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Cheap flights from Vancouver to Chicago from C$ 160

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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
23 May — 30 May1
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 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 23 April 2026.

Mon 29/67:50 a.m.
YVR
-
ORD
1 stop20h 29m
Multiple Airlines
Sat 4/79:13 p.m.
ORD
-
YVR
2 stops20h 42m
Multiple Airlines
Deal found 22/4C$ 490
Wed 27/56:00 a.m.
YVR
-
ORD
2 stops10h 05m
Delta
Thu 28/56:20 p.m.
ORD
-
YVR
1 stop6h 31m
Delta
Deal found 18/4C$ 499
Thu 18/611:57 p.m.
YVR
-
ORD
Nonstop4h 12m
American Airlines
Sun 21/68:14 p.m.
ORD
-
YVR
Nonstop4h 45m
American Airlines
Deal found 21/4C$ 500
Wed 1/77:50 a.m.
YVR
-
ORD
1 stop20h 29m
Multiple Airlines
Sat 4/79:13 p.m.
ORD
-
YVR
2 stops20h 42m
Multiple Airlines
Deal found 22/4C$ 501
Sun 10/510:40 a.m.
YVR
-
ORD
1 stop28h 00m
WestJet
Thu 14/55:30 p.m.
ORD
-
YVR
1 stop16h 10m
WestJet
Deal found 18/4C$ 503
Mon 1/67:30 a.m.
YVR
-
ORD
1 stop7h 10m
Multiple Airlines
Sat 13/67:52 a.m.
ORD
-
YVR
2 stops18h 52m
Multiple Airlines
Deal found 21/4C$ 505
Wed 10/66:00 a.m.
YVR
-
MDW
1 stop10h 18m
Delta
Wed 24/61:49 p.m.
MDW
-
YVR
1 stop8h 42m
Delta
Deal found 19/4C$ 507
Wed 6/55:00 a.m.
YVR
-
ORD
2 stops13h 32m
Multiple Airlines
Fri 8/55:30 p.m.
ORD
-
YVR
1 stop16h 10m
Multiple Airlines
Deal found 21/4C$ 507
Tue 25/83:35 p.m.
YVR
-
ORD
1 stop6h 24m
United Airlines
Wed 26/85:00 a.m.
ORD
-
YVR
1 stop6h 51m
United Airlines
Deal found 19/4C$ 508
Fri 1/510:55 p.m.
YVR
-
ORD
1 stop10h 38m
Multiple Airlines
Tue 5/57:15 a.m.
ORD
-
YVR
2 stops15h 25m
Multiple Airlines
Deal found 17/4C$ 511
Thu 18/611:35 p.m.
YVR
-
ORD
Nonstop4h 05m
United Airlines
Sun 21/65:00 a.m.
ORD
-
YVR
1 stop6h 51m
United Airlines
Deal found 21/4C$ 512
Mon 4/55:00 a.m.
YVR
-
ORD
1 stop9h 40m
WestJet
Fri 8/55:30 p.m.
ORD
-
YVR
2 stops15h 45m
WestJet
Deal found 18/4C$ 514

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 23 April 2026.

Round-trip from

C$ 490

One-way from

C$ 160

Popular in

December

Cheapest in

October

Average price

C$ 602
29/6-4/7
  • 29/6-4/7
  • 3 total stops
  • 41h 11m total
  • Vancouver to Chicago
Search Deals
WestJet
  • WestJet
  • 11/5
  • 1 total stop
  • 8h 40m total
  • Vancouver to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 126 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 April 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 23 April 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

Mon 4/5

1:59 p.m.-8:15 p.m.

Nonstop4h 16m

Chicago O'Hare Intl

Tue 5/5

6:20 a.m.-1:12 p.m.

1 stop8h 52m

C$ 529

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 4/6

6:00 a.m.-8:14 p.m.

2 stops12h 14m

Chicago O'Hare Intl

Thu 11/6

6:30 a.m.-1:30 p.m.

1 stop9h 00m

C$ 530
Quickest round-trip

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 28/7

11:35 p.m.-5:40 a.m.

Nonstop4h 05m

Chicago O'Hare Intl

Tue 11/8

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

Nonstop4h 37m

C$ 538

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 12/9

8:20 a.m.-6:58 p.m.

1 stop8h 38m

Chicago O'Hare Intl

Sat 12/9

9:30 p.m.-1:12 p.m.

1 stop17h 42m

C$ 546

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 11/6

7:23 a.m.-6:31 p.m.

2 stops9h 08m

Chicago Midway

Mon 22/6

9:17 a.m.-8:31 p.m.

2 stops13h 14m

C$ 560

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

7:35 p.m.-8:49 a.m.

2 stops11h 14m

Chicago Midway

Tue 13/10

12:30 p.m.-8:32 p.m.

1 stop10h 02m

C$ 564

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 22/5

1:45 p.m.-8:05 p.m.

Nonstop4h 20m

Chicago O'Hare Intl

Sun 24/5

6:13 a.m.-1:12 p.m.

1 stop8h 59m

C$ 568

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 27/5

6:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Sat 30/5

5:30 p.m.-12:15 a.m.

1 stop8h 45m

C$ 581

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 17/5

3:35 p.m.-11:57 p.m.

1 stop6h 22m

Chicago O'Hare Intl

Sun 24/5

5:30 p.m.-12:15 a.m.

1 stop8h 45m

C$ 583

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 18/9

6:15 a.m.-6:05 p.m.

1 stop9h 50m

Chicago Midway

Tue 22/9

2:00 p.m.-8:22 p.m.

1 stop8h 22m

C$ 589

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/4

Showing 1-10 of 44 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
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 17 April 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, August is the cheapest month in which you can book a flight from Vancouver to Chicago (average of C$ 104). Flying from Vancouver to Chicago in January is currently the most expensive (average of C$ 437). 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 23 April 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 23 April 2026.

The most flights from 8CA to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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

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 23 April 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
9,637 reviews
Check prices

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,637 reviews
United Airlines
7.4
Good
9,637 reviews
Check prices

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
WestJet
7.2
Good
3,324 reviews
United Airlines
7.4
Good
9,637 reviews
Check prices

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
American Airlines
7.1
Good
11,656 reviews
United Airlines
7.4
Good
9,637 reviews
Check prices

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
Air Canada
7.1
Good
10,957 reviews
United Airlines
7.4
Good
9,637 reviews
Check prices

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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 4h 16m. United Airlines provides one of the quickest options available for as low as C$ 529. 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$ 196 on this airline. Additional options worth looking into are WestJet and Air Canada, starting at C$ 207 and C$ 225 round-trip. These flights start at 63% 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$ 166. Users have also found prices from C$ 170 and C$ 223 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 (100%), United Airlines (90%) and Avianca (86%).

  • What are the cheapest flights from Vancouver to Chicago?

    While on average a flight from Vancouver to Chicago is generally C$ 552, our data shows the cheapest flight currently is C$ 211. When looking at the most popular route, (Vancouver Intl - Chicago O'Hare Intl), you can expect to pay C$ 407 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, August is the cheapest month in which you can book a flight from Vancouver to Chicago (average of C$ 104). Flying from Vancouver to Chicago in January is currently the most expensive (average of C$ 437). 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 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 23 April 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 196AverageC$ 472FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 207AverageC$ 362FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 225AverageC$ 530FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 252AverageC$ 418FlexibilityNo cancel feeOn-time71%
Search American 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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