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Cheap flights from Vancouver to Chicago from C$ 129

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 28/5. 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

Enter your travel dates to find the best prices.
WestJet Logo
5:55 p.m. - 1:35 p.m.YVR-ORD
17h 40m2 stops
WestJet Logo
5:30 p.m. - 10:35 p.m.ORD-YVR
7h 05m1 stop
C$ 283WestJet
Find Deal
Thu, 23 Apr - Sat, 2 May
Multiple Airlines Logo
3:45 p.m. - 4:51 p.m.YVR-ORD
23h 06m2 stops
Multiple Airlines Logo
2:20 p.m. - 7:45 p.m.ORD-YVR
7h 25m1 stop
C$ 287Multiple Airlines
Find Deal
Fri, 23 Jan - Fri, 30 Jan
WestJet Logo
7:45 p.m. - 1:35 p.m.YVR-ORD
15h 50m1 stop
WestJet Logo
5:30 p.m. - 10:35 p.m.ORD-YVR
7h 05m1 stop
C$ 290WestJet
Find Deal
Thu, 23 Apr - Sat, 2 May
WestJet Logo
10:10 p.m. - 4:43 p.m.YVR-ORD
16h 33m2 stops
WestJet Logo
5:30 p.m. - 10:35 p.m.ORD-YVR
7h 05m1 stop
C$ 291WestJet
Find Deal
Sat, 25 Apr - Sat, 2 May
Multiple Airlines Logo
7:45 p.m. - 10:23 p.m.YVR-ORD
24h 38m2 stops
Multiple Airlines Logo
2:20 p.m. - 7:40 p.m.ORD-YVR
7h 20m1 stop
C$ 294Multiple Airlines
Find Deal
Mon, 23 Feb - Mon, 9 Mar
Multiple Airlines Logo
7:45 p.m. - 10:23 p.m.YVR-ORD
24h 38m2 stops
Multiple Airlines Logo
2:20 p.m. - 8:55 p.m.ORD-YVR
8h 35m1 stop
C$ 301Multiple Airlines
Find Deal
Tue, 24 Feb - Fri, 6 Mar
Multiple Airlines Logo
5:30 p.m. - 8:29 p.m.YVR-ORD
24h 59m1 stop
Multiple Airlines Logo
9:38 p.m. - 10:20 p.m.ORD-YVR
26h 42m1 stop
C$ 304Multiple Airlines
Find Deal
Thu, 29 Jan - Sun, 1 Feb
Delta Logo
6:20 a.m. - 8:52 a.m.YVR-MDW
24h 32m2 stops
Delta Logo
9:33 a.m. - 11:59 p.m.MDW-YVR
16h 26m2 stops
C$ 434Delta
Find Deal
Thu, 22 Jan - Mon, 26 Jan
Delta Logo
6:20 a.m. - 5:37 p.m.YVR-MDW
9h 17m2 stops
Delta Logo
9:32 a.m. - 6:46 p.m.MDW-YVR
11h 14m2 stops
C$ 437Delta
Find Deal
Thu, 5 Mar - Tue, 10 Mar
Delta Logo
7:37 p.m. - 5:29 p.m.YVR-MDW
19h 52m2 stops
Delta Logo
1:49 p.m. - 10:47 a.m.MDW-YVR
22h 58m2 stops
C$ 438Delta
Find Deal
Thu, 22 Jan - Mon, 26 Jan

WestJet flights from Vancouver to Chicago

Our best WestJet deals on Vancouver to Chicago flight tickets
WestJet
23 Apr
YVR5:55 p.m.Vancouver Intl
17h 40m
2 stops
ORD1:35 p.m.Chicago O'Hare Intl
2 May
ORD5:30 p.m.Chicago O'Hare Intl
7h 05m
1 stop
YVR10:35 p.m.Vancouver Intl
C$ 283
Find similar
WestJet
23 Apr
YVR7:45 p.m.Vancouver Intl
15h 50m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
2 May
ORD5:30 p.m.Chicago O'Hare Intl
7h 05m
1 stop
YVR10:35 p.m.Vancouver Intl
C$ 290
Find similar
WestJet
25 Apr
YVR10:10 p.m.Vancouver Intl
16h 33m
2 stops
ORD4:43 p.m.Chicago O'Hare Intl
2 May
ORD5:30 p.m.Chicago O'Hare Intl
7h 05m
1 stop
YVR10:35 p.m.Vancouver Intl
C$ 291
Find similar

Alaska Airlines flights from Vancouver to Chicago

Our best Alaska Airlines deals on Vancouver to Chicago flight tickets
Alaska Airlines
23 Jan
YVR7:35 p.m.Vancouver Intl
26h 15m
1 stop
ORD11:50 p.m.Chicago O'Hare Intl
27 Jan
ORD8:00 a.m.Chicago O'Hare Intl
12h 45m
1 stop
YVR6:45 p.m.Vancouver Intl
C$ 368
Find similar
Alaska Airlines
23 Jan
YVR5:45 p.m.Vancouver Intl
28h 05m
1 stop
ORD11:50 p.m.Chicago O'Hare Intl
27 Jan
ORD6:06 p.m.Chicago O'Hare Intl
8h 04m
1 stop
YVR12:10 a.m.Vancouver Intl
C$ 372
Find similar
Alaska Airlines
23 Jan
YVR7:35 p.m.Vancouver Intl
26h 15m
1 stop
ORD11:50 p.m.Chicago O'Hare Intl
26 Jan
ORD3:35 p.m.Chicago O'Hare Intl
22h 55m
1 stop
YVR12:30 p.m.Vancouver Intl
C$ 393
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 96,600 searches. Data last updated 3 December 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

Thu 23/4

5:55 p.m.-1:35 p.m.

2 stops17h 40m

Chicago O'Hare Intl

Sat 2/5

5:30 p.m.-10:35 p.m.

1 stop7h 05m

C$ 283

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 23/1

3:45 p.m.-4:51 p.m.

2 stops23h 06m

Chicago O'Hare Intl

Fri 30/1

2:20 p.m.-7:45 p.m.

1 stop7h 25m

C$ 287

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 23/4

7:45 p.m.-1:35 p.m.

1 stop15h 50m

Chicago O'Hare Intl

Sat 2/5

5:30 p.m.-10:35 p.m.

1 stop7h 05m

C$ 290

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 25/4

10:10 p.m.-4:43 p.m.

2 stops16h 33m

Chicago O'Hare Intl

Sat 2/5

5:30 p.m.-10:35 p.m.

1 stop7h 05m

C$ 291

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 23/2

7:45 p.m.-10:23 p.m.

2 stops24h 38m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-7:40 p.m.

1 stop7h 20m

C$ 294

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 24/2

7:45 p.m.-10:23 p.m.

2 stops24h 38m

Chicago O'Hare Intl

Fri 6/3

2:20 p.m.-8:55 p.m.

1 stop8h 35m

C$ 301

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 29/1

5:30 p.m.-8:29 p.m.

1 stop24h 59m

Chicago O'Hare Intl

Sun 1/2

9:38 p.m.-10:20 p.m.

1 stop26h 42m

C$ 304

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 22/1

6:20 a.m.-8:52 a.m.

2 stops24h 32m

Chicago Midway

Mon 26/1

9:33 a.m.-11:59 p.m.

2 stops16h 26m

C$ 434

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/3

6:20 a.m.-5:37 p.m.

2 stops9h 17m

Chicago Midway

Tue 10/3

9:32 a.m.-6:46 p.m.

2 stops11h 14m

C$ 437

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 22/1

7:37 p.m.-5:29 p.m.

2 stops19h 52m

Chicago Midway

Mon 26/1

1:49 p.m.-10:47 a.m.

2 stops22h 58m

C$ 438

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 September is another great option to travel to Chicago, with average flight prices from Vancouver averaging around C$ 402.

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 Wednesday when prices can be found for as low as C$ 559. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around C$ 755. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

In the afternoon is the cheapest time of day to fly from Vancouver to Chicago when you can find flight prices for as low as C$ 409. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 658 per ticket.

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 C$ 491 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 C$ 360 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 straight-line distance from Vancouver to Chicago is 2850.5 km. By plane, this route typically takes 6h 13m.

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

    Prices for flights from Vancouver to Chicago are refreshed on a daily basis.

  • 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?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify 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 travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek 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 C$ 206Free CancellationRating
7.4
9,064 reviews
Search United Airlines flights
WestJetPriceFrom C$ 237Free CancellationRating
7.2
3,190 reviews
Search WestJet flights
American AirlinesPriceFrom C$ 238Free CancellationRating
7.2
11,045 reviews
Search American Airlines flights
Air CanadaPriceFrom C$ 258Free CancellationRating
7.1
10,497 reviews
Search Air Canada flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Vancouver to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo allows you to filter the results for Vancouver to Chicago flights to just show those with flexible booking policies.

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 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport