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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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
26 Nov — 3 Dec1
1 adult
1 adult, Economy, 0 bags

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

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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 27 October 2025.

Fri 5/129:15 p.m.YVR - ORD
2 stops12h 39mMultiple Airlines
Mon 8/1212:59 p.m.ORD - YVR
1 stop11h 21mMultiple Airlines
Deal found 24/10C$ 274
Sun 23/1111:00 p.m.YVR - ORD
1 stop23h 08mMultiple Airlines
Thu 27/116:45 p.m.ORD - YVR
1 stop29h 35mMultiple Airlines
Deal found 25/10C$ 290
Fri 5/1211:00 p.m.YVR - MDW
1 stop12h 59mMultiple Airlines
Mon 8/128:42 p.m.MDW - YVR
2 stops20h 03mMultiple Airlines
Deal found 24/10C$ 301
Mon 10/117:45 p.m.YVR - ORD
2 stops13h 29mMultiple Airlines
Wed 19/1112:37 p.m.ORD - YVR
1 stop24h 35mMultiple Airlines
Deal found 26/10C$ 316
Wed 24/121:45 p.m.YVR - ORD
Nonstop4h 09mUnited Airlines
Mon 12/13:40 p.m.ORD - YVR
Nonstop4h 35mUnited Airlines
Deal found 26/10C$ 323
Fri 14/1111:00 p.m.YVR - ORD
1 stop10h 30mMultiple Airlines
Wed 19/113:26 p.m.ORD - YVR
2 stops21h 46mMultiple Airlines
Deal found 26/10C$ 330
Sun 9/1111:00 p.m.YVR - ORD
2 stops23h 59mMultiple Airlines
Wed 19/1112:37 p.m.ORD - YVR
1 stop24h 35mMultiple Airlines
Deal found 26/10C$ 332
Sun 9/1111:00 p.m.YVR - ORD
1 stop9h 41mMultiple Airlines
Fri 14/115:11 a.m.ORD - YVR
2 stops19h 34mMultiple Airlines
Deal found 26/10C$ 333
Wed 24/121:45 p.m.YVR - ORD
Nonstop4h 09mUnited Airlines
Tue 13/17:00 a.m.ORD - YVR
1 stop8h 58mUnited Airlines
Deal found 25/10C$ 337
Fri 26/121:55 p.m.YVR - ORD
1 stop7h 05mUnited Airlines
Mon 12/13:40 p.m.ORD - YVR
Nonstop4h 35mUnited Airlines
Deal found 25/10C$ 344
Fri 26/127:32 p.m.YVR - MDW
2 stops11h 17mDelta
Mon 12/11:28 p.m.MDW - YVR
2 stops12h 35mDelta
Deal found 26/10C$ 365
Wed 24/129:15 p.m.YVR - MDW
2 stops18h 23mMultiple Airlines
Sun 11/18:26 p.m.MDW - YVR
1 stop22h 05mMultiple Airlines
Deal found 26/10C$ 389

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 27 October 2025.

Round-trip from

C$ 274

One-way from

C$ 165

Popular in

November

Cheapest in

September

Average price

C$ 430
5/12-8/12
  • 5/12-8/12
  • 3 total stops
  • 24h 00m total
  • Vancouver to Chicago
Search Deals
3/12
  • 3/12
  • 1 total stop
  • 21h 12m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 27 October 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 23/11

9:10 a.m.-2:48 p.m.

1 stop27h 38m

Chicago Midway

Thu 27/11

6:05 a.m.-10:45 p.m.

2 stops18h 40m

C$ 312

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 1/4

8:30 a.m.-2:43 p.m.

Nonstop4h 13m

Chicago O'Hare Intl

Sun 19/4

7:15 a.m.-1:55 p.m.

1 stop8h 40m

C$ 337

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 30/3

3:20 p.m.-11:57 p.m.

1 stop6h 37m

Chicago O'Hare Intl

Wed 15/4

8:45 a.m.-11:24 a.m.

Nonstop4h 39m

C$ 344

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 23/12

8:30 a.m.-2:41 p.m.

Nonstop4h 11m

Chicago O'Hare Intl

Sun 11/1

3:40 p.m.-6:15 p.m.

Nonstop4h 35m

C$ 357

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 22/12

8:30 a.m.-2:41 p.m.

Nonstop4h 11m

Chicago O'Hare Intl

Fri 16/1

3:40 p.m.-6:15 p.m.

Nonstop4h 35m

C$ 357

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 23/12

8:30 a.m.-2:41 p.m.

Nonstop4h 11m

Chicago O'Hare Intl

Sat 10/1

3:40 p.m.-6:15 p.m.

Nonstop4h 35m

C$ 357

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 31/3

11:39 a.m.-11:44 p.m.

1 stop10h 05m

Chicago O'Hare Intl

Sat 18/4

6:00 a.m.-10:59 a.m.

1 stop6h 59m

C$ 358

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 14/11

10:30 a.m.-4:44 p.m.

Nonstop4h 14m

Chicago O'Hare Intl

Tue 18/11

9:30 p.m.-10:53 a.m.

1 stop15h 23m

C$ 358

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 4/4

6:05 p.m.-6:08 a.m.

1 stop10h 03m

Chicago O'Hare Intl

Wed 15/4

7:15 a.m.-2:02 p.m.

1 stop8h 47m

C$ 358

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 4/4

6:05 p.m.-6:08 a.m.

1 stop10h 03m

Chicago O'Hare Intl

Sun 19/4

5:15 a.m.-5:48 p.m.

1 stop14h 33m

C$ 358

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/10

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 24 October 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$ 160). Flying from Vancouver to Chicago in January is currently the most expensive (average of C$ 355). 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 27 October 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 32% 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 27 October 2025.

The most flights from 8CA to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (7 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 27 October 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
7,996 reviews
Check prices

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Delta
7.9
Good
7,996 reviews
Delta
7.9
Good
7,996 reviews
Check prices

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
United Airlines
7.4
Good
8,997 reviews
Delta
7.9
Good
7,996 reviews
Check prices

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
American Airlines
7.2
Good
11,033 reviews
Delta
7.9
Good
7,996 reviews
Check prices

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
WestJet
7.2
Good
3,148 reviews
Delta
7.9
Good
7,996 reviews
Check prices

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Air Canada
7.1
Good
10,370 reviews
Delta
7.9
Good
7,996 reviews
Check prices

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!

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 4h 13m. United Airlines provides one of the quickest options available for as low as C$ 337. 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$ 208 on this airline. Additional options worth looking into are WestJet and American Airlines, starting at C$ 237 and C$ 238 round-trip. These flights start at 57% lower than the current average price 3 months from now.

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

    The top 3 most reliable airlines when flying from Vancouver to Chicago are Emirates (83%), American Airlines (75%) and Qatar Airways (65%).

  • What are the cheapest flights from Vancouver to Chicago?

    While on average a flight from Vancouver to Chicago is generally C$ 529, our data shows the cheapest flight currently is C$ 170. When looking at the most popular route, (Vancouver Intl - Chicago O'Hare Intl), you can expect to pay C$ 323 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$ 160). Flying from Vancouver to Chicago in January is currently the most expensive (average of C$ 355). 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 27 October 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 208AverageC$ 491FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 237AverageC$ 360FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 238AverageC$ 428FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 267AverageC$ 533FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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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.

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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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