YVR - CHI

$205 Find Cheap Flights from Vancouver to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Vancouver to Chicago departing on 10/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$285
Typical prices: $196-$485
WestJet
Fri 9/4Sun 9/13
YVR - ORD • 1 stop
Cheapest non-stop
$315
Typical prices: $208-$532
Air Canada
Thu 9/10Wed 9/16
YVR - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Basic Economy cuts fares, but late boarding and no seat assignment add tradeoffs.
United Economy Plus and Air Canada Premium Economy add legroom; both boost comfort.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $285 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Air Canada, American Airlines and United Airlines. Average duration is 4h 14m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $258 (round-trip)
Shortest trip • 6h 46m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 41% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 41% price drop
Most popular
Good to know
Good to know
+1
+1
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We hope you love your trip to Chicago!
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Flight Deals

Cheap Flights from Vancouver to Chicago (YVR-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Vancouver to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Vancouver to Chicago

Fri, Sep 4 - Sun, Sep 13
WestJet Logo
6:45 am - 4:40 pm
YVR
-
ORD
7h 55m
1 stop
WestJet Logo
5:30 pm - 10:35 pm
ORD
-
YVR
7h 05m
1 stop
$285WestJet
Thu, Oct 15 - Thu, Oct 22
WestJet Logo
6:00 am - 4:40 pm
YVR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 pm - 10:35 pm
ORD
-
YVR
7h 05m
1 stop
$287WestJet
Thu, Sep 10 - Wed, Sep 16
Air Canada Logo
8:25 am - 2:43 pm
YVR
-
ORD
4h 18mnonstop
Air Canada Logo
3:40 pm - 6:15 pm
ORD
-
YVR
4h 35mnonstop
$315Air Canada
Thu, Sep 10 - Wed, Sep 16
Air Canada Logo
8:25 am - 2:43 pm
YVR
-
ORD
4h 18mnonstop
Air Canada Logo
11:05 am - 8:15 pm
ORD
-
YVR
11h 10m
1 stop
$317Air Canada
Tue, Oct 6 - Tue, Oct 13
United Airlines Logo
1:45 pm - 8:06 pm
YVR
-
ORD
4h 21mnonstop
United Airlines Logo
7:45 pm - 10:26 pm
ORD
-
YVR
4h 41mnonstop
$322United Airlines
Wed, Oct 7 - Tue, Oct 13
United Airlines Logo
1:45 pm - 8:06 pm
YVR
-
ORD
4h 21mnonstop
United Airlines Logo
7:45 pm - 10:26 pm
ORD
-
YVR
4h 41mnonstop
$322United Airlines
Tue, Oct 6 - Thu, Oct 15
Multiple Airlines Logo
6:45 am - 4:40 pm
YVR
-
ORD
7h 55m
1 stop
Multiple Airlines Logo
6:05 am - 7:55 pm
ORD
-
YVR
15h 50m
2 stops
$325Multiple Airlines
Tue, Sep 15 - Tue, Sep 29
Delta Logo
6:00 am - 6:19 pm
YVR
-
MDW
10h 19m
1 stop
Delta Logo
9:59 am - 6:40 pm
MDW
-
YVR
10h 41m
2 stops
$331Delta
Sat, Sep 5 - Tue, Sep 8
American Airlines Logo
6:00 am - 6:29 pm
YVR
-
ORD
10h 29m
1 stop
American Airlines Logo
5:00 am - 10:45 am
ORD
-
YVR
7h 45m
1 stop
$353American Airlines
Thu, Sep 10 - Tue, Sep 22
American Airlines Logo
1:40 pm - 8:10 pm
YVR
-
ORD
4h 30mnonstop
American Airlines Logo
3:00 pm - 9:17 pm
ORD
-
YVR
8h 17m
1 stop
$353American Airlines
Booking Insights

KAYAK's insights & trends for Vancouver to Chicago flights

Get data-powered insights and trends into flights from Vancouver to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Vancouver Intl Airport to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Vancouver Intl Airport to Chicago departing in September.

Flight prices are typical for this route right now.

Flights to Chicago from Vancouver Intl Airport usually cost between $254 and $494 in September.
The lowest price found in the past 5 days was $285 on WestJet (Sep 4-Sep 13).

What is the cheapest Vancouver Intl Airport to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Vancouver Intl Airport to Chicago costs $356 on the route between Vancouver Intl Airport (YVR) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Vancouver to Chicago?

The average price of all round-trip flights from Vancouver Intl Airport to Chicago clicked on KAYAK for each day over the last 12 months.

For Vancouver to Chicago, Friday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago back to Vancouver, the best deals are generally found on Thursday, with Tuesday being the most expensive.

What is the cheapest month to fly from Vancouver Intl Airport to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Vancouver Intl Airport to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Vancouver Intl Airport to Chicago is October, where tickets cost $250 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $551 and $494 respectively.

Can I save money by flying with a layover from Vancouver Intl Airport to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $269 on average.

How far in advance should I book a flight from Vancouver Intl Airport to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Vancouver Intl Airport to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Vancouver Intl Airport to Chicago, you should book around 7 weeks before departure, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Expert advice

Expert advice for your flight from Vancouver to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Air Canada, United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Jessica Macdonald

Jessica Macdonald

Expert on YVR

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Good to know

Low season

January

Cheapest flight

$205
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 40% lower on average.
Flight from Vancouver to Chicago O'Hare Airport

When to book flights from Vancouver to Chicago

Are your dates flexible? Find out the best times to travel from Vancouver to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Vancouver to Chicago flights

  • What is the cheapest flight from Vancouver Intl Airport to Chicago?

    In the last 5 days, the lowest price for a flight from Vancouver Intl Airport to Chicago was $205 for a one-way ticket and $285 for a round-trip.

  • Do I need a passport to fly between Vancouver and Chicago?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Vancouver and on arrival in Chicago.

  • Which airports will I be using when flying from Vancouver to Chicago?

    On your way to Chicago, you’ll fly out from Vancouver Intl. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Vancouver to Chicago?

    American Airlines, Air Canada, Finnair, and Lufthansa offer inflight Wi-Fi service on the Vancouver to Chicago flight route.

  • Which aircraft models fly most regularly from Vancouver to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Vancouver to Chicago flight route.

  • Which airline alliances offer flights from Vancouver to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Vancouver and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Vancouver to Chicago?

    There are nonstop flights from Vancouver to Chicago on a daily basis.

  • Which is the best airline for flights from Vancouver to Chicago, United Airlines or Air Canada?

    The two airlines most popular with KAYAK users for flights from Vancouver to Chicago are United Airlines and Air Canada. With an average price for the route of $481 and an overall rating of 7.4, United Airlines is the most popular choice. Air Canada is also a great choice for the route, with an average price of $475 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Vancouver to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Vancouver to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Vancouver to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Vancouver is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Vancouver to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Vancouver with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Vancouver to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Vancouver up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Vancouver Intl Airport to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $278 or less one-way and $481 or less round-trip.

Prefer to fly direct from Vancouver to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Vancouver Intl to Chicago.
Find which airlines fly direct from Vancouver Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Vancouver Intl to Chicago

Monday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Tuesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Wednesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Thursday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Friday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Saturday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Sunday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

See more direct flights

Direct returns

Chicago to Vancouver Intl

Monday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Tuesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Wednesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Thursday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Friday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Saturday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Sunday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

See more direct flights

Reviews of the top 3 airlines serving from Vancouver to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Vancouver to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Vancouver to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 10057 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
6.7Food
8.1Crew
Airline reviews

We boarded the plane and were about to take off when we were notified that the tires had to be checked. Upon inspection, they were found to need replacement, so the entire plane had to be deboarded. After we exited the plane, United staff forced us to stay in the gate area by posting "Do Not Exit" signs on the doors connecting the gate area to the terminal. Many of us had already rebooked our flights and had no checked bags, but they told us we could not leave. This seemed inappropriate to hold people under false pretenses. When the agent told us we could leave, I asked them to please take down the "Do Not Exit" signs, as they were misleading. The agent refused, and I told them that it didn't feel right to hold people like that.

2.0 MediocreAnonymous, Jul 2026
YVR - SFO
Read more United Airlines reviews

We boarded the plane and were about to take off when we were notified that the tires had to be checked. Upon inspection, they were found to need replacement, so the entire plane had to be deboarded. After we exited the plane, United staff forced us to stay in the gate area by posting "Do Not Exit" signs on the doors connecting the gate area to the terminal. Many of us had already rebooked our flights and had no checked bags, but they told us we could not leave. This seemed inappropriate to hold people under false pretenses. When the agent told us we could leave, I asked them to please take down the "Do Not Exit" signs, as they were misleading. The agent refused, and I told them that it didn't feel right to hold people like that.

Friendly crew, but we were delayed for more than an hour and had to change planes due to maintenance issues.

Good but airlines getting smaller. I didn't like the meal but the service was fine. Flight was fine and luggage arrived. So good.

Reliable, nice crew, I fly often on that flight and I like it all.

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

Michael, our FA was very attentive, even finding me a chocolate brownie from economy class when the dessert selections were all dairy based. ( intolerant, not allergic so don’t usually need to order dairy free)

Cramped seats. Audio jack for the in -flight entertainment was broken.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

I got bumped by Qantas to American Airlines incurring a 6 hr layover at lax. I was not happy

Baggage allowances are terrible and the experience of only being allowed one bag and paying so much to take sporting equipment to a known ski area should be addressed.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

They cancelled my flight and downgraded me to economy and only gave me $250 for the downgrade

The luggage was completely damaged. It was ripped at the corner and the lock was stuck. We had to rip it open.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Incompetent crew at the boarding counter. Never flying AA again.

Everything was great except that I wasn’t issued a boarding pass for the second flight so they would not let me into customs until I had said boarding pass. Luckily a gate attendant from another Air Canada flight was able to print one for me so I could go through.

I suppose to board the plane AC5110 to San Francisco on July 16 2026 @07:00 am and arrive San Francisco at 09:25 am. At 9:30am still in YVR I was told the plane was delayed until 11:30 am to take off. Not until 11:35am the pilot of the plane declared that due to hydraulic system problem this plane was cancelled. After waited in a long pile up for negotiating with the counter-staff, I finally got the tickets for myself and my wife Yim Mei KONG firstly to Seattle and then transferred to San Francisco on the plane AS 2014 & AS 791 with Alaska Airlines. I suppose to attend the funeral of our friend in San Francisco on July 18 and a Memorial Gathering for the Birthday of the deceased on July 16, 2026. I arrived San Francisco at 9:40 pm that day (12 hours later) and couldn't joint the Memorial Gathering. This upset me a lot. I am seeking for compensation of this failing trip. Please let me know how to and where to forward my complaint.

not able to change flight, no customer service from KAYAK

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

Minimal food offered (crackers). Had to clean the seat with a wet wipe because of dried food.

TV Bathroom sink was full of water not draining. Counter all wet

unexplained delays rude staff (why do we have these people on board? No one needs the silly isle clogging drink cart) missed important appointments and spent nearly a day in the airport due to delays that were not made known prior to arriving reserved / paid -for seats not kept, but I was not reimbursed Will be writing to my local representatives, you need heavy federal regulations applied to your industry to protest customers.

I was never allowed to get checked in to United (Air Canada was booked but moved to United). Tried to check in amd was told our tickets was suspended. Called United and was told tickets were paid for but there was an unknown issue with Kayak. Called Kayak and could NEVER get to a live person. I WILL NEVER BOOK ANYTHING WITH KAYAK AGAIN! I had to spend another $2300 and book with Hotwire.

Delayed because of some passengers being held up or late coming to security. Not fair to all of us who arrived over 2 hours early

Everything you need to know for your flight from Vancouver to Chicago

Information on your arrival and departure airports