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Cheap flights from Vancouver Intl Airport to Chicago from $110

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Vancouver Intl Airport to Chicago departing on 3/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Vancouver Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
12:05 pm - 11:41 pm
YVR
-
MDW
9h 36m1 stop
Multiple Airlines Logo
9:22 pm - 7:13 am
MDW
-
YVR
35h 51m2 stops
$299Multiple Airlines
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
3:30 pm - 5:31 am
YVR
-
ORD
12h 01m2 stops
Multiple Airlines Logo
5:30 pm - 10:35 pm
ORD
-
YVR
7h 05m1 stop
$299Multiple Airlines
Mon, May 4 - Thu, May 7
Multiple Airlines Logo
11:00 pm - 9:13 pm
YVR
-
ORD
20h 13m2 stops
Multiple Airlines Logo
6:00 am - 7:29 pm
ORD
-
YVR
15h 29m1 stop
$306Multiple Airlines
Sun, Mar 1 - Thu, Mar 5
WestJet Logo
6:00 am - 4:43 pm
YVR
-
ORD
8h 43m2 stops
WestJet Logo
5:30 pm - 12:10 am
ORD
-
YVR
8h 40m1 stop
$307WestJet
Mon, May 18 - Wed, May 20
Multiple Airlines Logo
3:40 pm - 9:32 pm
YVR
-
ORD
27h 52m1 stop
Multiple Airlines Logo
2:18 pm - 10:20 pm
ORD
-
YVR
34h 02m2 stops
$308Multiple Airlines
Thu, Jan 8 - Wed, Jan 14
Alaska Airlines Logo
7:55 am - 11:50 pm
YVR
-
ORD
13h 55m1 stop
Alaska Airlines Logo
8:00 am - 12:10 am
ORD
-
YVR
18h 10m1 stop
$310Alaska Airlines
Thu, Jan 29 - Sun, Feb 1
Multiple Airlines Logo
11:00 pm - 9:03 pm
YVR
-
ORD
20h 03m2 stops
Multiple Airlines Logo
3:55 pm - 8:05 am
ORD
-
YVR
18h 10m2 stops
$311Multiple Airlines
Fri, Jan 16 - Sun, Jan 18
Alaska Airlines Logo
7:35 pm - 2:38 pm
YVR
-
ORD
17h 03m1 stop
Alaska Airlines Logo
6:06 pm - 12:10 am
ORD
-
YVR
8h 04m1 stop
$312Alaska Airlines
Wed, Jan 21 - Thu, Jan 22
Delta Logo
7:37 pm - 8:52 am
YVR
-
MDW
11h 15m2 stops
Delta Logo
9:50 am - 6:44 pm
MDW
-
YVR
10h 54m2 stops
$355Delta
Thu, Jan 15 - Wed, Jan 21
Delta Logo
3:30 pm - 8:52 am
YVR
-
MDW
15h 22m2 stops
Delta Logo
9:33 am - 11:59 pm
MDW
-
YVR
16h 26m2 stops
$356Delta
Thu, Jan 29 - Sun, Feb 1

WestJet flights from Vancouver Intl Airport to Chicago

Our best WestJet deals on Vancouver Intl Airport to Chicago flight tickets
WestJet
May 18
YVR6:00 amVancouver Intl
8h 43m
2 stops
ORD4:43 pmChicago O'Hare Intl
May 20
ORD5:30 pmChicago O'Hare Intl
8h 40m
1 stop
YVR12:10 amVancouver Intl
$307
Find similar
WestJet
May 14
YVR6:00 amVancouver Intl
8h 43m
2 stops
ORD4:43 pmChicago O'Hare Intl
May 24
ORD5:30 pmChicago O'Hare Intl
15h 25m
2 stops
YVR6:55 amVancouver Intl
$346
Find similar
WestJet
Jan 12
YVR10:30 pmVancouver Intl
12h 18m
2 stops
MDW12:48 pmChicago Midway
Jan 18
MDW9:32 amChicago Midway
13h 43m
2 stops
YVR9:15 pmVancouver Intl
$435
Find similar

Air Canada flights from Vancouver Intl Airport to Chicago

Our best Air Canada deals on Vancouver Intl Airport to Chicago flight tickets
Air Canada
Jan 15
YVR8:30 amVancouver Intl
4h 11m
ORD2:41 pmChicago O'Hare Intl
Jan 21
ORD3:35 pmChicago O'Hare Intl
4h 35m
YVR6:10 pmVancouver Intl
$335
Find similar
Air Canada
Feb 23
YVR8:30 amVancouver Intl
4h 11m
ORD2:41 pmChicago O'Hare Intl
Feb 26
ORD3:35 pmChicago O'Hare Intl
4h 35m
YVR6:10 pmVancouver Intl
$356
Find similar
Air Canada
Jan 8
YVR8:30 amVancouver Intl
4h 11m
ORD2:41 pmChicago O'Hare Intl
Jan 14
ORD3:35 pmChicago O'Hare Intl
4h 35m
YVR6:10 pmVancouver Intl
$358
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Vancouver Intl Airport 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, momondo users made 832,500 searches. Data last updated December 25, 2025.
Use the filters below to find and compare flights from Vancouver Intl Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 2/19

12:05 pm-11:41 pm

1 stop9h 36m

Chicago Midway

Mon 2/23

9:22 pm-7:13 am

2 stops35h 51m

$299

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 5/4

3:30 pm-5:31 am

2 stops12h 01m

Chicago O'Hare Intl

Thu 5/7

5:30 pm-10:35 pm

1 stop7h 05m

$299

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 3/1

11:00 pm-9:13 pm

2 stops20h 13m

Chicago O'Hare Intl

Thu 3/5

6:00 am-7:29 pm

1 stop15h 29m

$306

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 5/18

6:00 am-4:43 pm

2 stops8h 43m

Chicago O'Hare Intl

Wed 5/20

5:30 pm-12:10 am

1 stop8h 40m

$307

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 1/8

3:40 pm-9:32 pm

1 stop27h 52m

Chicago O'Hare Intl

Wed 1/14

2:18 pm-10:20 pm

2 stops34h 02m

$308

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 1/29

7:55 am-11:50 pm

1 stop13h 55m

Chicago O'Hare Intl

Sun 2/1

8:00 am-12:10 am

1 stop18h 10m

$310

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 1/16

11:00 pm-9:03 pm

2 stops20h 03m

Chicago O'Hare Intl

Sun 1/18

3:55 pm-8:05 am

2 stops18h 10m

$311

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 1/21

7:35 pm-2:38 pm

1 stop17h 03m

Chicago O'Hare Intl

Thu 1/22

6:06 pm-12:10 am

1 stop8h 04m

$312

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/15

7:37 pm-8:52 am

2 stops11h 15m

Chicago Midway

Wed 1/21

9:50 am-6:44 pm

2 stops10h 54m

$355

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/29

3:30 pm-8:52 am

2 stops15h 22m

Chicago Midway

Sun 2/1

9:33 am-11:59 pm

2 stops16h 26m

$356

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Vancouver Intl Airport 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

What is the typical price of a round-trip flight between Vancouver Intl Airport 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 Intl Airport, with most prices found around $261. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Vancouver Intl Airport to Chicago during September average around $286.

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 $336. 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 Intl Airport to Chicago for around $451.

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 Intl Airport 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 $424.

What is the cheapest Vancouver Intl to Chicago flight route?

Fly from Vancouver Intl to Chicago O'Hare Intl for the best Vancouver Intl - 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 Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $357 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Vancouver Intl Airport for as low as $257 on momondo.

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

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

Can stopping save me money on Vancouver Intl Airport to Chicago flights?

You could potentially save up to 22% on your flight if you consider stops on a Vancouver Intl Airport to Chicago flight.

How have Vancouver Intl Airport to Chicago flight prices changed over time?

As of December 2025, prices for Vancouver Intl Airport to Chicago flights are approximately 20% cheaper when compared to flights at the same time last year.

When to book flights from Vancouver Intl Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Vancouver Intl Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Vancouver Intl Airport to Chicago (YVR to CHI) flight deals and tips

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

Best Price Found

$251

Fastest flight time

4h 08m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Vancouver Intl Airport in the past 72 hours is $251. The best round-trip flight deal from Vancouver Intl Airport to Chicago found on momondo in the last 72 hours is $457.
The fastest flight from Vancouver Intl Airport to Chicago takes 4h 08m
Direct flights go from Vancouver Intl Airport to Chicago every day.
There are 3 airports in Chicago. From Vancouver Intl Airport there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • How far is Vancouver Intl to Chicago by plane?

    Vancouver Intl and Chicago are 1773.8 mi apart from one another. 4h 08m is a normal flight duration for this route.

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

    Prices for flights from Vancouver Intl Airport to Chicago refresh daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Vancouver Intl Airport to Chicago.

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

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Vancouver Intl Airport to Chicago?

  • What is the most popular airline from Vancouver Intl Airport to Chicago?

Best airlines flying from Vancouver Intl Airport to Chicago

Compare and see reviews for airlines that fly from Vancouver Intl Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $110Free CancellationRating
7.4
9,114 reviews
Search United Airlines flights
Air CanadaPriceFrom $155Free CancellationRating
7.1
10,555 reviews
Search Air Canada flights
American AirlinesPriceFrom $167Free CancellationRating
7.2
11,056 reviews
Search American Airlines flights

  • United Airlines Flights From Vancouver Intl Airport to Chicago

    The lowest priced United Airlines flight from Vancouver Intl Airport to Chicago from the last 72 hours was $110. Generally, United Airlines has 14 flights on this route every week with an average price of $379. United Airlines is rated 7.4/10 by our users.

  • Air Canada Flights From Vancouver Intl Airport to Chicago

    Across 10,555 Air Canada reviews on momondo, the average score is 7.1/10. Air Canada flies from Vancouver Intl Airport to Chicago about 14 times each week, with ticket deals ranging from $155 to $419. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
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?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Vancouver.

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

All flight searches from Vancouver to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

Once all potential Vancouver to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport