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$148+ Cheap flights from Calgary (YYC) 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Jun 20 — Jun 271
Sat 6/20
Sat 6/27
1 adult, Economy
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Cheapflights Tip: The best prices from Calgary to Chicago are usually found in November or January, booked 84 days in advance, depart on a Friday or Sunday and return on a Friday

Cheap flight deals from Calgary to Chicago

Cheapest flights from Calgary to Chicago
Explore the most affordable flight options available from Calgary to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 21, 2026.

This American Airlines deal was found by Cheapflights users on 5/18. 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.
Sun 5/246:15 am
YYC
-
ORD
Nonstop3h 30m
American Airlines
Mon 5/2510:00 am
ORD
-
YYC
Nonstop3h 44m
American Airlines
Deal found 5/18$244
This Delta deal was found by Cheapflights users on 5/20. 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 8/206:45 am
YYC
-
ORD
1 stop9h 19m
Delta
Wed 8/2612:29 pm
ORD
-
YYC
1 stop9h 06m
Delta
Deal found 5/20$245
This Delta deal was found by Cheapflights users on 5/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:45 am
YYC
-
ORD
1 stop9h 19m
Delta
Tue 8/188:48 am
ORD
-
YYC
2 stops12h 47m
Delta
Deal found 5/19$252
This Delta deal was found by Cheapflights users on 5/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:45 am
YYC
-
MDW
2 stops13h 00m
Delta
Sat 10/3112:30 pm
MDW
-
YYC
1 stop9h 24m
Delta
Deal found 5/19$252
This Delta deal was found by Cheapflights users on 5/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:45 am
YYC
-
ORD
1 stop9h 34m
Delta
Wed 8/191:59 pm
ORD
-
YYC
1 stop10h 00m
Delta
Deal found 5/19$253
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 6/812:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Sat 6/135:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 5/16$255
This Air Canada deal was found by Cheapflights users on 5/21. 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 10/63:45 pm
ORD
-
YYC
1 stop8h 12m
Air Canada
Deal found 5/21$257
This Delta deal was found by Cheapflights users on 5/20. 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.
Fri 8/217:45 am
YYC
-
ORD
1 stop9h 34m
Delta
Wed 8/2612:29 pm
ORD
-
YYC
1 stop9h 06m
Delta
Deal found 5/20$258
This oojo deal was found by Cheapflights users on 5/18. 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 9/1412:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Mon 9/215:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 5/18$259
This FlightHub deal was found by Cheapflights users on 5/18. 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 10/2312:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Sun 10/252:20 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 5/18$261
This oojo deal was found by Cheapflights users on 5/17. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Fri 10/235:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 5/17$262
This Trip.com deal was found by Cheapflights users on 5/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Sat 6/135:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 5/19$264

Find flight deals from Calgary to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$245
(Delta)

One-way from

$148
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$258

Good round-trip deal

$188 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 Calgary to Chicago (CHI)
Search Deals
One-way flight from Calgary to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 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 Calgary to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Calgary to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Calgary 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 21, 2026.
Use the filters below to find and compare flights from Calgary to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 10/27

7:45 am-9:45 pm

2 stops13h 00m

Chicago Midway

Sat 10/31

9:55 am-11:13 pm

2 stops14h 18m

$252

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 7/23

6:00 am-11:19 pm

1 stop16h 19m

Chicago O'Hare Intl

Sun 7/26

5:00 am-6:10 pm

1 stop14h 10m

$277

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/15

6:35 am-9:46 pm

2 stops14h 11m

Chicago Midway

Sat 9/19

10:35 am-11:06 pm

2 stops13h 31m

$292

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 7/29

7:45 am-6:57 pm

1 stop10h 12m

Chicago O'Hare Intl

Mon 8/3

12:29 pm-8:35 pm

1 stop9h 06m

$318
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 6/8

8:30 am-1:07 pm

Nonstop3h 37m

Chicago O'Hare Intl

Sat 6/13

7:45 pm-10:37 pm

Nonstop3h 52m

$319

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 6/3

6:45 am-4:51 pm

1 stop9h 06m

Chicago O'Hare Intl

Sat 6/6

12:30 pm-8:30 pm

1 stop9h 00m

$349

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 6/8

7:40 am-6:58 pm

1 stop10h 18m

Chicago O'Hare Intl

Sat 6/13

5:30 pm-8:25 pm

Nonstop3h 55m

$355

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 8/29

6:45 am-5:33 pm

1 stop9h 48m

Chicago O'Hare Intl

Sat 9/12

12:15 pm-11:06 pm

2 stops11h 51m

$364

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 6/5

7:45 am-6:50 pm

1 stop10h 05m

Chicago O'Hare Intl

Sun 6/7

2:09 pm-11:01 pm

1 stop9h 52m

$364

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 6/5

7:45 am-6:50 pm

1 stop10h 05m

Chicago O'Hare Intl

Mon 6/8

2:09 pm-11:01 pm

1 stop9h 52m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/20

Showing 1-10 of 33 resultsSorted by cheapest first
1
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3
4

Compare providers for flights from Calgary to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Calgary to Chicago in May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Calgary-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Calgary-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Calgary-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Calgary-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Calgary-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Calgary to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Calgary 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 Calgary to Chicago

What is the cheapest month to book a flight from Calgary to Chicago?

Currently, March is the cheapest month in which you can book a flight from Calgary to Chicago (average of $62). Flying from Calgary to Chicago in August is currently the most expensive (average of $127). 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 YYC to CHI?

Find hourly flight availability from Calgary 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 21, 2026.

When flying from Calgary to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How much does it cost to fly round-trip from Calgary to Chicago?

How far ahead should I book a flight from Calgary to Chicago?

To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 53 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

The best insider tips for Calgary to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Calgary to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Jenna Scatena

Jenna Scatena

Expert on YYC

Journalist and Travel Writer, Jenna Scatena is an award-winning travel writer with a love for sharing stories and exploring new places, especially by Vespa. Though she's from San Francisco, she has spent a significant chunk of her vacation days over the last decade eating her way through Texas and sleeping in hotels around the world—especially in California, the Middle East, and Europe.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 21, 2026.
Read reviews from past customers who have flown United Airlines,WestJet, andAmerican Airlines from Calgary to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,748 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,748 reviews
United Airlines
7.4
Good
9,748 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,341 reviews
United Airlines
7.4
Good
9,748 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,642 reviews
United Airlines
7.4
Good
9,748 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Calgary to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Calgary to Chicago?

    Most people fly from Calgary (YYC) if they book a flight from Calgary to Chicago. On average, Calgary has 5 outbound flights to Chicago per day from 5 airlines. Calgary is conveniently located just 5.8 mi from Calgary’s city center.

  • How long is the flight from Calgary to Chicago?

    There are many flights that can get you from Calgary to Chicago in 13h. Fly via Delta or United Airlines to get the fastest option. The distance between Calgary and Chicago is about 1396 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Calgary to Chicago round-trip?

    Our cheapest airline available from Calgary to Chicago is Air Canada. Our recent data shows that you can find tickets from as low as $134 on this airline. Additional options worth looking into are United Airlines and WestJet, starting at $135 and $137 round-trip. Air Canada is currently priced 51% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Calgary to Chicago one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $102. WestJet flights start at $106 while deals on United Airlines start at $123 one-way.

  • What are the most reliable airlines from Calgary to Chicago?

    Before booking your flight to Chicago from Calgary, check out the most reliable airlines to get you to your destination on time: Finnair (87%), British Airways (79%), Air Canada( 73%).

  • What are the cheapest flights from Calgary to Chicago?

    Looking for the cheapest flight from Calgary to Chicago? While on average our users pay $565, our data indicates the cheapest price to be $136. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $252.

  • Can I find deals for flights from Calgary to Chicago that include hotel bookings?

    Yes. In addition to deals on Calgary to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Chicago.

  • Can I find deals for business class flights from Calgary to Chicago?

    Yes. Cheapflights offers flight deals from Calgary 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 Calgary to Chicago?

    Currently, March is the cheapest month in which you can book a flight from Calgary to Chicago (average of $62). Flying from Calgary to Chicago in August is currently the most expensive (average of $127). 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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Alternative routes for Calgary to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Calgary to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Calgary to St. Louis flights

Top 5 airlines flying from Calgary to Chicago

Discover the top 5 airlines that operate flights from Calgary 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 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$134Average$335FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$135Average$460FlexibilityNo cancel feeOn-time69%
WestJetCheapest$137Average$274FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$208Average$391FlexibilityNo cancel feeOn-time71%
DeltaCheapest$241Average$371FlexibilityNo cancel feeOn-timeN/A

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