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Cheap flights from Vancouver to Chicago from $99

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 10/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

WestJet Logo
7:00 am - 4:43 pmYVR-ORD
7h 43m1 stop
WestJet Logo
5:30 pm - 10:36 pmORD-YVR
7h 06m1 stop
$149WestJet
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Fri, Oct 17 - Sun, Oct 19
WestJet Logo
7:00 am - 4:43 pmYVR-ORD
7h 43m1 stop
WestJet Logo
5:30 pm - 10:36 pmORD-YVR
7h 06m1 stop
$153WestJet
Find Deal
Sun, Oct 12 - Sun, Oct 19
Air Canada Logo
8:30 am - 2:41 pmYVR-ORD
4h 11mnonstop
Air Canada Logo
3:40 pm - 6:15 pmORD-YVR
4h 35mnonstop
$167Air Canada
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Tue, Nov 11 - Fri, Nov 14
American Airlines Logo
1:29 pm - 7:57 pmYVR-ORD
4h 28mnonstop
American Airlines Logo
9:52 am - 12:34 pmORD-YVR
4h 42mnonstop
$168American Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
Air Canada Logo
5:15 pm - 9:15 amYVR-ORD
14h 00m2 stops
Air Canada Logo
2:00 pm - 10:20 pmORD-YVR
10h 20m1 stop
$171Air Canada
Find Deal
Wed, Oct 29 - Wed, Nov 5
American Airlines Logo
1:29 pm - 7:57 pmYVR-ORD
4h 28mnonstop
American Airlines Logo
6:00 am - 12:45 pmORD-YVR
8h 45m1 stop
$178American Airlines
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Fri, Sep 26 - Mon, Sep 29
Multiple Airlines Logo
7:25 pm - 9:51 amYVR-ORD
12h 26m2 stops
Multiple Airlines Logo
5:30 pm - 12:11 amORD-YVR
8h 41m1 stop
$182Multiple Airlines
Find Deal
Fri, Oct 3 - Mon, Oct 6
United Airlines Logo
11:00 am - 7:55 pmYVR-ORD
6h 55m1 stop
United Airlines Logo
7:41 pm - 10:18 pmORD-YVR
4h 37mnonstop
$183United Airlines
Find Deal
Fri, Oct 17 - Mon, Oct 20
Multiple Airlines Logo
10:45 am - 11:44 pmYVR-ORD
10h 59m1 stop
Multiple Airlines Logo
5:30 pm - 10:36 pmORD-YVR
7h 06m1 stop
$192Multiple Airlines
Find Deal
Mon, Oct 13 - Thu, Oct 23
United Airlines Logo
1:45 pm - 8:04 pmYVR-ORD
4h 19mnonstop
United Airlines Logo
1:10 pm - 3:50 pmORD-YVR
4h 40mnonstop
$197United Airlines
Find Deal
Wed, Oct 15 - Tue, Oct 28

United Airlines flights from Vancouver to Chicago

Our best United Airlines deals on Vancouver to Chicago flight tickets
United Airlines
Sep 25
YVR2:20 pmVancouver Intl
6h 19m
1 stop
ORD10:39 pmChicago O'Hare Intl
Oct 1
ORD7:18 amChicago O'Hare Intl
7h 54m
1 stop
YVR1:12 pmVancouver Intl
$182
Find similar
United Airlines
Oct 17
YVR11:00 amVancouver Intl
6h 55m
1 stop
ORD7:55 pmChicago O'Hare Intl
Oct 20
ORD7:41 pmChicago O'Hare Intl
4h 37m
YVR10:18 pmVancouver Intl
$183
Find similar
United Airlines
Sep 25
YVR1:45 pmVancouver Intl
4h 19m
ORD8:04 pmChicago O'Hare Intl
Oct 1
ORD2:17 pmChicago O'Hare Intl
9h 32m
1 stop
YVR9:49 pmVancouver Intl
$188
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Lufthansa flights from Vancouver to Chicago

Our best Lufthansa deals on Vancouver to Chicago flight tickets
Lufthansa
Sep 25
YVR1:45 pmVancouver Intl
4h 19m
ORD8:04 pmChicago O'Hare Intl
Oct 1
ORD8:51 amChicago O'Hare Intl
4h 42m
YVR11:33 amVancouver Intl
$177
Find similar
Lufthansa
Sep 25
YVR1:45 pmVancouver Intl
4h 19m
ORD8:04 pmChicago O'Hare Intl
Oct 1
ORD2:53 pmChicago O'Hare Intl
8h 56m
1 stop
YVR9:49 pmVancouver Intl
$187
Find similar
Lufthansa
Sep 25
YVR11:00 amVancouver Intl
7h 18m
1 stop
ORD8:18 pmChicago O'Hare Intl
Oct 1
ORD5:01 amChicago O'Hare Intl
6h 50m
1 stop
YVR9:51 amVancouver Intl
$204
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 September 16, 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

Fri 10/17

7:00 am-4:43 pm

1 stop7h 43m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-10:36 pm

1 stop7h 06m

$149

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 10/12

7:00 am-4:43 pm

1 stop7h 43m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-10:36 pm

1 stop7h 06m

$153

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 11/11

8:30 am-2:41 pm

Nonstop4h 11m

Chicago O'Hare Intl

Fri 11/14

3:40 pm-6:15 pm

Nonstop4h 35m

$167

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 9/26

1:29 pm-7:57 pm

Nonstop4h 28m

Chicago O'Hare Intl

Mon 9/29

9:52 am-12:34 pm

Nonstop4h 42m

$168

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 10/29

5:15 pm-9:15 am

2 stops14h 00m

Chicago O'Hare Intl

Wed 11/5

2:00 pm-10:20 pm

1 stop10h 20m

$171

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 9/26

1:29 pm-7:57 pm

Nonstop4h 28m

Chicago O'Hare Intl

Mon 9/29

6:00 am-12:45 pm

1 stop8h 45m

$178

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 10/3

7:25 pm-9:51 am

2 stops12h 26m

Chicago O'Hare Intl

Mon 10/6

5:30 pm-12:11 am

1 stop8h 41m

$182

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 10/17

11:00 am-7:55 pm

1 stop6h 55m

Chicago O'Hare Intl

Mon 10/20

7:41 pm-10:18 pm

Nonstop4h 37m

$183

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 10/13

10:45 am-11:44 pm

1 stop10h 59m

Chicago O'Hare Intl

Thu 10/23

5:30 pm-10:36 pm

1 stop7h 06m

$192

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 10/15

1:45 pm-8:04 pm

Nonstop4h 19m

Chicago O'Hare Intl

Tue 10/28

1:10 pm-3:50 pm

Nonstop4h 40m

$197

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 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 $291. 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 $291.

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 $327. 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 $441.

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 $400.

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 $365 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 $264 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 09m

Direct flights

Every day

Airports in Chicago

1 airport
The fastest flight from Vancouver to Chicago takes 4h 09m
Direct flights go from Vancouver to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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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 4h 11m 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
United AirlinesPriceFrom $110Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
Air CanadaPriceFrom $151Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
American AirlinesPriceFrom $208Free CancellationRating
7.2
10,000 reviews
Search American 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
Lansing
Portage
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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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