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Illinois

$100+ Cheap flights from Calgary (YYC) to Illinois

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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Calgary to Illinois

Keep the following information in mind while searching for Calgary to Illinois flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$174
(Kiwi.com)

One-way from

$100
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$323

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.
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Provider most trusted by Cheapflights users for Calgary-Chicago (CHI) flights.
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From Calgary to Illinois
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One-way flight from Calgary to Illinois
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($85 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Calgary to Illinois.
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Price to beat on a one-way flight from Calgary to Illinois.
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Find flight deals from Calgary to Illinois

Cheapest flights from Calgary to Illinois
Explore the most affordable flight options available from Calgary to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2812:37 pmYYC - ORD
Nonstop3h 33mUnited Airlines
Sat 11/18:45 amORD - YYC
Nonstop3h 50mUnited Airlines
Deal found 10/27$192
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/112:54 pmYYC - ORD
1 stop9h 48mAmerican Airlines
Mon 11/310:05 pmORD - YYC
1 stop14h 39mAmerican Airlines
Deal found 10/28$207
This Kissandfly.com deal was found by Cheapflights users on 10/29. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/112:37 pmYYC - ORD
Nonstop3h 33mLufthansa
Sun 11/98:45 amORD - YYC
Nonstop3h 50mLufthansa
Deal found 10/29$210
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:45 amYYC - ORD
1 stop7h 21mAmerican Airlines
Sat 11/12:55 pmORD - YYC
1 stop7h 59mAmerican Airlines
Deal found 10/27$217
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/281:29 pmYYC - ORD
Nonstop3h 25mAmerican Airlines
Thu 10/309:49 amORD - YYC
Nonstop3h 45mAmerican Airlines
Deal found 10/27$219
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:30 amYYC - MDW
1 stop9h 49mDelta
Wed 12/3111:48 amMDW - YYC
1 stop10h 18mDelta
Deal found 10/27$222
This Delta deal was found by Cheapflights users on 10/29. 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 12/117:35 amYYC - ORD
2 stops13h 05mDelta
Mon 12/156:00 amORD - YYC
1 stop8h 40mDelta
Deal found 10/29$222
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/291:29 pmYYC - ORD
Nonstop3h 25mAmerican Airlines
Wed 11/57:25 amORD - YYC
1 stop15h 22mAmerican Airlines
Deal found 10/27$225
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/281:29 pmYYC - ORD
Nonstop3h 25mAmerican Airlines
Wed 10/299:49 amORD - YYC
Nonstop3h 45mAmerican Airlines
Deal found 10/27$227
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:30 amYYC - MDW
1 stop9h 49mDelta
Tue 12/306:00 amMDW - YYC
2 stops16h 06mDelta
Deal found 10/27$257
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:45 amYYC - MDW
1 stop5h 23mDelta
Wed 10/291:08 pmMDW - YYC
2 stops10h 54mDelta
Deal found 10/27$267
This Delta deal was found by Cheapflights users on 10/28. 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 11/112:30 amYYC - MDW
1 stop9h 15mDelta
Sun 11/99:34 amMDW - YYC
2 stops12h 19mDelta
Deal found 10/28$300

Cheapflights Fare Finder

 
Customize your flight search to find flights from Calgary to Illinois 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 October 29, 2025.
Use the filters below to find and compare flights from Calgary to Illinois that are best for you.

Fly from

Calgary

Fly to

Illinois

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 12/24

6:30 am-5:19 pm

1 stop9h 49m

Chicago Midway

Tue 12/30

11:48 am-9:06 pm

1 stop10h 18m

$222

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 1/29

6:30 am-1:09 pm

1 stop5h 39m

Chicago Midway

Sat 2/28

10:35 am-11:15 pm

2 stops13h 40m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 12/11

7:35 am-6:45 pm

1 stop10h 10m

Chicago O'Hare Intl

Mon 12/15

8:50 am-1:40 pm

1 stop5h 50m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/29

6:30 am-6:49 pm

2 stops11h 19m

Chicago O'Hare Intl

Sat 2/28

9:30 am-11:15 pm

2 stops14h 45m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 11/21

7:45 am-6:45 pm

1 stop10h 00m

Chicago O'Hare Intl

Mon 11/24

1:38 pm-11:10 pm

1 stop10h 32m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 3/10

1:14 pm-5:45 pm

Nonstop3h 31m

Chicago O'Hare Intl

Tue 3/31

9:40 am-12:37 pm

Nonstop3h 57m

$223

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/29

6:30 am-5:56 pm

1 stop10h 26m

Chicago O'Hare Intl

Mon 3/2

1:55 pm-11:15 pm

1 stop10h 20m

$242

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 11/10

6:35 am-4:52 pm

1 stop9h 17m

Chicago O'Hare Intl

Fri 11/14

6:00 am-1:53 pm

1 stop8h 53m

$267

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 12/11

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Mon 12/15

3:55 pm-11:58 pm

1 stop9h 03m

$269

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 1/31

10:00 am-11:25 pm

2 stops12h 25m

Chicago Midway

Sat 2/28

6:00 am-7:09 pm

1 stop14h 09m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 44 results
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Best time to book a flight from Calgary to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois

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

Currently, April is the cheapest month in which you can book a flight from Calgary to Illinois (average of $108). Flying from Calgary to Illinois in July is currently the most expensive (average of $156). 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 IL?

Find hourly flight availability from Calgary to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

One of the essential ways to save on airfare from Calgary to Illinois is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 65% on airfare.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated October 29, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Calgary to Illinois to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,992 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Delta
7.9
Good
7,992 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
United Airlines
7.4
Good
8,999 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
WestJet
7.2
Good
3,148 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Air Canada
7.1
Good
10,372 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!

Related info for your journey

Find useful and relevant information for your journey from Calgary to Illinois. 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 Illinois?

    Calgary (YYC) is the airport you will fly out of if you book a flight from Calgary to Illinois. It is only a 5.8 mi journey to Calgary (YYC) from Calgary’s city center.

  • How long is the flight from Calgary to Illinois?

    Airlines like Delta and American Airlines fly from Calgary to Illinois in about 9h 14m. The time it takes to get you to your destination can typically vary by up to 35m. There are 1427 mi between Calgary and Illinois. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airlines for a one-way flight from Calgary to Illinois are WestJet ($104), United Airlines ($113), and American Airlines ($114).

  • What are the most popular routes from Calgary to Illinois?

    Most travelers choose Calgary - Chicago O'Hare Intl, Calgary - Chicago Midway or Calgary - Lambert-St Louis when deciding on the best route from Calgary to Illinois.

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

    Consider United Airlines (88%), Emirates (85%) or Air Canada (83%) when booking your flight. These represent the most reliable airlines when flying from Calgary to Illinois.

  • What are the cheapest flights from Calgary to Illinois?

    Looking for the cheapest flight from Calgary to Illinois? While on average our users pay $447, our data indicates the cheapest price to be $112. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $187.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Calgary to Illinois (average of $108). Flying from Calgary to Illinois in July is currently the most expensive (average of $156). 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

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Top 4 airlines flying from Calgary to Illinois

Discover the top 4 airlines that operate flights from Calgary to Illinois. 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$468FlexibilityNo cancel feeOn-time67%
WestJetCheapest$138Average$219FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$185Average$376FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$491FlexibilityNo cancel feeOn-time69%

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