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Cheap flights from Whistler to Chicago from C$ 265

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 25/10. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
2 Jun — 9 Jun1
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 Friday or Thursday 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 3 May 2026.

Fri 11/97:30 a.m.
YVR
-
ORD
1 stop7h 10m
Multiple Airlines
Mon 14/911:49 a.m.
ORD
-
YVR
2 stops9h 21m
Multiple Airlines
Deal found 2/5C$ 481
Thu 3/97:30 a.m.
YVR
-
ORD
1 stop7h 10m
Multiple Airlines
Thu 10/912:01 p.m.
ORD
-
YVR
2 stops9h 09m
Multiple Airlines
Deal found 1/5C$ 484
Tue 1/97:30 a.m.
YVR
-
ORD
1 stop7h 10m
Multiple Airlines
Thu 10/912:01 p.m.
ORD
-
YVR
2 stops9h 09m
Multiple Airlines
Deal found 1/5C$ 487
Thu 15/107:30 a.m.
YVR
-
ORD
1 stop7h 10m
Multiple Airlines
Tue 20/107:30 p.m.
ORD
-
YVR
1 stop21h 00m
Multiple Airlines
Deal found 30/4C$ 488
Fri 4/97:30 a.m.
YVR
-
ORD
1 stop7h 10m
Multiple Airlines
Thu 10/912:01 p.m.
ORD
-
YVR
2 stops9h 09m
Multiple Airlines
Deal found 1/5C$ 493
Fri 11/96:00 a.m.
YVR
-
ORD
2 stops8h 40m
WestJet
Tue 15/95:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 2/5C$ 496
Tue 9/610:45 p.m.
YVR
-
ORD
2 stops15h 55m
WestJet
Mon 15/65:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 1/5C$ 497
Thu 28/510:15 p.m.
YVR
-
ORD
1 stop16h 25m
Multiple Airlines
Wed 3/69:37 p.m.
ORD
-
YVR
2 stops21h 13m
Multiple Airlines
Deal found 30/4C$ 499
Thu 10/99:30 a.m.
YVR
-
ORD
2 stops23h 28m
Multiple Airlines
Sun 13/95:30 p.m.
ORD
-
YVR
1 stop7h 05m
Multiple Airlines
Deal found 2/5C$ 500
Fri 29/57:30 a.m.
YVR
-
ORD
1 stop7h 10m
Multiple Airlines
Fri 5/66:25 p.m.
ORD
-
YVR
2 stops45h 45m
Multiple Airlines
Deal found 30/4C$ 501
Thu 21/510:30 p.m.
YVR
-
ORD
2 stops16h 10m
WestJet
Sat 30/55:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 2/5C$ 503
Thu 21/510:30 p.m.
YVR
-
ORD
2 stops16h 10m
WestJet
Fri 29/55:30 p.m.
ORD
-
YVR
1 stop16h 10m
WestJet
Deal found 28/4C$ 504

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 3 May 2026.

Round-trip from

C$ 481

One-way from

C$ 265

Popular in

December

Cheapest in

October

Average price

C$ 520
11/9-14/9
  • 11/9-14/9
  • 3 total stops
  • 16h 31m total
  • Whistler to Chicago
Search Deals
WestJet
  • WestJet
  • 25/10
  • 1 total stop
  • 15h 50m total
  • Whistler to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 122 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 May 2026
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 3 May 2026.
Use the filters below to find and compare flights from Whistler to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 19/6

11:35 p.m.-5:40 a.m.

Nonstop4h 05m

Chicago O'Hare Intl

Mon 22/6

7:40 p.m.-10:20 p.m.

Nonstop4h 40m

C$ 510

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 19/6

6:00 a.m.-8:31 p.m.

2 stops12h 31m

Chicago O'Hare Intl

Mon 22/6

7:45 a.m.-12:15 p.m.

1 stop6h 30m

C$ 537

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 22/6

7:36 p.m.-8:35 a.m.

2 stops10h 59m

Chicago O'Hare Intl

Sun 5/7

6:30 a.m.-1:30 p.m.

1 stop9h 00m

C$ 541

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 10/6

3:43 p.m.-11:39 p.m.

1 stop5h 56m

Chicago O'Hare Intl

Fri 12/6

3:55 p.m.-8:31 p.m.

1 stop6h 36m

C$ 567

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 22/5

6:45 a.m.-6:50 p.m.

1 stop10h 05m

Chicago O'Hare Intl

Mon 25/5

6:24 a.m.-10:39 a.m.

1 stop6h 15m

C$ 588

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 11/6

11:35 p.m.-5:40 a.m.

Nonstop4h 05m

Chicago O'Hare Intl

Wed 17/6

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

1 stop6h 51m

C$ 603

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 8/10

1:45 p.m.-7:53 p.m.

Nonstop4h 08m

Chicago O'Hare Intl

Sat 10/10

6:00 a.m.-2:06 p.m.

1 stop10h 06m

C$ 607

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 11/6

11:35 p.m.-5:40 a.m.

Nonstop4h 05m

Chicago O'Hare Intl

Mon 15/6

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

1 stop6h 51m

C$ 616

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 17/6

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

2 stops10h 16m

Chicago Midway

Wed 24/6

1:26 p.m.-8:31 p.m.

2 stops9h 05m

C$ 640

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

5:15 p.m.-8:49 a.m.

2 stops13h 34m

Chicago Midway

Tue 13/10

9:30 a.m.-8:32 p.m.

2 stops13h 02m

C$ 651

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/4

Showing 1-10 of 38 resultsSorted by cheapest first
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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

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 3 May 2026.

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 3 May 2026.

The most flights from WH1 to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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 3 May 2026.
Read reviews from past customers who have flown United Airlines,WestJet, andAmerican Airlines 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
9,684 reviews
Check prices

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,684 reviews
United Airlines
7.4
Good
9,684 reviews
Check prices

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
WestJet
7.2
Good
3,331 reviews
United Airlines
7.4
Good
9,684 reviews
Check prices

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
American Airlines
7.1
Good
11,673 reviews
United Airlines
7.4
Good
9,684 reviews
Check prices

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
Air Canada
7.1
Good
10,993 reviews
United Airlines
7.4
Good
9,684 reviews
Check prices

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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 4h 05m. United Airlines provides one of the quickest options available for as low as C$ 510. Airlines will cover a distance of 2829 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$ 165 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$ 169 and C$ 222, 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: Emirates (100%), United Airlines (89%), Air Canada( 79%).

  • What are the cheapest flights from Whistler to Chicago?

    On average you can expect to pay C$ 1,000 for a flight from Whistler to Chicago. The cheapest flight overall is C$ 222 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 470.

  • 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.

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 3 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 195AverageC$ 466FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 200AverageC$ 556FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 206AverageC$ 360FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 250AverageC$ 425FlexibilityNo cancel feeOn-time71%
Search American Airlines 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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