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Cheap flights from Alberta to Chicago from C$ 237

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 25/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
2 Sep — 9 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Alberta to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Alberta to Chicago
Explore the most affordable flight options available from Alberta to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 August 2026.

Fri 25/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 29/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 30/7C$ 293
Tue 15/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Thu 17/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 30/7C$ 294
Sun 20/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 29/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 31/7C$ 303
Wed 21/1012:30 p.m.
YYC
-
ORD
Nonstop3h 35m
United Airlines
Sat 24/108:40 a.m.
ORD
-
YYC
Nonstop3h 48m
United Airlines
Deal found 31/7C$ 321
Sun 22/1112:37 p.m.
YYC
-
ORD
Nonstop3h 33m
United Airlines
Sat 28/118:40 a.m.
ORD
-
YYC
Nonstop3h 55m
United Airlines
Deal found 30/7C$ 331
Wed 21/1012:30 p.m.
YYC
-
ORD
Nonstop3h 35m
Multiple Airlines
Sat 24/103:40 p.m.
ORD
-
YYC
1 stop8h 47m
Multiple Airlines
Deal found 31/7C$ 332
Sat 19/91:00 a.m.
YYC
-
ORD
1 stop8h 15m
Air Canada
Tue 29/98:45 a.m.
ORD
-
YYC
1 stop8h 12m
Air Canada
Deal found 31/7C$ 333
Thu 24/91:00 a.m.
YYC
-
ORD
1 stop8h 15m
Air Canada
Fri 2/102:15 p.m.
ORD
-
YYC
1 stop9h 42m
Air Canada
Deal found 1/8C$ 338
Sat 21/117:35 a.m.
YYC
-
MDW
1 stop8h 04m
Delta
Wed 25/1112:30 p.m.
MDW
-
YYC
2 stops11h 47m
Delta
Deal found 1/8C$ 406
Sun 20/99:10 a.m.
YEG
-
ORD
1 stop6h 30m
WestJet
Thu 24/95:30 p.m.
ORD
-
YEG
1 stop8h 14m
WestJet
Deal found 3/8C$ 425
Tue 15/97:30 a.m.
YEG
-
ORD
1 stop8h 10m
WestJet
Tue 22/95:30 p.m.
ORD
-
YEG
1 stop8h 14m
WestJet
Deal found 2/8C$ 427
Fri 4/97:00 a.m.
YEG
-
ORD
1 stop8h 40m
WestJet
Mon 14/95:30 p.m.
ORD
-
YEG
1 stop6h 25m
WestJet
Deal found 31/7C$ 432

Find flight deals from Alberta to Chicago

Keep the following information in mind while searching for Alberta to Chicago flight deals. Data was last updated 3 August 2026.

Round-trip from

C$ 293

One-way from

C$ 237

Popular in

June

Cheapest in

November

Average price

C$ 472

Good round-trip deal

C$ 587 or less

Good one-way deal

C$ 346 or less
WestJet
  • WestJet
  • 25/9-29/9
  • Nonstop
  • 7h 35m total
  • Alberta to Chicago
Search Deals
WestJet
  • WestJet
  • 25/9
  • 1 total stop
  • 6h 30m total
  • Alberta to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Alberta to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Alberta to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Alberta 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 3 August 2026.
Use the filters below to find and compare flights from Alberta to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 22/11

6:00 a.m.-10:59 p.m.

1 stop16h 59m

Chicago O'Hare Intl

Sat 28/11

8:40 a.m.-12:35 p.m.

Nonstop3h 55m

C$ 353

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Sun 20/9

9:10 a.m.-4:40 p.m.

1 stop6h 30m

Chicago O'Hare Intl

Thu 24/9

5:30 p.m.-12:44 a.m.

1 stop8h 14m

C$ 425

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 30/10

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

Chicago O'Hare Intl

Mon 2/11

8:40 a.m.-12:35 p.m.

Nonstop3h 55m

C$ 475

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Sat 5/9

4:45 p.m.-11:59 p.m.

1 stop6h 14m

Chicago O'Hare Intl

Sat 12/9

6:00 a.m.-2:08 p.m.

1 stop9h 08m

C$ 502

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Mon 31/8

3:17 p.m.-9:43 a.m.

1 stop17h 26m

Chicago O'Hare Intl

Tue 1/9

2:15 p.m.-11:03 p.m.

1 stop9h 48m

C$ 509

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 7/11

7:45 a.m.-9:33 p.m.

2 stops13h 48m

Chicago Midway

Tue 10/11

1:22 p.m.-12:17 a.m.

2 stops10h 55m

C$ 510

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Thu 20/8

6:00 a.m.-10:00 p.m.

1 stop15h 00m

Chicago O'Hare Intl

Thu 17/9

5:55 a.m.-10:04 p.m.

1 stop17h 09m

C$ 510

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Wed 2/9

3:28 p.m.-8:02 p.m.

Nonstop3h 34m

Chicago O'Hare Intl

Tue 8/9

2:15 p.m.-11:01 p.m.

1 stop9h 46m

C$ 513

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 26/8

8:00 a.m.-8:21 p.m.

1 stop11h 21m

Chicago O'Hare Intl

Wed 2/9

8:40 a.m.-6:30 p.m.

1 stop10h 50m

C$ 517

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 30/8

8:00 a.m.-10:46 p.m.

1 stop13h 46m

Chicago O'Hare Intl

Sat 5/9

5:35 p.m.-1:51 a.m.

1 stop9h 16m

C$ 528

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/7

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Alberta to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Alberta 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 Alberta to Chicago

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

Currently, February is the cheapest month in which you can book a flight from Alberta to Chicago (average of C$ 347). Flying from Alberta to Chicago in June is currently the most expensive (average of C$ 558). 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 AB to CHI?

Find hourly flight availability from Alberta 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 3 August 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Alberta to Chicago as you normally would.

Weekly flight availability from Alberta to Chicago

Explore weekly flight availability from Alberta to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 3 August 2026.

The most flights from CAAB to CHI are scheduled on a Friday (14 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Alberta to Chicago?

Airfare is below average for this route at the moment.
Alberta to Chicago flights typically cost between C$ 296 and C$ 567 in September.
The cheapest round-trip price found within the last 5 days was C$ 293 on WestJet (25 Sep-29 Sep).

How far ahead should I book a flight from Alberta to Chicago?

The price you pay for your flight from Alberta to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 59 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Related info for your journey

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

  • How long is the flight from Alberta to Chicago?

    Departing from Alberta to Chicago will take you 6h 30m. Airlines will cover a distance of 2279 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Alberta to Chicago one-way?

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as C$ 138. However, be on the lookout for offers from Air Canada and American Airlines, as they are both options that can get you from Alberta to Chicago for a low price.

  • What are the most popular routes from Alberta to Chicago?

    The most popular flight routes from Alberta to Chicago are Calgary - Chicago O'Hare Intl, Edmonton - Chicago O'Hare Intl and Calgary - Chicago Midway.

  • What are the most reliable airlines from Alberta to Chicago?

    Before booking your flight to Chicago from Alberta, check out the most reliable airlines to get you to your destination on time: Qatar Airways (81%), Air Canada (81%), United Airlines( 81%).

  • What are the cheapest flights from Alberta to Chicago?

    While on average a flight from Alberta to Chicago is generally C$ 1,732, our data shows the cheapest flight currently is C$ 264. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay C$ 321 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Alberta 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 Alberta to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Alberta to Chicago (average of C$ 347). Flying from Alberta to Chicago in June is currently the most expensive (average of C$ 558). 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

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Alternative routes for Alberta to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Region of Waterloo Intl to O'Hare Intl flights
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Halifax to O'Hare Intl flights
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Kelowna to Midway flights
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St John to O'Hare Intl flights
Vancouver Intl to Peoria flights
Kelowna to O'Hare Intl flights
Grande Prairie to Midway flights
Halifax to St. Louis flights
Edmonton to St. Louis flights
Pearson Intl to Bloomington flights
Québec City to St. Louis flights
Nanaimo to O'Hare Intl flights
St. John's to O'Hare Intl flights

Top 5 airlines flying from Alberta to Chicago

Discover the top 5 airlines that operate flights from Alberta 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 3 August 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 123AverageC$ 532FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 143AverageC$ 395FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 186AverageC$ 525FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 187AverageC$ 388FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 198AverageC$ 454FlexibilityNo cancel feeOn-time71%
Search American Airlines 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 Alberta to Chicago?

Cheapflights helps you search for flights from Alberta to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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

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

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

Yes, we can. To see specific flights from Alberta 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 Alberta to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Alberta 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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