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Cheap flights from Whistler to Chicago from C$ 198

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 16/7. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
17 Jun — 24 Jun1
1 adult

Cheapflights Tip: The best prices from Whistler to Chicago are usually found in April or January, 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 12 June 2025.

Round-trip from

C$ 327

One-way from

C$ 198

Popular in

December

Cheapest in

April

Average price

C$ 499
10/9-17/9
  • 10/9-17/9
  • 2 total stops
  • 16h 47m total
  • Whistler to Chicago
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16/7
  • 16/7
  • 1 total stop
  • 10h 28m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 12 June 2025.

Wed 10/97:00 a.m.YVR - ORD
1 stop7h 43mMultiple Airlines
Wed 17/93:21 p.m.ORD - YVR
1 stop9h 04mMultiple Airlines
Deal found 11/6C$ 327
Fri 27/610:25 p.m.YVR - ORD
1 stop23h 05mUnited Airlines
Sun 29/65:00 a.m.ORD - YVR
1 stop6h 51mUnited Airlines
Deal found 10/6C$ 328
Wed 17/97:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Mon 22/95:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Deal found 11/6C$ 332
Sun 15/61:40 p.m.YVR - ORD
1 stop7h 55mAmerican Airlines
Mon 16/69:55 a.m.ORD - YVR
Nonstop4h 35mAmerican Airlines
Deal found 11/6C$ 364
Tue 5/88:30 p.m.YVR - MDW
2 stops12h 10mMultiple Airlines
Tue 12/811:39 a.m.MDW - YVR
1 stop11h 13mMultiple Airlines
Deal found 11/6C$ 398
Mon 18/811:35 p.m.YVR - ORD
Nonstop4h 03mAir Canada
Mon 1/95:00 a.m.ORD - YVR
1 stop6h 51mAir Canada
Deal found 10/6C$ 407
Fri 20/61:45 p.m.YVR - ORD
Nonstop4h 16mLufthansa
Thu 26/67:35 p.m.ORD - YVR
Nonstop4h 43mLufthansa
Deal found 10/6C$ 424
Tue 12/83:31 p.m.YVR - ORD
1 stop6h 20mDelta
Tue 19/82:15 p.m.ORD - YVR
1 stop9h 55mDelta
Deal found 11/6C$ 433
Thu 24/76:15 a.m.YVR - MDW
1 stop9h 24mDelta
Tue 29/71:46 p.m.MDW - YVR
1 stop8h 45mDelta
Deal found 11/6C$ 435
Fri 25/77:07 p.m.YVR - ORD
2 stops8h 33mAlaska Airlines
Wed 30/77:00 a.m.ORD - YVR
2 stops13h 45mAlaska Airlines
Deal found 10/6C$ 511
Fri 20/68:40 a.m.YVR - MDW
2 stops22h 05mPorter Airlines
Thu 26/69:40 a.m.MDW - YVR
2 stops13h 21mPorter Airlines
Deal found 10/6C$ 662
Thu 24/79:30 a.m.YVR - MDW
1 stop10h 12mWestJet
Sun 27/712:43 p.m.MDW - YVR
1 stop10h 09mWestJet
Deal found 11/6C$ 946

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 12 June 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

Wed 10/9

7:00 a.m.-4:43 p.m.

1 stop7h 43m

Chicago O'Hare Intl

Wed 17/9

3:21 p.m.-10:25 p.m.

1 stop9h 04m

C$ 327

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 27/6

10:25 p.m.-11:30 p.m.

1 stop23h 05m

Chicago O'Hare Intl

Sun 29/6

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

1 stop6h 51m

C$ 328

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 17/9

7:00 a.m.-4:43 p.m.

1 stop7h 43m

Chicago O'Hare Intl

Mon 22/9

5:30 p.m.-10:36 p.m.

1 stop7h 06m

C$ 332

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 5/8

8:30 p.m.-10:40 a.m.

2 stops12h 10m

Chicago Midway

Tue 12/8

11:39 a.m.-8:52 p.m.

1 stop11h 13m

C$ 398

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 18/8

11:35 p.m.-5:38 a.m.

Nonstop4h 03m

Chicago O'Hare Intl

Mon 1/9

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

1 stop6h 51m

C$ 407

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 24/7

6:15 a.m.-5:39 p.m.

1 stop9h 24m

Chicago Midway

Wed 30/7

9:25 a.m.-8:31 p.m.

2 stops13h 06m

C$ 435

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 22/7

6:40 p.m.-7:49 a.m.

2 stops11h 09m

Chicago O'Hare Intl

Tue 29/7

2:00 p.m.-10:30 p.m.

2 stops10h 30m

C$ 451

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 28/7

6:00 a.m.-7:30 a.m.

1 stop23h 30m

Chicago O'Hare Intl

Sun 3/8

7:58 p.m.-10:45 p.m.

Nonstop4h 47m

C$ 461

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 25/7

7:07 p.m.-5:40 a.m.

2 stops8h 33m

Chicago O'Hare Intl

Wed 30/7

7:00 a.m.-6:45 p.m.

2 stops13h 45m

C$ 511

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 24/7

10:15 a.m.-8:45 a.m.

2 stops20h 30m

Chicago Midway

Thu 31/7

9:40 a.m.-9:01 p.m.

2 stops13h 21m

C$ 715

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 22 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 9 June 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$ 352). 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 12 June 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 12 June 2025.

The most flights from WH1 to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (11 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 12 June 2025.
See what other customers who have flown with Alaska Airlines, Porter Airlines and Delta from Whistler to Chicago have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Porter Airlines
8.0
Very good
288 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    C$ 219 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on Air Canada and United Airlines, with prices starting from C$ 227 and C$ 228, 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 (75%), Air Canada (65%), United Airlines( 65%).

  • What are the cheapest flights from Whistler to Chicago?

    On average you can expect to pay C$ 1,119 for a flight from Whistler to Chicago. The cheapest flight overall is C$ 214 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 354.

  • 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$ 352). 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 6 airlines flying from Whistler to Chicago

Discover the top 6 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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 232AverageC$ 423FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 281AverageC$ 543FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 296AverageC$ 387FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Alaska AirlinesCheapestC$ 355AverageC$ 494FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
United AirlinesCheapestC$ 361AverageC$ 540FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 386AverageC$ 623FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Whistler to Chicago?

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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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