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Cheap flights from Vancouver to Chicago from C$ 165

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 17/2. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

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

Cheap flight deals from Vancouver to Chicago

Enter your travel dates to find the best prices.

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 12 December 2025.

Mon 29/126:40 a.m.YVR - ORD
1 stop9h 20mDelta
Wed 14/12:20 p.m.ORD - YVR
1 stop6h 24mDelta
Deal found 11/12C$ 539
Sat 27/126:00 a.m.YVR - ORD
1 stop22h 29mMultiple Airlines
Wed 14/15:57 p.m.ORD - YVR
2 stops24h 57mMultiple Airlines
Deal found 10/12C$ 553
Sat 27/127:35 a.m.YVR - ORD
1 stop10h 10mAir Canada
Wed 14/110:00 a.m.ORD - YVR
1 stop8h 27mAir Canada
Deal found 10/12C$ 567
Mon 29/126:40 a.m.YVR - ORD
1 stop9h 20mDelta
Sat 3/16:00 a.m.ORD - YVR
1 stop16h 54mDelta
Deal found 10/12C$ 585
Thu 25/123:20 p.m.YVR - ORD
1 stop6h 39mUnited Airlines
Mon 5/17:57 p.m.ORD - YVR
1 stop17h 33mUnited Airlines
Deal found 10/12C$ 593
Fri 19/125:30 a.m.YVR - ORD
1 stop7h 40mAir Canada
Tue 6/13:55 p.m.ORD - YVR
1 stop8h 25mAir Canada
Deal found 10/12C$ 618
Sat 27/126:00 a.m.YVR - ORD
1 stop22h 29mAlaska Airlines
Wed 14/13:35 p.m.ORD - YVR
1 stop29h 10mAlaska Airlines
Deal found 10/12C$ 623
Sun 28/127:00 a.m.YVR - ORD
2 stops23h 31mMultiple Airlines
Mon 12/12:20 p.m.ORD - YVR
1 stop7h 25mMultiple Airlines
Deal found 10/12C$ 641
Sun 28/128:45 a.m.YVR - ORD
1 stop12h 15mUnited Airlines
Wed 14/18:50 a.m.ORD - YVR
1 stop14h 17mUnited Airlines
Deal found 11/12C$ 661
Fri 19/128:45 a.m.YVR - ORD
1 stop13h 14mUnited Airlines
Tue 23/129:40 p.m.ORD - YVR
1 stop15h 13mUnited Airlines
Deal found 10/12C$ 666
Sat 27/1210:55 p.m.YVR - MDW
1 stop14h 25mMultiple Airlines
Wed 14/16:14 p.m.MDW - YVR
2 stops19h 15mMultiple Airlines
Deal found 10/12C$ 894
Sat 27/1212:20 p.m.YVR - MDW
2 stops19h 45mPorter Airlines
Wed 14/111:00 a.m.MDW - YVR
2 stops12h 25mPorter Airlines
Deal found 10/12C$ 953

Find 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 12 December 2025.

Round-trip from

C$ 359

One-way from

C$ 165

Popular in

December

Cheapest in

October

Average price

C$ 658
WestJet
  • WestJet
  • 12/2-16/2
  • 3 total stops
  • 20h 45m total
  • Vancouver to Chicago
Search Deals
17/2
  • 17/2
  • 1 total stop
  • 26h 58m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 126 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 12 December 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 - MDW

YVRMDW

Vancouver Intl

Sun 25/1

11:00 p.m.-11:45 a.m.

1 stop10h 45m

Chicago Midway

Sun 1/2

7:30 a.m.-10:20 p.m.

2 stops16h 50m

C$ 368

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 9/1

9:15 p.m.-10:36 p.m.

2 stops23h 21m

Chicago O'Hare Intl

Fri 16/1

2:20 p.m.-7:45 p.m.

1 stop7h 25m

C$ 390

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 1/6

7:00 a.m.-4:43 p.m.

1 stop7h 43m

Chicago O'Hare Intl

Sun 7/6

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

1 stop7h 05m

C$ 407

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 2/6

8:30 a.m.-4:43 p.m.

1 stop6h 13m

Chicago O'Hare Intl

Sun 7/6

5:30 p.m.-12:10 a.m.

1 stop8h 40m

C$ 407

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 6/6

8:30 a.m.-4:43 p.m.

1 stop6h 13m

Chicago O'Hare Intl

Sun 7/6

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

1 stop7h 05m

C$ 407

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 15/2

10:55 p.m.-3:20 p.m.

1 stop14h 25m

Chicago Midway

Sun 22/2

3:02 p.m.-11:59 p.m.

2 stops34h 57m

C$ 429

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 17/1

7:55 a.m.-11:50 p.m.

1 stop13h 55m

Chicago O'Hare Intl

Wed 21/1

8:00 a.m.-12:10 a.m.

1 stop18h 10m

C$ 444

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 14/2

6:00 a.m.-2:11 p.m.

1 stop6h 11m

Chicago O'Hare Intl

Tue 17/2

5:29 p.m.-12:10 a.m.

1 stop8h 41m

C$ 445

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 13/1

6:00 a.m.-11:50 p.m.

1 stop15h 50m

Chicago O'Hare Intl

Tue 20/1

8:00 a.m.-8:55 p.m.

1 stop14h 55m

C$ 445

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 20/1

6:00 a.m.-2:38 p.m.

1 stop6h 38m

Chicago O'Hare Intl

Tue 27/1

6:06 p.m.-4:45 p.m.

1 stop24h 39m

C$ 445

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 37 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 5 December 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, October is the cheapest month in which you can book a flight from Vancouver to Chicago (average of C$ 152). Flying from Vancouver to Chicago in January is currently the most expensive (average of C$ 354). 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 12 December 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 38% 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 12 December 2025.

The most flights from 8CA to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

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 12 December 2025.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican Airlines 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.
Delta
7.9
Good
8,007 reviews
Check prices

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews
Check prices

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,095 reviews
Delta
7.9
Good
8,007 reviews
Check prices

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,050 reviews
Delta
7.9
Good
8,007 reviews
Check prices

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
WestJet
7.2
Good
3,195 reviews
Delta
7.9
Good
8,007 reviews
Check prices

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Air Canada
7.1
Good
10,516 reviews
Delta
7.9
Good
8,007 reviews
Check prices

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Vancouver to Chicago?

    A quick flight from Vancouver to Chicago can take about 7h 43m. WestJet provides one of the quickest options available for as low as C$ 407. The distance from Vancouver to Chicago is about 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 flying from Vancouver to Chicago round-trip?

    Our cheapest airline available from Vancouver to Chicago is United Airlines. Our recent data shows that you can find tickets from as low as C$ 198 on this airline. Additional options worth looking into are Air Canada and WestJet, starting at C$ 227 and C$ 234 round-trip. These flights start at 59% 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 United Airlines. According to our data, you can fly for as low as C$ 167. Users have also found prices from C$ 172 and C$ 193 on WestJet and Air Canada, respectively.

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

    The top 3 most reliable airlines when flying from Vancouver to Chicago are Avianca (89%), Emirates (87%) and American Airlines (85%).

  • What are the cheapest flights from Vancouver to Chicago?

    While on average a flight from Vancouver to Chicago is generally C$ 1,456, our data shows the cheapest flight currently is C$ 242. When looking at the most popular route, (Vancouver Intl - Chicago O'Hare Intl), you can expect to pay C$ 346 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, October is the cheapest month in which you can book a flight from Vancouver to Chicago (average of C$ 152). Flying from Vancouver to Chicago in January is currently the most expensive (average of C$ 354). 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 4 airlines flying from Vancouver to Chicago

Discover the top 4 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 12 December 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 202AverageC$ 482FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 234AverageC$ 339FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 235AverageC$ 422FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 254AverageC$ 476FlexibilityNo cancel feeOn-time67%
Search Air Canada 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 to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Vancouver to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Vancouver to Chicago.

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

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.

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

Not ready to book yet? You can track prices for flights from Vancouver to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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