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Cheap flights from Vancouver Intl Airport 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 10/8. 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 Vancouver Intl 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 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 3 May 2026.

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
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
Tue 2/611:57 p.m.
YVR
-
ORD
Nonstop4h 12m
American Airlines
Tue 9/610:34 p.m.
ORD
-
YVR
1 stop16h 11m
American Airlines
Deal found 1/5C$ 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
Fri 29/55:30 p.m.
ORD
-
YVR
1 stop16h 10m
WestJet
Deal found 28/4C$ 504
Fri 4/96:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Tue 8/95:30 p.m.
ORD
-
YVR
1 stop8h 45m
WestJet
Deal found 27/4C$ 506
Sat 5/96:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Fri 11/95:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 27/4C$ 507
Fri 22/51:25 p.m.
YVR
-
ORD
Nonstop4h 30m
American Airlines
Mon 25/58:15 p.m.
ORD
-
YVR
Nonstop4h 45m
American Airlines
Deal found 30/4C$ 508

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 3 May 2026.

Round-trip from

C$ 484

One-way from

C$ 265

Popular in

December

Cheapest in

October

Average price

C$ 526

Good round-trip deal

C$ 583 or less

Good one-way deal

C$ 249 or less
3/9-10/9
  • 3/9-10/9
  • 3 total stops
  • 16h 19m total
  • Vancouver to Chicago
Search Deals
10/8
  • 10/8
  • 3 total stops
  • 35h 48m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 124 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 May 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 3 May 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
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

1:20 p.m.-9:57 p.m.

1 stop6h 37m

Chicago O'Hare Intl

Mon 22/6

6:55 a.m.-2:53 p.m.

1 stop9h 58m

C$ 529

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

3:00 p.m.-12:58 a.m.

1 stop7h 58m

Chicago O'Hare Intl

Sat 10/10

12:45 p.m.-6:18 p.m.

1 stop7h 33m

C$ 614

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 - ORD

YVRORD

Vancouver Intl

Mon 22/6

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

Nonstop4h 05m

Chicago O'Hare Intl

Sun 5/7

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

1 stop6h 51m

C$ 618

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 26/8

2:20 p.m.-10:41 p.m.

1 stop6h 21m

Chicago O'Hare Intl

Sat 29/8

1:30 p.m.-10:56 p.m.

1 stop11h 26m

C$ 621

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 - ORD

YVRORD

Vancouver Intl

Sat 10/10

6:15 a.m.-4:49 p.m.

1 stop8h 34m

Chicago O'Hare Intl

Tue 13/10

7:00 a.m.-2:40 p.m.

1 stop9h 40m

C$ 641

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 1/6

6:20 a.m.-6:50 p.m.

2 stops10h 30m

Chicago O'Hare Intl

Thu 4/6

5:30 p.m.-12:15 a.m.

1 stop8h 45m

C$ 641

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/4

Showing 1-10 of 37 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

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

Booking 31 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.

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

Currently, August is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago (average of C$ 103). Flying from Vancouver Intl Airport to Chicago in January is currently the most expensive (average of C$ 435). 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 3 May 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 3 May 2026.

The most flights from YVR 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 Vancouver Intl Airport to Chicago?

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 80% 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$ 344.

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 02m.

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 15m.

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.
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
9,684 reviews
Check prices

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Entertainment

7.1

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
9,684 reviews
United Airlines
7.4
Good
9,684 reviews
Check prices

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Entertainment

7.1

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
3,331 reviews
United Airlines
7.4
Good
9,684 reviews
Check prices

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Entertainment

7.1

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
11,673 reviews
United Airlines
7.4
Good
9,684 reviews
Check prices

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Entertainment

7.1

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
10,993 reviews
United Airlines
7.4
Good
9,684 reviews
Check prices

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Entertainment

7.1

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$ 510, United Airlines can have you in Chicago from Vancouver Intl Airport in 4h 05m. The distance from Vancouver Intl Airport to Chicago is about 2829 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$ 195, was found to be the cheapest airline from Vancouver Intl Airport to Chicago.Alternate airlines to your destination round-trip include Air Canada and WestJet. United Airlines is 63% 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$ 165), WestJet (C$ 169), and Air Canada (C$ 222).

  • 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: Emirates (100%), United Airlines (89%), Air Canada (79%).

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

    On average you can expect to pay C$ 1,000 for a flight from Vancouver Intl Airport 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 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, August is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago (average of C$ 103). Flying from Vancouver Intl Airport to Chicago in January is currently the most expensive (average of C$ 435). 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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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 3 May 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 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 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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