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Cheap flights from Whistler to Chicago from C$ 113

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 23/5. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
17 Jan — 24 Jan1
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 Tuesday 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 18 December 2025.

Fri 19/128:30 a.m.YVR - ORD
Nonstop4h 11mAir Canada
Tue 6/13:35 p.m.ORD - YVR
Nonstop4h 35mAir Canada
Deal found 16/12C$ 643
Thu 25/121:45 p.m.YVR - ORD
Nonstop4h 09mUnited Airlines
Sun 4/16:00 a.m.ORD - YVR
1 stop11h 52mUnited Airlines
Deal found 16/12C$ 661
Wed 24/128:30 a.m.YVR - ORD
1 stop13h 29mUnited Airlines
Sun 4/18:08 p.m.ORD - YVR
1 stop16h 05mUnited Airlines
Deal found 15/12C$ 668
Fri 26/128:30 a.m.YVR - ORD
Nonstop4h 11mUnited Airlines
Sun 4/19:40 p.m.ORD - YVR
1 stop14h 33mUnited Airlines
Deal found 17/12C$ 672
Sun 28/128:45 a.m.YVR - ORD
1 stop12h 15mUnited Airlines
Tue 30/129:40 p.m.ORD - YVR
1 stop15h 13mUnited Airlines
Deal found 17/12C$ 716
Fri 19/123:20 p.m.YVR - ORD
1 stop6h 39mUnited Airlines
Tue 6/17:10 a.m.ORD - YVR
1 stop12h 53mUnited Airlines
Deal found 16/12C$ 718
Tue 30/128:30 a.m.YVR - ORD
Nonstop4h 11mUnited Airlines
Sat 3/18:08 p.m.ORD - YVR
1 stop16h 05mUnited Airlines
Deal found 17/12C$ 740
Wed 31/123:20 p.m.YVR - ORD
1 stop16h 24mUnited Airlines
Sat 3/18:08 p.m.ORD - YVR
1 stop16h 05mUnited Airlines
Deal found 16/12C$ 743
Wed 24/126:45 p.m.YVR - MDW
2 stops20h 34mWestJet
Sun 4/19:50 a.m.MDW - YVR
2 stops32h 10mWestJet
Deal found 16/12C$ 1,042
Sun 21/1212:45 p.m.YVR - MDW
1 stop20h 21mWestJet
Wed 31/125:59 p.m.MDW - YVR
1 stop19h 29mWestJet
Deal found 16/12C$ 1,112
Fri 26/1210:30 p.m.YVR - MDW
2 stops16h 56mWestJet
Sun 4/16:08 p.m.MDW - YVR
2 stops20h 56mWestJet
Deal found 17/12C$ 1,145
Fri 26/125:00 p.m.YVR - MDW
1 stop15h 05mMultiple Airlines
Sun 4/110:50 p.m.MDW - YVR
2 stops19h 41mMultiple Airlines
Deal found 17/12C$ 1,153

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 18 December 2025.

Round-trip from

C$ 384

One-way from

C$ 113

Popular in

December

Cheapest in

October

Average price

C$ 682
9/1-11/1
  • 9/1-11/1
  • 2 total stops
  • 21h 00m total
  • Whistler to Chicago
Search Deals
WestJet
  • WestJet
  • 23/5
  • 1 total stop
  • 6h 13m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 136 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 18 December 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

Tue 20/1

6:00 a.m.-2:38 p.m.

1 stop6h 38m

Chicago O'Hare Intl

Sat 31/1

8:00 a.m.-4:31 p.m.

1 stop10h 31m

C$ 404

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 13/1

7:00 a.m.-5:44 p.m.

1 stop8h 44m

Chicago O'Hare Intl

Thu 15/1

6:06 p.m.-12:10 a.m.

1 stop8h 04m

C$ 430

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 14/2

7:55 a.m.-11:56 p.m.

1 stop14h 01m

Chicago O'Hare Intl

Wed 25/2

5:29 p.m.-12:10 a.m.

1 stop8h 41m

C$ 457

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 15/1

3:40 p.m.-2:17 p.m.

2 stops20h 37m

Chicago O'Hare Intl

Mon 19/1

5:15 a.m.-12:15 a.m.

3 stops21h 00m

C$ 464

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 24/1

7:55 a.m.-2:38 p.m.

1 stop28h 43m

Chicago O'Hare Intl

Sun 25/1

6:06 p.m.-12:10 a.m.

1 stop8h 04m

C$ 466

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 23/1

7:55 a.m.-5:10 p.m.

1 stop7h 15m

Chicago O'Hare Intl

Tue 27/1

8:00 a.m.-6:45 p.m.

1 stop12h 45m

C$ 468

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 24/1

7:55 a.m.-11:50 p.m.

1 stop13h 55m

Chicago O'Hare Intl

Tue 27/1

8:00 a.m.-8:55 p.m.

1 stop14h 55m

C$ 468

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 17/1

5:45 p.m.-2:38 p.m.

1 stop18h 53m

Chicago O'Hare Intl

Wed 21/1

3:35 p.m.-12:10 a.m.

1 stop10h 35m

C$ 468

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 5/3

7:55 a.m.-11:56 p.m.

1 stop14h 01m

Chicago O'Hare Intl

Tue 10/3

5:29 p.m.-8:55 p.m.

1 stop29h 26m

C$ 470

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 21/1

7:37 p.m.-8:52 a.m.

2 stops11h 15m

Chicago Midway

Tue 27/1

9:50 a.m.-8:54 p.m.

2 stops13h 04m

C$ 488

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/12

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 12 December 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, October is the cheapest month in which you can book a flight from Whistler to Chicago (average of C$ 152). Flying from Whistler to Chicago in January is currently the most expensive (average of C$ 357). 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 18 December 2025.

A simple way to save on the total cost of your ticket is to fly from Whistler to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight in the morning.

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 18 December 2025.

The most flights from WH1 to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 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 18 December 2025.
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
9,095 reviews
Check prices

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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
9,095 reviews
United Airlines
7.4
Good
9,095 reviews
Check prices

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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
7.2
Good
11,054 reviews
United Airlines
7.4
Good
9,095 reviews
Check prices

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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
3,205 reviews
United Airlines
7.4
Good
9,095 reviews
Check prices

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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
10,534 reviews
United Airlines
7.4
Good
9,095 reviews
Check prices

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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 11h 15m. Alaska Airlines provides one of the quickest options available for as low as C$ 488. 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$ 167 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$ 172 and C$ 193, 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: Avianca (90%), American Airlines (88%), Qatar Airways( 88%).

  • What are the cheapest flights from Whistler to Chicago?

    On average you can expect to pay C$ 1,451 for a flight from Whistler to Chicago. The cheapest flight overall is C$ 233 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 287.

  • 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$ 152). Flying from Whistler to Chicago in January is currently the most expensive (average of C$ 357). 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 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 18 December 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 201AverageC$ 480FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 233AverageC$ 330FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 235AverageC$ 422FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 251AverageC$ 500FlexibilityNo cancel feeOn-time67%
Search Air Canada 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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