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Cheap flights from Alberta to Chicago from C$ 182

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 17/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
1 Jun — 8 Jun1
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 2 May 2026.

Mon 18/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Sun 24/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 1/5C$ 232
Wed 20/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 26/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 30/4C$ 235
Tue 26/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Fri 29/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 28/4C$ 240
Sat 23/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Sat 30/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 30/4C$ 243
Sat 23/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Sun 24/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 30/4C$ 244
Tue 19/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Sun 24/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 30/4C$ 253
Fri 29/56:15 a.m.
YYC
-
ORD
Nonstop3h 30m
American Airlines
Sun 7/68:50 p.m.
ORD
-
YYC
Nonstop3h 52m
American Airlines
Deal found 26/4C$ 273
Thu 28/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Thu 4/65:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 28/4C$ 289
Wed 20/512:34 p.m.
YYC
-
ORD
Nonstop3h 27m
United Airlines
Tue 26/56:00 a.m.
ORD
-
YYC
1 stop16h 48m
United Airlines
Deal found 29/4C$ 295
Sat 23/56:45 a.m.
YYC
-
MDW
1 stop10h 11m
Delta
Wed 27/51:59 p.m.
MDW
-
YYC
1 stop7h 31m
Delta
Deal found 28/4C$ 314
Sat 5/96:35 a.m.
YYC
-
MDW
2 stops14h 11m
Delta
Wed 9/96:00 a.m.
MDW
-
YYC
2 stops18h 06m
Delta
Deal found 27/4C$ 337
Thu 28/57:40 a.m.
YEG
-
ORD
1 stop8h 00m
WestJet
Wed 3/65:30 p.m.
ORD
-
YEG
1 stop6h 25m
WestJet
Deal found 29/4C$ 373

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 2 May 2026.

Round-trip from

C$ 232

One-way from

C$ 182

Popular in

March

Cheapest in

November

Average price

C$ 356

Good round-trip deal

C$ 452 or less

Good one-way deal

C$ 288 or less
WestJet
  • WestJet
  • 18/5-24/5
  • Nonstop
  • 7h 35m total
  • Alberta to Chicago
Search Deals
Air Canada
  • Air Canada
  • 17/5
  • 1 total stop
  • 7h 25m total
  • Alberta to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 2 May 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 - MDW

YYCMDW

Calgary

Sat 5/9

6:35 a.m.-9:46 p.m.

2 stops14h 11m

Chicago Midway

Wed 9/9

6:00 a.m.-11:06 p.m.

2 stops18h 06m

C$ 337

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 6/8

7:45 a.m.-6:57 p.m.

1 stop10h 12m

Chicago O'Hare Intl

Tue 11/8

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

1 stop10h 11m

C$ 337

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 21/5

12:27 p.m.-9:50 p.m.

1 stop8h 23m

Chicago O'Hare Intl

Tue 26/5

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

1 stop9h 00m

C$ 345

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 16/9

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

1 stop9h 46m

Chicago O'Hare Intl

Mon 21/9

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

1 stop10h 11m

C$ 373

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 25/5

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

Nonstop3h 40m

Chicago O'Hare Intl

Thu 28/5

7:12 a.m.-1:10 p.m.

1 stop6h 58m

C$ 384

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 19/5

8:45 a.m.-4:49 p.m.

1 stop7h 04m

Chicago O'Hare Intl

Fri 22/5

7:45 a.m.-7:40 p.m.

2 stops12h 55m

C$ 391

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 3/6

6:45 a.m.-8:14 p.m.

2 stops12h 29m

Chicago O'Hare Intl

Wed 17/6

2:09 p.m.-11:01 p.m.

1 stop9h 52m

C$ 394

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Wed 17/6

3:27 p.m.-8:01 p.m.

Nonstop3h 34m

Chicago O'Hare Intl

Tue 23/6

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

1 stop17h 04m

C$ 402

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 5/8

7:45 a.m.-6:57 p.m.

1 stop10h 12m

Chicago O'Hare Intl

Sun 9/8

2:02 p.m.-10:59 p.m.

1 stop9h 57m

C$ 405

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Wed 17/6

3:42 p.m.-8:16 p.m.

Nonstop3h 34m

Chicago O'Hare Intl

Sat 20/6

7:05 a.m.-10:04 p.m.

1 stop15h 59m

C$ 414

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/4

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

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 88 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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$ 84). Flying from Alberta to Chicago in February is currently the most expensive (average of C$ 139). 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 2 May 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 2 May 2026.

The most flights from CAAB to CHI are scheduled on a Friday (11 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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 3h 34m. 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$ 133. However, be on the lookout for offers from United Airlines 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: Delta (77%), WestJet (77%), Finnair( 75%).

  • What are the cheapest flights from Alberta to Chicago?

    While on average a flight from Alberta to Chicago is generally C$ 1,444, our data shows the cheapest flight currently is C$ 259. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay C$ 274 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$ 84). Flying from Alberta to Chicago in February is currently the most expensive (average of C$ 139). 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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Saskatoon to Midway flights
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St John to O'Hare Intl flights
Vancouver Intl to Peoria flights
Halifax to St. Louis flights
Nanaimo to O'Hare Intl flights
Saskatoon 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 2 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 119AverageC$ 351FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 146AverageC$ 379FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 165AverageC$ 451FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 181AverageC$ 342FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 192AverageC$ 405FlexibilityNo 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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