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

The number of flights available between Vancouver and Chicago is 42 per week as of November 2025. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.

What airlines fly to Chicago?

Air Canada, United Airlines and American Airlines 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 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

WestJet is the most popular carrier operating from Vancouver to Chicago

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

As of November 2025, 6 flights take off from Vancouver and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 96% of daily flights taking off at noon.

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

Prices for flights from Vancouver to Chicago were last updated today.

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

The number of operators available for flights from Vancouver to Chicago is 3 as of November 2025.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$113 Cheap Flights from Vancouver to Chicago in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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 pm - 5:27 pmYVR-ORD

16h 27m1 stop

4:01 pm - 4:54 pmORD-YVR

26h 53m2 stops

$203Multiple Airlines

Find Deal

mié., dic. 3 - mié., dic. 10

11:00 pm - 5:27 pmYVR-ORD

16h 27m1 stop

4:01 pm - 4:54 pmORD-YVR

26h 53m2 stops

$204Multiple Airlines

Find Deal

mié., dic. 3 - mié., dic. 10

11:00 pm - 10:12 pmYVR-MDW

21h 12m1 stop

7:23 pm - 3:45 pmMDW-YVR

22h 22m2 stops

$205Multiple Airlines

Find Deal

dom., dic. 7 - jue., dic. 11

11:00 pm - 5:27 pmYVR-ORD

16h 27m1 stop

4:22 pm - 2:45 pmORD-YVR

24h 23m2 stops

$205Multiple Airlines

Find Deal

mié., dic. 3 - mar., dic. 9

10:10 pm - 1:35 pmYVR-ORD

13h 25m1 stop

2:20 pm - 7:45 pmORD-YVR

7h 25m1 stop

$259WestJet

Find Deal

jue., dic. 4 - lun., ene. 12

5:45 pm - 1:35 pmYVR-ORD

17h 50m1 stop

2:20 pm - 7:45 pmORD-YVR

7h 25m1 stop

$276WestJet

Find Deal

jue., dic. 4 - vie., ene. 9

12:07 pm - 11:40 pmYVR-MDW

9h 33m2 stops

12:47 pm - 10:37 pmMDW-YVR

11h 50m2 stops

$426Delta

Find Deal

vie., nov. 21 - mar., nov. 25

11:00 pm - 9:52 amYVR-MDW

8h 52m1 stop

1:15 pm - 10:37 pmMDW-YVR

11h 22m2 stops

$478Delta

Find Deal

mié., nov. 19 - mié., nov. 26

4:20 pm - 10:05 amYVR-MDW

15h 45m1 stop

11:00 am - 9:23 pmMDW-YVR

12h 23m2 stops

$485Porter Airlines

Find Deal

lun., dic. 1 - lun., dic. 8

12:20 pm - 10:05 amYVR-MDW

19h 45m2 stops

11:00 am - 9:23 pmMDW-YVR

12h 23m2 stops

$518Porter Airlines

Find Deal

dom., nov. 30 - mié., dic. 3

WestJet flights from Vancouver to Chicago

Our best WestJet deals on Vancouver to Chicago flight tickets

WestJet

Dec 4

YVR10:10 pmVancouver Intl

13h 25m

1 stop

ORD1:35 pmChicago O'Hare Intl

Jan 12

ORD2:20 pmChicago O'Hare Intl

7h 25m

1 stop

YVR7:45 pmVancouver Intl

$259

Find similar

WestJet

Dec 4

YVR5:45 pmVancouver Intl

17h 50m

1 stop

ORD1:35 pmChicago O'Hare Intl

Jan 9

ORD2:20 pmChicago O'Hare Intl

7h 25m

1 stop

YVR7:45 pmVancouver Intl

$276

Find similar

WestJet

Mar 27

YVR11:00 pmVancouver Intl

8h 56m

1 stop

MDW9:56 amChicago Midway

Mar 31

MDW10:35 amChicago Midway

12h 33m

2 stops

YVR9:08 pmVancouver Intl

$591

Find similar

Alaska Airlines flights from Vancouver to Chicago

Our best Alaska Airlines deals on Vancouver to Chicago flight tickets

Alaska Airlines

Nov 15

YVR5:45 pmVancouver Intl

9h 16m

2 stops

ORD5:01 amChicago O'Hare Intl

Nov 25

ORD6:00 amChicago O'Hare Intl

16h 55m

1 stop

YVR8:55 pmVancouver Intl

$365

Find similar

Alaska Airlines

Nov 10

YVR7:35 pmVancouver Intl

8h 47m

1 stop

ORD6:22 amChicago O'Hare Intl

Nov 18

ORD2:05 pmChicago O'Hare Intl

12h 05m

2 stops

YVR12:10 amVancouver Intl

$378

Find similar

Alaska Airlines

Nov 17

YVR7:35 pmVancouver Intl

8h 47m

1 stop

ORD6:22 amChicago O'Hare Intl

Nov 26

ORD12:59 pmChicago O'Hare Intl

13h 11m

1 stop

YVR12:10 amVancouver Intl

$395

Find similar

Fly from

Fly to

Route

Depart

Return

Price

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

mié. 12/3

11:00 pm-5:27 pm

1 stop16h 27m

Chicago O'Hare Intl

mié. 12/10

4:01 pm-4:54 pm

2 stops26h 53m

$203

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

mié. 12/3

11:00 pm-5:27 pm

1 stop16h 27m

Chicago O'Hare Intl

mié. 12/10

4:01 pm-4:54 pm

2 stops26h 53m

$204

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

dom. 12/7

11:00 pm-10:12 pm

1 stop21h 12m

Chicago Midway

jue. 12/11

7:23 pm-3:45 pm

2 stops22h 22m

$205

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

mié. 12/3

11:00 pm-5:27 pm

1 stop16h 27m

Chicago O'Hare Intl

mar. 12/9

4:22 pm-2:45 pm

2 stops24h 23m

$205

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

jue. 12/4

10:10 pm-1:35 pm

1 stop13h 25m

Chicago O'Hare Intl

lun. 1/12

2:20 pm-7:45 pm

1 stop7h 25m

$259

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

jue. 12/4

5:45 pm-1:35 pm

1 stop17h 50m

Chicago O'Hare Intl

vie. 1/9

2:20 pm-7:45 pm

1 stop7h 25m

$276

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

vie. 11/21

12:07 pm-11:40 pm

2 stops9h 33m

Chicago Midway

mar. 11/25

12:47 pm-10:37 pm

2 stops11h 50m

$426

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

mié. 11/19

11:00 pm-9:52 am

1 stop8h 52m

Chicago Midway

mié. 11/26

1:15 pm-10:37 pm

2 stops11h 22m

$478

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

lun. 12/1

4:20 pm-10:05 am

1 stop15h 45m

Chicago Midway

lun. 12/8

11:00 am-9:23 pm

2 stops12h 23m

$485

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

dom. 11/30

12:20 pm-10:05 am

2 stops19h 45m

Chicago Midway

mié. 12/3

11:00 am-9:23 pm

2 stops12h 23m

$518

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 cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Vancouver, with most prices found around $287. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Vancouver to Chicago during October average around $307.

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 Tuesday when prices can be found for as low as $326. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Vancouver to Chicago for around $439.

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Vancouver to Chicago during this time can be as low as $301. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $417.

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 $360 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 $260 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 distance between Vancouver and Chicago is about 1771.2 mi. Typically, this will take 8h 52m by plane in normal conditions.
When did momondo last update prices for flights from Vancouver to Chicago?
Prices for flights from Vancouver to Chicago were last updated today.
How many operators does momondo search for flights from Vancouver to Chicago?
The number of operators available for flights from Vancouver to Chicago is 3 as of November 2025.
How old do you have to be to fly from Vancouver to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking 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 $110	Free Cancellation	Rating 7.4 8,997 reviews	Search United Airlines flights
Air Canada	PriceFrom $155	Free Cancellation	Rating 7.1 10,394 reviews	Search Air Canada flights
American Airlines	PriceFrom $167	Free Cancellation	Rating 7.2 11,036 reviews	Search American Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

Finding the right flight to Chicago from Vancouver is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

momondo does allow users to show only those flights to Chicago from Vancouver which offer a flexible booking policy as well as other useful filters and features.

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.