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Cheap flights from Vancouver Intl Airport to Chicago from C$ 287

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 26/8. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
30 Aug — 6 Sep1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Vancouver Intl to Chicago are usually found in September or October, booked 42 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap flight deals from Vancouver Intl to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Vancouver Intl to Chicago
Explore the most affordable flight options available from Vancouver Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 31 July 2026.

Fri 4/96:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Sun 13/95:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 31/7C$ 400
Thu 15/106:00 a.m.
YVR
-
ORD
1 stop8h 40m
WestJet
Thu 22/105:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 28/7C$ 402
Sun 6/96:00 a.m.
YVR
-
ORD
1 stop8h 40m
WestJet
Fri 11/95:30 p.m.
ORD
-
YVR
1 stop8h 45m
WestJet
Deal found 27/7C$ 411
Thu 10/96:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Fri 23/105:30 p.m.
ORD
-
YVR
1 stop8h 45m
WestJet
Deal found 27/7C$ 414
Tue 15/97:30 a.m.
YVR
-
ORD
1 stop7h 10m
WestJet
Tue 29/95:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 27/7C$ 422
Thu 10/96:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Tue 22/95:30 p.m.
ORD
-
YVR
1 stop18h 40m
WestJet
Deal found 31/7C$ 436
Fri 4/96:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Fri 11/95:30 p.m.
ORD
-
YVR
1 stop8h 45m
WestJet
Deal found 27/7C$ 439
Wed 9/97:30 p.m.
YVR
-
ORD
1 stop19h 10m
WestJet
Fri 23/105:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 31/7C$ 440
Thu 10/910:40 p.m.
YVR
-
ORD
2 stops16h 00m
WestJet
Mon 14/95:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 28/7C$ 442
Thu 10/98:25 a.m.
YVR
-
ORD
Nonstop4h 18m
Air Canada
Wed 16/911:05 a.m.
ORD
-
YVR
1 stop11h 10m
Air Canada
Deal found 31/7C$ 444
Fri 4/96:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Mon 7/95:30 p.m.
ORD
-
YVR
1 stop20h 15m
WestJet
Deal found 31/7C$ 446
Tue 15/96:00 a.m.
YVR
-
MDW
1 stop10h 19m
Delta
Tue 29/99:59 a.m.
MDW
-
YVR
2 stops10h 41m
Delta
Deal found 27/7C$ 464

Find flight deals from Vancouver Intl to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Vancouver Intl (YVR) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 31 July 2026.

Round-trip from

C$ 400

One-way from

C$ 287

Popular in

July

Cheapest in

September

Average price

C$ 719

Good round-trip deal

C$ 663 or less

Good one-way deal

C$ 363 or less
WestJet
  • WestJet
  • 4/9-13/9
  • 2 total stops
  • 15h 00m total
  • Vancouver to Chicago
Search Deals
26/8
  • 26/8
  • 2 total stops
  • 18h 44m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 78 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Vancouver Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Vancouver Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Vancouver Intl 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 31 July 2026.
Use the filters below to find and compare flights from Vancouver Intl Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 5/12

7:15 a.m.-3:39 p.m.

2 stops7h 24m

Chicago Midway

Wed 9/12

10:22 a.m.-12:59 a.m.

2 stops15h 37m

C$ 481

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 5/12

8:25 a.m.-7:25 p.m.

2 stops10h 00m

Chicago O'Hare Intl

Mon 7/12

2:03 p.m.-11:14 p.m.

2 stops10h 11m

C$ 499

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 5/9

6:00 a.m.-5:41 p.m.

1 stop9h 41m

Chicago O'Hare Intl

Sat 12/9

2:05 p.m.-10:59 p.m.

2 stops10h 54m

C$ 499

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 10/9

6:15 a.m.-6:01 p.m.

1 stop9h 46m

Chicago O'Hare Intl

Wed 16/9

5:44 p.m.-10:59 p.m.

1 stop7h 15m

C$ 509

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 19/10

2:20 p.m.-11:59 p.m.

1 stop7h 39m

Chicago O'Hare Intl

Sun 1/11

8:49 a.m.-1:45 p.m.

Nonstop5h 56m

C$ 515

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 10/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Wed 16/9

2:00 p.m.-8:26 p.m.

1 stop8h 26m

C$ 562

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 10/10

9:50 a.m.-9:36 p.m.

2 stops9h 46m

Chicago O'Hare Intl

Tue 13/10

5:30 p.m.-10:59 p.m.

1 stop7h 29m

C$ 565

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 21/8

7:00 a.m.-9:30 p.m.

1 stop12h 30m

Chicago O'Hare Intl

Tue 8/9

7:48 p.m.-10:25 p.m.

Nonstop4h 37m

C$ 569
Quickest round-trip

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 16/10

1:45 p.m.-8:06 p.m.

Nonstop4h 21m

Chicago O'Hare Intl

Mon 19/10

8:49 a.m.-11:33 a.m.

Nonstop4h 44m

C$ 571

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 4/12

7:15 a.m.-3:39 p.m.

2 stops7h 24m

Chicago Midway

Fri 11/12

12:30 p.m.-12:59 a.m.

2 stops13h 29m

C$ 583

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/7

Showing 1-10 of 34 resultsSorted by cheapest first
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Best time to book a flight from Vancouver Intl to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Vancouver Intl 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 Vancouver Intl Airport to Chicago

What is the cheapest month to book a flight from Vancouver Intl Airport to Chicago?

Currently, October is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago (average of C$ 350). Flying from Vancouver Intl Airport to Chicago in July is currently the most expensive (average of C$ 772). 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 YVR to CHI?

Find hourly flight availability from Vancouver Intl 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 2026.

When flying from Vancouver Intl Airport 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 Vancouver Intl Airport to Chicago

Explore weekly flight availability from Vancouver Intl 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 2026.

The most flights from YVR to CHI are scheduled on a Thursday (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 Vancouver Intl Airport to Chicago?

Airfare is typical for this route at the moment.
Vancouver Intl Airport to Chicago flights typically cost between C$ 356 and C$ 693 in September.
The cheapest round-trip price found within the last 5 days was C$ 400 on WestJet (4 Sep-13 Sep).

What’s the top layover airport for flights from Vancouver Intl Airport to Chicago?

Share of one-stop round-trip flights from Vancouver Intl Airport to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Calgary (YYC) – chosen by Cheapflights users on 89% of one-stop itineraries from Vancouver Intl Airport to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Vancouver Intl Airport to Chicago?

Average round-trip fare for 1-stop flights from Vancouver Intl Airport to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 351.

What’s the fastest layover option from Vancouver Intl Airport to Chicago?

Shortest average travel time for 1-stop one-way flights from Vancouver Intl Airport to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 7h 25m.

Which airport typically offers the quickest layover for flights from Vancouver Intl Airport to Chicago?

Average layover duration for 1-stop one-way flights from Vancouver Intl Airport to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 1h 30m.

How far ahead should I book a flight from Vancouver Intl Airport to Chicago?

Booking 44 days in advance of your planned departure date is, on average, the best time to get cheap flights from Vancouver Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 31 July 2026.
See what other customers who have flown with United Airlines,WestJet, andAmerican Airlines from Vancouver Intl Airport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,063 reviews
Check prices

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.7

Boarding

7.7

Crew

8.1

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
10,063 reviews
United Airlines
7.4
Good
10,063 reviews
Check prices

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.7

Boarding

7.7

Crew

8.1

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
3,423 reviews
United Airlines
7.4
Good
10,063 reviews
Check prices

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.7

Boarding

7.7

Crew

8.1

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
11,849 reviews
United Airlines
7.4
Good
10,063 reviews
Check prices

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.7

Boarding

7.7

Crew

8.1

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
11,415 reviews
United Airlines
7.4
Good
10,063 reviews
Check prices

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.7

Boarding

7.7

Crew

8.1

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 Vancouver Intl 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 Vancouver Intl Airport to Chicago?

    For as low as C$ 481, WestJet can have you in Chicago from Vancouver Intl Airport in 7h 24m. The distance from Vancouver Intl Airport to Chicago is about 2850 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the cheapest airlines flying from Vancouver Intl Airport to Chicago round-trip?

    United Airlines, at C$ 201, was found to be the cheapest airline from Vancouver Intl Airport to Chicago.Alternate airlines to your destination round-trip include WestJet and Air Canada. United Airlines is 65% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Vancouver Intl Airport to Chicago one-way?

    The cheapest airlines for a one-way flight from Vancouver Intl Airport to Chicago are United Airlines (C$ 170), Air Canada (C$ 170), and WestJet (C$ 178).

  • What are the most reliable airlines from Vancouver Intl Airport to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Vancouver Intl Airport to Chicago on time: American Airlines (65%), Finnair (60%), Air Canada (57%).

  • What are the cheapest flights from Vancouver Intl Airport to Chicago?

    On average you can expect to pay C$ 869 for a flight from Vancouver Intl Airport to Chicago. The cheapest flight overall is C$ 276 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 464.

  • Can I find deals for flights from Vancouver Intl to Chicago that include hotel bookings?

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

  • How can I find direct flights from Vancouver Intl to Chicago?

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

  • Can I find deals for business class flights from Vancouver Intl to Chicago?

    Yes. Cheapflights offers flight deals from Vancouver Intl 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 Vancouver Intl Airport to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago (average of C$ 350). Flying from Vancouver Intl Airport to Chicago in July is currently the most expensive (average of C$ 772). 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

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Fly from Vancouver Intl to Chicago on these airlines

Choose from the following airlines for your flight from Vancouver Intl to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 31 July 2026.
Air Canada flights from Vancouver Intl to Chicago
United Airlines flights from Vancouver Intl to Chicago
WestJet flights from Vancouver Intl to Chicago

Top 4 airlines flying from Vancouver Intl to Chicago

Discover the top 4 airlines that operate flights from Vancouver Intl 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 31 July 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 201AverageC$ 546FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 212AverageC$ 415FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 274AverageC$ 671FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 275AverageC$ 603FlexibilityNo 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 Vancouver Intl to Chicago?

Cheapflights makes it easy to find Vancouver Intl to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Vancouver Intl to Chicago for you. Better yet — we are completely free to use.

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

Yes, we can. To see specific flights from Vancouver Intl to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes! Start tracking prices for Vancouver Intl 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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