Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Vancouver to Chicago from C$ 290

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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
23 Aug — 30 Aug1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Vancouver to Chicago are usually found in September or October, booked 42 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap flight deals from Vancouver to Chicago

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 24 July 2026.

Thu 15/107:30 a.m.
YVR
-
ORD
1 stop7h 10m
WestJet
Thu 22/105:30 p.m.
ORD
-
YVR
1 stop8h 45m
WestJet
Deal found 22/7C$ 405
Thu 10/96:00 a.m.
YVR
-
ORD
1 stop8h 40m
WestJet
Fri 23/105:30 p.m.
ORD
-
YVR
1 stop8h 45m
WestJet
Deal found 22/7C$ 420
Fri 18/96:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Mon 21/95:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 22/7C$ 425
Tue 15/97:30 a.m.
YVR
-
ORD
1 stop7h 10m
WestJet
Tue 29/95:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 22/7C$ 428
Tue 15/98:25 a.m.
YVR
-
ORD
Nonstop4h 18m
Air Canada
Tue 22/93:40 p.m.
ORD
-
YVR
Nonstop4h 35m
Air Canada
Deal found 20/7C$ 434
Mon 24/86:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Wed 26/85:30 p.m.
ORD
-
YVR
1 stop18h 40m
WestJet
Deal found 20/7C$ 435
Fri 28/86:00 a.m.
YVR
-
ORD
1 stop8h 40m
WestJet
Tue 1/95:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 23/7C$ 441
Tue 15/97:20 a.m.
YVR
-
ORD
1 stop8h 41m
Delta
Tue 22/92:05 p.m.
ORD
-
YVR
1 stop10h 29m
Delta
Deal found 20/7C$ 442
Thu 10/98:25 a.m.
YVR
-
ORD
Nonstop4h 18m
Air Canada
Wed 16/93:40 p.m.
ORD
-
YVR
Nonstop4h 35m
Air Canada
Deal found 18/7C$ 443
Sat 5/96:00 a.m.
YVR
-
ORD
1 stop8h 40m
WestJet
Thu 10/95:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 20/7C$ 445
Fri 21/86:45 a.m.
YVR
-
ORD
1 stop7h 55m
WestJet
Mon 24/85:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 23/7C$ 455
Tue 15/96:05 a.m.
YVR
-
MDW
1 stop10h 19m
WestJet
Tue 22/92:05 p.m.
MDW
-
YVR
1 stop8h 26m
WestJet
Deal found 20/7C$ 483

Find 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 24 July 2026.

Round-trip from

C$ 405

One-way from

C$ 290

Popular in

July

Cheapest in

September

Average price

C$ 719
WestJet
  • WestJet
  • 15/10-22/10
  • 2 total stops
  • 15h 55m total
  • Vancouver to Chicago
Search Deals
12/9
  • 12/9
  • 3 total stops
  • 14h 27m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 75 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 24 July 2026.
Use the filters below to find and compare flights from Vancouver to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 1/9

5:44 p.m.-8:30 a.m.

2 stops12h 46m

Chicago O'Hare Intl

Tue 8/9

5:44 p.m.-10:59 p.m.

1 stop7h 15m

C$ 442

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 10/9

6:15 a.m.-6:01 p.m.

1 stop9h 46m

Chicago O'Hare Intl

Wed 16/9

5:44 p.m.-10:59 p.m.

1 stop7h 15m

C$ 459

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 15/9

7:30 p.m.-8:48 a.m.

2 stops11h 18m

Chicago Midway

Tue 29/9

9:59 a.m.-6:40 p.m.

2 stops10h 41m

C$ 522

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 10/9

8:35 a.m.-10:46 p.m.

1 stop12h 11m

Chicago O'Hare Intl

Wed 16/9

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

Nonstop4h 35m

C$ 524
Quickest round-trip

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 31/8

3:35 p.m.-11:59 p.m.

1 stop6h 24m

Chicago O'Hare Intl

Tue 8/9

7:48 p.m.-10:25 p.m.

Nonstop4h 37m

C$ 536

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 5/10

6:45 a.m.-6:04 p.m.

1 stop9h 19m

Chicago O'Hare Intl

Wed 7/10

2:03 p.m.-9:13 p.m.

2 stops9h 10m

C$ 543

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 19/10

10:30 a.m.-4:45 p.m.

Nonstop4h 15m

Chicago O'Hare Intl

Mon 19/10

10:00 p.m.-9:51 a.m.

1 stop13h 51m

C$ 549

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 31/8

3:35 p.m.-11:59 p.m.

1 stop6h 24m

Chicago O'Hare Intl

Sun 6/9

10:00 p.m.-9:51 a.m.

1 stop13h 51m

C$ 562

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 5/9

6:00 a.m.-3:57 p.m.

1 stop7h 57m

Chicago Midway

Thu 10/9

2:00 p.m.-8:26 p.m.

1 stop8h 26m

C$ 584

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 5/10

7:30 p.m.-8:47 a.m.

2 stops11h 17m

Chicago Midway

Wed 7/10

12:28 p.m.-11:08 p.m.

2 stops12h 40m

C$ 597

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/7

Showing 1-10 of 27 resultsSorted by cheapest first
1
2
3

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

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$ 352). Flying from Vancouver to Chicago in July is currently the most expensive (average of C$ 777). 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 24 July 2026.

When flying from Vancouver to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 24 July 2026.

The most flights from 8CA to CHI are scheduled on a Thursday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 on average).

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

Airfare is below average for this route at the moment.
Vancouver to Chicago flights typically cost between C$ 468 and C$ 786 in October.
The cheapest round-trip price found within the last 5 days was C$ 405 on WestJet (15 Oct-22 Oct).

How far ahead should I book a flight from Vancouver to Chicago?

To ensure you get the cheapest price possible for a flight from Vancouver to Chicago, you should look to book at least 44 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.

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 24 July 2026.
Read reviews from past customers who have flown United Airlines,WestJet, 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.
United Airlines
7.4
Good
10,026 reviews
Check prices

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

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
10,026 reviews
United Airlines
7.4
Good
10,026 reviews
Check prices

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

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
3,413 reviews
United Airlines
7.4
Good
10,026 reviews
Check prices

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

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
7.1
Good
11,833 reviews
United Airlines
7.4
Good
10,026 reviews
Check prices

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

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
11,375 reviews
United Airlines
7.4
Good
10,026 reviews
Check prices

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

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 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 12h 46m. Delta provides one of the quickest options available for as low as C$ 442. The distance from Vancouver to Chicago is about 2829 km.

  • 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$ 202 on this airline. Additional options worth looking into are WestJet and American Airlines, starting at C$ 213 and C$ 275 round-trip. These flights start at 65% lower than the current average price 3 months from now.

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

    For one-way options, check prices for WestJet. According to our data, you can fly for as low as C$ 167. Users have also found prices from C$ 171 and C$ 171 on United Airlines and Air Canada, respectively.

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

    The top 3 most reliable airlines when flying from Vancouver to Chicago are American Airlines (65%), Finnair (60%) and Air Canada (57%).

  • What are the cheapest flights from Vancouver to Chicago?

    While on average a flight from Vancouver to Chicago is generally C$ 868, our data shows the cheapest flight currently is C$ 278. When looking at the most popular route, (Vancouver Intl - Chicago O'Hare Intl), you can expect to pay C$ 458 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$ 352). Flying from Vancouver to Chicago in July is currently the most expensive (average of C$ 777). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 24 July 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 202AverageC$ 541FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 213AverageC$ 416FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 275AverageC$ 606FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 276AverageC$ 678FlexibilityNo 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 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.

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

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.