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$109+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Alberta to Chicago

Keep the following information in mind while searching for Alberta to Chicago flight deals. Data was last updated September 16, 2025.

Round-trip from

$156
(FlightHub)

One-way from

$109
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$230

Good round-trip deal

$155 or less

Good one-way deal

$208 or less
From Alberta to Chicago (CHI)
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One-way flight from Alberta to Chicago (CHI)
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Highest demand for flights based on searches. 23% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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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Find 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 September 16, 2025.

This FlightHub deal was found by Cheapflights users on 9/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:15 pmYYC - ORD
Nonstop3h 28mWestJet
Sun 10/55:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 9/15$156
This Trip.com deal was found by Cheapflights users on 9/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:00 amYEG - ORD
1 stop7h 43mWestJet
Sat 10/255:30 pmORD - YEG
1 stop7h 57mWestJet
Deal found 9/14$160
This Mytrip deal was found by Cheapflights users on 9/15. 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.
Sat 10/111:00 amYEG - ORD
1 stop7h 51mAir Canada
Sat 10/189:55 amORD - YEG
2 stops11h 08mAir Canada
Deal found 9/15$162
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/146:00 amYEG - ORD
1 stop16h 59mUnited Airlines
Tue 10/217:10 amORD - YEG
1 stop7h 58mUnited Airlines
Deal found 9/16$165
This Booking.com deal was found by Cheapflights users on 9/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/129:30 amYEG - ORD
1 stop6h 13mWestJet
Sat 10/185:30 pmORD - YEG
1 stop7h 57mWestJet
Deal found 9/15$169
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 12/1112:35 pmYYC - ORD
Nonstop3h 35mUnited Airlines
Mon 12/157:10 amORD - YYC
1 stop15h 43mUnited Airlines
Deal found 9/15$172
This Mytrip deal was found by Cheapflights users on 9/15. 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.
Sun 10/129:30 amYEG - ORD
1 stop6h 13mMultiple Airlines
Sat 10/189:55 amORD - YEG
2 stops11h 08mMultiple Airlines
Deal found 9/15$172
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/153:17 pmYEG - ORD
1 stop6h 22mUnited Airlines
Wed 10/221:27 pmORD - YEG
Nonstop3h 58mUnited Airlines
Deal found 9/15$179
This FlightHub deal was found by Cheapflights users on 9/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:00 amYEG - ORD
1 stop7h 43mWestJet
Sun 10/195:30 pmORD - YEG
1 stop7h 57mWestJet
Deal found 9/15$186
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2711:15 amYYC - ORD
1 stop11h 29mMultiple Airlines
Fri 10/312:20 pmORD - YYC
Nonstop3h 55mMultiple Airlines
Deal found 9/14$190
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/58:55 amYYC - ORD
1 stop23h 42mMultiple Airlines
Sun 10/125:30 pmORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 9/14$197
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Tue 10/148:00 pmYEG - ORD
2 stops12h 51mAir Canada
Tue 10/219:55 amORD - YEG
2 stops11h 08mAir Canada
Deal found 9/16$198

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 September 16, 2025.
Use the filters below to find and compare flights from Alberta to Chicago that are best for you.

Fly from

Alberta

Fly to

Chicago

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/3

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sun 10/5

5:30 pm-8:19 pm

Nonstop3h 49m

$156

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 12/11

12:35 pm-5:10 pm

Nonstop3h 35m

Chicago O'Hare Intl

Mon 12/15

7:10 am-9:53 pm

1 stop15h 43m

$172

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Sun 10/12

9:30 am-4:43 pm

1 stop6h 13m

Chicago O'Hare Intl

Sat 10/18

9:55 am-8:03 pm

2 stops11h 08m

$172

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 1/2

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Mon 1/5

2:20 pm-5:15 pm

Nonstop3h 55m

$174

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Thu 10/16

6:00 am-8:25 pm

1 stop13h 25m

Chicago O'Hare Intl

Sun 10/19

5:01 am-2:08 pm

1 stop10h 07m

$179

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Fri 10/17

3:17 pm-11:59 pm

1 stop7h 42m

Chicago O'Hare Intl

Sat 10/25

1:27 pm-4:25 pm

Nonstop3h 58m

$179

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Wed 10/15

3:17 pm-10:39 pm

1 stop6h 22m

Chicago O'Hare Intl

Wed 10/22

5:01 am-2:08 pm

1 stop10h 07m

$179

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Wed 10/1

3:17 pm-10:39 pm

1 stop6h 22m

Chicago O'Hare Intl

Sun 10/12

1:27 pm-4:25 pm

Nonstop3h 58m

$179

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Tue 10/14

6:00 am-10:39 pm

1 stop15h 39m

Chicago O'Hare Intl

Tue 10/21

7:10 am-2:08 pm

1 stop7h 58m

$180

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/17

12:38 pm-5:10 pm

Nonstop3h 32m

Chicago O'Hare Intl

Sun 10/19

5:01 am-1:53 pm

1 stop9h 52m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
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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, August is the cheapest month in which you can book a flight from Alberta to Chicago (average of $245). Flying from Alberta to Chicago in March is currently the most expensive (average of $321). 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 September 16, 2025.

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 September 16, 2025.

The most flights from CAAB to CHI are scheduled on a Sunday (15 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 on average).

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 28m. 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 WestJet. According to our data, you can fly for as low as $109. Users have also found prices from $110 and $113 on United Airlines and Air Canada, 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 Avianca (80%), Air Canada (79%) or United Airlines (79%) 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 $418, our data shows the cheapest flight currently is $117. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay $172 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, August is the cheapest month in which you can book a flight from Alberta to Chicago (average of $245). Flying from Alberta to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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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St. John's to Midway flights
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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$468FlexibilityNo cancel feeOn-time67%
WestJetCheapest$138Average$217FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$143Average$359FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$208Average$385FlexibilityNo cancel feeOn-time71%

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