Find flights
Deals
When to book
FAQs

Cheap flights from Alberta to Chicago from C$ 216

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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
19 Jul — 26 Jul1
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 19 June 2026.

Fri 30/109:00 a.m.
YYC
-
ORD
Nonstop3h 35m
WestJet
Mon 2/112:20 p.m.
ORD
-
YYC
Nonstop4h 55m
WestJet
Deal found 18/6C$ 356
Mon 28/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 6/105:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 17/6C$ 376
Fri 11/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 15/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 15/6C$ 383
Thu 10/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 15/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 15/6C$ 384
Thu 2/712:28 p.m.
YYC
-
ORD
Nonstop3h 36m
United Airlines
Sat 4/77:45 p.m.
ORD
-
YYC
Nonstop3h 52m
United Airlines
Deal found 17/6C$ 393
Mon 28/911:55 p.m.
YYC
-
ORD
1 stop8h 05m
Air Canada
Tue 6/108:45 a.m.
ORD
-
YYC
1 stop8h 12m
Air Canada
Deal found 17/6C$ 407
Thu 24/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Thu 8/105:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 15/6C$ 408
Thu 24/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Mon 5/105:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 15/6C$ 409
Fri 30/106:00 a.m.
YYC
-
ORD
1 stop7h 56m
Air Canada
Mon 2/114:00 p.m.
ORD
-
YYC
1 stop8h 24m
Air Canada
Deal found 18/6C$ 414
Wed 21/107:45 a.m.
YYC
-
MDW
1 stop8h 05m
Delta
Sat 24/1012:30 p.m.
MDW
-
YYC
2 stops11h 43m
Delta
Deal found 16/6C$ 415
Wed 23/96:45 a.m.
YYC
-
ORD
1 stop9h 38m
Delta
Thu 8/101:55 p.m.
ORD
-
YYC
1 stop10h 18m
Delta
Deal found 15/6C$ 415
Mon 31/87:45 a.m.
YYC
-
ORD
1 stop9h 34m
Delta
Tue 8/92:05 p.m.
ORD
-
YYC
1 stop10h 01m
Delta
Deal found 15/6C$ 417

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 19 June 2026.

Round-trip from

C$ 354

One-way from

C$ 216

Popular in

July

Cheapest in

November

Average price

C$ 494

Good round-trip deal

C$ 504 or less

Good one-way deal

C$ 288 or less
WestJet
  • WestJet
  • 30/10-2/11
  • Nonstop
  • 8h 30m total
  • Alberta to Chicago
Search Deals
WestJet
  • WestJet
  • 11/10
  • Nonstop
  • 3h 40m total
  • Alberta to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 119 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 19 June 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

Thu 2/7

12:28 p.m.-5:04 p.m.

Nonstop3h 36m

Chicago O'Hare Intl

Sat 4/7

7:45 p.m.-10:37 p.m.

Nonstop3h 52m

C$ 393

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 21/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Sat 24/10

12:30 p.m.-11:13 p.m.

2 stops11h 43m

C$ 415

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 23/11

2:50 p.m.-9:34 p.m.

1 stop5h 44m

Chicago O'Hare Intl

Sat 5/12

3:50 p.m.-8:54 p.m.

1 stop6h 04m

C$ 418

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 26/11

7:45 a.m.-6:37 p.m.

2 stops9h 52m

Chicago Midway

Sat 5/12

9:55 a.m.-11:13 p.m.

2 stops14h 18m

C$ 418

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 30/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Mon 2/11

12:30 p.m.-8:54 p.m.

1 stop9h 24m

C$ 418

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 2/7

12:28 p.m.-5:04 p.m.

Nonstop3h 36m

Chicago O'Hare Intl

Sat 4/7

2:15 p.m.-1:21 a.m.

1 stop12h 06m

C$ 445

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 13/11

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Tue 17/11

10:35 a.m.-11:13 p.m.

2 stops13h 38m

C$ 460

Fort McMurrayChicago

YMM - ORD

YMMORD

Fort Mcmurray

Tue 8/9

8:45 a.m.-4:40 p.m.

1 stop6h 55m

Chicago O'Hare Intl

Mon 14/9

5:30 p.m.-5:25 p.m.

1 stop24h 55m

C$ 494

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 28/9

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Tue 6/10

12:15 p.m.-8:54 p.m.

1 stop9h 39m

C$ 500

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 3/9

7:45 a.m.-6:19 p.m.

1 stop9h 34m

Chicago O'Hare Intl

Mon 7/9

12:29 p.m.-8:35 p.m.

1 stop9h 06m

C$ 503

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/6

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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, March is the cheapest month in which you can book a flight from Alberta to Chicago (average of C$ 88). Flying from Alberta to Chicago in August is currently the most expensive (average of C$ 188). 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 19 June 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 19 June 2026.

The most flights from CAAB to CHI are scheduled on a Monday (14 on average). You will have fewer flight options on Saturday, 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?

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 3h 36m. 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$ 139. 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: Qatar Airways (87%), American Airlines (87%), Envoy Air( 86%).

  • What are the cheapest flights from Alberta to Chicago?

    While on average a flight from Alberta to Chicago is generally C$ 582, our data shows the cheapest flight currently is C$ 227. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay C$ 414 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, March is the cheapest month in which you can book a flight from Alberta to Chicago (average of C$ 88). Flying from Alberta to Chicago in August is currently the most expensive (average of C$ 188). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Alberta to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to Midway flights
Toronto Island to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Calgary to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Vancouver Intl to Midway flights
Ottawa to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Halifax to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Pearson Intl to St. Louis flights
Calgary to Midway flights
Edmonton to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Halifax to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Québec City to O'Hare Intl flights
Edmonton to Midway flights
Ottawa to Midway flights
Victoria to O'Hare Intl flights
Québec City to Midway flights
St. John's to O'Hare Intl flights
London to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Calgary to St. Louis flights
Saskatoon to O'Hare Intl flights
Pearson Intl to Bloomington flights
Regina to O'Hare Intl flights
Comox to O'Hare Intl flights
Halifax to Peoria flights
Kelowna to Midway flights
Ottawa to St. Louis flights
Edmonton to St. Louis flights
Halifax to St. Louis flights
Moncton to O'Hare Intl flights
Sudbury to O'Hare Intl flights
St John to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Victoria to Midway flights
Pearson Intl to Moline flights
Victoria to St. Louis flights
Saskatoon to Midway 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 19 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 123AverageC$ 469FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 151AverageC$ 376FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 188AverageC$ 504FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 189AverageC$ 398FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 200AverageC$ 393FlexibilityNo 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.