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Cheap flights from Vancouver Intl Airport to Chicago from C$ 123

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 22/5. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
14 Jan — 21 Jan1
1 adult
1 adult, Economy, 0 bags

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 Wednesday or Tuesday and return on a Thursday

Cheap flight deals from Vancouver Intl to Chicago

Enter your travel dates to find the best prices.

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 15 December 2025.

Wed 17/123:40 p.m.YVR - ORD
2 stops16h 38mMultiple Airlines
Wed 7/17:57 p.m.ORD - YVR
1 stop28h 23mMultiple Airlines
Deal found 13/12C$ 472
Sun 14/127:35 p.m.YVR - ORD
1 stop8h 46mMultiple Airlines
Sun 18/110:41 p.m.ORD - YVR
1 stop25h 39mMultiple Airlines
Deal found 14/12C$ 558
Sat 27/128:30 a.m.YVR - ORD
Nonstop4h 11mAir Canada
Mon 5/13:35 p.m.ORD - YVR
Nonstop4h 35mAir Canada
Deal found 14/12C$ 563
Tue 23/121:45 p.m.YVR - ORD
Nonstop4h 09mUnited Airlines
Wed 7/16:47 a.m.ORD - YVR
1 stop8h 48mUnited Airlines
Deal found 13/12C$ 587
Tue 23/121:45 p.m.YVR - ORD
Nonstop4h 09mUnited Airlines
Tue 6/17:10 a.m.ORD - YVR
2 stops16h 08mUnited Airlines
Deal found 13/12C$ 595
Sun 28/1211:24 a.m.YVR - ORD
1 stop10h 35mDelta
Wed 14/12:20 p.m.ORD - YVR
1 stop8h 34mDelta
Deal found 14/12C$ 599
Sun 28/125:30 a.m.YVR - ORD
1 stop7h 40mAir Canada
Wed 14/13:35 p.m.ORD - YVR
Nonstop4h 35mAir Canada
Deal found 14/12C$ 613
Wed 17/123:40 p.m.YVR - ORD
2 stops16h 38mMultiple Airlines
Tue 6/17:44 p.m.ORD - YVR
1 stop21h 09mMultiple Airlines
Deal found 13/12C$ 633
Sun 14/1212:13 p.m.YVR - MDW
2 stops9h 34mDelta
Wed 14/11:49 p.m.MDW - YVR
2 stops12h 26mDelta
Deal found 14/12C$ 804
Sun 14/1210:55 p.m.YVR - MDW
1 stop14h 25mMultiple Airlines
Sun 18/16:01 p.m.MDW - YVR
2 stops23h 44mMultiple Airlines
Deal found 14/12C$ 951
Wed 24/122:25 p.m.YVR - MDW
2 stops24h 54mWestJet
Sun 4/16:08 p.m.MDW - YVR
2 stops20h 56mWestJet
Deal found 13/12C$ 972
Sun 14/1211:00 p.m.YVR - MDW
2 stops11h 34mDelta
Sun 18/19:32 a.m.MDW - YVR
2 stops13h 22mDelta
Deal found 14/12C$ 983

Find 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 15 December 2025.

Round-trip from

C$ 361

One-way from

C$ 123

Popular in

December

Cheapest in

October

Average price

C$ 682

Good round-trip deal

C$ 569 or less

Good one-way deal

C$ 457 or less
29/1-5/2
  • 29/1-5/2
  • 3 total stops
  • 53h 13m total
  • Vancouver to Chicago
Search Deals
WestJet
  • WestJet
  • 22/5
  • 1 total stop
  • 6h 13m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 135 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 629,999 searches. Data last updated 15 December 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 - MDW

YVRMDW

Vancouver Intl

Thu 19/2

12:05 p.m.-11:51 p.m.

1 stop9h 46m

Chicago Midway

Tue 24/2

11:05 a.m.-11:25 p.m.

1 stop14h 20m

C$ 365

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 19/2

12:05 p.m.-11:51 p.m.

1 stop9h 46m

Chicago Midway

Wed 25/2

11:05 a.m.-11:25 p.m.

1 stop14h 20m

C$ 365

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 27/1

9:00 p.m.-9:03 p.m.

3 stops22h 03m

Chicago O'Hare Intl

Tue 3/2

2:00 p.m.-8:05 a.m.

2 stops20h 05m

C$ 430

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 5/3

5:55 p.m.-1:35 p.m.

2 stops17h 40m

Chicago O'Hare Intl

Tue 10/3

10:00 a.m.-11:50 p.m.

2 stops15h 50m

C$ 434

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 29/1

3:40 p.m.-8:29 p.m.

1 stop26h 49m

Chicago O'Hare Intl

Thu 5/2

6:06 p.m.-12:10 a.m.

1 stop8h 04m

C$ 442

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 14/5

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

2 stops8h 43m

Chicago O'Hare Intl

Sun 24/5

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

1 stop8h 40m

C$ 443

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 12/1

10:05 p.m.-5:52 p.m.

3 stops17h 47m

Chicago O'Hare Intl

Mon 19/1

5:15 a.m.-12:15 a.m.

3 stops21h 00m

C$ 450

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 27/1

7:55 a.m.-5:10 p.m.

1 stop7h 15m

Chicago O'Hare Intl

Tue 3/2

6:06 p.m.-12:10 a.m.

1 stop8h 04m

C$ 456

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 12/1

7:30 a.m.-11:09 p.m.

1 stop13h 39m

Chicago Midway

Mon 19/1

10:07 a.m.-9:04 a.m.

2 stops24h 57m

C$ 456

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 17/1

7:35 p.m.-2:38 p.m.

1 stop17h 03m

Chicago O'Hare Intl

Wed 21/1

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

1 stop14h 55m

C$ 457

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/12

Showing 1-10 of 32 results
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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 12 December 2025.

Booking 32 days in advance of your planned departure date is, on average, the best time to get cheap flights from Vancouver Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 C$ 151). Flying from Vancouver Intl Airport to Chicago in January is currently the most expensive (average of C$ 357). 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 15 December 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 38% 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 15 December 2025.

The most flights from YVR to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).

What’s the top layover airport for flights from Vancouver Intl Airport to Chicago?

Share of one-stop round-trip flights from Vancouver Intl Airport to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Calgary (YYC) – chosen by Cheapflights users on 79% of one-stop itineraries from Vancouver Intl Airport to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Vancouver Intl Airport to Chicago?

Average round-trip fare for 1-stop flights from Vancouver Intl Airport to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 320.

What’s the fastest layover option from Vancouver Intl Airport to Chicago?

Shortest average travel time for 1-stop one-way flights from Vancouver Intl Airport to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Seattle (SEA) have the shortest average one-way travel time for 1-stop routes: 7h 31m.

Which airport typically offers the quickest layover for flights from Vancouver Intl Airport to Chicago?

Average layover duration for 1-stop one-way flights from Vancouver Intl Airport to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 1h 45m.

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 15 December 2025.
See what other customers who have flown with United Airlines,American Airlines, andWestJet from Vancouver Intl Airport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,092 reviews
Check prices

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

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
9,092 reviews
United Airlines
7.4
Good
9,092 reviews
Check prices

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

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
11,048 reviews
United Airlines
7.4
Good
9,092 reviews
Check prices

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

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
3,202 reviews
United Airlines
7.4
Good
9,092 reviews
Check prices

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

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
10,526 reviews
United Airlines
7.4
Good
9,092 reviews
Check prices

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

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 C$ 443, WestJet can have you in Chicago from Vancouver Intl Airport in 8h 43m. The distance from Vancouver Intl Airport to Chicago is about 2829 km. Both multi-stop and direct flights can be found to your destination and back.

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

    United Airlines, at C$ 197, was found to be the cheapest airline from Vancouver Intl Airport to Chicago.Alternate airlines to your destination round-trip include Air Canada and WestJet. United Airlines is 59% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest airlines for a one-way flight from Vancouver Intl Airport to Chicago are United Airlines (C$ 167), WestJet (C$ 172), and Air Canada (C$ 193).

  • 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 (89%), Emirates (87%), American Airlines (85%).

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

    On average you can expect to pay C$ 1,450 for a flight from Vancouver Intl Airport to Chicago. The cheapest flight overall is C$ 233 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 241.

  • 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 C$ 151). Flying from Vancouver Intl Airport to Chicago in January is currently the most expensive (average of C$ 357). 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

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Fly from Vancouver Intl to Chicago on these airlines

Choose from the following airlines for your flight from Vancouver Intl to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 15 December 2025.
Air Canada flights from Vancouver Intl to Chicago
United Airlines flights from Vancouver Intl to Chicago
WestJet flights from Vancouver Intl to Chicago

Top 4 airlines flying from Vancouver Intl to Chicago

Discover the top 4 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 629,999 searches. Data last updated 15 December 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 201AverageC$ 481FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 233AverageC$ 339FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 234AverageC$ 421FlexibilityNo 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 Intl to Chicago?

Cheapflights makes it easy to find Vancouver Intl to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Vancouver Intl to Chicago for you. Better yet — we are completely free to use.

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

Yes, we can. To see specific flights from Vancouver Intl 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 Intl to Chicago become cheaper?

Yes! Start tracking prices for Vancouver Intl to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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