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Cheap flights from Victoria to Chicago from C$ 242

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 16/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYJ — CHI
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 28 October 2025.

Sun 23/119:35 a.m.YYJ - ORD
1 stop26h 00mMultiple Airlines
Thu 27/116:45 p.m.ORD - YYJ
2 stops41h 05mMultiple Airlines
Deal found 28/10C$ 354
Sun 16/113:55 p.m.YYJ - ORD
2 stops37h 33mMultiple Airlines
Sat 22/116:00 a.m.ORD - YYJ
1 stop9h 10mMultiple Airlines
Deal found 27/10C$ 501
Thu 4/129:55 p.m.YYJ - ORD
1 stop14h 46mAir Canada
Sun 7/128:15 p.m.ORD - YYJ
1 stop16h 35mAir Canada
Deal found 26/10C$ 512
Sun 16/116:09 a.m.YYJ - ORD
1 stop22h 13mAlaska Airlines
Sat 22/116:00 a.m.ORD - YYJ
1 stop9h 10mAlaska Airlines
Deal found 27/10C$ 548
Thu 4/1210:10 a.m.YYJ - ORD
2 stops8h 58mUnited Airlines
Sun 7/123:40 p.m.ORD - YYJ
1 stop6h 46mUnited Airlines
Deal found 26/10C$ 606
Sun 16/1112:10 p.m.YYJ - MDW
2 stops19h 55mMultiple Airlines
Sat 22/119:41 a.m.MDW - YYJ
3 stops29h 14mMultiple Airlines
Deal found 27/10C$ 773
Sun 16/111:25 p.m.YYJ - MDW
3 stops26h 53mWestJet
Sat 22/119:41 a.m.MDW - YYJ
3 stops29h 14mWestJet
Deal found 27/10C$ 843
Sat 1/118:00 p.m.YYJ - MDW
2 stops12h 45mWestJet
Sat 8/113:00 p.m.MDW - YYJ
2 stops23h 55mWestJet
Deal found 25/10C$ 979
Sun 23/117:00 p.m.YYJ - MDW
2 stops12h 52mWestJet
Thu 27/1110:47 a.m.MDW - YYJ
2 stops15h 37mWestJet
Deal found 28/10C$ 1,125
Fri 19/127:00 p.m.YYJ - MDW
2 stops12h 05mDelta
Fri 2/111:48 a.m.MDW - YYJ
2 stops14h 36mDelta
Deal found 26/10C$ 2,699

Cheap 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 28 October 2025.

Round-trip from

C$ 347

One-way from

C$ 242
WestJet
  • WestJet
  • 15/1-19/1
  • 2 total stops
  • 32h 54m total
  • Victoria to Chicago
Search Deals
16/11
  • 16/11
  • 2 total stops
  • 43h 08m 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 28 October 2025.
Use the filters below to find and compare flights from Victoria to Chicago that are best for you.

Fly from

Victoria

Fly to

Chicago

Route

Depart

Return

Price

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Thu 15/1

9:35 a.m.-1:35 p.m.

1 stop26h 00m

Chicago O'Hare Intl

Mon 19/1

2:20 p.m.-7:14 p.m.

1 stop6h 54m

C$ 347

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Sun 23/11

9:35 a.m.-1:35 p.m.

1 stop26h 00m

Chicago O'Hare Intl

Thu 27/11

6:45 p.m.-9:50 a.m.

2 stops41h 05m

C$ 354

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Wed 21/1

5:40 a.m.-2:41 p.m.

1 stop7h 01m

Chicago O'Hare Intl

Sat 24/1

3:40 p.m.-10:11 p.m.

1 stop8h 31m

C$ 393

VictoriaChicago

YYJ - ORD

YYJORD

Victoria Intl

Wed 21/1

5:40 a.m.-9:15 p.m.

2 stops13h 35m

Chicago O'Hare Intl

Sat 24/1

12:53 p.m.-8:26 p.m.

2 stops9h 33m

C$ 491

VictoriaChicago

YYJ - MDW

YYJMDW

Victoria Intl

Sun 16/11

12:10 p.m.-10:05 a.m.

2 stops19h 55m

Chicago Midway

Sat 22/11

9:41 a.m.-12:55 p.m.

3 stops29h 14m

C$ 773

VictoriaChicago

YYJ - MDW

YYJMDW

Victoria Intl

Sun 16/11

1:25 p.m.-6:18 p.m.

3 stops26h 53m

Chicago Midway

Sat 22/11

9:41 a.m.-12:55 p.m.

3 stops29h 14m

C$ 843

VictoriaChicago

YYJ - MDW

YYJMDW

Victoria Intl

Thu 15/1

8:00 p.m.-10:34 a.m.

2 stops12h 34m

Chicago Midway

Mon 19/1

9:50 a.m.-12:24 a.m.

2 stops16h 34m

C$ 979

VictoriaChicago

YYJ - MDW

YYJMDW

Victoria Intl

Sun 23/11

7:00 p.m.-9:52 a.m.

2 stops12h 52m

Chicago Midway

Thu 27/11

10:47 a.m.-12:24 a.m.

2 stops15h 37m

C$ 1,125

VictoriaChicago

YYJ - MDW

YYJMDW

Victoria Intl

Wed 21/1

7:00 p.m.-9:58 a.m.

2 stops12h 58m

Chicago Midway

Sat 24/1

11:45 a.m.-12:24 a.m.

2 stops14h 39m

C$ 1,127

VictoriaChicago

YYJ - MDW

YYJMDW

Victoria Intl

Fri 19/12

7:00 p.m.-9:05 a.m.

2 stops12h 05m

Chicago Midway

Fri 2/1

11:48 a.m.-12:24 a.m.

2 stops14h 36m

C$ 2,699

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/10

Showing 1-10 of 16 results
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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 is the cheapest month to book a flight from Victoria to Chicago?

Currently, October is the cheapest month in which you can book a flight from Victoria to Chicago (average of C$ 159). Flying from Victoria to Chicago in January is currently the most expensive (average of C$ 355). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YYJ to CHI?

Find hourly flight availability from Victoria to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 28 October 2025.

A simple way to save on the total cost of your ticket is to fly from Victoria to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 38% on your trip compared to booking a flight at noon.

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.

Vancouver (YVR) – chosen by Cheapflights users on 79% 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$ 454.

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 28 October 2025.
See what other customers who have flown with WestJet and 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.
WestJet
7.2
Good
3,148 reviews
Check prices

Boarding

7.4

Crew

7.9

Overall

7.2

Comfort

7.1

Food

6.2

Entertainment

6.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon
WestJet
7.2
Good
3,148 reviews
WestJet
7.2
Good
3,148 reviews
Check prices

Boarding

7.4

Crew

7.9

Overall

7.2

Comfort

7.1

Food

6.2

Entertainment

6.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon
Air Canada
7.1
Good
10,371 reviews
WestJet
7.2
Good
3,148 reviews
Check prices

Boarding

7.4

Crew

7.9

Overall

7.2

Comfort

7.1

Food

6.2

Entertainment

6.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon

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 2 different airlines.

  • How long is the flight from Victoria to Chicago?

    Departing from Victoria to Chicago will take you 26h. There are 2845 km between Victoria and Chicago.

  • What are the cheapest airlines flying from Victoria to Chicago round-trip?

    WestJet, at C$ 253, was found to be the cheapest airline from Victoria to Chicago. An alternate airline flying to your destination would be Air Canada.

  • 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.

  • What is the cheapest month to book a flight from Victoria to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Victoria to Chicago (average of C$ 159). Flying from Victoria to Chicago in January is currently the most expensive (average of C$ 355). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Victoria to Chicago

Discover the top 2 airlines 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 28 October 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 253AverageC$ 432FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 391AverageC$ 544FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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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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