Find flights
Deals
When to book
FAQs

Cheap flights from Alberta to Chicago from C$ 157

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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
16 Apr — 23 Apr1
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 17 March 2026.

Sun 26/412:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Thu 30/45:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 13/3C$ 289
Mon 20/49:00 a.m.
YYC
-
ORD
Nonstop3h 35m
WestJet
Mon 27/45:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 13/3C$ 293
Thu 30/412:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Sun 3/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 13/3C$ 304
Thu 30/412:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Thu 7/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 12/3C$ 308
Fri 17/41:27 p.m.
YYC
-
ORD
1 stop10h 03m
United Airlines
Tue 21/48:42 a.m.
ORD
-
YYC
Nonstop3h 50m
United Airlines
Deal found 12/3C$ 311
Mon 20/411:40 p.m.
YYC
-
ORD
1 stop8h 30m
Multiple Airlines
Mon 27/45:30 p.m.
ORD
-
YYC
Nonstop3h 55m
Multiple Airlines
Deal found 13/3C$ 324
Fri 17/45:35 a.m.
YYC
-
ORD
1 stop8h 40m
Air Canada
Tue 21/44:15 p.m.
ORD
-
YYC
1 stop9h 08m
Air Canada
Deal found 12/3C$ 326
Fri 17/46:00 a.m.
YEG
-
ORD
1 stop6h 35m
WestJet
Fri 24/42:20 p.m.
ORD
-
YEG
1 stop7h 57m
WestJet
Deal found 13/3C$ 329
Tue 28/47:00 a.m.
YYC
-
ORD
1 stop7h 15m
Air Canada
Tue 5/53:50 p.m.
ORD
-
YYC
1 stop8h 08m
Air Canada
Deal found 14/3C$ 330
Mon 27/411:40 p.m.
YYC
-
ORD
1 stop8h 30m
Air Canada
Mon 4/58:20 p.m.
ORD
-
YYC
1 stop14h 11m
Air Canada
Deal found 13/3C$ 331
Fri 17/46:00 a.m.
YYC
-
ORD
1 stop15h 54m
United Airlines
Mon 20/410:04 p.m.
ORD
-
YYC
1 stop16h 49m
United Airlines
Deal found 12/3C$ 337
Fri 29/57:00 a.m.
YEG
-
ORD
1 stop8h 40m
WestJet
Tue 2/65:30 p.m.
ORD
-
YEG
1 stop6h 25m
WestJet
Deal found 14/3C$ 353

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 17 March 2026.

Round-trip from

C$ 289

One-way from

C$ 157

Popular in

March

Cheapest in

November

Average price

C$ 498

Good round-trip deal

C$ 350 or less

Good one-way deal

C$ 215 or less
WestJet
  • WestJet
  • 26/4-30/4
  • Nonstop
  • 7h 35m total
  • Alberta to Chicago
Search Deals
WestJet
  • WestJet
  • 10/5
  • Nonstop
  • 3h 40m total
  • Alberta to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 17 March 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

Fri 17/4

1:27 p.m.-12:30 a.m.

1 stop10h 03m

Chicago O'Hare Intl

Tue 21/4

8:42 a.m.-11:32 a.m.

Nonstop3h 50m

C$ 311

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 22/4

7:40 a.m.-7:52 p.m.

2 stops11h 12m

Chicago O'Hare Intl

Wed 29/4

2:09 p.m.-11:00 p.m.

1 stop9h 51m

C$ 387

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 19/8

9:30 a.m.-10:41 p.m.

1 stop12h 11m

Chicago O'Hare Intl

Sun 23/8

5:00 a.m.-6:30 p.m.

1 stop14h 30m

C$ 400

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Fri 29/5

6:00 a.m.-10:49 p.m.

1 stop15h 49m

Chicago O'Hare Intl

Fri 5/6

6:00 a.m.-10:04 p.m.

1 stop17h 04m

C$ 411

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Fri 10/4

6:00 a.m.-11:28 p.m.

1 stop16h 28m

Chicago O'Hare Intl

Mon 13/4

11:03 p.m.-2:08 p.m.

1 stop16h 05m

C$ 416

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 3/4

6:30 a.m.-6:07 p.m.

1 stop10h 37m

Chicago O'Hare Intl

Fri 17/4

2:09 p.m.-11:00 p.m.

1 stop9h 51m

C$ 423

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 2/5

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

2 stops13h 00m

Chicago O'Hare Intl

Fri 8/5

2:11 p.m.-10:57 p.m.

1 stop9h 46m

C$ 429

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 6/8

7:15 a.m.-6:01 p.m.

1 stop9h 46m

Chicago O'Hare Intl

Sun 9/8

1:55 p.m.-11:06 p.m.

1 stop10h 11m

C$ 429

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Fri 29/5

6:00 a.m.-11:19 p.m.

1 stop16h 19m

Chicago O'Hare Intl

Sat 13/6

12:40 p.m.-3:47 p.m.

Nonstop4h 07m

C$ 437
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 14/4

1:27 p.m.-9:20 p.m.

1 stop6h 53m

Chicago O'Hare Intl

Tue 21/4

8:42 a.m.-11:32 a.m.

Nonstop3h 50m

C$ 445

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

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, April is the cheapest month in which you can book a flight from Alberta to Chicago (average of C$ 125). Flying from Alberta to Chicago in July is currently the most expensive (average of C$ 215). 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 17 March 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 17 March 2026.

The most flights from CAAB to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).

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

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 9h 55m. Airlines will cover a distance of 2326 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$ 116. However, be on the lookout for offers from United Airlines and Air Canada, 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 (82%), Delta( 76%).

  • What are the cheapest flights from Alberta to Chicago?

    While on average a flight from Alberta to Chicago is generally C$ 505, our data shows the cheapest flight currently is C$ 143. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay C$ 340 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, April is the cheapest month in which you can book a flight from Alberta to Chicago (average of C$ 125). Flying from Alberta to Chicago in July is currently the most expensive (average of C$ 215). 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
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pearson Intl to Midway flights
Calgary to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Pearson Intl to St. Louis flights
Vancouver Intl to Midway flights
Edmonton to O'Hare Intl flights
Halifax to O'Hare Intl flights
Calgary to Midway flights
Ottawa to Midway flights
Vancouver Intl to St. Louis flights
Pierre Elliott Trudeau Intl to St. Louis flights
Edmonton to Midway flights
Québec City to O'Hare Intl flights
Regina to O'Hare Intl flights
Halifax to Midway flights
Halifax to St. Louis flights
Hamilton to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Victoria to O'Hare Intl flights
Québec City to Midway flights
Edmonton to St. Louis flights
Saskatoon to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Ottawa to St. Louis flights
Pearson Intl to Moline flights
Victoria to Midway flights
Québec City to St. Louis flights
Saskatoon to St. Louis flights
Grande Prairie to O'Hare Intl flights
Grande Prairie to Midway flights
Calgary to St. Louis flights
Pearson Intl to Champaign flights
Pearson Intl to Peoria flights
Kelowna to O'Hare Intl flights
Victoria to St. Louis flights
London to O'Hare Intl flights
Calgary to Decatur flights
Kelowna to Midway flights
Charlottetown to St. Louis 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 17 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 121AverageC$ 306FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 147AverageC$ 378FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 167AverageC$ 430FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 169AverageC$ 357FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 176AverageC$ 322FlexibilityNo cancel feeOn-time60%
Search WestJet 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.