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Cheap flights from Whistler to Chicago from C$ 152

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 18/11. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

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 Wednesday

Find 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 30 October 2025.

Wed 3/1211:00 p.m.YVR - ORD
1 stop16h 27mMultiple Airlines
Mon 8/1212:59 p.m.ORD - YVR
1 stop11h 21mMultiple Airlines
Deal found 30/10C$ 279
Sun 7/1211:00 p.m.YVR - ORD
1 stop21h 24mMultiple Airlines
Wed 10/124:01 p.m.ORD - YVR
2 stops26h 53mMultiple Airlines
Deal found 28/10C$ 285
Mon 15/127:10 a.m.YVR - ORD
1 stop15h 03mMultiple Airlines
Wed 17/124:01 p.m.ORD - YVR
2 stops32h 44mMultiple Airlines
Deal found 29/10C$ 295
Wed 26/1111:00 p.m.YVR - MDW
1 stop21h 43mMultiple Airlines
Thu 4/126:15 a.m.MDW - YVR
2 stops18h 30mMultiple Airlines
Deal found 30/10C$ 303
Thu 11/127:45 p.m.YVR - MDW
2 stops24h 27mMultiple Airlines
Mon 15/126:15 a.m.MDW - YVR
1 stop12h 16mMultiple Airlines
Deal found 30/10C$ 338
Fri 12/129:15 p.m.YVR - ORD
2 stops12h 39mMultiple Airlines
Mon 15/122:20 p.m.ORD - YVR
1 stop7h 25mMultiple Airlines
Deal found 29/10C$ 338
Thu 11/1210:10 p.m.YVR - ORD
1 stop13h 25mWestJet
Mon 15/122:20 p.m.ORD - YVR
1 stop8h 40mWestJet
Deal found 30/10C$ 349
Fri 12/129:10 a.m.YVR - ORD
1 stop9h 45mMultiple Airlines
Tue 13/14:11 p.m.ORD - YVR
2 stops56h 09mMultiple Airlines
Deal found 30/10C$ 357
Fri 12/1210:10 p.m.YVR - MDW
2 stops21h 12mMultiple Airlines
Mon 15/126:15 a.m.MDW - YVR
1 stop12h 16mMultiple Airlines
Deal found 29/10C$ 369
Wed 26/1111:00 p.m.YVR - ORD
1 stop10h 34mMultiple Airlines
Thu 4/125:05 a.m.ORD - YVR
2 stops19h 40mMultiple Airlines
Deal found 30/10C$ 369
Mon 10/119:15 p.m.YVR - ORD
2 stops11h 59mMultiple Airlines
Sun 16/115:01 a.m.ORD - YVR
1 stop32h 11mMultiple Airlines
Deal found 28/10C$ 387
Thu 20/118:00 a.m.YVR - ORD
1 stop20h 25mMultiple Airlines
Thu 27/116:45 p.m.ORD - YVR
1 stop29h 35mMultiple Airlines
Deal found 30/10C$ 391

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 30 October 2025.

Round-trip from

C$ 278

One-way from

C$ 152

Popular in

November

Cheapest in

September

Average price

C$ 429
3/12-6/12
  • 3/12-6/12
  • 3 total stops
  • 45h 57m total
  • Whistler to Chicago
Search Deals
18/11
  • 18/11
  • 2 total stops
  • 25h 21m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 30 October 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 - MDW

YVRMDW

Vancouver Intl

Fri 5/12

11:00 p.m.-1:59 p.m.

1 stop12h 59m

Chicago Midway

Mon 8/12

8:42 p.m.-2:45 p.m.

2 stops20h 03m

C$ 296

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 26/11

11:00 p.m.-10:43 p.m.

1 stop21h 43m

Chicago Midway

Thu 4/12

6:15 a.m.-10:45 p.m.

2 stops18h 30m

C$ 303

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 11/1

9:10 a.m.-7:21 p.m.

1 stop8h 11m

Chicago Midway

Sun 18/1

11:30 a.m.-4:31 p.m.

1 stop31h 01m

C$ 314

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 16/11

11:00 p.m.-2:33 p.m.

2 stops13h 33m

Chicago Midway

Wed 19/11

1:56 p.m.-11:12 a.m.

1 stop23h 16m

C$ 331

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 1/2

11:40 a.m.-11:53 p.m.

1 stop10h 13m

Chicago O'Hare Intl

Mon 9/2

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

1 stop6h 24m

C$ 364

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 9/1

3:30 p.m.-11:53 p.m.

1 stop6h 23m

Chicago O'Hare Intl

Fri 16/1

2:20 p.m.-8:54 p.m.

1 stop8h 34m

C$ 364

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 29/1

3:30 p.m.-11:53 p.m.

1 stop6h 23m

Chicago O'Hare Intl

Wed 4/2

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

1 stop6h 24m

C$ 364

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 18/1

3:30 p.m.-11:53 p.m.

1 stop6h 23m

Chicago O'Hare Intl

Sat 24/1

6:12 a.m.-11:01 a.m.

1 stop6h 49m

C$ 364

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 9/1

3:30 p.m.-11:53 p.m.

1 stop6h 23m

Chicago O'Hare Intl

Sat 17/1

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

1 stop7h 54m

C$ 364

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 23/1

3:30 p.m.-11:53 p.m.

1 stop6h 23m

Chicago O'Hare Intl

Thu 29/1

2:20 p.m.-8:54 p.m.

1 stop8h 34m

C$ 364

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/10

Showing 1-10 of 42 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 24 October 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$ 159). Flying from Whistler to Chicago in January is currently the most expensive (average of C$ 355). 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 30 October 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 29% on your trip compared to booking a flight in the morning.

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

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 30 October 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
8,998 reviews
Check prices

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

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
8,998 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

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
11,030 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

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
3,149 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

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
10,376 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

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 10h 13m. Delta provides one of the quickest options available for as low as C$ 364. Airlines will cover a distance of 2829 km.

  • 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 (83%), American Airlines (75%), Qatar Airways( 65%).

  • What are the cheapest flights from Whistler to Chicago?

    On average you can expect to pay C$ 528 for a flight from Whistler to Chicago. The cheapest flight overall is C$ 170 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 327.

  • 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$ 159). Flying from Whistler to Chicago in January is currently the most expensive (average of C$ 355). 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 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 30 October 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 208AverageC$ 489FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 236AverageC$ 360FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 238AverageC$ 427FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 267AverageC$ 528FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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

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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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