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Cheap flights from Whistler to Chicago from C$ 223

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
2 Apr — 9 Apr1
1 adult

Cheapflights Tip: The best prices from Whistler to Chicago are usually found in January or October, booked 66 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 28 March 2025.

Round-trip from

C$ 290

One-way from

C$ 223

Popular in

December

Cheapest in

January

Average price

C$ 556
WestJet
  • WestJet
  • 1/5-4/5
  • 2 total stops
  • 17h 24m total
  • Whistler to Chicago
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23/5
  • 23/5
  • 1 total stop
  • 21h 02m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 28 March 2025.

Thu 1/56:00 a.m.YVR - ORD
1 stop8h 44mWestJet
Sun 4/55:30 p.m.ORD - YVR
1 stop8h 40mWestJet
Deal found 27/3C$ 290
Wed 30/45:35 p.m.YVR - ORD
1 stop10h 58mMultiple Airlines
Fri 2/55:30 p.m.ORD - YVR
1 stop16h 05mMultiple Airlines
Deal found 27/3C$ 356
Fri 1/89:30 a.m.YVR - MDW
1 stop11h 51mMultiple Airlines
Tue 5/812:15 p.m.MDW - YVR
1 stop10h 37mMultiple Airlines
Deal found 27/3C$ 379
Mon 14/45:20 p.m.YVR - ORD
1 stop10h 39mAlaska Airlines
Tue 15/47:16 p.m.ORD - YVR
1 stop6h 31mAlaska Airlines
Deal found 26/3C$ 393
Wed 23/48:30 a.m.YVR - ORD
Nonstop4h 13mAir Canada
Wed 30/47:00 a.m.ORD - YVR
1 stop17h 54mAir Canada
Deal found 27/3C$ 400
Sat 12/46:15 a.m.YVR - ORD
Nonstop4h 16mUnited Airlines
Sun 13/48:52 a.m.ORD - YVR
Nonstop4h 41mUnited Airlines
Deal found 27/3C$ 403
Thu 10/47:25 p.m.YVR - MDW
2 stops12h 31mDelta
Sat 19/49:20 a.m.MDW - YVR
2 stops13h 48mDelta
Deal found 27/3C$ 450
Thu 17/43:30 p.m.YVR - ORD
1 stop6h 29mDelta
Tue 22/41:55 p.m.ORD - YVR
2 stops11h 02mDelta
Deal found 27/3C$ 483
Sat 17/56:00 a.m.YVR - ORD
2 stops13h 09mAmerican Airlines
Tue 27/57:05 a.m.ORD - YVR
1 stop17h 45mAmerican Airlines
Deal found 27/3C$ 606
Mon 12/57:00 a.m.YVR - MDW
2 stops23h 45mPorter Airlines
Thu 15/59:40 a.m.MDW - YVR
2 stops13h 15mPorter Airlines
Deal found 27/3C$ 728
Wed 28/56:15 a.m.YVR - MDW
1 stop9h 30mWestJet
Sat 31/56:30 p.m.MDW - YVR
1 stop27h 45mWestJet
Deal found 27/3C$ 1,112

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 28 March 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

Thu 1/5

6:00 a.m.-4:44 p.m.

1 stop8h 44m

Chicago O'Hare Intl

Sun 4/5

5:30 p.m.-12:10 a.m.

1 stop8h 40m

C$ 290

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 30/4

5:35 p.m.-6:33 a.m.

1 stop10h 58m

Chicago O'Hare Intl

Fri 2/5

5:30 p.m.-7:35 a.m.

1 stop16h 05m

C$ 356

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 1/8

9:30 a.m.-11:21 p.m.

1 stop11h 51m

Chicago Midway

Tue 5/8

12:15 p.m.-8:52 p.m.

1 stop10h 37m

C$ 379

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 14/4

5:20 p.m.-5:59 a.m.

1 stop10h 39m

Chicago O'Hare Intl

Tue 15/4

7:16 p.m.-11:47 p.m.

1 stop6h 31m

C$ 393

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 23/4

8:30 a.m.-2:43 p.m.

Nonstop4h 13m

Chicago O'Hare Intl

Wed 30/4

7:00 a.m.-10:54 p.m.

1 stop17h 54m

C$ 400

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 12/4

6:15 a.m.-12:31 p.m.

Nonstop4h 16m

Chicago O'Hare Intl

Sun 13/4

8:52 a.m.-11:33 a.m.

Nonstop4h 41m

C$ 403

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 10/4

7:25 p.m.-9:56 a.m.

2 stops12h 31m

Chicago Midway

Sat 19/4

9:20 a.m.-9:08 p.m.

2 stops13h 48m

C$ 450

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 17/4

3:30 p.m.-11:59 p.m.

1 stop6h 29m

Chicago O'Hare Intl

Tue 22/4

1:55 p.m.-10:57 p.m.

2 stops11h 02m

C$ 483

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 17/5

6:00 a.m.-9:09 p.m.

2 stops13h 09m

Chicago O'Hare Intl

Tue 27/5

7:05 a.m.-10:50 p.m.

1 stop17h 45m

C$ 606

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 12/5

7:00 a.m.-8:45 a.m.

2 stops23h 45m

Chicago Midway

Thu 15/5

9:40 a.m.-8:55 p.m.

2 stops13h 15m

C$ 728

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/3

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 21 March 2025.

To ensure you get the cheapest price possible for a flight from Whistler to Chicago, you should look to book at least 66 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$ 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 28 March 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.

What is the cheapest day to fly from Whistler to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Whistler to Chicago. Price data was last updated on 10 November 2024.

Travelers seeking maximum savings on their Whistler to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 28 March 2025.
See what other customers who have flown with Alaska Airlines, Delta and Porter Airlines 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
9,798 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,798 reviews
Alaska Airlines
8.0
Very good
9,798 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,896 reviews
Alaska Airlines
8.0
Very good
9,798 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Porter Airlines
7.9
Good
276 reviews
Alaska Airlines
8.0
Very good
9,798 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,603 reviews
Alaska Airlines
8.0
Very good
9,798 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,798 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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$ 223 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 Alaska Airlines, with prices starting from C$ 227 and C$ 242, 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 (100%), Emirates (90%), Air Canada( 87%).

  • What are the cheapest flights from Whistler to Chicago?

    On average you can expect to pay C$ 1,185 for a flight from Whistler to Chicago. The cheapest flight overall is C$ 212 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 367.

  • 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$ 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 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 28 March 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 309AverageC$ 430FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 340AverageC$ 579FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Alaska AirlinesCheapestC$ 371AverageC$ 621FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
United AirlinesCheapestC$ 380AverageC$ 563FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 403AverageC$ 554FlexibilityNo 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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