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Cheap flights from Victoria to Chicago from C$ 300

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
YYJ — CHI
21 Jul — 28 Jul1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Victoria to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Victoria to Chicago
Explore the most affordable flight options available from Victoria to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 21 June 2026.

Mon 14/96:00 a.m.
YYJ
-
ORD
1 stop8h 40m
WestJet
Fri 18/95:30 p.m.
ORD
-
YYJ
1 stop8h 10m
WestJet
Deal found 19/6C$ 423
Fri 18/96:00 a.m.
YYJ
-
ORD
1 stop8h 40m
WestJet
Sun 20/95:30 p.m.
ORD
-
YYJ
1 stop8h 10m
WestJet
Deal found 17/6C$ 460
Mon 31/84:30 p.m.
YYJ
-
ORD
2 stops22h 10m
WestJet
Sat 5/95:30 p.m.
ORD
-
YYJ
1 stop8h 10m
WestJet
Deal found 16/6C$ 481
Thu 23/76:50 p.m.
YYJ
-
MDW
3 stops17h 45m
Multiple Airlines
Mon 27/710:25 a.m.
MDW
-
YYJ
3 stops24h 35m
Multiple Airlines
Deal found 17/6C$ 985
Mon 21/96:00 a.m.
YYJ
-
MDW
2 stops10h 33m
Delta
Tue 22/97:13 p.m.
MDW
-
YYJ
2 stops30h 12m
Delta
Deal found 20/6C$ 1,071
Sun 19/711:55 a.m.
YYJ
-
MDW
2 stops19h 45m
Multiple Airlines
Sat 25/78:49 p.m.
MDW
-
YYJ
3 stops28h 51m
Multiple Airlines
Deal found 19/6C$ 1,138
Sun 9/88:25 p.m.
YYJ
-
MDW
2 stops11h 34m
WestJet
Thu 13/81:51 p.m.
MDW
-
YYJ
2 stops11h 49m
WestJet
Deal found 17/6C$ 1,201
Mon 14/97:50 a.m.
YYJ
-
MDW
2 stops12h 35m
WestJet
Fri 18/910:48 a.m.
MDW
-
YYJ
2 stops10h 47m
WestJet
Deal found 20/6C$ 1,214
Fri 17/72:40 p.m.
YYJ
-
MDW
3 stops16h 33m
WestJet
Fri 24/79:19 a.m.
MDW
-
YYJ
3 stops16h 21m
WestJet
Deal found 19/6C$ 1,217

Find flight deals from Victoria to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Victoria (YYJ) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 21 June 2026.

Round-trip from

C$ 423

One-way from

C$ 300
WestJet
  • WestJet
  • 14/9-18/9
  • 2 total stops
  • 16h 50m total
  • Victoria to Chicago
Search Deals
WestJet
  • WestJet
  • 4/8
  • 2 total stops
  • 22h 10m total
  • Victoria to Chicago
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Victoria 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, Cheapflights users made 629,999 searches. Data last updated 21 June 2026.
Use the filters below to find and compare flights from Victoria to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Mon 14/9

4:30 p.m.-4:40 p.m.

2 stops22h 10m

Chicago O'Hare Intl

Fri 18/9

5:30 p.m.-10:05 a.m.

2 stops18h 35m

C$ 453

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Mon 31/8

6:55 p.m.-4:40 p.m.

2 stops19h 45m

Chicago O'Hare Intl

Sat 5/9

5:30 p.m.-10:05 a.m.

2 stops18h 35m

C$ 484

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Fri 14/8

7:50 a.m.-4:40 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Mon 17/8

5:30 p.m.-3:55 p.m.

2 stops24h 25m

C$ 492

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Wed 23/9

10:40 a.m.-9:47 p.m.

2 stops9h 07m

Chicago O'Hare Intl

Sat 26/9

2:00 p.m.-11:40 p.m.

2 stops11h 40m

C$ 583

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Fri 18/9

2:55 p.m.-9:43 a.m.

2 stops16h 48m

Chicago O'Hare Intl

Sun 20/9

5:00 a.m.-6:31 p.m.

2 stops15h 31m

C$ 601
Quickest round-trip

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Mon 31/8

6:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Sat 5/9

5:30 p.m.-11:40 p.m.

1 stop8h 10m

C$ 608

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Wed 23/9

9:10 p.m.-2:43 p.m.

1 stop15h 33m

Chicago O'Hare Intl

Sat 26/9

2:15 p.m.-9:27 p.m.

1 stop9h 12m

C$ 621

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Wed 23/9

5:45 p.m.-9:35 a.m.

2 stops13h 50m

Chicago O'Hare Intl

Sat 26/9

7:45 p.m.-9:16 a.m.

1 stop15h 31m

C$ 630

VictoriaChicago

YYJ - MDW

YYJMDW

Victoria Intl

Mon 21/9

6:00 a.m.-6:33 p.m.

2 stops10h 33m

Chicago Midway

Tue 22/9

7:13 p.m.-11:40 p.m.

2 stops30h 27m

C$ 1,070

VictoriaChicago

YYJ - MDW

YYJMDW

Victoria Intl

Sun 9/8

8:25 p.m.-9:59 a.m.

2 stops11h 34m

Chicago Midway

Thu 13/8

1:51 p.m.-11:40 p.m.

2 stops11h 49m

C$ 1,201

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/6

Showing 1-10 of 31 resultsSorted by cheapest first
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3
4

Best time to book a flight from Victoria to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Victoria with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Victoria to Chicago

What’s the top layover airport for flights from Victoria to Chicago?

Share of one-stop round-trip flights from Victoria to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Seattle (SEA) – chosen by Cheapflights users on 50% of one-stop itineraries from Victoria to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Victoria to Chicago?

Average round-trip fare for 1-stop flights from Victoria to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Vancouver (YVR) is the most affordable 1-stop option, with an average round-trip price of C$ 483.

What’s the fastest layover option from Victoria to Chicago?

Shortest average travel time for 1-stop one-way flights from Victoria to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Calgary (YYC) have the shortest average one-way travel time for 1-stop routes: 6h 19m.

Which airport typically offers the quickest layover for flights from Victoria to Chicago?

Average layover duration for 1-stop one-way flights from Victoria to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Calgary (YYC) offer the fastest connection on this route, with an average layover time of 1h 23m.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 21 June 2026.
See what other customers who have flown with Air Canada from Victoria to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
11,231 reviews
Check prices

Comfort

7.1

Crew

7.8

Entertainment

6.8

Boarding

7.3

Overall

7.1

Food

6.3

Reviews

1 / 20
4.0
Okay

Anonymous,May 2026

YYJ - YUL

The pouch in front of my seat was never cleaned. The hospitality I requested wasn't there for me. Perhaps as looking at me you wouldn't think I needed it. I push myself then pay for it later. Like last night and today....... The flight had a generator problem, we had to debark the plane as there was no staff to repair it , therefore we had to wait for staff to come from Vancouver to repair it. The staff on hand though were very good at keeping us informed and making sure of any questions we had at that point. Once repaired all went well. Then just the hospitality wasn't there. When I did ask at the desk after the long walk from the plane the young person attending said baggage is just over there. Well just over there to a 30 year old and a 76 year old with mobility problems is quite different !
Air Canada
7.1
Good
11,231 reviews
Air Canada
7.1
Good
11,231 reviews
Check prices

Comfort

7.1

Crew

7.8

Entertainment

6.8

Boarding

7.3

Overall

7.1

Food

6.3

Reviews

1 / 20
4.0
Okay

Anonymous,May 2026

YYJ - YUL

The pouch in front of my seat was never cleaned. The hospitality I requested wasn't there for me. Perhaps as looking at me you wouldn't think I needed it. I push myself then pay for it later. Like last night and today....... The flight had a generator problem, we had to debark the plane as there was no staff to repair it , therefore we had to wait for staff to come from Vancouver to repair it. The staff on hand though were very good at keeping us informed and making sure of any questions we had at that point. Once repaired all went well. Then just the hospitality wasn't there. When I did ask at the desk after the long walk from the plane the young person attending said baggage is just over there. Well just over there to a 30 year old and a 76 year old with mobility problems is quite different !

Related info for your journey

Find useful and relevant information for your journey from Victoria to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Victoria to Chicago?

    If you book a flight to Chicago from Victoria, you will be flying from Victoria Intl, which is the city’s only airport. Victoria Intl (YYJ) is located 24.8 km from the centre of Victoria. There are 0 flights from Victoria Intl to Chicago per day from 1 airline.

  • How long is the flight from Victoria to Chicago?

    Departing from Victoria to Chicago will take you 9h 07m. There are 2845 km between Victoria and Chicago. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What is the cheapest airline to fly from Victoria to Chicago round-trip?

    Air Canada, at C$ 396, was found to be the cheapest airline from Victoria to Chicago..

  • Can I find deals for flights from Victoria to Chicago that include hotel bookings?

    Yes. In addition to deals on Victoria to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Victoria to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Victoria to Chicago.

  • Can I find deals for business class flights from Victoria to Chicago?

    Yes. Cheapflights offers flight deals from Victoria to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Victoria to Chicago

Discover the top airline that operate flights from Victoria to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 21 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 396AverageC$ 790FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Victoria to Chicago?

When you search for this flight from Victoria to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Victoria to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Victoria to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Victoria to Chicago with no change fees?

Yes, we can. To see specific flights from Victoria to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Victoria to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Victoria to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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