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Cheap flights from Vancouver to Chicago from C$ 266

YVR — CHI
4 Oct — 11 Oct1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Vancouver to Chicago are usually found in October or September, booked 42 days in advance, depart on a Wednesday 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

Thu 8/106:00 a.m. -
2 stops8h 40m
Mon 12/105:30 p.m. -
1 stop8h 45m
Deal found 30/8C$ 384
Thu 15/107:30 a.m. -
1 stop7h 10m
Thu 22/105:30 p.m. -
1 stop17h 30m
Deal found 31/8C$ 391
Sun 4/103:40 p.m. -
1 stop23h 00m
Thu 8/105:30 p.m. -
1 stop7h 05m
Deal found 30/8C$ 398
Sat 10/1010:45 p.m. -
2 stops15h 55m
Mon 12/105:30 p.m. -
1 stop22h 10m
Deal found 3/9C$ 402
Wed 21/108:25 p.m. -
1 stop18h 15m
Fri 23/105:30 p.m. -
1 stop7h 05m
Deal found 2/9C$ 407
Thu 15/107:30 a.m. -
1 stop7h 10m
Sat 17/108:01 p.m. -
2 stops19h 34m
Deal found 3/9C$ 409
Fri 9/1010:45 p.m. -
2 stops39h 55m
Mon 12/105:30 p.m. -
1 stop8h 45m
Deal found 2/9C$ 411
Thu 15/107:30 a.m. -
1 stop7h 10m
Sun 18/105:30 p.m. -
2 stops15h 30m
Deal found 31/8C$ 414
Sat 24/106:00 a.m. -
1 stop8h 47m
Tue 27/1012:27 p.m. -
2 stops10h 46m
Deal found 1/9C$ 496
Wed 30/96:00 a.m. -
1 stop10h 19m
Sat 3/102:00 p.m. -
1 stop8h 26m
Deal found 1/9C$ 500
Sat 10/107:36 p.m. -
2 stops11h 08m
Tue 13/101:27 p.m. -
2 stops11h 32m
Deal found 4/9C$ 519
Fri 13/118:26 a.m. -
2 stops7h 38m
Mon 16/1112:30 p.m. -
2 stops13h 26m
Deal found 2/9C$ 551

Find flight deals from Vancouver to Chicago

Round-trip from

C$ 384

One-way from

C$ 266

Popular in

December

Cheapest in

October

Average price

C$ 507
WestJet
  • WestJet
  • 8/10-12/10
  • 3 total stops
  • 17h 25m total
  • Vancouver to Chicago
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WestJet
  • WestJet
  • 10/10-31/12
  • 1 total stop
  • 22h 10m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 61 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 16 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Cheapflights Fare Finder

 
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 Vancouver Intl - ORD Chicago O'Hare Intl

YVRORD

Vancouver Intl

Tue 2/3

7:00 a.m.-4:43 p.m.

1 stop8h 43m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 269

VancouverChicago

YVR Vancouver Intl - ORD Chicago O'Hare Intl

YVRORD

Vancouver Intl

Fri 26/2

7:00 a.m.-4:43 p.m.

1 stop8h 43m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 269

VancouverChicago

YVR Vancouver Intl - ORD Chicago O'Hare Intl

YVRORD

Vancouver Intl

Fri 26/2

5:15 p.m.-7:58 a.m.

2 stops13h 43m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 278

VancouverChicago

YVR Vancouver Intl - ORD Chicago O'Hare Intl

YVRORD

Vancouver Intl

Tue 3/11

4:44 p.m.-10:34 p.m.

1 stop4h 50m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 278

VancouverChicago

YVR Vancouver Intl - ORD Chicago O'Hare Intl

YVRORD

Vancouver Intl

Sun 28/2

7:35 p.m.-7:58 a.m.

2 stops11h 23m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 278

VancouverChicago

YVR Vancouver Intl - ORD Chicago O'Hare Intl

YVRORD

Vancouver Intl

Wed 14/10

6:15 a.m.-4:53 p.m.

1 stop8h 38m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 278
Quickest round-trip

VancouverChicago

YVR Vancouver Intl - ORD Chicago O'Hare Intl

YVRORD

Vancouver Intl

Fri 23/10

1:45 p.m.-8:06 p.m.

Nonstop4h 21m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 279

VancouverChicago

YVR Vancouver Intl - ORD Chicago O'Hare Intl

YVRORD

Vancouver Intl

Sat 10/10

1:45 p.m.-8:06 p.m.

Nonstop4h 21m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 280

VancouverChicago

YVR Vancouver Intl - ORD Chicago O'Hare Intl

YVRORD

Vancouver Intl

Wed 14/10

10:55 a.m.-9:52 p.m.

1 stop8h 57m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 282

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Sat 24/10

6:00 a.m.-4:47 p.m.

1 stop8h 47m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 282

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/9

Showing 1-10 of 34 resultsSorted by cheapest first
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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

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$ 432). Flying from Vancouver to Chicago in July is currently the most expensive (average of C$ 751). 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?

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

The most flights from 8CA to CHI are scheduled on a Wednesday (13 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).

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

Airfare is typical for this route at the moment.
Vancouver to Chicago flights typically cost between C$ 351 and C$ 675 in October.
The cheapest round-trip price found within the last 5 days was C$ 384 on WestJet (8 Oct-12 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 41 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

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
10,165 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.7

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
United Airlines
7.4
Good
10,165 reviews
United Airlines
7.4
Good
10,165 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.7

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
WestJet
7.2
Good
3,445 reviews
United Airlines
7.4
Good
10,165 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.7

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
American Airlines
7.1
Good
12,042 reviews
United Airlines
7.4
Good
10,165 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.7

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
Air Canada
7.1
Good
11,579 reviews
United Airlines
7.4
Good
10,165 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.7

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!

Related info for your journey

  • How long is the flight from Vancouver to Chicago?

    A quick flight from Vancouver to Chicago can take about 4h 15m. United Airlines provides one of the quickest options available for as low as C$ 475. The distance from Vancouver to Chicago is about 2829 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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$ 197 on this airline. Additional options worth looking into are WestJet and American Airlines, starting at C$ 200 and C$ 271 round-trip. These flights start at 67% 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$ 175. Users have also found prices from C$ 259 and C$ 285 on Air Canada and American Airlines, respectively.

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

    The top 3 most reliable airlines when flying from Vancouver to Chicago are Emirates (77%), Finnair (75%) and American Airlines (73%).

  • What are the cheapest flights from Vancouver to Chicago?

    While on average a flight from Vancouver to Chicago is generally C$ 652, our data shows the cheapest flight currently is C$ 355. When looking at the most popular route, (Vancouver Intl - Chicago O'Hare Intl), you can expect to pay C$ 409 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$ 432). Flying from Vancouver to Chicago in July is currently the most expensive (average of C$ 751). 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

Top 4 airlines flying from Vancouver to Chicago

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 197AverageC$ 559FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 200AverageC$ 408FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 271AverageC$ 587FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 271AverageC$ 685FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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.

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