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Illinois

$134+ 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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
May 28 — Jun 41
Thu 5/28
Thu 6/4
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 April 28, 2026.

This FlightHub deal was found by Cheapflights users on 4/27. 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.
Wed 5/2012:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 5/265:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 4/27$175
This Trip.com deal was found by Cheapflights users on 4/24. 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.
Thu 5/216:30 am
YYC
-
ORD
1 stop7h 25m
Multiple Airlines
Wed 5/275:30 pm
ORD
-
YYC
Nonstop3h 55m
Multiple Airlines
Deal found 4/24$195
This American Airlines deal was found by Cheapflights users on 4/26. 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.
Fri 5/296:15 am
YYC
-
ORD
Nonstop3h 30m
American Airlines
Sun 6/78:50 pm
ORD
-
YYC
Nonstop3h 52m
American Airlines
Deal found 4/26$201
This American Airlines deal was found by Cheapflights users on 4/23. 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 6/77:00 am
YYC
-
ORD
Nonstop3h 35m
American Airlines
Sun 6/148:50 pm
ORD
-
YYC
Nonstop3h 52m
American Airlines
Deal found 4/23$214
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 5/2212:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Fri 6/125:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 4/25$227
This Delta deal was found by Cheapflights users on 4/23. 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 5/96:45 am
YYC
-
ORD
1 stop9h 06m
Delta
Mon 5/1112:30 pm
ORD
-
YYC
1 stop9h 00m
Delta
Deal found 4/23$230
This Delta deal was found by Cheapflights users on 4/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:45 am
YYC
-
MDW
1 stop10h 11m
Delta
Sat 5/169:22 am
MDW
-
YYC
2 stops12h 08m
Delta
Deal found 4/26$231
This FlightHub deal was found by Cheapflights users on 4/24. 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 5/2212:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Fri 7/35:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 4/24$234
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 5/2712:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Fri 6/125:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 4/25$236
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 5/2912:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Fri 6/125:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 4/25$237
This Delta deal was found by Cheapflights users on 4/25. 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 5/236:45 am
YYC
-
ORD
2 stops12h 39m
Delta
Thu 6/42:11 pm
ORD
-
YYC
1 stop9h 46m
Delta
Deal found 4/25$239
This Air Canada deal was found by Cheapflights users on 4/27. 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.
Fri 9/186:30 am
YYC
-
ORD
1 stop7h 25m
Air Canada
Tue 9/222:15 pm
ORD
-
YYC
1 stop7h 45m
Air Canada
Deal found 4/27$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 April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$175
(FlightHub)

One-way from

$134
(Air Canada)

Popular in

March

Cheapest in

November

Average price

$252

Good round-trip deal

$320 or less

Good one-way deal

$197 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. 6% potential increase in price ($20 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 April 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 April 28, 2026.
Use the filters below to find and compare flights from Calgary to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 9/16

6:00 am-9:12 pm

1 stop14h 12m

Chicago O'Hare Intl

Mon 9/21

7:45 pm-10:36 pm

Nonstop3h 51m

$248

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 9/5

6:35 am-9:46 pm

2 stops14h 11m

Chicago Midway

Wed 9/9

6:00 am-11:06 pm

2 stops18h 06m

$248

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 10/24

7:45 am-4:50 pm

1 stop8h 05m

Chicago Midway

Tue 12/8

12:30 pm-8:54 pm

1 stop9h 24m

$255

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 5/24

12:30 am-10:16 am

1 stop8h 46m

Chicago O'Hare Intl

Thu 5/28

7:12 am-1:10 pm

1 stop6h 58m

$288

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 5/21

11:00 am-8:14 pm

1 stop8h 14m

Chicago O'Hare Intl

Thu 5/28

2:00 pm-8:05 pm

1 stop7h 05m

$289

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/15

11:00 am-8:14 pm

1 stop8h 14m

Chicago O'Hare Intl

Sun 5/17

2:00 pm-8:05 pm

1 stop7h 05m

$289

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 6/3

6:45 am-8:14 pm

2 stops12h 29m

Chicago O'Hare Intl

Wed 6/17

2:09 pm-11:01 pm

1 stop9h 52m

$290
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/23

1:27 pm-10:49 pm

1 stop8h 22m

Chicago O'Hare Intl

Sat 5/30

7:44 pm-10:37 pm

Nonstop3h 53m

$297

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/8

7:45 am-6:50 pm

1 stop10h 05m

Chicago O'Hare Intl

Sun 5/10

12:30 pm-8:30 pm

1 stop9h 00m

$311

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 5/12

6:45 am-5:56 pm

1 stop10h 11m

Chicago Midway

Tue 5/26

6:23 am-8:30 pm

2 stops15h 07m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 57 resultsSorted by cheapest first
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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

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

The price you pay for your flight from Calgary to Illinois may vary depending on when you book. For the best chance of a lower fare, look to book 53 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, March is the cheapest month in which you can book a flight from Calgary to Illinois (average of $62). Flying from Calgary to Illinois in February is currently the most expensive (average of $102). 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 April 28, 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 April 28, 2026.

The most flights from YYC to USIL are scheduled on a Monday (11 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

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

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 April 28, 2026.
Peruse reviews from past customers who have flown with United Airlines,WestJet, andAmerican 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.
United Airlines
7.4
Good
9,672 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

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
9,672 reviews
United Airlines
7.4
Good
9,672 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

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
3,327 reviews
United Airlines
7.4
Good
9,672 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

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
11,673 reviews
United Airlines
7.4
Good
9,672 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

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
10,974 reviews
United Airlines
7.4
Good
9,672 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

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 United Airlines, Delta, and American Airlines fly from Calgary to Illinois in about 14h 11m. The time it takes to get you to your destination can typically vary by up to 2h 05m. There are 1396 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), Air Canada ($101), and American Airlines ($102).

  • 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 Delta (77%), WestJet (77%) or Finnair (75%) 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 $678, our data indicates the cheapest price to be $152. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $205.

  • 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, March is the cheapest month in which you can book a flight from Calgary to Illinois (average of $62). Flying from Calgary to Illinois in February is currently the most expensive (average of $102). 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 April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$101Average$321FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$121Average$461FlexibilityNo cancel feeOn-time69%
WestJetCheapest$137Average$267FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$208Average$389FlexibilityNo cancel feeOn-time71%

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