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$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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 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 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 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
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:15 pm
YYC
-
ORD
Nonstop3h 28m
WestJet
Sun 8/95:30 pm
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 1/28$239
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/277:00 am
YYC
-
ORD
1 stop9h 44m
Multiple Airlines
Fri 4/32:20 pm
ORD
-
YYC
Nonstop3h 55m
Multiple Airlines
Deal found 1/27$240

Find flight deals from Calgary to Illinois

Keep the following information in mind while searching for Calgary to Illinois 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

$216 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 Illinois
Search Deals
One-way flight from Calgary to Illinois
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 Calgary to Illinois.
Search Deals
Price to beat on a one-way flight from Calgary to Illinois.
Search Deals

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 January 29, 2026.
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 - 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

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

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 5/9

6:35 am-1:07 pm

1 stop5h 32m

Chicago Midway

Sat 5/16

9:20 am-11:06 pm

2 stops14h 46m

$273

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/15

7:15 am-6:01 pm

1 stop9h 46m

Chicago O'Hare Intl

Tue 5/19

1:55 pm-11:06 pm

1 stop10h 11m

$274

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 6/30

7:15 am-6:01 pm

1 stop9h 46m

Chicago O'Hare Intl

Sun 7/5

1:55 pm-11:06 pm

1 stop10h 11m

$303

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/9

6:35 am-4:48 pm

1 stop9h 13m

Chicago O'Hare Intl

Sat 5/16

10:35 am-8:05 pm

1 stop10h 30m

$308

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/15

7:15 am-6:01 pm

1 stop9h 46m

Chicago O'Hare Intl

Sun 5/17

10:35 am-8:05 pm

1 stop10h 30m

$308

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 5/9

6:35 am-1:07 pm

1 stop5h 32m

Chicago Midway

Sun 5/17

9:20 am-7:40 pm

2 stops11h 20m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 57 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 $102). Flying from Calgary to Illinois in July is currently the most expensive (average of $155). 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 January 29, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Calgary to Illinois as you normally would.

Weekly flight availability from Calgary to Illinois

Explore weekly flight availability from Calgary to Illinois. 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 YYC to USIL 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).

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 January 29, 2026.
Peruse reviews from past customers who have flown with United Airlines, American Airlines, and WestJet 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.
United Airlines
7.4
Good
9,215 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

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
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

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
7.2
Good
11,206 reviews
United Airlines
7.4
Good
9,215 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

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
3,253 reviews
United Airlines
7.4
Good
9,215 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

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.
Air Canada
7.1
Good
10,667 reviews
United Airlines
7.4
Good
9,215 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

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 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 12h 49m. The time it takes to get you to your destination can typically vary by up to 7h 55m. There are 1381 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 ($95), American Airlines ($102), and Air Canada ($105).

  • 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 WestJet (77%), Delta (76%) or Air Canada (65%) 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 $330, our data indicates the cheapest price to be $116. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $226.

  • 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 $102). Flying from Calgary to Illinois in July is currently the most expensive (average of $155). 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.

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$101Average$321FlexibilityNo cancel feeOn-time67%
WestJetCheapest$138Average$237FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$168Average$457FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$185Average$376FlexibilityNo cancel feeOn-time71%

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