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Cheap flights from Chicago to Calgary from $64

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 4/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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 from Chicago to Calgary

The cheapest plane tickets from Chicago to Calgary found on KAYAK recently.
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$158WestJet
Find Deal
Mon, Mar 10 - Mon, Mar 24
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$161WestJet
Find Deal
Thu, Apr 10 - Thu, Apr 17
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$162WestJet
Find Deal
Thu, Feb 27 - Thu, Mar 6
7:10 am - 9:48 pmORD-YYC
15h 38m1 stop
8:30 am - 12:49 pmYYC-ORD
3h 19mnonstop
$204United Airlines
Find Deal
Sat, May 17 - Sat, May 24
8:47 am - 11:39 amORD-YYC
3h 52mnonstop
2:09 pm - 12:23 amYYC-ORD
9h 14m1 stop
$210United Airlines
Find Deal
Tue, Mar 11 - Wed, Mar 12
2:05 pm - 9:18 pmORD-YYC
8h 13m1 stop
8:30 am - 6:38 pmYYC-ORD
9h 08m1 stop
$235Air Canada
Find Deal
Sat, Feb 8 - Tue, Feb 11
2:40 pm - 11:03 pmORD-YYC
9h 23m1 stop
6:00 am - 2:54 pmYYC-ORD
7h 54m1 stop
$243Air Canada
Find Deal
Mon, Jul 14 - Sat, Jul 19
1:45 pm - 11:16 pmORD-YYC
10h 31m1 stop
6:30 am - 5:28 pmYYC-ORD
9h 58m1 stop
$249Delta
Find Deal
Wed, Mar 19 - Sat, Mar 22
1:26 pm - 8:53 pmMDW-YYC
8h 27m1 stop
6:35 am - 5:43 pmYYC-MDW
10h 08m1 stop
$250Delta
Find Deal
Mon, Feb 10 - Sun, Feb 16
5:00 am - 11:50 amORD-YYC
7h 50m1 stop
1:32 pm - 6:03 pmYYC-ORD
3h 31mnonstop
$339American Airlines
Find Deal
Tue, Feb 18 - Tue, Feb 25
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
$64WestJet
Find Deal
Sun, Apr 20
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$65WestJet
Find Deal
Wed, May 14
8:47 am - 11:39 amORD-YYC
3h 52mnonstop
$75United Airlines
Find Deal
Tue, Mar 11
1:05 pm - 9:41 pmORD-YYC
9h 36m1 stop
$85United Airlines
Find Deal
Tue, Mar 11
2:40 pm - 11:03 pmORD-YYC
9h 23m1 stop
$96Air Canada
Find Deal
Sun, Jul 20
1:45 pm - 11:15 pmORD-YYC
10h 30m1 stop
$100Delta
Find Deal
Wed, Feb 19
1:45 pm - 11:18 pmORD-YYC
10h 33m1 stop
$101Delta
Find Deal
Thu, Jan 30
6:39 pm - 1:18 amORD-YYC
7h 39m1 stop
$103Air Canada
Find Deal
Fri, Feb 28
8:20 pm - 11:20 pmORD-YYC
4h 00mnonstop
$204American Airlines
Find Deal
Sun, Jul 20
9:50 am - 12:32 pmORD-YYC
3h 42mnonstop
$223American Airlines
Find Deal
Thu, Apr 17
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
6:19 am - 7:31 pmYYC-ORD
12h 12m1 stop
$274United Airlines
Find Deal
Thu, Jan 23 - Thu, Jan 30
7:10 am - 2:21 pmORD-YYC
8h 11m1 stop
8:30 am - 6:38 pmYYC-ORD
9h 08m1 stop
Thu, Jan 23 - Thu, Jan 30
1:26 pm - 8:53 pmMDW-YYC
8h 27m1 stop
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
$284Delta
Find Deal
Thu, Jan 23 - Thu, Jan 30
4:15 pm - 8:53 pmORD-YYC
5h 38m1 stop
6:35 am - 5:29 pmYYC-ORD
9h 54m1 stop
$284Delta
Find Deal
Sun, Jan 26 - Fri, Jan 31
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
$294Delta
Find Deal
Thu, Jan 23 - Thu, Jan 30
2:05 pm - 9:18 pmORD-YYC
8h 13m1 stop
12:50 am - 10:10 amYYC-ORD
8h 20m1 stop
$309Air Canada
Find Deal
Sun, Jan 26 - Thu, Jan 30
2:05 pm - 9:18 pmORD-YYC
8h 13m1 stop
8:30 am - 6:38 pmYYC-ORD
9h 08m1 stop
$361Air Canada
Find Deal
Sat, Jan 25 - Sun, Jan 26
11:19 am - 8:53 pmMDW-YYC
10h 34m1 stop
9:45 pm - 10:12 amYYC-MDW
11h 27m2 stops
$983WestJet
Find Deal
Sat, Jan 25 - Mon, Jan 27
11:19 am - 8:53 pmMDW-YYC
10h 34m1 stop
12:30 am - 10:12 amYYC-MDW
8h 42m1 stop
$1,097WestJet
Find Deal
Sat, Jan 25 - Sat, Jan 25
1:05 pm - 11:30 pmMDW-YYC
11h 25m1 stop
4:20 pm - 12:10 pmYYC-MDW
18h 50m1 stop
$1,386Porter Airlines
Find Deal
Fri, Jan 24 - Sun, Jan 26
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$158WestJet
Find Deal
Mon, Mar 10 - Mon, Mar 24
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$161WestJet
Find Deal
Thu, Apr 10 - Thu, Apr 17
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$285Delta
Find Deal
Thu, Mar 6 - Mon, Mar 10
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
$306Delta
Find Deal
Fri, May 16 - Sat, May 24
8:47 am - 11:39 amORD-YYC
3h 52mnonstop
12:41 pm - 5:10 pmYYC-ORD
3h 29mnonstop
$314United Airlines
Find Deal
Tue, Mar 11 - Wed, Mar 12
7:45 pm - 10:29 pmORD-YYC
3h 44mnonstop
8:30 am - 12:49 pmYYC-ORD
3h 19mnonstop
$376United Airlines
Find Deal
Fri, Jun 13 - Thu, Jun 19
9:50 am - 12:32 pmORD-YYC
3h 42mnonstop
1:20 pm - 5:45 pmYYC-ORD
3h 25mnonstop
$418American Airlines
Find Deal
Thu, May 1 - Tue, May 6
9:45 am - 12:42 pmORD-YYC
3h 57mnonstop
1:17 pm - 5:49 pmYYC-ORD
3h 32mnonstop
$420American Airlines
Find Deal
Tue, Apr 1 - Tue, Apr 8
8:52 am - 11:41 amORD-YYC
3h 49mnonstop
12:43 pm - 5:10 pmYYC-ORD
3h 27mnonstop
$593Air Canada
Find Deal
Wed, Apr 16 - Sat, Apr 19
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
$640Air Canada
Find Deal
Sat, Feb 8 - Tue, Feb 11

WestJet flights from Chicago to Calgary

Our best WestJet deals on Chicago to Calgary flight tickets
WestJet
Mar 10
ORD4:45 pmChicago O'Hare Intl
3h 51m
YYC7:36 pmCalgary
Mar 24
YYC11:30 amCalgary
3h 26m
ORD3:56 pmChicago O'Hare Intl
WestJet
Apr 10
ORD4:45 pmChicago O'Hare Intl
3h 51m
YYC7:36 pmCalgary
Apr 17
YYC11:30 amCalgary
3h 26m
ORD3:56 pmChicago O'Hare Intl
WestJet
Feb 27
ORD4:45 pmChicago O'Hare Intl
3h 51m
YYC7:36 pmCalgary
Mar 6
YYC11:30 amCalgary
3h 26m
ORD3:56 pmChicago O'Hare Intl

United Airlines flights from Chicago to Calgary

Our best United Airlines deals on Chicago to Calgary flight tickets
United Airlines
May 17
ORD7:10 amChicago O'Hare Intl
15h 38m
1 stop
YYC9:48 pmCalgary
May 24
YYC8:30 amCalgary
3h 19m
ORD12:49 pmChicago O'Hare Intl
United Airlines
Mar 11
ORD8:47 amChicago O'Hare Intl
3h 52m
YYC11:39 amCalgary
Mar 12
YYC2:09 pmCalgary
9h 14m
1 stop
ORD12:23 amChicago O'Hare Intl
United Airlines
Mar 11
ORD10:50 amChicago O'Hare Intl
11h 51m
1 stop
YYC9:41 pmCalgary
Mar 12
YYC6:14 amCalgary
12h 41m
1 stop
ORD7:55 pmChicago 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 typical price of a round-trip flight between Chicago and Calgary?

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 $285. If you aren’t able to travel during the month of September, then book flights to Calgary from Chicago during March instead. Flights to Calgary in March, while not as cheap as those in September, still average around $292.

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 $346. 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 $376. 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 morning when prices are $503 on average. Flights to Calgary from Chicago in the morning 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?

You are more likely to see cheaper flights to Calgary from Chicago when booking 18 weeks ahead of your departure date. In general, you can expect to find flights to Calgary for around $334 when searching 18 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Calgary from Chicago for as low as $290 on momondo.

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.

How have Chicago to Calgary flight prices changed over time?

As of January 2025, prices for Chicago to Calgary flights are approximately 19% cheaper 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

$64

Fastest flight time

3h 42m

Direct flights

Every day

Airports in Calgary

1 airport
The best one-way flight to Calgary from Chicago in the past 72 hours is $64. The best round-trip flight deal from Chicago to Calgary found on momondo in the last 72 hours is $158.
The fastest flight from Chicago to Calgary takes 3h 42m
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 $114Free CancellationRating
7.0
8,635 reviews
Search Air Canada flights
WestJetPriceFrom $125Free CancellationRating
7.2
2,829 reviews
Search WestJet flights
DeltaPriceFrom $155Free CancellationRating
8.0
8,521 reviews
Search Delta flights
American AirlinesPriceFrom $187Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $210Free CancellationRating
7.4
8,985 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 $464, with the best United Airlines deals starting from $210 round-trip. 8,985 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 $114 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around $370. Air Canada operates 6 flights to Calgary from Chicago in an average week. Users have rated it 7.0/10 across 8,635 reviews.


Traveling to a place near Calgary?

Book flights to Calgary if you plan to visit one of these locations
Banff
Lake Louise
Canmore
Radium Hot Springs
Drumheller
Airdrie
Kananaskis

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.


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