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Cheap flights from Vancouver to Chicago from C$ 166

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 20/5. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
26 Feb — 5 Mar1
1 adult

The best prices from Vancouver to Chicago are usually found in January or October, booked 66 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

Cheap 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 February 2025.

Round-trip from

C$ 284

One-way from

C$ 166

Popular in

December

Cheapest in

January

Average price

C$ 476
2/4-8/4
  • 2/4-8/4
  • 2 total stops
  • 39h 08m total
  • Vancouver to Chicago
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WestJet
  • WestJet
  • 20/5
  • 1 total stop
  • 7h 44m total
  • Vancouver to Chicago
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Highest demand for flights based on searches. 1% potential increase in price (C$ 12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 14 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Vancouver to Chicago

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 February 2025.

Wed 2/43:55 p.m.YVR - MDW
1 stop11h 28mMultiple Airlines
Tue 8/48:50 p.m.MDW - YVR
1 stop27h 40mMultiple Airlines
Deal found 20/2C$ 284
Wed 11/67:00 a.m.YVR - ORD
1 stop7h 44mWestJet
Wed 18/61:40 p.m.ORD - YVR
1 stop7h 30mWestJet
Deal found 20/2C$ 300
Mon 28/43:55 p.m.YVR - ORD
1 stop12h 38mMultiple Airlines
Tue 29/49:04 p.m.ORD - YVR
2 stops27h 21mMultiple Airlines
Deal found 20/2C$ 310
Wed 2/48:05 a.m.YVR - ORD
1 stop6h 43mAir Canada
Sat 5/410:53 a.m.ORD - YVR
1 stop10h 57mAir Canada
Deal found 20/2C$ 381
Sun 6/46:15 a.m.YVR - ORD
Nonstop4h 16mUnited Airlines
Sun 13/43:45 p.m.ORD - YVR
Nonstop4h 34mUnited Airlines
Deal found 20/2C$ 409
Thu 20/37:25 p.m.YVR - MDW
2 stops12h 20mDelta
Tue 1/410:25 a.m.MDW - YVR
2 stops14h 29mDelta
Deal found 20/2C$ 446
Sun 2/33:43 p.m.YVR - ORD
1 stop6h 13mDelta
Wed 12/32:20 p.m.ORD - YVR
1 stop6h 14mDelta
Deal found 19/2C$ 447
Mon 17/310:05 p.m.YVR - MDW
1 stop10h 15mPorter Airlines
Thu 20/311:15 a.m.MDW - YVR
2 stops12h 10mPorter Airlines
Deal found 20/2C$ 697
Mon 28/411:00 p.m.YVR - MDW
1 stop8h 07mWestJet
Tue 29/41:16 p.m.MDW - YVR
2 stops12h 54mWestJet
Deal found 20/2C$ 835

Find flights from Vancouver to Chicago within your budget

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 February 2025.

Fly from

Vancouver

Fly to

Chicago

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 2/4

3:55 p.m.-5:23 a.m.

1 stop11h 28m

Chicago Midway

Tue 8/4

8:50 p.m.-10:30 p.m.

1 stop27h 40m

C$ 284

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 21/5

7:00 a.m.-4:44 p.m.

1 stop7h 44m

Chicago O'Hare Intl

Mon 26/5

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

1 stop7h 05m

C$ 303

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 28/4

3:55 p.m.-6:33 a.m.

1 stop12h 38m

Chicago O'Hare Intl

Tue 29/4

9:04 p.m.-10:25 p.m.

2 stops27h 21m

C$ 310

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 2/4

8:05 a.m.-4:48 p.m.

1 stop6h 43m

Chicago O'Hare Intl

Sat 5/4

10:53 a.m.-7:50 p.m.

1 stop10h 57m

C$ 381

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 6/4

6:15 a.m.-12:31 p.m.

Nonstop4h 16m

Chicago O'Hare Intl

Sun 13/4

3:45 p.m.-6:19 p.m.

Nonstop4h 34m

C$ 409

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 20/3

7:25 p.m.-9:45 a.m.

2 stops12h 20m

Chicago Midway

Tue 1/4

10:25 a.m.-10:54 p.m.

2 stops14h 29m

C$ 446

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 2/3

3:43 p.m.-11:56 p.m.

1 stop6h 13m

Chicago O'Hare Intl

Wed 12/3

2:20 p.m.-6:34 p.m.

1 stop6h 14m

C$ 447

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 19/3

4:59 p.m.-5:40 a.m.

1 stop10h 41m

Chicago O'Hare Intl

Wed 26/3

7:40 a.m.-4:09 p.m.

1 stop10h 29m

C$ 626

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 17/3

10:05 p.m.-10:20 a.m.

1 stop10h 15m

Chicago Midway

Thu 20/3

11:15 a.m.-9:25 p.m.

2 stops12h 10m

C$ 697

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 28/4

11:00 p.m.-9:07 a.m.

1 stop8h 07m

Chicago Midway

Tue 29/4

1:16 p.m.-12:10 a.m.

2 stops12h 54m

C$ 835

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/2

Showing 1-10 of 21 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.

Travel insights for flights from Vancouver to Chicago

Get recent, data-driven insights about flights from Vancouver to Chicago including ideal travel times, pricing trends, and more.

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 14 February 2025.

To ensure you get the cheapest price possible for a flight from Vancouver to Chicago, you should look to book at least 66 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, January is the cheapest month in which you can book a flight from Vancouver to Chicago (average of C$ 261). Flying from Vancouver to Chicago in March 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 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 February 2025.

When flying from Vancouver 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 36% versus a flight at noon.

What is the cheapest day to fly from Vancouver to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Vancouver to Chicago. Price data was last updated on 10 November 2024.

Travelers seeking maximum savings on their Vancouver to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 February 2025.

The most flights from 8CA to CHI are scheduled on a Thursday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 February 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta and Porter Airlines from Vancouver to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,696 reviews
Check prices

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,696 reviews
Alaska Airlines
8.0
Very good
9,696 reviews
Check prices

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,217 reviews
Alaska Airlines
8.0
Very good
9,696 reviews
Check prices

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Porter Airlines
7.9
Good
276 reviews
Alaska Airlines
8.0
Very good
9,696 reviews
Check prices

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,757 reviews
Alaska Airlines
8.0
Very good
9,696 reviews
Check prices

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,696 reviews
Check prices

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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.

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

    Our cheapest airline available from Vancouver to Chicago is WestJet. Our recent data shows that you can find tickets from as low as C$ 303 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at C$ 381 and C$ 409 round-trip. These flights start at 44% 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$ 166. Users have also found prices from C$ 232 and C$ 236 on United Airlines and Delta, respectively.

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

    The top 3 most reliable airlines when flying from Vancouver to Chicago are Avianca (100%), Emirates (90%) and United Airlines (85%).

  • What are the cheapest flights from Vancouver to Chicago?

    While on average a flight from Vancouver to Chicago is generally C$ 1,094, our data shows the cheapest flight currently is C$ 205. When looking at the most popular route, (Vancouver Intl - Chicago O'Hare Intl), you can expect to pay C$ 310 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, January is the cheapest month in which you can book a flight from Vancouver to Chicago (average of C$ 261). Flying from Vancouver to Chicago in March 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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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 February 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 307AverageC$ 430FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 365AverageC$ 578FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Alaska AirlinesCheapestC$ 369AverageC$ 617FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
United AirlinesCheapestC$ 381AverageC$ 559FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 401AverageC$ 551FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

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How does Cheapflights help users find flights from Vancouver to Chicago?

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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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