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Cheap flights from Alberta to Chicago from C$ 218

YYC — CHI
18 Oct — 25 Oct1
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

Mon 12/1012:50 a.m. -
1 stop7h 10m
Tue 20/108:45 a.m. -
1 stop8h 12m
Deal found 15/9C$ 353
Wed 14/1012:50 a.m. -
1 stop7h 10m
Thu 22/108:45 a.m. -
1 stop8h 12m
Deal found 18/9C$ 358
Wed 21/1012:50 a.m. -
1 stop7h 10m
Sat 24/102:15 p.m. -
1 stop7h 50m
Deal found 15/9C$ 360
Wed 28/1012:20 a.m. -
1 stop8h 03m
Thu 5/114:30 p.m. -
1 stop8h 36m
Deal found 14/9C$ 361
Thu 15/1012:00 p.m. -
Nonstop3h 40m
Thu 22/105:30 p.m. -
Nonstop3h 55m
Deal found 15/9C$ 362
Thu 22/1012:00 p.m. -
Nonstop3h 40m
Tue 27/105:46 p.m. -
1 stop17h 57m
Deal found 17/9C$ 364
Sat 31/107:45 a.m. -
1 stop8h 02m
Fri 6/1112:27 p.m. -
2 stops12h 43m
Deal found 15/9C$ 365
Thu 29/1012:33 p.m. -
1 stop8h 32m
Tue 3/112:03 p.m. -
1 stop11h 07m
Deal found 14/9C$ 365
Tue 13/1012:50 a.m. -
1 stop7h 10m
Wed 21/108:45 a.m. -
1 stop8h 12m
Deal found 16/9C$ 369
Wed 23/97:00 a.m. -
Nonstop3h 29m
Wed 30/98:30 p.m. -
Nonstop3h 59m
Deal found 14/9C$ 372
Sun 18/1012:00 p.m. -
Nonstop3h 40m
Thu 22/105:30 p.m. -
Nonstop3h 55m
Deal found 16/9C$ 374
Fri 30/1012:37 p.m. -
Nonstop3h 33m
Mon 2/118:40 a.m. -
Nonstop4h 55m
Deal found 16/9C$ 375

Find flight deals from Alberta to Chicago

Round-trip from

C$ 353

One-way from

C$ 218

Popular in

June

Cheapest in

January

Average price

C$ 432

Good round-trip deal

C$ 521 or less

Good one-way deal

C$ 266 or less
Air Canada
  • Air Canada
  • 12/10-20/10
  • 2 total stops
  • 15h 22m total
  • Alberta to Chicago
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Alaska Airlines
  • Alaska Airlines
  • 17/11-31/12
  • 1 total stop
  • 7h 28m total
  • Alberta to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (C$ 50 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 17 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Price to beat on a round-trip flight from Alberta to Chicago (CHI).
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Price to beat on a one-way flight from Alberta to Chicago (CHI).
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Cheapflights Fare Finder

 
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
Quickest round-trip

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Mon 23/11

1:37 p.m.-5:10 p.m.

Nonstop2h 33m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 220

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sun 22/11

8:45 a.m.-10:54 p.m.

2 stops13h 09m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 222

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 3/10

6:35 a.m.-6:22 p.m.

2 stops10h 47m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 222

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Wed 7/10

7:45 a.m.-4:47 p.m.

1 stop8h 02m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 222

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sun 13/12

7:25 a.m.-6:26 p.m.

2 stops10h 01m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 222

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Wed 21/10

6:35 a.m.-8:30 p.m.

2 stops12h 55m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 222

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sat 14/11

8:45 a.m.-4:18 p.m.

2 stops6h 33m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 222

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Wed 21/10

7:45 a.m.-4:47 p.m.

1 stop8h 02m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 229

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sat 14/11

3:06 p.m.-10:46 p.m.

1 stop6h 40m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 231

EdmontonChicago

YEG Edmonton - ORD Chicago O'Hare Intl

YEGORD

Edmonton

Sat 24/10

1:00 a.m.-9:23 a.m.

1 stop7h 23m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 243

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

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

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$ 567). 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?

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

The most flights from CAAB to CHI are scheduled on a Thursday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).

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

Airfare is typical for this route at the moment.
Alberta to Chicago flights typically cost between C$ 353 and C$ 523 in October.
The cheapest round-trip price found within the last 5 days was C$ 353 on Air Canada (12 Oct-20 Oct).

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

  • How long is the flight from Alberta to Chicago?

    Departing from Alberta to Chicago will take you 8h 17m. 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$ 145. 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, Calgary - Chicago Midway and Edmonton - Chicago O'Hare Intl.

  • 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: Avianca (79%), Qatar Airways (78%), Air Canada( 76%).

  • What are the cheapest flights from Alberta to Chicago?

    While on average a flight from Alberta to Chicago is generally C$ 645, 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$ 374 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$ 567). 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

Alternative routes for Alberta to Chicago

Pearson Intl to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Vancouver Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Vancouver Intl to Midway flights
Calgary to O'Hare Intl flights
Québec City to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Pearson Intl to St. Louis flights
Winnipeg to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Calgary to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Edmonton to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Ottawa to Midway flights
Calgary to St. Louis flights
Halifax to O'Hare Intl flights
Edmonton to Midway flights
Québec City to Midway flights
Kelowna to O'Hare Intl flights
Halifax to Midway flights
Regina to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Saskatoon to Midway flights
Ottawa to St. Louis flights
Victoria to O'Hare Intl flights
St. John's to O'Hare Intl flights
Pearson Intl to Moline flights
Nanaimo to O'Hare Intl flights
St John to O'Hare Intl flights
Halifax to St. Louis flights
Calgary to Decatur flights
Sudbury to O'Hare Intl flights
Saskatoon to St. Louis flights
Kelowna to Midway flights
London to O'Hare Intl flights
Vancouver Intl to Peoria flights
Pearson Intl to Bloomington flights
Comox to O'Hare Intl flights
Moncton to O'Hare Intl flights
Victoria to St. Louis flights

Top 6 airlines flying from Alberta to Chicago

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 122AverageC$ 527FlexibilityNo cancel feeOn-time67%
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DeltaCheapestC$ 143AverageC$ 387FlexibilityNo cancel feeOn-timeN/A
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United AirlinesCheapestC$ 186AverageC$ 531FlexibilityNo cancel feeOn-time69%
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American AirlinesCheapestC$ 198AverageC$ 461FlexibilityNo cancel feeOn-time71%
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WestJetCheapestC$ 206AverageC$ 392FlexibilityNo cancel feeOn-time60%
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Porter AirlinesCheapestC$ 263AverageC$ 498FlexibilityNo cancel feeOn-time52%
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Fly with Cheapflights

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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