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

Airfare is below average for this route at the moment. Whistler to Chicago flights typically cost between C$ 387 and C$ 706 in September. The cheapest round-trip price found within the last 3 days was C$ 313 on WestJet (13 Sep-20 Sep).

Question 1

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

Accepted Answer

Airfare is below average for this route at the moment.Whistler to Chicago flights typically cost between C$ 387 and C$ 706 in September.
The cheapest round-trip price found within the last 3 days was C$ 313 on WestJet (13 Sep-20 Sep).

Question 2

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

Accepted Answer

C$ 250 is the cheapest one-way deal found within the past few days, from Alaska Airlines. You may also be able to find cheap deals on United Airlines and WestJet, with prices starting from C$ 252 and C$ 256, respectively.

Question 3

How far ahead should I book a flight from Whistler to Chicago?

Accepted Answer

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.

Question 4

What is the cheapest month to book a flight from Whistler to Chicago?

Accepted Answer

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.

Question 5

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

Accepted Answer

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.

Question 6

Weekly flight availability from Whistler to Chicago

Accepted Answer

The most flights from WH1 to CHI are scheduled on a Tuesday (12 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (11 on average).

Question 7

E

Accepted Answer

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.

Question 8

E

Accepted Answer

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).

Question 9

What are the cheapest flights from Whistler to Chicago?

Accepted Answer

On average you can expect to pay C$ 1,669 for a flight from Whistler to Chicago. The cheapest flight overall is C$ 249 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 316.

Question 10

What are the most reliable airlines from Whistler to Chicago?

Accepted Answer

Before booking your flight to Chicago from Whistler, check out the most reliable airlines to get you to your destination on time: Air Canada (70%), United Airlines (70%), Avianca( 53%).

Question 11

What are the most popular airlines that fly from Whistler to Chicago?

Accepted Answer

The most popular airlines flying from Whistler to Chicago are American Airlines, Air Canada and Delta. Something to consider prior to booking your flight.

Question 12

How far in advance should I book a flight from Whistler to Chicago?

Accepted Answer

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 33 days in advance, which can save you up to 61% on flights from Whistler to Chicago compared to booking the week you need them. Waiting 33 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at C$ 435. For sooner than that we have options available in the next 3 days from C$ 608.

Question 13

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

Accepted Answer

The best pricing can be found in the month of April. Prices to Chicago from Whistler average C$ 502. You can even find prices in April for less than C$ 502, as users have found deals to Chicago from as low as C$ 228. The month of July appears to be one of the more expensive times to travel to Chicago from Whistler. Flying in the targeted month can save you up to 25%.

Question 14

What is the cheapest time of day to fly from WH1 to CHI?

Accepted Answer

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.

Question 15

Can I find deals for flights from Whistler to Chicago that include hotel bookings?

Accepted Answer

Yes. In addition to deals on Whistler to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

Question 16

How can I find direct flights from Whistler to Chicago?

Accepted Answer

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Whistler to Chicago.

Question 17

Can I find deals for business class flights from Whistler to Chicago?

Accepted Answer

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.

Question 18

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

Accepted Answer

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.

Question 19

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

Accepted Answer

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.

Question 20

Can Cheapflights find flights from Whistler to Chicago with no change fees?

Accepted Answer

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.

Question 21

Can Cheapflights notify me if prices for flights from Whistler to Chicago become cheaper?

Accepted Answer

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.

Round-trip from	C$ 313
One-way from	C$ 248
Popular in	July
Cheapest in	April
Average price	C$ 632

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	CheapestC$ 235	AverageC$ 446	FlexibilityNo cancel fee	On-time71%	Search American Airlines flights
WestJet	CheapestC$ 292	AverageC$ 367	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
Air Canada	CheapestC$ 316	AverageC$ 545	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
United Airlines	CheapestC$ 366	AverageC$ 532	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights
Delta	CheapestC$ 390	AverageC$ 693	FlexibilityNo cancel fee	On-timeN/A	Search Delta flights

Cheap flights from Whistler to Chicago

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 31 July 2025.

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One-way from

Popular in

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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 25 July 2025.

What is the cheapest month to book a flight from Whistler to Chicago?

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 31 July 2025.

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 31 July 2025.

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

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Alaska Airlines,Porter Airlines, andDelta 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.

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?

What are the most reliable airlines from Whistler to Chicago?

What are the cheapest flights from Whistler to Chicago?

Can I find deals for flights from Whistler to Chicago that include hotel bookings?

How can I find direct flights from Whistler to Chicago?

Can I find deals for business class flights from Whistler to Chicago?

What is the cheapest month to book a flight from Whistler to Chicago?

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Whistler to Chicago

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Top 5 airlines flying from Whistler to Chicago

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

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

Can Cheapflights find flights from Whistler to Chicago with no change fees?

Can Cheapflights notify me if prices for flights from Whistler to Chicago become cheaper?

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