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Cheap flights from Vancouver to Chicago from C$ 182

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 20/2. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
20 Feb — 27 Feb1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Vancouver 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 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 21 January 2026.

Wed 11/24:35 p.m.
YVR
-
ORD
1 stop20h 19m
Multiple Airlines
Wed 11/34:28 p.m.
ORD
-
YVR
2 stops31h 52m
Multiple Airlines
Deal found 21/1C$ 324
Wed 18/212:30 p.m.
YVR
-
ORD
2 stops30h 33m
Multiple Airlines
Thu 26/26:34 p.m.
ORD
-
YVR
1 stop29h 46m
Multiple Airlines
Deal found 19/1C$ 329
Fri 20/24:35 p.m.
YVR
-
ORD
1 stop22h 18m
Multiple Airlines
Tue 24/29:05 a.m.
ORD
-
YVR
1 stop16h 54m
Multiple Airlines
Deal found 20/1C$ 340
Thu 7/56:00 a.m.
YVR
-
ORD
1 stop8h 43m
WestJet
Sun 10/55:30 p.m.
ORD
-
YVR
1 stop8h 40m
WestJet
Deal found 20/1C$ 342
Thu 19/27:00 a.m.
YVR
-
ORD
2 stops38h 03m
Multiple Airlines
Thu 26/26:34 p.m.
ORD
-
YVR
1 stop29h 46m
Multiple Airlines
Deal found 19/1C$ 343
Wed 27/58:30 a.m.
YVR
-
ORD
1 stop6h 13m
WestJet
Fri 5/65:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 19/1C$ 347
Thu 5/35:30 p.m.
YVR
-
ORD
1 stop10h 38m
Multiple Airlines
Mon 9/36:30 p.m.
ORD
-
YVR
2 stops45h 25m
Multiple Airlines
Deal found 19/1C$ 361
Wed 18/212:30 p.m.
YVR
-
ORD
2 stops30h 33m
Multiple Airlines
Tue 24/29:05 a.m.
ORD
-
YVR
1 stop16h 54m
Multiple Airlines
Deal found 19/1C$ 364
Wed 27/58:30 a.m.
YVR
-
ORD
1 stop6h 13m
WestJet
Wed 3/65:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 19/1C$ 365
Thu 30/46:00 a.m.
YVR
-
ORD
1 stop8h 43m
WestJet
Mon 4/55:30 p.m.
ORD
-
YVR
1 stop7h 05m
WestJet
Deal found 20/1C$ 368
Fri 27/23:40 p.m.
YVR
-
MDW
2 stops21h 39m
Multiple Airlines
Sun 1/33:21 p.m.
MDW
-
YVR
1 stop10h 38m
Multiple Airlines
Deal found 20/1C$ 419
Fri 27/23:40 p.m.
YVR
-
MDW
2 stops21h 39m
Multiple Airlines
Mon 2/37:25 p.m.
MDW
-
YVR
1 stop23h 02m
Multiple Airlines
Deal found 19/1C$ 434

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 21 January 2026.

Round-trip from

C$ 324

One-way from

C$ 182

Popular in

December

Cheapest in

October

Average price

C$ 460
11/2-11/3
  • 11/2-11/3
  • 3 total stops
  • 52h 11m total
  • Vancouver to Chicago
Search Deals
20/2
  • 20/2
  • 1 total stop
  • 22h 18m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 19% potential increase in price (C$ 154 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 21 January 2026.
Use the filters below to find and compare flights from Vancouver to Chicago that are best for you.

Fly from

Vancouver

Fly to

Chicago

Route

Depart

Return

Price

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 11/2

4:35 p.m.-2:54 p.m.

1 stop20h 19m

Chicago O'Hare Intl

Wed 11/3

4:28 p.m.-10:20 p.m.

2 stops31h 52m

C$ 324

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 27/2

3:40 p.m.-3:19 p.m.

2 stops21h 39m

Chicago Midway

Sun 1/3

3:21 p.m.-11:59 p.m.

1 stop10h 38m

C$ 419

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 21/4

7:00 a.m.-7:33 p.m.

1 stop10h 33m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-10:35 p.m.

1 stop7h 05m

C$ 447

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 17/2

3:35 p.m.-11:52 p.m.

1 stop6h 17m

Chicago O'Hare Intl

Sat 28/2

7:40 a.m.-6:47 p.m.

1 stop13h 07m

C$ 456

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 8/2

6:00 a.m.-2:38 p.m.

1 stop6h 38m

Chicago O'Hare Intl

Mon 9/2

6:06 p.m.-6:45 p.m.

1 stop26h 39m

C$ 467

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 18/2

7:25 a.m.-11:52 p.m.

1 stop14h 27m

Chicago O'Hare Intl

Thu 26/2

7:40 a.m.-9:00 p.m.

1 stop15h 20m

C$ 467

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 5/3

3:35 p.m.-11:52 p.m.

1 stop6h 17m

Chicago O'Hare Intl

Tue 10/3

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

1 stop6h 24m

C$ 467

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 23/2

4:35 p.m.-5:58 p.m.

1 stop23h 23m

Chicago O'Hare Intl

Mon 2/3

6:00 a.m.-11:59 p.m.

1 stop19h 59m

C$ 467

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 5/3

7:55 a.m.-12:01 p.m.

1 stop26h 06m

Chicago O'Hare Intl

Tue 10/3

7:00 a.m.-4:45 p.m.

1 stop11h 45m

C$ 469

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 24/2

3:35 p.m.-11:52 p.m.

1 stop6h 17m

Chicago O'Hare Intl

Thu 5/3

2:20 p.m.-11:59 p.m.

1 stop11h 39m

C$ 469

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/1

Showing 1-10 of 39 results
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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
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

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

Use this chart to determine the optimal time to book a round-trip flight from Vancouver to Chicago. Price data was last updated on 16 January 2026.

To ensure you get the cheapest price possible for a flight from Vancouver to Chicago, you should look to book at least 32 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.

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$ 151). Flying from Vancouver to Chicago in January is currently the most expensive (average of C$ 405). 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 21 January 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 21 January 2026.

The most flights from 8CA to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 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 21 January 2026.
Read reviews from past customers who have flown United Airlines,American Airlines, andWestJet 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
9,191 reviews
Check prices

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

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
9,191 reviews
United Airlines
7.4
Good
9,191 reviews
Check prices

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

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
11,174 reviews
United Airlines
7.4
Good
9,191 reviews
Check prices

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

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
3,247 reviews
United Airlines
7.4
Good
9,191 reviews
Check prices

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

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
10,646 reviews
United Airlines
7.4
Good
9,191 reviews
Check prices

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

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 6h 17m. Delta provides one of the quickest options available for as low as C$ 456. 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$ 198 on this airline. Additional options worth looking into are WestJet and American Airlines, starting at C$ 234 and C$ 235 round-trip. These flights start at 58% 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 United Airlines. According to our data, you can fly for as low as C$ 168. Users have also found prices from C$ 172 and C$ 196 on WestJet 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 Emirates (90%), Avianca (82%) and Air Canada (80%).

  • What are the cheapest flights from Vancouver to Chicago?

    While on average a flight from Vancouver to Chicago is generally C$ 589, our data shows the cheapest flight currently is C$ 215. When looking at the most popular route, (Vancouver Intl - Chicago O'Hare Intl), you can expect to pay C$ 340 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$ 151). Flying from Vancouver to Chicago in January is currently the most expensive (average of C$ 405). 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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Top 5 airlines flying from Vancouver to Chicago

Discover the top 5 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 21 January 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 198AverageC$ 482FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 234AverageC$ 327FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 235AverageC$ 401FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 238AverageC$ 497FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Alaska AirlinesCheapestC$ 387AverageC$ 499FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines 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.

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