HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$113+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
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

Keep the following information in mind while searching for Alberta to Chicago flight deals. Data was last updated November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$147
(FlightHub)

One-way from

$113
(United Airlines)

Popular in

December

Cheapest in

April

Average price

$405

Good round-trip deal

$268 or less

Good one-way deal

$160 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. 24% potential increase in price ($87 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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

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 November 2, 2025.

This FlightHub deal was found by Cheapflights users on 10/31. 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 12/269:00 amYYC - ORD
Nonstop3h 35mWestJet
Mon 1/52:20 pmORD - YYC
Nonstop3h 55mWestJet
Deal found 10/31$147
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/59:00 amYYC - ORD
Nonstop3h 35mWestJet
Fri 12/122:20 pmORD - YYC
Nonstop3h 55mWestJet
Deal found 11/1$158
This Kiwi.com deal was found by Cheapflights users on 10/31. 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
Mon 1/52:20 pmORD - YYC
Nonstop3h 55mWestJet
Deal found 10/31$164
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Fri 12/269:00 amYYC - ORD
Nonstop3h 35mWestJet
Fri 1/22:20 pmORD - YYC
Nonstop3h 55mWestJet
Deal found 10/31$177
This Mytrip deal was found by Cheapflights users on 10/31. 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.
Fri 12/129:00 amYYC - ORD
Nonstop3h 35mWestJet
Mon 12/152:20 pmORD - YYC
Nonstop3h 55mWestJet
Deal found 10/31$180
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 1/22:20 pmORD - YYC
Nonstop3h 55mWestJet
Deal found 10/31$187
This Air Canada deal was found by Cheapflights users on 10/31. 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 11/275:35 amYYC - ORD
1 stop8h 35mAir Canada
Sat 12/63:55 pmORD - YYC
1 stop9h 19mAir Canada
Deal found 10/31$191
This Trip.com deal was found by Cheapflights users on 11/1. 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.
Fri 12/55:35 amYYC - ORD
1 stop8h 35mMultiple Airlines
Fri 12/122:20 pmORD - YYC
Nonstop3h 55mMultiple Airlines
Deal found 11/1$193
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Fri 11/289:00 amYYC - ORD
Nonstop3h 35mWestJet
Fri 12/122:20 pmORD - YYC
Nonstop3h 55mWestJet
Deal found 10/31$195
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Fri 12/269:00 amYYC - ORD
Nonstop3h 35mMultiple Airlines
Wed 1/75:05 amORD - YYC
1 stop15h 04mMultiple Airlines
Deal found 10/31$203
This Delta deal was found by Cheapflights users on 10/31. 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.
Tue 12/26:35 amYYC - MDW
1 stop5h 35mDelta
Fri 12/51:50 pmMDW - YYC
1 stop8h 07mDelta
Deal found 10/31$214
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Fri 12/129:45 pmYYC - MDW
2 stops22h 37mMultiple Airlines
Mon 12/158:42 pmMDW - YYC
1 stop16h 02mMultiple Airlines
Deal found 10/31$219

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 November 2, 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 - MDW

YYCMDW

Calgary

Tue 12/2

6:35 am-1:10 pm

1 stop5h 35m

Chicago Midway

Tue 12/9

1:50 pm-8:57 pm

1 stop8h 07m

$214

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 12/17

7:35 am-6:45 pm

1 stop10h 10m

Chicago O'Hare Intl

Sun 1/11

1:50 pm-11:02 pm

1 stop10h 12m

$214

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 12/3

12:41 pm-9:21 pm

1 stop7h 40m

Chicago O'Hare Intl

Fri 12/5

8:50 am-1:40 pm

1 stop5h 50m

$214

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 12/2

6:35 am-1:10 pm

1 stop5h 35m

Chicago Midway

Sat 12/6

1:14 pm-8:57 pm

2 stops8h 43m

$222

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 12/24

6:30 am-5:19 pm

1 stop9h 49m

Chicago Midway

Wed 1/7

1:49 pm-8:56 pm

1 stop8h 07m

$222

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 12/2

6:35 am-1:10 pm

1 stop5h 35m

Chicago Midway

Fri 12/5

1:14 pm-8:57 pm

2 stops8h 43m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 12/11

12:41 pm-9:21 pm

1 stop7h 40m

Chicago O'Hare Intl

Mon 12/15

1:35 pm-11:13 pm

1 stop10h 38m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 12/17

7:35 am-9:40 pm

2 stops13h 05m

Chicago O'Hare Intl

Wed 12/24

12:30 pm-11:15 pm

2 stops11h 45m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 12/2

12:41 pm-9:21 pm

1 stop7h 40m

Chicago O'Hare Intl

Thu 12/11

1:35 pm-11:13 pm

1 stop10h 38m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 12/8

2:45 pm-9:40 pm

1 stop5h 55m

Chicago O'Hare Intl

Thu 12/11

1:35 pm-11:13 pm

1 stop10h 38m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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 $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 November 2, 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 5h 35m. The distance from Alberta to Chicago is about 1396 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 United Airlines. According to our data, you can fly for as low as $114. Users have also found prices from $118 and $137 on Air Canada and Delta, 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 Edmonton - 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 United Airlines (88%), Emirates (85%) or Air Canada (83%) 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 $447, our data shows the cheapest flight currently is $112. When looking at the most popular route, (Calgary - Chicago O'Hare Intl), you can expect to pay $190 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
Merrillville
Lansing
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.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island to Midway flights
Vancouver Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Ottawa to O'Hare Intl flights
Calgary to O'Hare Intl flights
Québec City to O'Hare Intl flights
Pearson Intl to St. Louis flights
Winnipeg to O'Hare Intl flights
Vancouver Intl to Midway flights
Ottawa to Midway flights
Abbotsford to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Halifax to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Halifax to Midway flights
Kelowna to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Edmonton to Midway flights
Calgary to Midway flights
Grande Prairie to O'Hare Intl flights
Winnipeg to Midway flights
Québec City to Midway flights
Ottawa to St. Louis flights
Vancouver Intl to St. Louis flights
Calgary to St. Louis flights
Regina to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Winnipeg to St. Louis flights
Edmonton to St. Louis flights
London to O'Hare Intl flights
Victoria to O'Hare Intl flights
Pearson Intl to Peoria flights
London to Midway flights
Vancouver Intl to Peoria flights
Halifax to St. Louis flights
Vancouver Intl to Paducah flights
Victoria to St. Louis flights
St John to O'Hare Intl flights
Moncton to O'Hare Intl 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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$479FlexibilityNo cancel feeOn-time67%
WestJetCheapest$138Average$234FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$143Average$370FlexibilityNo 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.