Which airlines fly to Chicago?

Air Canada, United Airlines and WestJet are the top three most popular airlines that fly to Chicago from Vancouver according to our data. Air Canada is the first choice among our users, with 53% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Vancouver to Chicago on average per day?

As of November 2025, there are 6 flights per day flying from Vancouver to Chicago. The most common time of day flights depart is 10:00a.m., with 96% of flights taking off at noon.

How many flights depart from Vancouver to Chicago on average per week?

As of November 2025, 42 flights take off from Vancouver and land in Chicago each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.

What is the cheapest airline that flies from Vancouver to Chicago?

WestJet is the most popular carrier operating from Vancouver to Chicago

When did momondo last update prices for flights from Vancouver to Chicago?

Prices for flights from Vancouver to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from Vancouver to Chicago?

The number of operators available for flights from Vancouver to Chicago is 4 as of November 2025.

How old do you have to be to fly from Vancouver to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Vancouver to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

C$ 166 Cheap Flights from Vancouver to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Vancouver and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from C$ 457 to C$ 710. The lowest price recently found on this route was C$ 292.

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Find the cheapest flights from Vancouver to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:00 p.m. - 5:27 p.m.YVR-ORD

16h 27m1 stop

4:01 p.m. - 4:54 p.m.ORD-YVR

26h 53m2 stops

C$ 295Multiple Airlines

Find Deal

Wed, 3 Dec - Wed, 10 Dec

11:00 p.m. - 5:27 p.m.YVR-ORD

16h 27m1 stop

4:01 p.m. - 4:54 p.m.ORD-YVR

26h 53m2 stops

C$ 296Multiple Airlines

Find Deal

Wed, 3 Dec - Wed, 10 Dec

11:00 p.m. - 5:27 p.m.YVR-ORD

16h 27m1 stop

4:01 p.m. - 11:12 a.m.ORD-YVR

21h 11m1 stop

C$ 302Multiple Airlines

Find Deal

Wed, 3 Dec - Wed, 10 Dec

11:00 p.m. - 5:27 p.m.YVR-ORD

16h 27m1 stop

4:01 p.m. - 11:12 a.m.ORD-YVR

21h 11m1 stop

C$ 303Multiple Airlines

Find Deal

Wed, 3 Dec - Wed, 10 Dec

7:45 p.m. - 3:12 p.m.YVR-ORD

17h 27m2 stops

9:27 p.m. - 4:31 p.m.ORD-YVR

21h 04m1 stop

C$ 305Multiple Airlines

Find Deal

Mon, 1 Dec - Mon, 8 Dec

11:24 a.m. - 11:59 p.m.YVR-ORD

10h 35m1 stop

2:20 p.m. - 8:54 p.m.ORD-YVR

8h 34m1 stop

C$ 433Delta

Find Deal

Wed, 24 Dec - Tue, 13 Jan

3:31 p.m. - 11:59 p.m.YVR-ORD

6h 28m1 stop

7:30 a.m. - 2:36 p.m.ORD-YVR

9h 06m1 stop

C$ 435Delta

Find Deal

Tue, 16 Dec - Wed, 7 Jan

4:20 p.m. - 10:05 a.m.YVR-MDW

15h 45m1 stop

11:00 a.m. - 9:23 p.m.MDW-YVR

12h 23m2 stops

C$ 578Porter Airlines

Find Deal

Sat, 6 Dec - Mon, 8 Dec

6:00 a.m. - 1:10 p.m.YVR-MDW

29h 10m2 stops

10:49 a.m. - 12:44 a.m.MDW-YVR

15h 55m2 stops

C$ 753WestJet

Find Deal

Fri, 12 Dec - Sun, 14 Dec

5:00 p.m. - 1:10 p.m.YVR-MDW

18h 10m2 stops

9:59 a.m. - 10:44 p.m.MDW-YVR

14h 45m3 stops

C$ 769WestJet

Find Deal

Fri, 12 Dec - Sun, 14 Dec

Delta flights from Vancouver to Chicago

Our best Delta deals on Vancouver to Chicago flight tickets

Delta

24 Dec

YVR11:24 a.m.Vancouver Intl

10h 35m

1 stop

ORD11:59 p.m.Chicago O'Hare Intl

13 Jan

ORD2:20 p.m.Chicago O'Hare Intl

8h 34m

1 stop

YVR8:54 p.m.Vancouver Intl

C$ 433

Find similar

Delta

16 Dec

YVR3:31 p.m.Vancouver Intl

6h 28m

1 stop

ORD11:59 p.m.Chicago O'Hare Intl

7 Jan

ORD7:30 a.m.Chicago O'Hare Intl

9h 06m

1 stop

YVR2:36 p.m.Vancouver Intl

C$ 434

Find similar

Delta

16 Dec

YVR3:31 p.m.Vancouver Intl

6h 28m

1 stop

ORD11:59 p.m.Chicago O'Hare Intl

9 Jan

ORD2:20 p.m.Chicago O'Hare Intl

8h 34m

1 stop

YVR8:54 p.m.Vancouver Intl

C$ 447

Find similar

Alaska Airlines flights from Vancouver to Chicago

Our best Alaska Airlines deals on Vancouver to Chicago flight tickets

Alaska Airlines

13 Nov

YVR7:35 p.m.Vancouver Intl

8h 47m

1 stop

ORD6:22 a.m.Chicago O'Hare Intl

19 Nov

ORD1:10 p.m.Chicago O'Hare Intl

4h 40m

YVR3:50 p.m.Vancouver Intl

C$ 519

Find similar

Alaska Airlines

13 Nov

YVR7:35 p.m.Vancouver Intl

8h 47m

1 stop

ORD6:22 a.m.Chicago O'Hare Intl

20 Nov

ORD10:00 a.m.Chicago O'Hare Intl

8h 45m

1 stop

YVR4:45 p.m.Vancouver Intl

C$ 559

Find similar

Fly from

Fly to

Route

Depart

Return

Price

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 3/12

11:00 p.m.-5:27 p.m.

1 stop16h 27m

Chicago O'Hare Intl

Wed 10/12

4:01 p.m.-4:54 p.m.

2 stops26h 53m

C$ 295

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 3/12

11:00 p.m.-5:27 p.m.

1 stop16h 27m

Chicago O'Hare Intl

Wed 10/12

4:01 p.m.-4:54 p.m.

2 stops26h 53m

C$ 296

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 3/12

11:00 p.m.-5:27 p.m.

1 stop16h 27m

Chicago O'Hare Intl

Wed 10/12

4:01 p.m.-11:12 a.m.

1 stop21h 11m

C$ 302

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 3/12

11:00 p.m.-5:27 p.m.

1 stop16h 27m

Chicago O'Hare Intl

Wed 10/12

4:01 p.m.-11:12 a.m.

1 stop21h 11m

C$ 303

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 1/12

7:45 p.m.-3:12 p.m.

2 stops17h 27m

Chicago O'Hare Intl

Mon 8/12

9:27 p.m.-4:31 p.m.

1 stop21h 04m

C$ 305

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 24/12

11:24 a.m.-11:59 p.m.

1 stop10h 35m

Chicago O'Hare Intl

Tue 13/1

2:20 p.m.-8:54 p.m.

1 stop8h 34m

C$ 433

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 16/12

3:31 p.m.-11:59 p.m.

1 stop6h 28m

Chicago O'Hare Intl

Wed 7/1

7:30 a.m.-2:36 p.m.

1 stop9h 06m

C$ 434

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 6/12

4:20 p.m.-10:05 a.m.

1 stop15h 45m

Chicago Midway

Mon 8/12

11:00 a.m.-9:23 p.m.

2 stops12h 23m

C$ 578

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 12/12

6:00 a.m.-1:10 p.m.

2 stops29h 10m

Chicago Midway

Sun 14/12

10:49 a.m.-12:44 a.m.

2 stops15h 55m

C$ 753

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 12/12

5:00 p.m.-1:10 p.m.

2 stops18h 10m

Chicago Midway

Sun 14/12

9:59 a.m.-10:44 p.m.

3 stops14h 45m

C$ 769

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Vancouver to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Vancouver and Chicago?

What is the cheapest month to fly to Chicago?

The month of October is another great option to travel to Chicago, with average flight prices from Vancouver averaging around C$ 433.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as C$ 570. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 773. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the afternoon is the cheapest time of day to fly from Vancouver to Chicago when you can find flight prices for as low as C$ 413. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 667 per ticket.

What is the cheapest Vancouver to Chicago flight route?

Fly from Vancouver Intl to Chicago O'Hare Intl for the best Vancouver - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Vancouver when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 508 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Vancouver for as low as C$ 367 on momondo.

What cabin class options are available on Vancouver to Chicago flights?

There are 4 cabin classes available to choose from on Vancouver to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Vancouver to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Vancouver to Chicago

Fastest flight time	4h 08m
Direct flights	Every day
Airports in Chicago	1 airport

The fastest flight from Vancouver to Chicago takes 4h 08m

Direct flights go from Vancouver to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

How far is Vancouver to Chicago by plane?
The straight-line distance from Vancouver to Chicago is 2850.5 km. By plane, this route typically takes 6h 28m.
When did momondo last update prices for flights from Vancouver to Chicago?
Prices for flights from Vancouver to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Vancouver to Chicago?
The number of operators available for flights from Vancouver to Chicago is 4 as of November 2025.
How old do you have to be to fly from Vancouver to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Vancouver to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Vancouver to Chicago

Compare and see reviews for airlines that fly from Vancouver to Chicago with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom C$ 210	Free Cancellation	Rating 7.4 9,007 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 239	Free Cancellation	Rating 7.2 3,155 reviews	Search WestJet flights
American Airlines	PriceFrom C$ 240	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights
Air Canada	PriceFrom C$ 269	Free Cancellation	Rating 7.1 10,416 reviews	Search Air Canada flights

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Why use momondo?

Why should I use momondo to find a flight deal from Vancouver to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Vancouver to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Vancouver to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Vancouver to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Vancouver to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Vancouver.

I’m not ready to book a flight from Vancouver to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Vancouver. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.