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Cheap flights from Vancouver to Chicago from $111

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 to Chicago departing on 9/30. 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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Find the cheapest flights from Vancouver to Chicago

Cheap round-trip flights

WestJet Logo
6:00 am - 4:43 pmYVR-ORD
8h 43m1 stop
WestJet Logo
5:30 pm - 12:11 amORD-YVR
8h 41m1 stop
$203WestJet
Find Deal
Wed, Sep 24 - Tue, Sep 30
WestJet Logo
6:00 am - 4:43 pmYVR-ORD
8h 43m1 stop
WestJet Logo
5:30 pm - 12:11 amORD-YVR
8h 41m1 stop
$204WestJet
Find Deal
Wed, Sep 24 - Tue, Sep 30
Logo
6:00 am - 4:43 pmYVR-ORD
8h 43m1 stop
Logo
12:53 pm - 10:26 pmORD-YVR
11h 33m2 stops
$262
Find Deal
Wed, Sep 17 - Sun, Sep 21
Logo
5:35 pm - 4:50 amYVR-ORD
9h 15m1 stop
Logo
1:40 pm - 7:11 pmORD-YVR
7h 31m1 stop
$265
Find Deal
Wed, Aug 27 - Sat, Sep 6
Air Canada Logo
11:05 pm - 9:51 amYVR-ORD
8h 46m1 stop
Air Canada Logo
3:45 pm - 6:15 pmORD-YVR
4h 30mnonstop
$267Air Canada
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Tue, Sep 16 - Wed, Sep 17
Air Canada Logo
12:25 am - 10:53 amYVR-ORD
8h 28m1 stop
Air Canada Logo
3:45 pm - 6:15 pmORD-YVR
4h 30mnonstop
$273Air Canada
Find Deal
Mon, Sep 15 - Wed, Sep 17
Delta Logo
6:15 am - 5:37 pmYVR-MDW
9h 22m1 stop
Delta Logo
1:43 pm - 8:33 pmMDW-YVR
8h 50m1 stop
$308Delta
Find Deal
Fri, Aug 29 - Wed, Sep 3
Delta Logo
6:10 am - 5:35 pmYVR-MDW
9h 25m1 stop
Delta Logo
1:43 pm - 8:31 pmMDW-YVR
8h 48m1 stop
$347Delta
Find Deal
Wed, Sep 24 - Tue, Sep 30
Porter Airlines Logo
7:00 am - 10:05 amYVR-MDW
25h 05m2 stops
Porter Airlines Logo
4:15 pm - 11:15 amMDW-YVR
21h 00m2 stops
$555Porter Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30
Porter Airlines Logo
12:10 pm - 10:05 amYVR-MDW
19h 55m2 stops
Porter Airlines Logo
11:00 am - 11:15 amMDW-YVR
26h 15m2 stops
$556Porter Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30

WestJet flights from Vancouver to Chicago

Our best WestJet deals on Vancouver to Chicago flight tickets
WestJet
Sep 24
YVR6:00 amVancouver Intl
8h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl
Sep 30
ORD5:30 pmChicago O'Hare Intl
8h 41m
1 stop
YVR12:11 amVancouver Intl
$203
Find similar
WestJet
Sep 24
YVR6:00 amVancouver Intl
8h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl
Sep 30
ORD5:30 pmChicago O'Hare Intl
8h 41m
1 stop
YVR12:11 amVancouver Intl
$204
Find similar
WestJet
Sep 24
YVR6:00 amVancouver Intl
8h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl
Sep 30
ORD5:30 pmChicago O'Hare Intl
7h 06m
1 stop
YVR10:36 pmVancouver Intl
$205
Find similar

United Airlines flights from Vancouver to Chicago

Our best United Airlines deals on Vancouver to Chicago flight tickets
United Airlines
Aug 13
YVR11:35 pmVancouver Intl
4h 03m
ORD5:38 amChicago O'Hare Intl
Aug 21
ORD5:00 amChicago O'Hare Intl
13h 00m
1 stop
YVR4:00 pmVancouver Intl
$334
Find similar
United Airlines
Aug 13
YVR11:35 pmVancouver Intl
4h 03m
ORD5:38 amChicago O'Hare Intl
Aug 20
ORD6:15 amChicago O'Hare Intl
11h 39m
1 stop
YVR3:54 pmVancouver Intl
$341
Find similar
United Airlines
Aug 13
YVR11:35 pmVancouver Intl
4h 03m
ORD5:38 amChicago O'Hare Intl
Aug 15
ORD7:35 pmChicago O'Hare Intl
4h 43m
YVR10:18 pmVancouver Intl
$342
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated July 31, 2025.
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

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 9/24

6:00 am-4:43 pm

1 stop8h 43m

Chicago O'Hare Intl

Tue 9/30

5:30 pm-12:11 am

1 stop8h 41m

$203

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 9/24

6:00 am-4:43 pm

1 stop8h 43m

Chicago O'Hare Intl

Tue 9/30

5:30 pm-12:11 am

1 stop8h 41m

$204

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 9/17

6:00 am-4:43 pm

1 stop8h 43m

Chicago O'Hare Intl

Sun 9/21

12:53 pm-10:26 pm

2 stops11h 33m

$262

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 8/27

5:35 pm-4:50 am

1 stop9h 15m

Chicago O'Hare Intl

Sat 9/6

1:40 pm-7:11 pm

1 stop7h 31m

$265

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 9/16

11:05 pm-9:51 am

1 stop8h 46m

Chicago O'Hare Intl

Wed 9/17

3:45 pm-6:15 pm

Nonstop4h 30m

$267

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 9/15

12:25 am-10:53 am

1 stop8h 28m

Chicago O'Hare Intl

Wed 9/17

3:45 pm-6:15 pm

Nonstop4h 30m

$273

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 8/29

6:15 am-5:37 pm

1 stop9h 22m

Chicago Midway

Wed 9/3

1:43 pm-8:33 pm

1 stop8h 50m

$308

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 9/24

6:10 am-5:35 pm

1 stop9h 25m

Chicago Midway

Tue 9/30

1:43 pm-8:31 pm

1 stop8h 48m

$347

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 11/26

7:00 am-10:05 am

2 stops25h 05m

Chicago Midway

Sun 11/30

4:15 pm-11:15 am

2 stops21h 00m

$555

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 11/26

12:10 pm-10:05 am

2 stops19h 55m

Chicago Midway

Sun 11/30

11:00 am-11:15 am

2 stops26h 15m

$556

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 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 and Chicago?

What is the cheapest month to fly to Chicago?

The month of April is, on average, the cheapest month to fly to Chicago from Vancouver, with most prices found around $311. If you’re not able to fly to Chicago in April, then January is your next best option. Flight prices from Vancouver to Chicago during January average around $318.

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 Saturday, the most expensive travel day of the week, you can expect to see flight prices from Vancouver to Chicago for around $438.

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 in the evening when prices are around $395.

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 $379 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 $274 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

Best Price Found

$111

Fastest flight time

4h 09m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Vancouver in the past 72 hours is $111. The best round-trip flight deal from Vancouver to Chicago found on momondo in the last 72 hours is $203.
The fastest flight from Vancouver to Chicago takes 4h 09m
Direct flights go from Vancouver to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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  • How far is Vancouver to Chicago by plane?

    The distance between Vancouver and Chicago is about 1771.2 mi. Typically, this will take 7h 43m 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?

  • 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
Air CanadaPriceFrom $166Free CancellationRating
7.1
9,851 reviews
Search Air Canada flights
American AirlinesPriceFrom $167Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $261Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights

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
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.

An easier way to manage your Chicago trip

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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