Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Calgary from $59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Calgary departing on 1/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Chicago to Calgary

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Calgary that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Calgary.

Cheap last minute flights

Planning a quick getaway from Chicago to Calgary? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Calgary, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Calgary

Find recent round-trip train or bus tickets from Chicago to Calgary.

All round-trip flight deals to Calgary

The cheapest plane tickets to Calgary found on KAYAK recently.
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$135WestJet
Find Deal
Thu, Apr 17 - Mon, Apr 21
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$136WestJet
Find Deal
Thu, Mar 13 - Sun, Mar 16
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$140WestJet
Find Deal
Thu, Mar 20 - Sun, Mar 23
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$151WestJet
Find Deal
Sun, Mar 16 - Thu, Mar 20
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
12:05 am - 10:10 amYYC-ORD
9h 05m1 stop
$173Air Canada
Find Deal
Tue, Jan 28 - Sat, Feb 1
4:00 pm - 11:18 pmORD-YYC
8h 18m1 stop
12:50 am - 10:54 amYYC-ORD
9h 04m1 stop
$178Air Canada
Find Deal
Tue, Jan 7 - Mon, Jan 27
5:00 am - 6:16 pmORD-YYC
14h 16m1 stop
6:04 am - 10:51 pmYYC-ORD
15h 47m1 stop
$187United Airlines
Find Deal
Thu, Mar 6 - Sat, Mar 15
11:19 am - 8:53 pmMDW-YYC
10h 34m1 stop
6:35 am - 12:46 pmYYC-MDW
5h 11m1 stop
$249Delta
Find Deal
Sat, Jan 11 - Thu, Jan 30
11:50 am - 8:53 pmORD-YYC
10h 03m1 stop
6:35 am - 5:29 pmYYC-ORD
9h 54m1 stop
$249Delta
Find Deal
Thu, Jan 9 - Sun, Feb 2
5:00 am - 11:50 amORD-YYC
7h 50m1 stop
1:32 pm - 6:03 pmYYC-ORD
3h 31mnonstop
$397American Airlines
Find Deal
Wed, Feb 26 - Sat, Mar 1
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$59Air Canada
Find Deal
Mon, Jan 20
3:35 pm - 11:02 pmORD-YYC
8h 27m1 stop
$64Air Canada
Find Deal
Mon, Jan 20
7:00 am - 9:41 pmORD-YYC
15h 41m1 stop
$68United Airlines
Find Deal
Tue, Feb 18
1:40 pm - 11:15 pmORD-YYC
10h 35m1 stop
$99Delta
Find Deal
Thu, Feb 20
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
$104Delta
Find Deal
Sun, Mar 16
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$220WestJet
Find Deal
Sun, May 25
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$221WestJet
Find Deal
Sun, May 25
9:45 am - 12:42 pmORD-YYC
3h 57mnonstop
$225American Airlines
Find Deal
Tue, Mar 18
5:00 am - 6:17 pmORD-YYC
14h 17m1 stop
$296United Airlines
Find Deal
Sun, Mar 23
9:50 am - 12:50 pmORD-YYC
4h 00mnonstop
$303American Airlines
Find Deal
Wed, Feb 19
1:55 pm - 11:16 pmORD-YYC
10h 21m1 stop
7:00 am - 5:09 pmYYC-ORD
9h 09m1 stop
$491Delta
Find Deal
Mon, Dec 23 - Fri, Dec 27
7:20 pm - 11:59 amORD-YYC
17h 39m1 stop
12:45 pm - 8:25 amYYC-ORD
18h 40m1 stop
$521American Airlines
Find Deal
Mon, Dec 23 - Fri, Dec 27
10:00 am - 10:39 pmORD-YYC
13h 39m2 stops
4:35 pm - 5:40 amYYC-ORD
12h 05m1 stop
Tue, Dec 24 - Sun, Dec 29
8:34 pm - 10:55 pmORD-YYC
27h 21m1 stop
4:35 pm - 5:40 amYYC-ORD
12h 05m1 stop
Sun, Dec 22 - Sun, Dec 29
7:20 am - 5:15 pmORD-YYC
10h 55m1 stop
6:00 pm - 8:05 amYYC-ORD
13h 05m1 stop
$720Air Canada
Find Deal
Mon, Dec 23 - Sun, Dec 29
9:50 am - 5:08 pmORD-YYC
8h 18m1 stop
6:00 pm - 8:05 amYYC-ORD
13h 05m1 stop
$726Air Canada
Find Deal
Tue, Dec 24 - Sun, Dec 29
1:55 pm - 11:04 amORD-YYC
22h 09m2 stops
11:00 am - 9:39 pmYYC-ORD
9h 39m2 stops
$1,003WestJet
Find Deal
Mon, Dec 23 - Sat, Dec 28
1:55 pm - 9:04 amORD-YYC
20h 09m2 stops
11:00 am - 9:39 pmYYC-ORD
9h 39m2 stops
$1,079WestJet
Find Deal
Mon, Dec 23 - Sun, Dec 29
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
$1,124United Airlines
Find Deal
Mon, Dec 23 - Fri, Dec 27
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
6:19 am - 11:59 pmYYC-ORD
16h 40m1 stop
$1,133United Airlines
Find Deal
Mon, Dec 23 - Wed, Jan 1
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$135WestJet
Find Deal
Thu, Apr 17 - Mon, Apr 21
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$136WestJet
Find Deal
Thu, Mar 13 - Sun, Mar 16
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$253Delta
Find Deal
Sun, Mar 2 - Thu, Mar 6
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
$278Delta
Find Deal
Thu, May 29 - Sat, Jun 7
9:50 am - 12:50 pmORD-YYC
4h 00mnonstop
1:32 pm - 6:03 pmYYC-ORD
3h 31mnonstop
$401American Airlines
Find Deal
Tue, Feb 18 - Fri, Feb 21
9:45 am - 12:30 pmORD-YYC
3h 45mnonstop
1:20 pm - 5:45 pmYYC-ORD
3h 25mnonstop
$409American Airlines
Find Deal
Tue, Apr 1 - Tue, Apr 8
7:45 pm - 10:29 pmORD-YYC
3h 44mnonstop
8:30 am - 12:49 pmYYC-ORD
3h 19mnonstop
$436Air Canada
Find Deal
Mon, Jun 2 - Wed, Jun 4
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
$451United Airlines
Find Deal
Sat, Jan 18 - Fri, Jan 24
8:52 am - 11:41 amORD-YYC
3h 49mnonstop
12:43 pm - 5:10 pmYYC-ORD
3h 27mnonstop
$466United Airlines
Find Deal
Tue, Apr 8 - Fri, Apr 11
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
$597Air Canada
Find Deal
Mon, Jan 20 - Wed, Jan 29

United Airlines flights from Chicago to Calgary

Our best United Airlines deals on Chicago to Calgary flight tickets
United Airlines
Mar 6
ORD5:00 amChicago O'Hare Intl
14h 16m
1 stop
YYC6:16 pmCalgary
Mar 15
YYC6:04 amCalgary
15h 47m
1 stop
ORD10:51 pmChicago O'Hare Intl
United Airlines
Dec 23
ORD8:45 amChicago O'Hare Intl
3h 54m
YYC11:39 amCalgary
Dec 27
YYC12:41 pmCalgary
3h 34m
ORD5:15 pmChicago O'Hare Intl
United Airlines
Dec 23
ORD8:45 amChicago O'Hare Intl
3h 54m
YYC11:39 amCalgary
Jan 1
YYC6:19 amCalgary
16h 40m
1 stop
ORD11:59 pmChicago O'Hare Intl

American Airlines flights from Chicago to Calgary

Our best American Airlines deals on Chicago to Calgary flight tickets
American Airlines
Feb 26
ORD5:00 amChicago O'Hare Intl
7h 50m
1 stop
YYC11:50 amCalgary
Mar 1
YYC1:32 pmCalgary
3h 31m
ORD6:03 pmChicago O'Hare Intl
American Airlines
Dec 23
ORD7:20 pmChicago O'Hare Intl
17h 39m
1 stop
YYC11:59 amCalgary
Dec 27
YYC12:45 pmCalgary
18h 40m
1 stop
ORD8:25 amChicago O'Hare Intl
American Airlines
Dec 23
ORD7:20 pmChicago O'Hare Intl
17h 39m
1 stop
YYC11:59 amCalgary
Dec 28
YYC6:24 amCalgary
16h 55m
1 stop
ORD12:19 amChicago O'Hare Intl

See travel insights to Calgary from

How to get the cheapest flight ticket from Chicago to Calgary

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Calgary?

The month of September is, on average, the cheapest month to fly to Calgary from Chicago, with most prices found around $283. If you aren’t able to travel during the month of September, then book flights to Calgary from Chicago during April instead. Flights to Calgary in April, while not as cheap as those in September, still average around $301.

What is the cheapest day to depart on your flight to Calgary?

The cheapest day to depart on your flight to Calgary is on a Thursday when prices can be found for as low as $320. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago to Calgary on a Monday will generally be more expensive and average around $352. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Calgary?

The cheapest time of day to fly to Calgary is at noon when flights can be purchased for as low as $282. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are $395 on average. Flights to Calgary from Chicago in the evening are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to Calgary flight route?

Fly from Chicago O'Hare Intl to Calgary for the best Chicago - Calgary flight prices

How far in advance should I book a flight to Calgary?

Most flyers found that booking tickets 49 days in advance of their planned departure date is the best time to get cheap flights to Calgary. During this timeframe, flight prices are around $335. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $185.

What cabin class options are available on Chicago to Calgary flights?

There are 4 cabin classes available to choose from on Chicago to Calgary flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Calgary flights?

You could potentially save up to 20% on your flight if you consider stops on a Chicago to Calgary flight.

How have Chicago to Calgary flight prices changed over time?

As of December 2024, prices for Chicago to Calgary flights are approximately 27% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Calgary

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Calgary according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Calgary (CHI to YYC) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Calgary

Best Price Found

$59

Fastest flight time

3h 46m

Direct flights

Every day

Airports in Calgary

1 airport
The best one-way flight to Calgary from Chicago in the past 72 hours is $59. The best round-trip flight deal from Chicago to Calgary found on momondo in the last 72 hours is $135.
The fastest flight from Chicago to Calgary takes 3h 46m
Direct flights go from Chicago to Calgary every day.
There is 1 airport near Calgary: Calgary (YYC)

  • How far is Chicago to Calgary by plane?

    Chicago and Calgary are 1397.6 mi apart from one another. Flights usually cover this in 3h 49m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Calgary Airport?

    Prices for flights from Chicago to Calgary Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Calgary Airport?

  • How old do you have to be to fly from Chicago to Calgary Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Calgary Airport.

  • What documentation or ID do you need to fly to Calgary Airport?

    The travel and health documents required for your trip to Calgary Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Calgary Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to Calgary?

  • What is the most popular airline from Chicago to Calgary?


Best airlines flying from Chicago to Calgary

Compare and see reviews for airlines that fly from Chicago to Calgary with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $107Free CancellationRating
7.0
8,391 reviews
Search Air Canada flights
WestJetPriceFrom $123Free CancellationRating
7.2
2,819 reviews
Search WestJet flights
DeltaPriceFrom $154Free CancellationRating
8.0
8,600 reviews
Search Delta flights
American AirlinesPriceFrom $187Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $205Free CancellationRating
7.4
9,048 reviews
Search United Airlines flights
  • United Airlines Flights From Chicago to Calgary

    Across 6 United Airlines flights from Chicago to Calgary this week, the average price was $450, with the best United Airlines deals starting from $205 round-trip. 9,048 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • Air Canada Flights From Chicago to Calgary

    Air Canada is also a popular choice for this route. Air Canada flight deals for Chicago to Calgary start from as low as $107 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around $371. Air Canada operates 6 flights to Calgary from Chicago in an average week. Users have rated it 7.0/10 across 8,391 reviews.


Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Calgary?

Finding the right flight to Calgary from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Calgary quick and easy, saving you time and money.

Can I find flights from Chicago to Calgary with flexible booking policies on momondo?

Yes. All flights to Calgary from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Calgary?

momondo helps you find the best flight between Chicago and Calgary by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Calgary right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Calgary flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


An easier way to manage your Calgary trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 12/24
Tue 12/31
Email me momondo's favorite deals

Find better results for your trip to Canada