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$97+ Cheap flights from Vancouver Intl (YVR) to Chicago (CHI)

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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
Dec 24 — Dec 311
Wed 12/24
Wed 12/31
1 adult, Economy
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1. Tell us where you want to go

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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 Tuesday or Friday and return on a Thursday

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 November 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1110:10 pmYVR - ORD
1 stop13h 25mMultiple Airlines
Mon 12/1511:44 amORD - YVR
2 stops29h 01mMultiple Airlines
Deal found 11/24$245
This Kiwi.com deal was found by Cheapflights users on 11/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/410:10 pmYVR - ORD
1 stop13h 25mMultiple Airlines
Wed 12/104:01 pmORD - YVR
2 stops26h 53mMultiple Airlines
Deal found 11/23$263
This Kiwi.com deal was found by Cheapflights users on 11/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/59:15 pmYVR - ORD
2 stops12h 39mMultiple Airlines
Mon 12/89:06 pmORD - YVR
1 stop19h 47mMultiple Airlines
Deal found 11/23$293
This Kiwi.com deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:00 pmYVR - ORD
1 stop16h 27mMultiple Airlines
Sat 12/69:06 pmORD - YVR
1 stop18h 49mMultiple Airlines
Deal found 11/22$308
This Delta deal was found by Cheapflights users on 11/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/412:13 pmYVR - MDW
2 stops9h 34mDelta
Wed 12/101:50 pmMDW - YVR
2 stops12h 09mDelta
Deal found 11/23$423
This Delta deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:45 amYVR - MDW
2 stops14h 55mDelta
Thu 12/41:14 pmMDW - YVR
2 stops12h 45mDelta
Deal found 11/24$498
This Mytrip deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/410:55 pmYVR - MDW
1 stop14h 25mMultiple Airlines
Sun 12/711:00 amMDW - YVR
1 stop14h 25mMultiple Airlines
Deal found 11/22$531
This Kiwi.com deal was found by Cheapflights users on 11/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/410:55 pmYVR - MDW
1 stop14h 25mMultiple Airlines
Wed 12/102:49 pmMDW - YVR
2 stops11h 21mMultiple Airlines
Deal found 11/23$532
This Kiwi.com deal was found by Cheapflights users on 11/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:45 pmYVR - MDW
2 stops26h 13mMultiple Airlines
Wed 12/316:12 amMDW - YVR
1 stop31h 00mMultiple Airlines
Deal found 11/23$554
This Mytrip deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:55 pmYVR - MDW
1 stop10h 55mMultiple Airlines
Sun 12/711:00 amMDW - YVR
1 stop14h 25mMultiple Airlines
Deal found 11/22$564

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 November 24, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$226
(Kiwi.com)

One-way from

$97
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$424

Good round-trip deal

$299 or less

Good one-way deal

$108 or less
Provider with most accurate pricing for Vancouver Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Vancouver Intl-Chicago (CHI) flights.
Search Deals
From Vancouver Intl to Chicago (CHI)
Search Deals
One-way flight from Vancouver Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 2,558,603 searches. Data last updated November 24, 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

Thu 1/8

7:55 am-5:10 pm

1 stop7h 15m

Chicago O'Hare Intl

Thu 1/15

3:35 pm-8:55 pm

1 stop7h 20m

$323

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 12/5

8:00 am-12:13 am

1 stop14h 13m

Chicago O'Hare Intl

Mon 12/8

9:06 pm-2:53 pm

1 stop19h 47m

$327

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 3/5

3:31 pm-11:55 pm

1 stop6h 24m

Chicago O'Hare Intl

Tue 3/10

2:20 pm-10:53 pm

1 stop10h 33m

$333

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 2/12

7:35 pm-1:11 pm

2 stops15h 36m

Chicago O'Hare Intl

Tue 2/17

2:07 pm-12:10 am

2 stops12h 03m

$349

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 2/12

5:45 pm-1:11 pm

2 stops17h 26m

Chicago O'Hare Intl

Thu 2/19

7:00 am-8:55 pm

1 stop15h 55m

$352

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 1/9

7:25 am-5:44 pm

2 stops8h 19m

Chicago O'Hare Intl

Sat 1/17

6:50 am-6:44 pm

2 stops13h 54m

$359

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/5

7:37 pm-8:54 am

2 stops11h 17m

Chicago Midway

Tue 3/10

9:20 am-8:52 pm

2 stops13h 32m

$391

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 12/4

12:13 pm-11:47 pm

2 stops9h 34m

Chicago Midway

Wed 12/10

1:50 pm-11:59 pm

2 stops12h 09m

$423

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 3/13

3:45 pm-11:20 am

2 stops17h 35m

Chicago Midway

Sun 3/22

12:33 pm-11:12 am

1 stop24h 39m

$461

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 1/17

6:20 am-10:07 pm

2 stops13h 47m

Chicago Midway

Thu 1/29

1:26 pm-11:59 pm

2 stops12h 33m

$464

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 32 results
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Compare providers for flights from Vancouver Intl to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Vancouver Intl to Chicago in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Vancouver Intl Airport-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Vancouver Intl Airport-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Vancouver Intl Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Vancouver Intl Airport-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Vancouver Intl Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 November 21, 2025.

The price you pay for your flight from Vancouver Intl Airport to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 32 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, October is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago (average of $113). Flying from Vancouver Intl Airport to Chicago in January is currently the most expensive (average of $257). 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 November 24, 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 40% 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 November 24, 2025.

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

The best insider tips for Vancouver Intl Airport to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Vancouver Intl Airport to Chicago trip
Airports
YVR

Security screenings at YVR are usually quick, averaging under ten minutes. Check live wait times online to plan your arrival accordingly.

Read more about YVRby Brandon Schultz
ORD

At ORD, Global Entry lanes are always open for expedited immigration. Prepare for long walks to reach immigration in Terminal 5.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on YVR

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

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 November 24, 2025.
Get a feel of what it's like to fly with United Airlines, American Airlines, and WestJet from Vancouver Intl Airport to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,039 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,039 reviews
United Airlines
7.4
Good
9,039 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,043 reviews
United Airlines
7.4
Good
9,039 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,172 reviews
United Airlines
7.4
Good
9,039 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,466 reviews
United Airlines
7.4
Good
9,039 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 $333, Alaska Airlines can have you in Chicago from Vancouver Intl Airport in 6h 24m. Airlines will cover a distance of 1758 mi. This flight may include one or multiple stops.

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

    Cheapflights users have booked flights from Vancouver Intl Airport to Chicago round-trip from $110. Other airlines that can offer you cheap pricing are Air Canada, from $155, and American Airlines, from $167. Users have found that United Airlines is 68% cheaper than the other options available to this destination.

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

    For one-way options, check prices for WestJet. According to our data, you can fly for as low as $112. Users have also found prices from $178 and $195 on Alaska Airlines and Delta, respectively.

  • 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: Avianca (91%), American Airlines (86%), Emirates (84%).

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

    While on average a flight from Vancouver Intl Airport to Chicago is generally $566, our data shows the cheapest flight currently is $106. When looking at the most popular route, (Vancouver Intl - Chicago O'Hare Intl), you can expect to pay $266 for that flight.

  • 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, October is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago (average of $113). Flying from Vancouver Intl Airport to Chicago in January is currently the most expensive (average of $257). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Alternative routes for Vancouver Intl to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Vancouver Intl to O'Hare Intl flights
Vancouver Intl to Midway flights
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Top 3 airlines flying from Vancouver Intl to Chicago

Discover the top 3 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 2,558,603 searches. Data last updated November 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$110Average$366FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$155Average$413FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$167Average$370FlexibilityNo cancel feeOn-time71%

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