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Cheap flights from Vancouver to Chicago from C$ 240

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 30/8. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
3 Aug — 10 Aug1
1 adult

Cheapflights Tip: The best prices from Vancouver to Chicago are usually found in April or January, booked 32 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from Vancouver to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Vancouver (8CA) 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 29 July 2025.

Round-trip from

C$ 320

One-way from

C$ 240

Popular in

July

Cheapest in

April

Average price

C$ 627
WestJet
  • WestJet
  • 10/9-14/9
  • 3 total stops
  • 17h 24m total
  • Vancouver to Chicago
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30/8
  • 30/8
  • 2 total stops
  • 17h 56m total
  • Vancouver to Chicago
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Highest demand for flights based on searches. 3% potential increase in price (C$ 25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 18 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Vancouver to Chicago

Cheapest flights from Vancouver to Chicago
Explore the most affordable flight options available from Vancouver to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 29 July 2025.

Wed 10/96:00 a.m.YVR - ORD
2 stops8h 43mWestJet
Sun 14/95:30 p.m.ORD - YVR
1 stop8h 41mWestJet
Deal found 29/7C$ 320
Tue 19/88:30 p.m.YVR - ORD
2 stops17h 56mMultiple Airlines
Thu 21/85:30 p.m.ORD - YVR
1 stop7h 05mMultiple Airlines
Deal found 27/7C$ 331
Wed 17/98:45 a.m.YVR - ORD
Nonstop4h 15mAir Canada
Sat 20/93:45 p.m.ORD - YVR
Nonstop4h 30mAir Canada
Deal found 29/7C$ 359
Tue 19/811:00 p.m.YVR - MDW
1 stop13h 01mMultiple Airlines
Thu 21/811:03 a.m.MDW - YVR
1 stop11h 49mMultiple Airlines
Deal found 27/7C$ 390
Wed 13/811:50 p.m.YVR - ORD
Nonstop4h 08mAmerican Airlines
Thu 21/88:20 p.m.ORD - YVR
Nonstop4h 34mAmerican Airlines
Deal found 27/7C$ 414
Tue 9/96:20 a.m.YVR - MDW
2 stops10h 17mDelta
Tue 16/99:20 a.m.MDW - YVR
2 stops11h 33mDelta
Deal found 27/7C$ 446
Wed 26/117:00 a.m.YVR - MDW
2 stops30h 20mPorter Airlines
Sun 30/1111:00 a.m.MDW - YVR
2 stops26h 15mPorter Airlines
Deal found 27/7C$ 776

Cheapflights Fare Finder

 
Customize your flight search to find flights from Vancouver 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 29 July 2025.
Use the filters below to find and compare flights from Vancouver to Chicago that are best for you.

Fly from

Vancouver

Fly to

Chicago

Route

Depart

Return

Price

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 10/9

6:00 a.m.-4:43 p.m.

2 stops8h 43m

Chicago O'Hare Intl

Sun 14/9

5:30 p.m.-12:11 a.m.

1 stop8h 41m

C$ 320

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 19/8

8:30 p.m.-4:26 p.m.

2 stops17h 56m

Chicago O'Hare Intl

Thu 21/8

5:30 p.m.-10:35 p.m.

1 stop7h 05m

C$ 331

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 17/9

8:45 a.m.-3:00 p.m.

Nonstop4h 15m

Chicago O'Hare Intl

Sat 20/9

3:45 p.m.-6:15 p.m.

Nonstop4h 30m

C$ 359

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 19/8

11:00 p.m.-2:01 p.m.

1 stop13h 01m

Chicago Midway

Thu 21/8

11:03 a.m.-8:52 p.m.

1 stop11h 49m

C$ 390

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 13/8

11:50 p.m.-5:58 a.m.

Nonstop4h 08m

Chicago O'Hare Intl

Thu 21/8

8:20 p.m.-10:54 p.m.

Nonstop4h 34m

C$ 414

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 9/9

6:20 a.m.-6:37 p.m.

2 stops10h 17m

Chicago Midway

Tue 16/9

9:20 a.m.-6:53 p.m.

2 stops11h 33m

C$ 446

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 26/11

7:00 a.m.-3:20 p.m.

2 stops30h 20m

Chicago Midway

Sun 30/11

11:00 a.m.-11:15 a.m.

2 stops26h 15m

C$ 776

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 30/8

8:30 p.m.-4:26 p.m.

2 stops17h 56m

C$ 240

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 31/8

7:07 p.m.-5:00 a.m.

1 stop7h 53m

C$ 241

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 17/8

7:00 a.m.-4:44 p.m.

1 stop7h 44m

C$ 246

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

Showing 1-10 of 18 results
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Best time to book a flight from Vancouver to Chicago

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

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

Use this chart to determine the optimal time to book a round-trip flight from Vancouver to Chicago. Price data was last updated on 25 July 2025.

To ensure you get the cheapest price possible for a flight from Vancouver to Chicago, you should look to book at least 32 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, January is the cheapest month in which you can book a flight from Vancouver to Chicago (average of C$ 261). Flying from Vancouver to Chicago in March is currently the most expensive (average of C$ 352). 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 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 29 July 2025.

When flying from Vancouver 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 to Chicago

Explore weekly flight availability from Vancouver 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 29 July 2025.

The most flights from 8CA to CHI are scheduled on a Monday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (11 on average).

How much does it cost to fly round-trip from Vancouver 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 29 July 2025.
Read reviews from past customers who have flown Alaska Airlines,Porter Airlines, andDelta from Vancouver 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.
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Overall

8.0

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Overall

8.0

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Porter Airlines
8.0
Very good
317 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Overall

8.0

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Delta
8.0
Very good
7,977 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Overall

8.0

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
United Airlines
7.4
Good
8,893 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Overall

8.0

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Overall

8.0

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave

Related info for your journey

Find useful and relevant information for your journey from Vancouver to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Our cheapest airline available from Vancouver to Chicago is WestJet. Our recent data shows that you can find tickets from as low as C$ 320 on this airline. Additional options worth looking into are Air Canada and American Airlines, starting at C$ 359 and C$ 414 round-trip. These flights start at 35% lower than the current average price 3 months from now.

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

    For one-way options, check prices for Alaska Airlines. According to our data, you can fly for as low as C$ 241. Users have also found prices from C$ 246 and C$ 247 on WestJet and American Airlines, respectively.

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

    The top 3 most reliable airlines when flying from Vancouver to Chicago are Air Canada (70%), United Airlines (70%) and Avianca (53%).

  • What are the cheapest flights from Vancouver to Chicago?

    While on average a flight from Vancouver to Chicago is generally C$ 1,655, our data shows the cheapest flight currently is C$ 246. When looking at the most popular route, (Vancouver Intl - Chicago O'Hare Intl), you can expect to pay C$ 309 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Vancouver 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 to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Vancouver to Chicago (average of C$ 261). Flying from Vancouver to Chicago in March is currently the most expensive (average of C$ 352). 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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Top 5 airlines flying from Vancouver to Chicago

Discover the top 5 airlines that operate flights from Vancouver 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 29 July 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 233AverageC$ 442FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 289AverageC$ 364FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 313AverageC$ 540FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 363AverageC$ 527FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 387AverageC$ 687FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

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How does Cheapflights help users find flights from Vancouver to Chicago?

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

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