
1 stop12h 11mMultiple Airlines
Tue 7/108:05 a.m.MDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 13/9C$ 285
Wed 29/1011:00 p.m.YVR - MDW
1 stop17h 39mMultiple Airlines
Mon 3/111:37 p.m.MDW - YVR
2 stops29h 17mMultiple Airlines
Deal found 13/9C$ 319

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 15 September 2025.
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

Fri 17/10

2:20 p.m.-10:39 p.m.

1 stop6h 19m

Chicago O'Hare Intl

Sat 18/10

8:51 a.m.-11:33 a.m.

Nonstop4h 42m

C$ 246

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 30/12

8:30 a.m.-9:19 p.m.

1 stop10h 49m

Chicago O'Hare Intl

Sun 4/1

7:10 a.m.-6:02 p.m.

1 stop12h 52m

C$ 267

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 2/10

2:20 p.m.-10:39 p.m.

1 stop6h 19m

Chicago O'Hare Intl

Sat 4/10

5:01 a.m.-9:51 a.m.

1 stop6h 50m

C$ 267

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 17/10

11:00 a.m.-7:55 p.m.

1 stop6h 55m

Chicago O'Hare Intl

Wed 22/10

6:15 a.m.-1:12 p.m.

1 stop8h 57m

C$ 267

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 30/10

12:35 p.m.-11:59 p.m.

1 stop9h 24m

Chicago O'Hare Intl

Thu 6/11

6:15 a.m.-1:39 p.m.

1 stop9h 24m

C$ 267

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 17/10

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

1 stop7h 39m

Chicago O'Hare Intl

Mon 20/10

5:01 a.m.-9:51 a.m.

1 stop6h 50m

C$ 267

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 25/9

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Tue 30/9

5:01 a.m.-9:51 a.m.

1 stop6h 50m

C$ 272

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 14/11

10:30 a.m.-4:44 p.m.

Nonstop4h 14m

Chicago O'Hare Intl

Mon 17/11

7:10 a.m.-6:45 p.m.

1 stop13h 35m

C$ 272

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 16/10

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Wed 22/10

5:01 a.m.-9:51 a.m.

1 stop6h 50m

C$ 272

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 14/10

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Thu 23/10

5:01 a.m.-9:51 a.m.

1 stop6h 50m

C$ 272

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

Showing 1-10 of 39 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 12 September 2025.

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, January is the cheapest month in which you can book a flight from Whistler to Chicago (average of C$ 261). Flying from Whistler to Chicago in March is currently the most expensive (average of C$ 348). 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 15 September 2025.

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 15 September 2025.

The most flights from WH1 to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 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 15 September 2025.
Read reviews from past customers who have flown Delta,United Airlines, 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.
Delta
8.0
Very good
7,954 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,954 reviews
Delta
8.0
Very good
7,954 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,929 reviews
Delta
8.0
Very good
7,954 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,954 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
WestJet
7.2
Good
3,091 reviews
Delta
8.0
Very good
7,954 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Air Canada
7.1
Good
10,000 reviews
Delta
8.0
Very good
7,954 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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 6h 19m. United Airlines provides one of the quickest options available for as low as C$ 246. 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$ 142 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 Delta, with prices starting from C$ 142 and C$ 202, 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 (86%), Air Canada (67%), United Airlines( 67%).

  • What are the cheapest flights from Whistler to Chicago?

    On average you can expect to pay C$ 639 for a flight from Whistler to Chicago. The cheapest flight overall is C$ 198 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 232.

  • 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, January is the cheapest month in which you can book a flight from Whistler to Chicago (average of C$ 261). Flying from Whistler to Chicago in March is currently the most expensive (average of C$ 348). 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

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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 15 September 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 209AverageC$ 497FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 234AverageC$ 356FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 235AverageC$ 432FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 264AverageC$ 536FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 390AverageC$ 692FlexibilityNo cancel feeOn-timeN/A
Search Delta 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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