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$85+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:35 amYYC - ORD
1 stop10h 10mDelta
Wed 1/712:30 pmORD - YYC
1 stop9h 24mDelta
Deal found 12/15$270
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:35 amYYC - ORD
1 stop10h 10mDelta
Mon 1/51:35 pmORD - YYC
1 stop10h 27mDelta
Deal found 12/15$282
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:00 amYYC - ORD
Nonstop3h 35mWestJet
Fri 1/92:20 pmORD - YYC
Nonstop3h 55mWestJet
Deal found 12/16$330
This Air Canada deal was found by Cheapflights users on 12/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:35 amYYC - ORD
1 stop8h 35mAir Canada
Tue 1/62:00 pmORD - YYC
1 stop7h 59mAir Canada
Deal found 12/15$358
This Air Canada deal was found by Cheapflights users on 12/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:15 amYYC - ORD
1 stop7h 55mAir Canada
Tue 1/610:00 amORD - YYC
1 stop9h 54mAir Canada
Deal found 12/15$363
This Air Canada deal was found by Cheapflights users on 12/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:15 amYYC - ORD
1 stop7h 55mAir Canada
Wed 1/77:15 amORD - YYC
2 stops14h 04mAir Canada
Deal found 12/15$365
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:35 amYYC - MDW
2 stops16h 12mDelta
Wed 1/79:50 amMDW - YYC
2 stops10h 25mDelta
Deal found 12/15$376
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:35 amYYC - MDW
2 stops16h 12mDelta
Tue 1/69:50 amMDW - YYC
2 stops14h 12mDelta
Deal found 12/15$394
This Air Canada deal was found by Cheapflights users on 12/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/268:00 amYEG - ORD
1 stop10h 45mAir Canada
Wed 1/78:00 amORD - YEG
2 stops14h 43mAir Canada
Deal found 12/15$400
This Air Canada deal was found by Cheapflights users on 12/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2011:40 pmYYC - ORD
1 stop8h 33mAir Canada
Tue 1/62:00 pmORD - YYC
1 stop7h 59mAir Canada
Deal found 12/15$423
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/182:13 pmYYC - ORD
1 stop6h 06mUnited Airlines
Tue 1/68:45 amORD - YYC
Nonstop3h 50mUnited Airlines
Deal found 12/15$425
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:00 amYYC - ORD
Nonstop3h 35mMultiple Airlines
Fri 1/95:50 amORD - YYC
1 stop14h 19mMultiple Airlines
Deal found 12/16$428

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$147
(FlightHub)

One-way from

$85
(Kiwi.com)

Popular in

July

Cheapest in

April

Average price

$291

Good round-trip deal

$195 or less

Good one-way deal

$154 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. 14% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 18, 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

Thu 5/21

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sat 5/30

5:30 pm-8:19 pm

Nonstop3h 49m

$147

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 2/3

2:13 pm-11:59 pm

1 stop8h 46m

Chicago O'Hare Intl

Wed 2/4

8:45 am-11:35 am

Nonstop3h 50m

$161

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 1/13

6:15 am-5:04 pm

1 stop9h 49m

Chicago O'Hare Intl

Tue 1/20

1:55 pm-9:53 pm

1 stop8h 58m

$188

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 1/14

6:15 am-7:51 pm

1 stop12h 36m

Chicago O'Hare Intl

Sun 1/18

5:40 am-1:08 pm

1 stop8h 28m

$188

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 2/2

6:15 am-9:15 pm

1 stop14h 00m

Chicago O'Hare Intl

Wed 2/4

8:45 am-11:35 am

Nonstop3h 50m

$188

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 2/2

6:15 am-11:59 pm

1 stop16h 44m

Chicago O'Hare Intl

Tue 2/3

12:53 pm-9:53 pm

1 stop10h 00m

$188

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/15

6:15 am-7:51 pm

1 stop12h 36m

Chicago O'Hare Intl

Thu 1/22

8:45 am-11:35 am

Nonstop3h 50m

$195

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 3/21

6:15 am-8:00 pm

1 stop12h 45m

Chicago O'Hare Intl

Tue 3/24

7:00 am-9:53 pm

1 stop15h 53m

$195

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 2/11

6:15 am-11:59 pm

1 stop16h 44m

Chicago O'Hare Intl

Tue 2/17

7:10 am-9:53 pm

1 stop15h 43m

$196

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Thu 6/11

8:00 am-4:43 pm

1 stop7h 43m

Chicago O'Hare Intl

Tue 6/16

5:30 pm-12:25 am

1 stop7h 55m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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, May is the cheapest month in which you can book a flight from Alberta to Chicago (average of $89). Flying from Alberta to Chicago in August is currently the most expensive (average of $150). 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 December 18, 2025.

When flying from Alberta to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 62% versus a flight at noon.

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 $94. Users have also found prices from $102 and $102 on American 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 Delta (85%), WestJet (79%) or Avianca (74%) 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 $443, our data shows the cheapest flight currently is $102. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay $158 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, May is the cheapest month in which you can book a flight from Alberta to Chicago (average of $89). Flying from Alberta to Chicago in August is currently the most expensive (average of $150). 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

Browse thousands of different options on Cheapflights for your next trip

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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.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island to Midway flights
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Pearson Intl 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$101Average$414FlexibilityNo cancel feeOn-time67%
WestJetCheapest$138Average$244FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$143Average$355FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$185Average$376FlexibilityNo cancel feeOn-time71%

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