Cheap flights from Whistler to Chicago from C$ 266
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 24/10. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
17 Oct — 24 Oct1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Whistler to Chicago are usually found in September or October, booked 42 days in advance, depart on a Friday or Wednesday and return on a Friday
Cheap flight deals from Whistler to Chicago
Enter your travel dates to find the best prices.
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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 17 September 2026.
Thu 29/107:55 a.m. -
1 stop6h 55m
Sat 31/107:00 a.m. -
1 stop7h 40m
Deal found 17/9C$ 411
Tue 20/108:05 a.m. -
1 stop8h 15m
Sat 24/109:00 a.m. -
1 stop9h 29m
Deal found 16/9C$ 414
Mon 19/105:00 a.m. -
1 stop9h 40m
Fri 23/105:30 p.m. -
1 stop8h 45m
Deal found 16/9C$ 417
Wed 14/1012:45 p.m. -
1 stop25h 55m
Fri 16/105:30 p.m. -
1 stop8h 45m
Deal found 17/9C$ 418
Thu 1/1010:10 p.m. -
2 stops13h 13m
Wed 7/103:40 p.m. -
Nonstop4h 35m
Deal found 16/9C$ 420
Tue 20/108:05 a.m. -
1 stop8h 15m
Wed 28/103:49 p.m. -
1 stop7h 06m
Deal found 16/9C$ 425
Fri 23/106:45 a.m. -
1 stop7h 55m
Mon 26/104:20 p.m. -
2 stops23h 40m
Deal found 16/9C$ 431
Thu 1/101:45 p.m. -
Nonstop4h 21m
Wed 7/108:49 a.m. -
Nonstop4h 44m
Deal found 17/9C$ 432
Thu 1/108:25 a.m. -
Nonstop4h 18m
Sun 4/103:40 p.m. -
Nonstop4h 35m
Deal found 17/9C$ 434
Sun 8/119:25 a.m. -
Nonstop3h 12m
Mon 16/113:30 p.m. -
Nonstop5h 47m
Deal found 16/9C$ 435
Fri 4/122:35 p.m. -
2 stops20h 35m
Sun 6/126:00 a.m. -
1 stop9h 35m
Deal found 17/9C$ 438
Sat 24/106:00 a.m. -
1 stop8h 47m
Tue 27/1012:27 p.m. -
1 stop10h 06m
Deal found 16/9C$ 469
Best flights from Whistler to Chicago
Discover carefully curated flight deals from Whistler to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 17 September 2026.
Thu 29/101:50 p.m. -
Nonstop4h 11m
Sun 1/117:00 a.m. -
2 stops12h 19m
Deal found 16/9C$ 462
Sat 24/106:00 a.m. -
1 stop8h 47m
Tue 27/1012:27 p.m. -
1 stop10h 06m
Deal found 16/9C$ 469
Thu 3/1212:55 p.m. -
1 stop9h 04m
Tue 8/126:00 a.m. -
1 stop9h 35m
Deal found 13/9C$ 485
Fri 13/112:50 p.m. -
Nonstop3h 09m
Sun 15/118:49 a.m. -
Nonstop5h 56m
Deal found 17/9C$ 462
Sat 14/111:36 p.m. -
1 stop7h 10m
Sun 15/118:49 a.m. -
Nonstop5h 56m
Deal found 15/9C$ 462
Wed 28/107:36 p.m. -
2 stops11h 08m
Wed 4/1112:27 p.m. -
1 stop11h 06m
Deal found 12/9C$ 526
Thu 12/112:50 p.m. -
Nonstop3h 09m
Fri 20/118:49 a.m. -
Nonstop5h 56m
Deal found 16/9C$ 462
Mon 5/106:15 a.m. -
1 stop9h 46m
Wed 7/106:35 a.m. -
1 stop10h 20m
Deal found 13/9C$ 526
Fri 13/111:36 p.m. -
1 stop7h 10m
Mon 16/118:49 a.m. -
Nonstop5h 56m
Deal found 17/9C$ 469
Sat 3/107:35 p.m. -
2 stops11h 13m
Sat 10/1012:27 p.m. -
1 stop10h 06m
Deal found 14/9C$ 554
Sat 14/111:36 p.m. -
1 stop7h 10m
Tue 17/117:00 a.m. -
1 stop9h 59m
Deal found 15/9C$ 470
Mon 5/1010:55 a.m. -
1 stop9h 51m
Wed 7/107:44 a.m. -
1 stop10h 39m
Deal found 16/9C$ 471
Sat 10/107:36 p.m. -
2 stops11h 08m
Tue 13/1012:27 p.m. -
2 stops8h 43m
Deal found 14/9C$ 609
Thu 21/12:50 p.m. -
Nonstop3h 14m
Sun 24/17:25 a.m. -
1 stop11h 54m
Deal found 14/9C$ 496
Thu 3/127:15 a.m. -
2 stops7h 35m
Tue 8/1212:39 p.m. -
2 stops13h 12m
Deal found 13/9C$ 609
Sat 31/106:00 a.m. -
1 stop8h 47m
Sat 7/1112:27 p.m. -
1 stop11h 06m
Deal found 16/9C$ 628
Direct flights from Whistler to Chicago
Explore direct flight options from Whistler to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 17 September 2026.
Thu 1/108:25 a.m. -
Nonstop4h 18m
Wed 7/103:40 p.m. -
Nonstop4h 35m
Deal found 17/9C$ 428
Thu 1/101:45 p.m. -
Nonstop4h 21m
Wed 7/108:49 a.m. -
Nonstop4h 44m
Deal found 17/9C$ 432
Thu 1/108:25 a.m. -
Nonstop4h 18m
Sun 4/103:40 p.m. -
Nonstop4h 35m
Deal found 17/9C$ 434
Sun 8/119:25 a.m. -
Nonstop3h 12m
Sun 15/113:30 p.m. -
Nonstop5h 47m
Deal found 16/9C$ 435
Sat 14/112:50 p.m. -
Nonstop3h 09m
Fri 20/118:49 a.m. -
Nonstop5h 56m
Deal found 16/9C$ 462
Thu 1/101:45 p.m. -
Nonstop4h 21m
Wed 7/103:40 p.m. -
Nonstop4h 35m
Deal found 16/9C$ 463
Fri 16/108:25 a.m. -
Nonstop4h 18m
Sat 17/103:40 p.m. -
Nonstop4h 35m
Deal found 15/9C$ 485
Tue 29/98:25 a.m. -
Nonstop4h 18m
Tue 6/103:40 p.m. -
Nonstop4h 35m
Deal found 14/9C$ 495
Fri 2/108:25 a.m. -
Nonstop4h 18m
Mon 5/103:40 p.m. -
Nonstop4h 35m
Deal found 14/9C$ 496
Sat 10/108:25 a.m. -
Nonstop4h 18m
Tue 13/103:40 p.m. -
Nonstop4h 35m
Deal found 15/9C$ 516
Sat 14/112:50 p.m. -
Nonstop3h 09m
Tue 17/118:49 a.m. -
Nonstop5h 56m
Deal found 15/9C$ 517
Last-minute flights from Whistler to Chicago
Discover last-minute flight deals from Whistler to Chicago. Data last updated 17 September 2026 and is based on user searches.
Thu 1/1010:10 p.m. -
2 stops13h 13m
Wed 7/103:40 p.m. -
Nonstop4h 35m
Deal found 16/9C$ 420
Thu 1/101:45 p.m. -
Nonstop4h 21m
Wed 7/108:49 a.m. -
Nonstop4h 44m
Deal found 17/9C$ 432
Thu 1/108:25 a.m. -
Nonstop4h 18m
Sun 4/103:40 p.m. -
Nonstop4h 35m
Deal found 17/9C$ 434
Sat 10/101:45 p.m. -
Nonstop4h 21m
Tue 13/107:45 p.m. -
Nonstop4h 41m
Deal found 16/9C$ 435
Wed 14/1012:45 p.m. -
1 stop25h 55m
Fri 16/105:30 p.m. -
1 stop8h 45m
Deal found 17/9C$ 418
Mon 19/105:00 a.m. -
1 stop9h 40m
Fri 23/105:30 p.m. -
1 stop8h 45m
Deal found 16/9C$ 417
Tue 20/108:05 a.m. -
1 stop8h 15m
Sat 24/109:00 a.m. -
1 stop9h 29m
Deal found 16/9C$ 414
Tue 20/108:05 a.m. -
1 stop8h 15m
Fri 30/109:00 a.m. -
1 stop9h 30m
Deal found 16/9C$ 425
Fri 23/106:45 a.m. -
1 stop7h 55m
Mon 26/104:20 p.m. -
2 stops23h 40m
Deal found 16/9C$ 431
Sat 24/106:00 a.m. -
1 stop8h 47m
Tue 27/1012:27 p.m. -
1 stop10h 06m
Deal found 16/9C$ 469
Thu 29/107:55 a.m. -
1 stop6h 55m
Sat 31/107:00 a.m. -
1 stop7h 40m
Deal found 17/9C$ 411
Sat 31/109:20 a.m. -
1 stop8h 32m
Sat 7/113:30 p.m. -
Nonstop5h 47m
Deal found 16/9C$ 441
One-way flights from Whistler to Chicago
Search for one-way flight options from Whistler to Chicago. Find affordable one-way fares based on user searches. Data last updated 17 September 2026.
Sat 24/106:00 a.m. -
1 stop8h 47m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 17/9C$ 266
Fri 30/108:30 a.m. -
1 stop9h 35m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 17/9C$ 266
Sat 3/108:25 a.m. -
Nonstop4h 18m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 13/9C$ 268
Tue 15/1211:05 a.m. -
3 stops22h 41m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 15/9C$ 269
Mon 30/118:00 p.m. -
2 stops11h 08m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 16/9C$ 271
Mon 26/1011:00 a.m. -
3 stops22h 22m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 16/9C$ 272
Tue 13/1010:55 p.m. -
1 stop22h 48m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 15/9C$ 273
Mon 12/1010:55 p.m. -
1 stop22h 48m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 15/9C$ 276
Tue 13/101:45 p.m. -
Nonstop4h 21m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 13/9C$ 276
Sun 11/106:00 a.m. -
2 stops22h 34m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 14/9C$ 278
Sun 13/127:45 a.m. -
3 stops26h 01m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 15/9C$ 279
Fri 2/109:00 a.m. -
1 stop9h 20m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 13/9C$ 280
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 17 September 2026.
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 7,457,451 searches. Data last updated 17 September 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
VancouverChicago
YVR Vancouver Intl - MDW Chicago Midway
YVRMDW
Vancouver Intl
Sat 24/10
6:00 a.m.-6:00 p.m.
2 stops10h 00m
Chicago Midway
Wed 31/12
12:00 a.m.-10:00 p.m.
Nonstop0h 00m
C$ 266
VancouverChicago
YVR Vancouver Intl - ORD Chicago O'Hare Intl
YVRORD
Vancouver Intl
Tue 17/11
8:00 a.m.-10:59 p.m.
2 stops13h 59m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-10:00 p.m.
Nonstop0h 00m
C$ 266
VancouverChicago
YVR Vancouver Intl - ORD Chicago O'Hare Intl
YVRORD
Vancouver Intl
Fri 30/10
8:30 a.m.-8:05 p.m.
1 stop9h 35m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-10:00 p.m.
Nonstop0h 00m
C$ 266
VancouverChicago
YVR Vancouver Intl - ORD Chicago O'Hare Intl
YVRORD
Vancouver Intl
Wed 16/12
7:15 a.m.-8:56 p.m.
2 stops12h 41m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-10:00 p.m.
Nonstop0h 00m
C$ 266
VancouverChicago
YVR Vancouver Intl - ORD Chicago O'Hare Intl
YVRORD
Vancouver Intl
Sat 24/10
5:25 p.m.-5:40 a.m.
1 stop10h 15m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-10:00 p.m.
Nonstop0h 00m
C$ 275
VancouverChicago
YVR Vancouver Intl - ORD Chicago O'Hare Intl
YVRORD
Vancouver Intl
Wed 11/11
2:35 p.m.-10:59 p.m.
1 stop7h 24m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-10:00 p.m.
Nonstop0h 00m
C$ 275
Quickest round-trip
VancouverChicago
YVR Vancouver Intl - ORD Chicago O'Hare Intl
YVRORD
Vancouver Intl
Wed 13/1
2:50 p.m.-7:04 p.m.
Nonstop3h 14m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-10:00 p.m.
Nonstop0h 00m
C$ 276
VancouverChicago
YVR Vancouver Intl - ORD Chicago O'Hare Intl
YVRORD
Vancouver Intl
Wed 13/1
11:30 a.m.-8:37 p.m.
2 stops8h 07m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-10:00 p.m.
Nonstop0h 00m
C$ 284
VancouverChicago
YVR Vancouver Intl - MDW Chicago Midway
YVRMDW
Vancouver Intl
Mon 12/10
7:36 p.m.-8:44 a.m.
2 stops11h 08m
Chicago Midway
Wed 31/12
12:00 a.m.-10:00 p.m.
Nonstop0h 00m
C$ 294
VancouverChicago
YVR Vancouver Intl - ORD Chicago O'Hare Intl
YVRORD
Vancouver Intl
Fri 13/11
2:00 p.m.-10:27 p.m.
1 stop7h 27m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-10:00 p.m.
Nonstop0h 00m
C$ 294
Flights are sorted by cheapest round-trip flights first.
Deals found on 17/9
Showing 1-10 of 29 resultsSorted by cheapest first
1
2
3
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.
YVR-ORD
YVR-MDW
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
WH1-CHI
YVR-ORD
YVR-MDW
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 17 September 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 17 September 2026.
The most flights from WH1 to CHI are scheduled on a Wednesday (11 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 on average).
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$ 508 and C$ 676 in October.The cheapest round-trip price found within the last 5 days was C$ 414 on Alaska Airlines (20 Oct-24 Oct).
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 17 September 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.
Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
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 21m. United Airlines provides one of the quickest options available for as low as C$ 448. 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$ 177 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 American Airlines, with prices starting from C$ 262 and C$ 288, 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 (78%), Air Canada Rouge (75%), Finnair( 71%).
What are the cheapest flights from Whistler to Chicago?
On average you can expect to pay C$ 653 for a flight from Whistler to Chicago. The cheapest flight overall is C$ 359 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 435.
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.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 17 September 2026.
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 7,457,451 searches. Data last updated 17 September 2026.
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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