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$123+ Cheap flights from Alberta to Chicago (CHI)

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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Apr 20 — Apr 271
Mon 4/20
Mon 4/27
1 adult, Economy
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Cheap flight deals from Alberta to Chicago

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 March 21, 2026.

This Mytrip deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2212:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Wed 5/275:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 3/20$203
This Air Canada deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
YYC
-
ORD
1 stop7h 55m
Air Canada
Sat 5/22:15 pm
ORD
-
YYC
1 stop9h 43m
Air Canada
Deal found 3/19$246
This American Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:40 pm
YYC
-
ORD
Nonstop3h 45m
American Airlines
Mon 6/18:50 pm
ORD
-
YYC
Nonstop3h 48m
American Airlines
Deal found 3/20$248
This Air Canada deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:45 am
YYC
-
ORD
1 stop8h 30m
Air Canada
Sat 5/22:15 pm
ORD
-
YYC
1 stop9h 43m
Air Canada
Deal found 3/21$249
This Air Canada deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:45 am
YYC
-
ORD
1 stop8h 30m
Air Canada
Tue 5/59:55 am
ORD
-
YYC
1 stop9h 48m
Air Canada
Deal found 3/19$251
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/221:27 pm
YYC
-
ORD
1 stop6h 53m
United Airlines
Sat 4/257:00 am
ORD
-
YYC
1 stop15h 48m
United Airlines
Deal found 3/20$252
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
YYC
-
ORD
1 stop11h 59m
United Airlines
Sat 4/2510:04 pm
ORD
-
YYC
1 stop16h 49m
United Airlines
Deal found 3/18$254
This oojo deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/37:00 am
YEG
-
ORD
1 stop8h 40m
WestJet
Sun 5/105:30 pm
ORD
-
YEG
1 stop6h 25m
WestJet
Deal found 3/17$254
This Air Canada deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:35 am
YYC
-
ORD
1 stop8h 40m
Air Canada
Tue 4/214:15 pm
ORD
-
YYC
1 stop9h 08m
Air Canada
Deal found 3/19$256
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:40 am
YYC
-
ORD
2 stops12h 36m
Delta
Wed 4/292:09 pm
ORD
-
YYC
1 stop9h 51m
Delta
Deal found 3/18$257
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
YYC
-
ORD
1 stop16h 28m
United Airlines
Mon 4/2711:03 pm
ORD
-
YYC
1 stop15h 50m
United Airlines
Deal found 3/18$259
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
YYC
-
ORD
1 stop14h 17m
United Airlines
Sun 4/197:00 am
ORD
-
YYC
1 stop15h 48m
United Airlines
Deal found 3/20$260

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 March 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$203
(Mytrip)

One-way from

$123
(Kiwi.com)

Popular in

March

Cheapest in

November

Average price

$364

Good round-trip deal

$266 or less

Good one-way deal

$210 or less
Provider with most accurate pricing for Calgary-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Calgary-Chicago (CHI) flights.
Search Deals
From Alberta to Chicago (CHI)
Search Deals
One-way flight from Alberta to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 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 2,558,603 searches. Data last updated March 21, 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

Sat 4/18

7:40 am-6:11 pm

2 stops9h 31m

Chicago O'Hare Intl

Wed 4/29

2:09 pm-11:00 pm

1 stop9h 51m

$256

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 4/22

7:40 am-7:52 pm

2 stops11h 12m

Chicago O'Hare Intl

Wed 4/29

2:09 pm-11:00 pm

1 stop9h 51m

$278

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 4/1

6:30 am-6:02 pm

1 stop10h 32m

Chicago O'Hare Intl

Wed 4/15

2:09 pm-11:00 pm

1 stop9h 51m

$285
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 5/27

8:30 am-1:07 pm

Nonstop3h 37m

Chicago O'Hare Intl

Sun 5/31

7:42 pm-10:37 pm

Nonstop3h 55m

$288

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 4/24

1:27 pm-10:54 pm

1 stop8h 27m

Chicago O'Hare Intl

Sat 4/25

8:42 am-11:32 am

Nonstop3h 50m

$300

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 4/22

6:40 am-9:25 pm

2 stops13h 45m

Chicago O'Hare Intl

Sat 4/25

2:09 pm-11:00 pm

1 stop9h 51m

$332

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 7/29

6:35 am-4:48 pm

1 stop9h 13m

Chicago O'Hare Intl

Mon 8/3

1:55 pm-11:06 pm

1 stop10h 11m

$334

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Sat 5/30

7:40 am-4:40 pm

1 stop8h 00m

Chicago O'Hare Intl

Sat 6/13

5:30 pm-12:44 am

1 stop8h 14m

$337

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 4/3

6:30 am-6:07 pm

1 stop10h 37m

Chicago O'Hare Intl

Fri 4/17

2:09 pm-11:00 pm

1 stop9h 51m

$339

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Mon 5/4

6:10 am-5:58 pm

2 stops10h 48m

Chicago Midway

Mon 5/11

1:22 pm-10:55 pm

2 stops10h 33m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

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

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 $91). Flying from Alberta to Chicago in July is currently the most expensive (average of $157). 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 March 21, 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 March 21, 2026.

The most flights from CAAB to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, 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 3h 37m. The distance from Alberta to Chicago is about 1381 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Alberta to Chicago one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $102. Users have also found prices from $102 and $106 on WestJet and United Airlines, respectively.

  • What are the most popular routes from Alberta to Chicago?

    The most popular route from Alberta to Chicago is Calgary - Chicago O'Hare Intl. You may also consider Edmonton - Chicago O'Hare Intl or Calgary - Chicago Midway.

  • What are the most reliable airlines from Alberta to Chicago?

    No one likes to see their flight delayed. When booking a flight from Alberta to Chicago consider choosing Scandinavian Airlines (83%), WestJet (82%) or Delta (76%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Alberta to Chicago?

    While on average a flight from Alberta to Chicago is generally $654, our data shows the cheapest flight currently is $132. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay $244 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 $91). Flying from Alberta to Chicago in July is currently the most expensive (average of $157). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top 4 airlines flying from Alberta to Chicago

Discover the top 4 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 2,558,603 searches. Data last updated March 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$83Average$398FlexibilityNo cancel feeOn-time67%
WestJetCheapest$137Average$252FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$143Average$353FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$185Average$389FlexibilityNo cancel feeOn-time71%

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