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Cheap flights from Vancouver Intl Airport to Chicago from C$ 152

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 18/11. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

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 Wednesday or Tuesday and return on a Wednesday

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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 30 October 2025.

Wed 3/1211:00 p.m.YVR - ORD
1 stop16h 27mMultiple Airlines
Mon 8/1212:59 p.m.ORD - YVR
1 stop11h 21mMultiple Airlines
Deal found 30/10C$ 279
Sun 7/1211:00 p.m.YVR - ORD
1 stop21h 24mMultiple Airlines
Wed 10/124:01 p.m.ORD - YVR
2 stops26h 53mMultiple Airlines
Deal found 28/10C$ 285
Mon 15/127:10 a.m.YVR - ORD
1 stop15h 03mMultiple Airlines
Wed 17/124:01 p.m.ORD - YVR
2 stops32h 44mMultiple Airlines
Deal found 29/10C$ 295
Wed 26/1111:00 p.m.YVR - MDW
1 stop21h 43mMultiple Airlines
Thu 4/126:15 a.m.MDW - YVR
2 stops18h 30mMultiple Airlines
Deal found 30/10C$ 303
Thu 11/127:45 p.m.YVR - MDW
2 stops24h 27mMultiple Airlines
Mon 15/126:15 a.m.MDW - YVR
1 stop12h 16mMultiple Airlines
Deal found 30/10C$ 338
Fri 12/129:15 p.m.YVR - ORD
2 stops12h 39mMultiple Airlines
Mon 15/122:20 p.m.ORD - YVR
1 stop7h 25mMultiple Airlines
Deal found 29/10C$ 338
Thu 11/1210:10 p.m.YVR - ORD
1 stop13h 25mWestJet
Mon 15/122:20 p.m.ORD - YVR
1 stop8h 40mWestJet
Deal found 30/10C$ 349
Fri 12/129:10 a.m.YVR - ORD
1 stop9h 45mMultiple Airlines
Tue 13/14:11 p.m.ORD - YVR
2 stops56h 09mMultiple Airlines
Deal found 30/10C$ 357
Fri 12/1210:10 p.m.YVR - MDW
2 stops21h 12mMultiple Airlines
Mon 15/126:15 a.m.MDW - YVR
1 stop12h 16mMultiple Airlines
Deal found 29/10C$ 369
Wed 26/1111:00 p.m.YVR - ORD
1 stop10h 34mMultiple Airlines
Thu 4/125:05 a.m.ORD - YVR
2 stops19h 40mMultiple Airlines
Deal found 30/10C$ 369
Mon 10/119:15 p.m.YVR - ORD
2 stops11h 59mMultiple Airlines
Sun 16/115:01 a.m.ORD - YVR
1 stop32h 11mMultiple Airlines
Deal found 28/10C$ 387
Thu 20/118:00 a.m.YVR - ORD
1 stop20h 25mMultiple Airlines
Thu 27/116:45 p.m.ORD - YVR
1 stop29h 35mMultiple Airlines
Deal found 30/10C$ 391

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 30 October 2025.

Round-trip from

C$ 278

One-way from

C$ 152

Popular in

November

Cheapest in

September

Average price

C$ 429

Good round-trip deal

C$ 450 or less

Good one-way deal

C$ 267 or less
3/12-6/12
  • 3/12-6/12
  • 3 total stops
  • 45h 57m total
  • Vancouver to Chicago
Search Deals
18/11
  • 18/11
  • 2 total stops
  • 25h 21m 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
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 30 October 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

Fri 5/12

11:00 p.m.-1:59 p.m.

1 stop12h 59m

Chicago Midway

Mon 8/12

8:42 p.m.-2:45 p.m.

2 stops20h 03m

C$ 296

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 26/11

11:00 p.m.-10:43 p.m.

1 stop21h 43m

Chicago Midway

Thu 4/12

6:15 a.m.-10:45 p.m.

2 stops18h 30m

C$ 303

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 11/1

9:10 a.m.-7:21 p.m.

1 stop8h 11m

Chicago Midway

Sun 18/1

11:30 a.m.-4:31 p.m.

1 stop31h 01m

C$ 314

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 16/11

11:00 p.m.-2:33 p.m.

2 stops13h 33m

Chicago Midway

Wed 19/11

1:56 p.m.-11:12 a.m.

1 stop23h 16m

C$ 331

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 1/2

11:40 a.m.-11:53 p.m.

1 stop10h 13m

Chicago O'Hare Intl

Mon 9/2

2:20 p.m.-6:44 p.m.

1 stop6h 24m

C$ 364

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 9/1

3:30 p.m.-11:53 p.m.

1 stop6h 23m

Chicago O'Hare Intl

Fri 16/1

2:20 p.m.-8:54 p.m.

1 stop8h 34m

C$ 364

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 29/1

3:30 p.m.-11:53 p.m.

1 stop6h 23m

Chicago O'Hare Intl

Wed 4/2

2:20 p.m.-6:44 p.m.

1 stop6h 24m

C$ 364

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 18/1

3:30 p.m.-11:53 p.m.

1 stop6h 23m

Chicago O'Hare Intl

Sat 24/1

6:12 a.m.-11:01 a.m.

1 stop6h 49m

C$ 364

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 9/1

3:30 p.m.-11:53 p.m.

1 stop6h 23m

Chicago O'Hare Intl

Sat 17/1

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

1 stop7h 54m

C$ 364

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 23/1

3:30 p.m.-11:53 p.m.

1 stop6h 23m

Chicago O'Hare Intl

Thu 29/1

2:20 p.m.-8:54 p.m.

1 stop8h 34m

C$ 364

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/10

Showing 1-10 of 42 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 24 October 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$ 159). Flying from Vancouver Intl Airport 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 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 30 October 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.

How much does it cost to fly round-trip from Vancouver Intl Airport to Chicago?

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 80% 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$ 332.

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: 6h 25m.

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 Seattle (SEA) offer the fastest connection on this route, with an average layover time of 1h 11m.

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 30 October 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
8,998 reviews
Check prices

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

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
8,998 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

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
11,030 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

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
3,149 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

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
10,377 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

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$ 364, Delta can have you in Chicago from Vancouver Intl Airport in 10h 13m. The distance from Vancouver Intl Airport to Chicago is about 2829 km.

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

    United Airlines, at C$ 208, was found to be the cheapest airline from Vancouver Intl Airport to Chicago.Alternate airlines to your destination round-trip include WestJet and American Airlines. United Airlines is 57% cheaper than the average price of flights available within the next 90 days to this destination.

  • 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 (83%), American Airlines (75%), Qatar Airways (65%).

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

    On average you can expect to pay C$ 528 for a flight from Vancouver Intl Airport to Chicago. The cheapest flight overall is C$ 170 while the most popular route, (Vancouver Intl - Chicago O'Hare Intl) is currently priced at C$ 327.

  • 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$ 159). Flying from Vancouver Intl Airport 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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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 30 October 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 30 October 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 208AverageC$ 489FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 236AverageC$ 360FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 238AverageC$ 427FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 267AverageC$ 528FlexibilityNo 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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