HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$100+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This oojo deal was found by Cheapflights users on 1/28. 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.
Mon 4/2712:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Fri 5/15:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 1/28$182
This Air Canada deal was found by Cheapflights users on 1/27. 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 3/75:35 am
YYC
-
ORD
1 stop8h 35m
Air Canada
Tue 3/103:55 pm
ORD
-
YYC
1 stop9h 04m
Air Canada
Deal found 1/27$197
This WestJet deal was found by Cheapflights users on 1/28. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/279:10 am
YEG
-
ORD
1 stop6h 30m
WestJet
Fri 5/15:30 pm
ORD
-
YEG
1 stop6h 25m
WestJet
Deal found 1/28$209
This FlightHub deal was found by Cheapflights users on 1/27. 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 7/1612:15 pm
YYC
-
ORD
Nonstop3h 28m
WestJet
Fri 7/175:30 pm
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 1/27$216
This Air Canada deal was found by Cheapflights users on 1/28. 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 3/511:40 pm
YYC
-
ORD
1 stop8h 33m
Air Canada
Sat 3/73:55 pm
ORD
-
YYC
1 stop9h 04m
Air Canada
Deal found 1/28$217
This FlightHub deal was found by Cheapflights users on 1/27. 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.
Mon 6/2912:15 pm
YYC
-
ORD
Nonstop3h 28m
WestJet
Tue 7/75:30 pm
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 1/27$218
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 7/2212:15 pm
YYC
-
ORD
Nonstop3h 28m
WestJet
Sat 7/255:30 pm
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 1/27$222
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 7/2212:15 pm
YYC
-
ORD
Nonstop3h 28m
WestJet
Mon 7/275:30 pm
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 1/27$226
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Tue 2/241:40 pm
YYC
-
ORD
Nonstop3h 40m
American Airlines
Tue 3/35:00 am
ORD
-
YYC
1 stop7h 44m
American Airlines
Deal found 1/26$233
This WestJet deal was found by Cheapflights users on 1/28. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:35 am
YQU
-
ORD
1 stop7h 00m
WestJet
Fri 4/242:20 pm
ORD
-
YQU
1 stop6h 49m
WestJet
Deal found 1/28$234
This Air Canada deal was found by Cheapflights users on 1/27. 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 3/319:00 am
YYC
-
ORD
1 stop8h 53m
Air Canada
Wed 4/810:43 am
ORD
-
YYC
1 stop10h 15m
Air Canada
Deal found 1/27$237
This Delta deal was found by Cheapflights users on 1/28. 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.
Sat 5/96:35 am
YYC
-
ORD
1 stop9h 13m
Delta
Mon 5/111:55 pm
ORD
-
YYC
1 stop10h 11m
Delta
Deal found 1/28$238

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$182
(oojo)

One-way from

$100
(Kiwi.com)

Popular in

July

Cheapest in

April

Average price

$234

Good round-trip deal

$185 or less

Good one-way deal

$172 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 ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 29, 2026.
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

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Mon 4/27

9:10 am-4:40 pm

1 stop6h 30m

Chicago O'Hare Intl

Fri 5/1

5:30 pm-10:55 pm

1 stop6h 25m

$209

Grande PrairieChicago

YQU - ORD

YQUORD

Grande Prairie

Mon 4/20

5:35 am-1:35 pm

1 stop7h 00m

Chicago O'Hare Intl

Fri 4/24

2:20 pm-8:09 pm

1 stop6h 49m

$234

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Thu 4/30

7:30 am-4:40 pm

1 stop8h 10m

Chicago O'Hare Intl

Mon 5/4

5:30 pm-10:55 pm

1 stop6h 25m

$241

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Fri 4/10

6:00 am-1:35 pm

1 stop6h 35m

Chicago O'Hare Intl

Mon 4/13

2:20 pm-9:16 pm

1 stop7h 56m

$247

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/9

6:35 am-8:24 pm

2 stops12h 49m

Chicago O'Hare Intl

Thu 5/14

1:55 pm-11:06 pm

1 stop10h 11m

$250

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/9

7:15 am-9:34 pm

2 stops13h 19m

Chicago O'Hare Intl

Fri 5/15

1:55 pm-11:06 pm

1 stop10h 11m

$250

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 2/24

6:30 am-1:05 pm

1 stop5h 35m

Chicago Midway

Tue 3/3

1:49 pm-8:54 pm

1 stop8h 05m

$251

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Thu 6/11

7:30 am-4:40 pm

1 stop8h 10m

Chicago O'Hare Intl

Tue 6/16

5:30 pm-12:40 am

1 stop8h 10m

$255

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 7/21

7:15 am-6:01 pm

1 stop9h 46m

Chicago O'Hare Intl

Mon 7/27

1:55 pm-11:06 pm

1 stop10h 11m

$257

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Fri 4/10

3:17 pm-9:37 am

1 stop17h 20m

Chicago O'Hare Intl

Mon 4/13

9:49 pm-2:08 pm

1 stop17h 19m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 60 results
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, May is the cheapest month in which you can book a flight from Alberta to Chicago (average of $93). Flying from Alberta to Chicago in August is currently the most expensive (average of $149). 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 January 29, 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 January 29, 2026.

The most flights from CAAB to CHI are scheduled on a Wednesday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 6h 30m. 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 WestJet. According to our data, you can fly for as low as $98. Users have also found prices from $102 and $112 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 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 WestJet (77%), Delta (76%) or Air Canada (65%) 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 $330, our data shows the cheapest flight currently is $116. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay $226 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 $93). Flying from Alberta to Chicago in August is currently the most expensive (average of $149). 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

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

Alternative routes for Alberta to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pearson Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Pearson Intl to Midway flights
Pearson Intl to St. Louis flights
Toronto Island to O'Hare Intl flights
Vancouver Intl to Midway flights
Ottawa to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Québec City to O'Hare Intl flights
Calgary to Midway flights
Ottawa to Midway flights
Vancouver Intl to St. Louis flights
Edmonton to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Abbotsford to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Hamilton to O'Hare Intl flights
Winnipeg to Midway flights
Halifax to O'Hare Intl flights
Québec City to Midway flights
Halifax to Midway flights
Ottawa to St. Louis flights
Edmonton to Midway flights
Calgary to St. Louis flights
London to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Winnipeg to St. Louis flights
Victoria to O'Hare Intl flights
St. John's to Midway flights
Edmonton to St. Louis flights
Vancouver Intl to Paducah flights
Halifax to St. Louis flights
Nanaimo to O'Hare Intl flights
Victoria to Midway flights
Pearson Intl to Peoria flights
Vancouver Intl to Peoria flights
Regina to O'Hare Intl flights
Charlottetown to St. Louis flights
Edmonton to Moline flights
Victoria to St. Louis flights

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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$83Average$391FlexibilityNo cancel feeOn-time67%
WestJetCheapest$138Average$237FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$143Average$351FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$185Average$376FlexibilityNo cancel feeOn-time71%

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.