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Cheap flights from Alberta to Chicago from C$ 246

YYC — CHI
3 Dec — 10 Dec1
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

Fri 4/129:07 a.m. -
1 stop8h 42m
Mon 7/126:47 p.m. -
1 stop26h 50m
Deal found 31/10C$ 422
Sat 21/118:45 a.m. -
1 stop6h 10m
Wed 25/112:03 p.m. -
1 stop10h 14m
Deal found 1/11C$ 425
Mon 16/119:09 a.m. -
2 stops28h 00m
Wed 18/117:00 a.m. -
1 stop14h 39m
Deal found 2/11C$ 435
Wed 2/129:07 a.m. -
1 stop7h 24m
Fri 11/126:47 p.m. -
1 stop26h 50m
Deal found 2/11C$ 439
Fri 4/129:07 a.m. -
1 stop7h 24m
Sun 6/126:00 a.m. -
1 stop15h 37m
Deal found 3/11C$ 440
Thu 3/121:37 p.m. -
Nonstop3h 33m
Tue 8/1212:29 p.m. -
1 stop10h 24m
Deal found 1/11C$ 446
Thu 3/127:25 a.m. -
2 stops12h 50m
Tue 8/122:04 p.m. -
1 stop10h 17m
Deal found 1/11C$ 447
Tue 22/128:45 a.m. -
1 stop9h 44m
Tue 9/29:59 a.m. -
2 stops14h 24m
Deal found 30/10C$ 449
Fri 11/121:37 p.m. -
Nonstop3h 33m
Sun 13/124:30 p.m. -
1 stop7h 51m
Deal found 31/10C$ 451
Thu 12/111:35 p.m. -
1 stop8h 12m
Tue 24/112:03 p.m. -
1 stop10h 14m
Deal found 1/11C$ 456
Mon 14/124:30 p.m. -
2 stops32h 24m
Mon 21/125:40 a.m. -
2 stops18h 50m
Deal found 30/10C$ 565
Fri 20/114:17 p.m. -
1 stop17h 22m
Mon 23/119:47 p.m. -
1 stop17h 28m
Deal found 2/11C$ 566

Find flight deals from Alberta to Chicago

Round-trip from

C$ 422

One-way from

C$ 240

Popular in

December

Cheapest in

April

Average price

C$ 479

Good round-trip deal

C$ 582 or less

Good one-way deal

C$ 377 or less
Alaska Airlines
  • Alaska Airlines
  • 4/12-7/12
  • 2 total stops
  • 35h 32m total
  • Alberta to Chicago
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13/12-31/12
  • 13/12-31/12
  • 1 total stop
  • 19h 37m total
  • Alberta to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 57 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 11 potential savings vs. average RT price).
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Average for round-trip flights in November 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

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 15/1

7:15 a.m.-6:09 p.m.

1 stop10h 54m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 252

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sun 6/12

7:25 a.m.-6:06 p.m.

1 stop10h 41m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 252

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Tue 9/3

6:25 a.m.-5:57 p.m.

1 stop11h 32m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 253

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Mon 30/11

7:25 a.m.-6:05 p.m.

1 stop10h 40m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 253

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 10/12

7:25 a.m.-6:06 p.m.

1 stop10h 41m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 253

EdmontonChicago

YEG Edmonton - ORD Chicago O'Hare Intl

YEGORD

Edmonton

Sun 6/12

7:00 a.m.-10:24 a.m.

1 stop27h 24m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 256

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 17/12

3:06 p.m.-12:30 a.m.

1 stop9h 24m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 274
Quickest round-trip

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Tue 17/11

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

Nonstop3h 33m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 275

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Tue 2/3

7:25 a.m.-9:32 p.m.

2 stops14h 07m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 289

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Wed 23/12

7:25 a.m.-6:01 p.m.

1 stop10h 36m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 309

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 58 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$ 570). 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.

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$ 296 and C$ 583 in December.
The cheapest round-trip price found within the last 5 days was C$ 422 on Alaska Airlines (4 Dec-7 Dec).

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 3h 33m. Airlines will cover a distance of 2223 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, 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: Scandinavian Airlines (83%), WestJet (76%), Delta( 72%).

  • What are the cheapest flights from Alberta to Chicago?

    While on average a flight from Alberta to Chicago is generally C$ 1,842, our data shows the cheapest flight currently is C$ 260. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay C$ 425 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$ 570). 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
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Québec City to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Pearson Intl to St. Louis flights
Ottawa to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Vancouver Intl to Midway flights
Calgary to Midway flights
Halifax to O'Hare Intl flights
Ottawa to Midway flights
Québec City to Midway flights
Toronto Island to Midway flights
Victoria to O'Hare Intl flights
Edmonton to Midway flights
Kelowna to O'Hare Intl flights
Kelowna to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights
Halifax to Midway flights
Edmonton to St. Louis flights
London to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Pearson Intl to Peoria flights
Moncton to O'Hare Intl flights
Calgary to St. Louis flights
Pearson Intl to Bloomington flights
St. John's to O'Hare Intl flights
Pearson Intl to Moline flights
Victoria to St. Louis flights
Victoria to Midway flights
Nanaimo to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Ottawa to St. Louis flights
Vancouver Intl to Peoria flights
Saskatoon to St. Louis flights
Fort McMurray to O'Hare Intl flights
Regina to O'Hare Intl flights
St John to O'Hare Intl flights
Sudbury to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights

Top 6 airlines flying from Alberta to Chicago

AirlineCheapestAverageFlexibilityOn-time
DeltaCheapestC$ 143AverageC$ 386FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 186AverageC$ 559FlexibilityNo cancel feeOn-time67%
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United AirlinesCheapestC$ 189AverageC$ 546FlexibilityNo cancel feeOn-time69%
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WestJetCheapestC$ 228AverageC$ 396FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 243AverageC$ 490FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 263AverageC$ 498FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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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