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 41% 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, Porter Airlines, and Delta are the most popular carriers operating from Vancouver to Chicago

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

The number of flights available between Vancouver and Chicago is 39 per week as of January 2026. The most frequent departure day is Mon, with 15% of weekly flights leaving on this day.

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

As of January 2026, 5 flights take off from Vancouver and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 100% 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 January 2026.

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.

$109 Cheap Flights from Vancouver to Chicago in 2026

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

Prices are currently typical for flights on this route. Typical prices usually range from $225 to $425. The lowest price recently found on this route was $239.

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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.

12:30 pm - 11:41 pm

YVR

MDW

33h 11m

2 stops

3:29 pm - 11:59 pm

MDW

YVR

10h 30m

1 stop

$239Multiple Airlines

Wed, Feb 25 - Mon, Mar 2

7:30 am - 4:40 pm

YVR

ORD

7h 10m

1 stop

5:30 pm - 10:35 pm

ORD

YVR

7h 05m

1 stop

$239WestJet

Thu, May 7 - Mon, May 11

8:55 am - 1:35 pm

YVR

ORD

26h 40m

2 stops

6:00 am - 11:59 pm

ORD

YVR

19h 59m

1 stop

$241Multiple Airlines

Thu, Feb 26 - Mon, Mar 2

4:35 pm - 5:03 pm

YVR

ORD

22h 28m

1 stop

9:15 am - 4:27 pm

ORD

YVR

9h 12m

1 stop

$242Multiple Airlines

Tue, Feb 24 - Tue, Mar 3

8:00 am - 6:30 pm

YVR

MDW

32h 30m

2 stops

3:29 pm - 11:59 pm

MDW

YVR

10h 30m

1 stop

$244Multiple Airlines

Thu, Feb 26 - Mon, Mar 2

6:55 am - 1:35 pm

YVR

ORD

28h 40m

2 stops

7:55 am - 7:29 pm

ORD

YVR

13h 34m

1 stop

$244Multiple Airlines

Thu, Feb 26 - Sat, Feb 28

12:05 pm - 7:54 am

YVR

ORD

17h 49m

2 stops

6:00 am - 11:59 pm

ORD

YVR

19h 59m

1 stop

$249Multiple Airlines

Sat, Feb 28 - Mon, Mar 2

7:30 am - 4:40 pm

YVR

ORD

7h 10m

1 stop

5:30 pm - 10:10 am

ORD

YVR

18h 40m

1 stop

$251WestJet

Mon, Jun 1 - Mon, Jun 8

7:30 am - 4:40 pm

YVR

ORD

7h 10m

1 stop

5:30 pm - 7:40 am

ORD

YVR

16h 10m

1 stop

$252WestJet

Sun, Apr 26 - Fri, May 1

5:30 pm - 5:03 pm

YVR

ORD

45h 33m

2 stops

6:00 am - 11:59 pm

ORD

YVR

19h 59m

1 stop

$254Multiple Airlines

Mon, Feb 23 - Mon, Mar 2

WestJet flights from Vancouver to Chicago

Our best WestJet deals on Vancouver to Chicago flight tickets

WestJet

May 7

YVR7:30 amVancouver Intl

7h 10m

1 stop

ORD4:40 pmChicago O'Hare Intl

May 11

ORD5:30 pmChicago O'Hare Intl

7h 05m

1 stop

YVR10:35 pmVancouver Intl

$239

WestJet

Jun 1

YVR7:30 amVancouver Intl

7h 10m

1 stop

ORD4:40 pmChicago O'Hare Intl

Jun 8

ORD5:30 pmChicago O'Hare Intl

18h 40m

1 stop

YVR10:10 amVancouver Intl

$251

WestJet

Apr 26

YVR7:30 amVancouver Intl

7h 10m

1 stop

ORD4:40 pmChicago O'Hare Intl

May 1

ORD5:30 pmChicago O'Hare Intl

16h 10m

1 stop

YVR7:40 amVancouver Intl

$252

Delta flights from Vancouver to Chicago

Our best Delta deals on Vancouver to Chicago flight tickets

Delta

Apr 20

YVR7:30 pmVancouver Intl

15h 13m

2 stops

MDW12:43 pmChicago Midway

Apr 28

MDW9:27 amChicago Midway

15h 34m

2 stops

YVR11:01 pmVancouver Intl

$438

Delta

Apr 20

YVR7:30 pmVancouver Intl

15h 13m

2 stops

MDW12:43 pmChicago Midway

Apr 25

MDW9:27 amChicago Midway

13h 43m

2 stops

YVR9:10 pmVancouver Intl

$445

Delta

Apr 22

YVR7:30 pmVancouver Intl

15h 13m

2 stops

MDW12:43 pmChicago Midway

Apr 28

MDW9:27 amChicago Midway

15h 34m

2 stops

YVR11:01 pmVancouver Intl

$450

Fly from

Fly to

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 2/25

12:30 pm-11:41 pm

2 stops33h 11m

Chicago Midway

Mon 3/2

3:29 pm-11:59 pm

1 stop10h 30m

$239

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 5/7

7:30 am-4:40 pm

1 stop7h 10m

Chicago O'Hare Intl

Mon 5/11

5:30 pm-10:35 pm

1 stop7h 05m

$239

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 2/26

8:55 am-1:35 pm

2 stops26h 40m

Chicago O'Hare Intl

Mon 3/2

6:00 am-11:59 pm

1 stop19h 59m

$241

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 2/24

4:35 pm-5:03 pm

1 stop22h 28m

Chicago O'Hare Intl

Tue 3/3

9:15 am-4:27 pm

1 stop9h 12m

$242

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 2/26

8:00 am-6:30 pm

2 stops32h 30m

Chicago Midway

Mon 3/2

3:29 pm-11:59 pm

1 stop10h 30m

$244

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 2/26

6:55 am-1:35 pm

2 stops28h 40m

Chicago O'Hare Intl

Sat 2/28

7:55 am-7:29 pm

1 stop13h 34m

$244

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 2/28

12:05 pm-7:54 am

2 stops17h 49m

Chicago O'Hare Intl

Mon 3/2

6:00 am-11:59 pm

1 stop19h 59m

$249

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 6/1

7:30 am-4:40 pm

1 stop7h 10m

Chicago O'Hare Intl

Mon 6/8

5:30 pm-10:10 am

1 stop18h 40m

$251

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 4/26

7:30 am-4:40 pm

1 stop7h 10m

Chicago O'Hare Intl

Fri 5/1

5:30 pm-7:40 am

1 stop16h 10m

$252

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 2/23

5:30 pm-5:03 pm

2 stops45h 33m

Chicago O'Hare Intl

Mon 3/2

6:00 am-11:59 pm

1 stop19h 59m

$254

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, on average, the cheapest month to fly to Chicago from Vancouver, with most prices found around $264. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Vancouver to Chicago during September average around $287.

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 $340. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Vancouver to Chicago for around $512.

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 morning. Flights from Vancouver to Chicago during this time can be as low as $378. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $421.

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 $272 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 05m
Direct flights	Every day
Airports in Chicago	3 airports

The fastest flight from Vancouver to Chicago takes 4h 05m

Direct flights go from Vancouver to Chicago every day.

There are 3 airports in Chicago. From Vancouver there are direct flights to 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 4h 05m 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 January 2026.
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 $90	Free Cancellation	Rating 7.4 9,207 reviews	Search United Airlines flights
Air Canada	PriceFrom $151	Free Cancellation	Rating 7.1 10,660 reviews	Search Air Canada flights
American Airlines	PriceFrom $167	Free Cancellation	Rating 7.2 11,198 reviews	Search American Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

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.