HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$153+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Jul 19 — Jul 261
Sun 7/19
Sun 7/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Alberta to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 19, 2026.

This Justfly.com deal was found by Cheapflights users on 6/19. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:00 am
YYC
-
ORD
Nonstop3h 35m
WestJet
Mon 11/22:20 pm
ORD
-
YYC
Nonstop4h 55m
WestJet
Deal found 6/19$251
This Super.com deal was found by Cheapflights users on 6/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/512:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 10/65:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 6/19$262
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2812:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 10/65:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 6/17$266
This oojo deal was found by Cheapflights users on 6/15. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 9/155:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 6/15$271
This FlightHub deal was found by Cheapflights users on 6/15. 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 9/1012:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 9/155:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 6/15$272
This United Airlines deal was found by Cheapflights users on 6/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:37 pm
YYC
-
ORD
Nonstop3h 33m
United Airlines
Mon 11/29:47 pm
ORD
-
YYC
1 stop17h 09m
United Airlines
Deal found 6/19$276
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:28 pm
YYC
-
ORD
Nonstop3h 36m
United Airlines
Sat 7/47:45 pm
ORD
-
YYC
Nonstop3h 52m
United Airlines
Deal found 6/17$278
This Air Canada deal was found by Cheapflights users on 6/19. 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.
Mon 10/56:30 am
YYC
-
ORD
1 stop7h 25m
Air Canada
Tue 10/68:45 am
ORD
-
YYC
1 stop8h 12m
Air Canada
Deal found 6/19$286
This Air Canada deal was found by Cheapflights users on 6/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2811:55 pm
YYC
-
ORD
1 stop8h 05m
Air Canada
Tue 10/68:45 am
ORD
-
YYC
1 stop8h 12m
Air Canada
Deal found 6/17$288
This Justfly.com deal was found by Cheapflights users on 6/15. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Thu 10/85:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 6/15$289
This oojo deal was found by Cheapflights users on 6/15. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Mon 10/55:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 6/15$290
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:45 am
YYC
-
MDW
1 stop8h 05m
Delta
Sat 10/2412:30 pm
MDW
-
YYC
2 stops11h 43m
Delta
Deal found 6/16$294

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 June 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$251
(Justfly.com)

One-way from

$153

Popular in

July

Cheapest in

November

Average price

$350

Good round-trip deal

$335 or less

Good one-way deal

$214 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. 17% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 19, 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

Wed 10/21

7:45 am-10:10 pm

2 stops13h 25m

Chicago Midway

Sat 10/24

12:30 pm-11:13 pm

2 stops11h 43m

$294

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 11/23

7:15 am-7:34 pm

2 stops11h 19m

Chicago O'Hare Intl

Sat 12/5

3:50 pm-11:13 pm

2 stops8h 23m

$296

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 10/30

7:45 am-4:50 pm

1 stop8h 05m

Chicago Midway

Mon 11/2

12:30 pm-8:54 pm

1 stop9h 24m

$296

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 11/26

7:45 am-6:37 pm

2 stops9h 52m

Chicago Midway

Mon 11/30

9:30 am-8:54 pm

2 stops12h 24m

$326

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 11/27

7:45 am-10:10 pm

2 stops13h 25m

Chicago Midway

Wed 12/2

12:30 pm-11:13 pm

2 stops11h 43m

$326

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 11/13

7:45 am-4:50 pm

1 stop8h 05m

Chicago Midway

Tue 11/17

10:35 am-11:13 pm

2 stops13h 38m

$326

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 9/2

8:30 am-1:05 pm

Nonstop3h 35m

Chicago O'Hare Intl

Tue 9/8

2:15 pm-1:17 am

1 stop12h 02m

$334

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 9/28

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 10/6

12:15 pm-8:54 pm

1 stop9h 39m

$354

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 10/6

12:20 am-12:06 pm

1 stop10h 46m

Chicago O'Hare Intl

Thu 10/8

1:55 pm-11:13 pm

1 stop10h 18m

$360

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 9/28

7:00 am-11:29 am

Nonstop3h 29m

Chicago O'Hare Intl

Tue 10/6

5:00 am-11:55 am

1 stop7h 55m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/19

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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, 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 August is currently the most expensive (average of $133). 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 June 19, 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 June 19, 2026.

The most flights from CAAB to CHI are scheduled on a Monday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

How much does it cost to fly round-trip 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 59 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 29m. 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 $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 Calgary - Chicago Midway or Edmonton - Chicago O'Hare Intl.

  • 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 Qatar Airways (87%), American Airlines (87%) or Envoy Air (86%) 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 $384, our data shows the cheapest flight currently is $149. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay $293 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 August is currently the most expensive (average of $133). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 2,558,603 searches. Data last updated June 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$135Average$444FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$135Average$434FlexibilityNo cancel feeOn-time69%
WestJetCheapest$138Average$331FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$208Average$389FlexibilityNo cancel feeOn-time71%
DeltaCheapest$241Average$288FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.