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$139+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
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 May 5, 2026.

This Trip.com deal was found by Cheapflights users on 5/1. 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.
Mon 5/1812:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Sun 5/245:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 5/1$171
This FlightHub deal was found by Cheapflights users on 4/30. 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.
Wed 5/2012:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 5/265:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 4/30$173
This FlightHub deal was found by Cheapflights users on 5/1. 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.
Sat 5/3012:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Sun 5/315:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 5/1$175
This Mytrip deal was found by Cheapflights users on 4/30. 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 5/2312:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Sat 5/305:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 4/30$179
This Gotogate deal was found by Cheapflights users on 4/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Sun 5/245:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 4/30$180
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Tue 5/1912:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Sun 5/245:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 4/30$186
This Trip.com deal was found by Cheapflights users on 5/3. 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.
Thu 5/216:30 am
YYC
-
ORD
1 stop7h 25m
Multiple Airlines
Sat 5/305:30 pm
ORD
-
YYC
Nonstop3h 55m
Multiple Airlines
Deal found 5/3$195
This Flightnetwork deal was found by Cheapflights users on 4/30. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:30 am
YYC
-
ORD
1 stop7h 25m
Multiple Airlines
Sun 5/245:30 pm
ORD
-
YYC
Nonstop3h 55m
Multiple Airlines
Deal found 4/30$217
This Mytrip deal was found by Cheapflights users on 4/30. 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 5/236:30 am
YYC
-
ORD
1 stop7h 25m
Multiple Airlines
Sat 5/305:30 pm
ORD
-
YYC
Nonstop3h 55m
Multiple Airlines
Deal found 4/30$218
This Trip.com deal was found by Cheapflights users on 4/30. 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 5/197:05 am
YYC
-
ORD
1 stop8h 13m
Multiple Airlines
Sun 5/245:30 pm
ORD
-
YYC
Nonstop3h 55m
Multiple Airlines
Deal found 4/30$230
This Delta deal was found by Cheapflights users on 4/30. 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 12/247:45 am
YYC
-
MDW
2 stops13h 00m
Delta
Thu 12/3111:20 am
MDW
-
YYC
2 stops12h 53m
Delta
Deal found 4/30$279
This oojo deal was found by Cheapflights users on 4/30. 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.
Wed 5/277:40 am
YEG
-
ORD
1 stop8h 00m
WestJet
Sat 5/305:30 pm
ORD
-
YEG
1 stop16h 40m
WestJet
Deal found 4/30$280

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 May 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$171
(Trip.com)

One-way from

$139
(Air Canada)

Popular in

July

Cheapest in

November

Average price

$262

Good round-trip deal

$278 or less

Good one-way deal

$178 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. 12% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 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 2,558,603 searches. Data last updated May 5, 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

Thu 8/6

7:45 am-6:57 pm

1 stop10h 12m

Chicago O'Hare Intl

Tue 8/11

1:55 pm-11:06 pm

1 stop10h 11m

$248

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/2

7:15 am-6:01 pm

1 stop9h 46m

Chicago O'Hare Intl

Fri 10/16

1:55 pm-11:13 pm

1 stop10h 18m

$255

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 5/19

8:45 am-4:49 pm

1 stop7h 04m

Chicago O'Hare Intl

Fri 5/22

7:45 am-7:40 pm

2 stops12h 55m

$288

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 8/14

7:15 am-6:01 pm

1 stop9h 46m

Chicago O'Hare Intl

Sun 8/16

1:55 pm-11:06 pm

1 stop10h 11m

$299

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Wed 6/17

3:42 pm-8:16 pm

Nonstop3h 34m

Chicago O'Hare Intl

Sat 6/20

7:05 am-10:04 pm

1 stop15h 59m

$305

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Fri 5/29

6:00 am-10:49 pm

1 stop15h 49m

Chicago O'Hare Intl

Tue 6/2

12:56 pm-10:04 pm

1 stop10h 08m

$310

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Thu 5/28

7:40 am-4:40 pm

1 stop8h 00m

Chicago O'Hare Intl

Tue 6/2

5:30 pm-6:30 pm

1 stop26h 00m

$321

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 7/22

6:45 am-4:59 pm

1 stop9h 14m

Chicago O'Hare Intl

Wed 8/5

2:02 pm-10:59 pm

1 stop9h 57m

$325

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 5/28

6:45 am-4:51 pm

1 stop9h 06m

Chicago O'Hare Intl

Mon 6/1

12:30 pm-8:30 pm

1 stop9h 00m

$331

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Thu 6/11

3:17 pm-12:44 am

1 stop8h 27m

Chicago O'Hare Intl

Tue 6/16

7:05 am-10:04 pm

1 stop15h 59m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 $62). Flying from Alberta to Chicago in February is currently the most expensive (average of $102). 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 May 5, 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 May 5, 2026.

The most flights from CAAB to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Tuesday, 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. The distance from Alberta to Chicago is about 1416 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 $106 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 Finnair (79%), British Airways (74%) or American Airlines (73%) 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 $564, our data shows the cheapest flight currently is $133. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay $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 $62). Flying from Alberta to Chicago in February is currently the most expensive (average of $102). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$444FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$135Average$374FlexibilityNo cancel feeOn-time69%
WestJetCheapest$137Average$330FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$208Average$391FlexibilityNo cancel feeOn-time71%

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