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$102+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Vancouver Intl to Chicago are usually found in September or October, booked 32 days in advance, depart on a Tuesday or Wednesday 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 September 15, 2025.

Round-trip from

$149
(Trip.com)

One-way from

$102
(Gotogate)

Popular in

November

Cheapest in

September

Average price

$291

Good round-trip deal

$225 or less

Good one-way deal

$188 or less
From Vancouver Intl to Chicago (CHI)
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One-way flight from Vancouver Intl to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 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 September 15, 2025.

This Trip.com deal was found by Cheapflights users on 9/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/127:00 amYVR - ORD
1 stop7h 43mWestJet
Sun 10/195:30 pmORD - YVR
1 stop8h 41mWestJet
Deal found 9/13$149
This Booking.com deal was found by Cheapflights users on 9/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/288:30 amYVR - ORD
Nonstop4h 11mAir Canada
Tue 11/43:40 pmORD - YVR
Nonstop4h 35mAir Canada
Deal found 9/13$154
This Trip.com deal was found by Cheapflights users on 9/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:00 amYVR - ORD
1 stop7h 43mWestJet
Mon 10/272:20 pmORD - YVR
1 stop7h 25mWestJet
Deal found 9/14$156
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 10/127:00 amYVR - ORD
1 stop7h 43mWestJet
Fri 10/175:30 pmORD - YVR
1 stop7h 06mWestJet
Deal found 9/14$157
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/177:00 amYVR - ORD
1 stop7h 43mWestJet
Thu 10/235:30 pmORD - YVR
1 stop7h 06mWestJet
Deal found 9/14$160
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/167:00 amYVR - ORD
1 stop7h 43mWestJet
Thu 10/235:30 pmORD - YVR
1 stop8h 41mWestJet
Deal found 9/14$161
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sat 10/187:00 amYVR - ORD
1 stop7h 43mWestJet
Fri 10/245:30 pmORD - YVR
1 stop7h 06mWestJet
Deal found 9/14$165
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/2911:00 pmYVR - MDW
1 stop17h 39mMultiple Airlines
Wed 11/52:06 pmMDW - YVR
1 stop23h 06mMultiple Airlines
Deal found 9/14$200
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 10/208:30 pmYVR - MDW
2 stops15h 08mMultiple Airlines
Wed 10/228:05 amMDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 9/14$202
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/29:30 amYVR - MDW
1 stop12h 11mMultiple Airlines
Mon 10/66:20 amMDW - YVR
1 stop16h 28mMultiple Airlines
Deal found 9/13$204
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sat 10/49:30 amYVR - MDW
1 stop12h 11mMultiple Airlines
Tue 10/78:05 amMDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 9/13$206
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/2911:00 pmYVR - MDW
1 stop17h 39mMultiple Airlines
Mon 11/31:37 pmMDW - YVR
2 stops29h 17mMultiple Airlines
Deal found 9/13$231

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 September 15, 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

Tue 9/30

1:45 pm-8:04 pm

Nonstop4h 19m

Chicago O'Hare Intl

Sun 10/12

8:51 am-11:33 am

Nonstop4h 42m

$168

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 10/30

12:35 pm-11:59 pm

1 stop9h 24m

Chicago O'Hare Intl

Thu 11/6

1:10 pm-3:50 pm

Nonstop4h 40m

$183

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 10/17

1:25 pm-10:39 pm

1 stop7h 14m

Chicago O'Hare Intl

Wed 10/22

8:51 am-11:33 am

Nonstop4h 42m

$183

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 12/9

8:30 am-9:08 pm

1 stop10h 38m

Chicago O'Hare Intl

Thu 12/11

9:00 am-6:45 pm

1 stop11h 45m

$193

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 9/25

1:45 pm-8:04 pm

Nonstop4h 19m

Chicago O'Hare Intl

Tue 10/7

6:15 am-1:12 pm

1 stop8h 57m

$197

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 10/20

1:45 pm-8:04 pm

Nonstop4h 19m

Chicago O'Hare Intl

Wed 10/22

7:41 pm-10:18 pm

Nonstop4h 37m

$197

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 10/16

1:45 pm-8:04 pm

Nonstop4h 19m

Chicago O'Hare Intl

Wed 10/22

5:01 am-9:51 am

1 stop6h 50m

$197

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 10/31

3:05 pm-5:16 am

1 stop12h 11m

Chicago O'Hare Intl

Sat 11/1

1:10 pm-3:50 pm

Nonstop4h 40m

$197

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 9/25

1:45 pm-8:04 pm

Nonstop4h 19m

Chicago O'Hare Intl

Mon 10/6

7:41 pm-10:18 pm

Nonstop4h 37m

$197

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 9/25

1:45 pm-8:04 pm

Nonstop4h 19m

Chicago O'Hare Intl

Sun 9/28

5:01 am-9:51 am

1 stop6h 50m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 40 results
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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

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 September 12, 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, August is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago (average of $245). Flying from Vancouver Intl Airport to Chicago in March is currently the most expensive (average of $321). 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 September 15, 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 25% versus a flight in the evening.

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 September 15, 2025.

The most flights from YVR to CHI are scheduled on a Tuesday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 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 September 15, 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
8,931 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,931 reviews
United Airlines
7.4
Good
8,931 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,931 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
WestJet
7.2
Good
3,091 reviews
United Airlines
7.4
Good
8,931 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,931 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 $168, United Airlines can have you in Chicago from Vancouver Intl Airport in 4h 19m. 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 $155. Other airlines that can offer you cheap pricing are United Airlines, from $186, and American Airlines, from $208. Users have found that Air Canada is 55% 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 United Airlines. According to our data, you can fly for as low as $103. Users have also found prices from $103 and $146 on Air Canada 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: Emirates (86%), Air Canada (67%), United Airlines (67%).

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

    While on average a flight from Vancouver Intl Airport to Chicago is generally $504, our data shows the cheapest flight currently is $104. When looking at the most popular route, (Vancouver Intl - Chicago O'Hare Intl), you can expect to pay $167 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, August is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago (average of $245). Flying from Vancouver Intl Airport to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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
Vancouver Intl to St. Louis flights
Vancouver Intl to Paducah flights
Vancouver Intl to Peoria flights

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$155Average$402FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$186Average$381FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$208Average$370FlexibilityNo cancel feeOn-time71%

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