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Cheap flights from Vancouver Intl Airport to Chicago from C$ 143

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 29/12. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
11 Oct — 18 Oct1
1 adult
1 adult, Economy

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 Wednesday or Friday and return on a Thursday

Cheap 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 11 September 2025.

Round-trip from

C$ 222

One-way from

C$ 143

Popular in

December

Cheapest in

October

Average price

C$ 417

Good round-trip deal

C$ 360 or less

Good one-way deal

C$ 388 or less
Air Canada
  • Air Canada
  • 22/10-25/10
  • 1 total stop
  • 13h 36m total
  • Vancouver to Chicago
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Air Canada
  • Air Canada
  • 9/12
  • Nonstop
  • 4h 11m total
  • Vancouver to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (C$ 63 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Vancouver Intl to Chicago (CHI).
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Price to beat on a one-way flight from Vancouver Intl to Chicago (CHI).
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Find flight deals from Vancouver Intl to Chicago

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 11 September 2025.

Wed 22/108:45 a.m.YVR - ORD
Nonstop4h 15mAir Canada
Sat 25/103:50 p.m.ORD - YVR
1 stop9h 21mAir Canada
Deal found 10/9C$ 222
Sat 22/118:30 a.m.YVR - ORD
Nonstop4h 11mAir Canada
Tue 25/1112:50 p.m.ORD - YVR
1 stop10h 00mAir Canada
Deal found 10/9C$ 224
Mon 20/108:45 a.m.YVR - ORD
Nonstop4h 15mAir Canada
Thu 23/103:45 p.m.ORD - YVR
Nonstop4h 30mAir Canada
Deal found 11/9C$ 231
Sat 20/91:45 p.m.YVR - ORD
Nonstop4h 19mUnited Airlines
Wed 24/98:51 a.m.ORD - YVR
Nonstop4h 42mUnited Airlines
Deal found 10/9C$ 233
Fri 17/1010:45 p.m.YVR - ORD
2 stops15h 58mWestJet
Sun 19/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Deal found 10/9C$ 234
Thu 23/109:30 a.m.YVR - MDW
1 stop8h 51mMultiple Airlines
Wed 29/102:06 p.m.MDW - YVR
2 stops28h 48mMultiple Airlines
Deal found 9/9C$ 238
Sat 25/108:45 a.m.YVR - ORD
Nonstop4h 15mAir Canada
Sat 1/113:55 p.m.ORD - YVR
1 stop8h 25mAir Canada
Deal found 9/9C$ 238
Fri 14/1110:30 a.m.YVR - ORD
Nonstop4h 14mUnited Airlines
Mon 17/119:18 p.m.ORD - YVR
1 stop16h 12mUnited Airlines
Deal found 10/9C$ 241
Fri 19/99:15 p.m.YVR - ORD
1 stop13h 24mWestJet
Mon 29/95:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Deal found 11/9C$ 245
Fri 17/109:30 a.m.YVR - MDW
1 stop12h 16mMultiple Airlines
Sun 19/106:20 a.m.MDW - YVR
2 stops17h 31mMultiple Airlines
Deal found 9/9C$ 247
Sat 20/91:45 p.m.YVR - ORD
Nonstop4h 19mUnited Airlines
Sun 21/97:10 a.m.ORD - YVR
1 stop8h 43mUnited Airlines
Deal found 10/9C$ 247
Tue 7/108:30 p.m.YVR - MDW
2 stops15h 08mMultiple Airlines
Tue 14/108:05 a.m.MDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 9/9C$ 248

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 11 September 2025.
Use the filters below to find and compare flights from Vancouver Intl Airport to Chicago that are best for you.

Fly from

Vancouver Intl

Fly to

Chicago

Route

Depart

Return

Price

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 3/10

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Mon 6/10

5:01 a.m.-9:51 a.m.

1 stop6h 50m

C$ 247

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 4/10

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Sun 12/10

5:01 a.m.-9:51 a.m.

1 stop6h 50m

C$ 247

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 10/10

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Fri 17/10

5:01 a.m.-9:51 a.m.

1 stop6h 50m

C$ 247

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 20/10

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Thu 23/10

5:01 a.m.-9:51 a.m.

1 stop6h 50m

C$ 247

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 8/10

2:20 p.m.-10:39 p.m.

1 stop6h 19m

Chicago O'Hare Intl

Wed 15/10

2:17 p.m.-9:49 p.m.

1 stop9h 32m

C$ 267

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 3/10

11:00 a.m.-9:30 p.m.

1 stop8h 30m

Chicago O'Hare Intl

Wed 8/10

2:17 p.m.-9:49 p.m.

1 stop9h 32m

C$ 267

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 20/9

3:00 p.m.-6:10 a.m.

1 stop13h 10m

Chicago O'Hare Intl

Mon 22/9

7:10 a.m.-1:53 p.m.

1 stop8h 43m

C$ 267

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 26/9

2:20 p.m.-10:39 p.m.

1 stop6h 19m

Chicago O'Hare Intl

Mon 29/9

5:01 a.m.-6:18 p.m.

1 stop15h 17m

C$ 267

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 4/10

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Thu 9/10

7:41 p.m.-10:18 p.m.

Nonstop4h 37m

C$ 272

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 25/9

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Fri 26/9

9:44 p.m.-9:51 a.m.

1 stop14h 07m

C$ 272

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

Showing 1-10 of 41 results
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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?

Use this chart to determine the optimal time to book a round-trip flight from Vancouver Intl to Chicago. Price data was last updated on 29 August 2025.

Booking 32 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, January is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago (average of C$ 261). Flying from Vancouver Intl Airport to Chicago in March is currently the most expensive (average of C$ 349). 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 11 September 2025.

When flying from Vancouver Intl Airport to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 34% versus a flight in the morning.

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 11 September 2025.

The most flights from YVR to CHI are scheduled on a Tuesday (11 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (10 on average).

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 73% 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$ 338.

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 Winnipeg (YWG) have the shortest average one-way travel time for 1-stop routes: 6h 35m.

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 Seattle (SEA) offer the fastest connection on this route, with an average layover time of 1h 26m.

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 11 September 2025.
See what other customers who have flown with Delta,United Airlines, 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.
Delta
8.0
Very good
7,960 reviews
Check prices

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews
Check prices

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews
Check prices

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews
Check prices

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
WestJet
7.2
Good
3,091 reviews
Delta
8.0
Very good
7,960 reviews
Check prices

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Air Canada
7.1
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews
Check prices

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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$ 247, United Airlines can have you in Chicago from Vancouver Intl Airport in 4h 19m. 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$ 211, was found to be the cheapest airline from Vancouver Intl Airport to Chicago.Alternate airlines to your destination round-trip include American Airlines and WestJet. United Airlines is 56% 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$ 143), Air Canada (C$ 143), and Delta (C$ 201).

  • 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 (86%), Air Canada (67%), United Airlines (67%).

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

    On average you can expect to pay C$ 641 for a flight from Vancouver Intl Airport to Chicago. The cheapest flight overall is C$ 198 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 226.

  • 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, January is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago (average of C$ 261). Flying from Vancouver Intl Airport to Chicago in March is currently the most expensive (average of C$ 349). 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 11 September 2025.
Air Canada flights from Vancouver Intl to Chicago
United Airlines flights from Vancouver Intl to Chicago
WestJet flights from Vancouver Intl to Chicago

Top 5 airlines flying from Vancouver Intl to Chicago

Discover the top 5 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 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 211AverageC$ 496FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 236AverageC$ 434FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 253AverageC$ 367FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 265AverageC$ 534FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 391AverageC$ 694FlexibilityNo cancel feeOn-timeN/A
Search Delta 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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