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Cheap flights from Chicago to Calgary from $50

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 3/9. 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

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Find the cheapest flights from Chicago to Calgary

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
5:30 pm - 8:19 pm
ORD
-
YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:43 pm
YYC
-
ORD
3h 28mnonstop
$159WestJet
Sun, May 17 - Tue, Jun 2
WestJet Logo
5:30 pm - 8:19 pm
ORD
-
YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:43 pm
YYC
-
ORD
3h 28mnonstop
$160WestJet
Sun, May 17 - Sat, May 30
WestJet Logo
5:30 pm - 8:19 pm
ORD
-
YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:43 pm
YYC
-
ORD
3h 28mnonstop
$161WestJet
Fri, May 22 - Mon, Jun 1
WestJet Logo
5:30 pm - 8:19 pm
ORD
-
YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:43 pm
YYC
-
ORD
3h 28mnonstop
$162WestJet
Sat, May 23 - Sun, May 31
WestJet Logo
5:30 pm - 8:19 pm
ORD
-
YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:43 pm
YYC
-
ORD
3h 28mnonstop
$163WestJet
Sat, May 23 - Sat, May 30
United Airlines Logo
8:45 am - 11:35 am
ORD
-
YYC
3h 50mnonstop
United Airlines Logo
2:13 pm - 11:59 pm
YYC
-
ORD
8h 46m1 stop
$164United Airlines
Wed, Jan 21 - Wed, Jan 21
Multiple Airlines Logo
2:20 pm - 5:15 pm
ORD
-
YYC
3h 55mnonstop
Multiple Airlines Logo
5:35 am - 3:10 pm
YYC
-
ORD
8h 35m1 stop
$165Multiple Airlines
Mon, Jan 19 - Wed, Jan 28
Delta Logo
11:45 am - 8:54 pm
MDW
-
YYC
10h 09m1 stop
Delta Logo
6:30 am - 1:06 pm
YYC
-
MDW
5h 36m1 stop
$251Delta
Sat, Jan 31 - Tue, Feb 3
Delta Logo
11:45 am - 8:54 pm
MDW
-
YYC
10h 09m1 stop
Delta Logo
6:30 am - 4:14 pm
YYC
-
MDW
8h 44m1 stop
$252Delta
Sun, Feb 8 - Sat, Feb 14
Multiple Airlines Logo
1:20 pm - 4:15 pm
MDW
-
YYC
27h 55m2 stops
Multiple Airlines Logo
12:30 am - 11:45 am
YYC
-
MDW
10h 15m1 stop
$281Multiple Airlines
Wed, Jan 21 - Sat, Jan 24

Air Canada flights from Chicago to Calgary

Our best Air Canada deals on Chicago to Calgary flight tickets
Air Canada
Jan 19
ORD2:00 pmChicago O'Hare Intl
7h 59m
1 stop
YYC8:59 pmCalgary
Jan 23
YYC5:35 amCalgary
8h 35m
1 stop
ORD3:10 pmChicago O'Hare Intl
$174
Find similar
Air Canada
May 9
ORD2:15 pmChicago O'Hare Intl
9h 43m
1 stop
YYC10:58 pmCalgary
May 12
YYC6:30 amCalgary
7h 25m
1 stop
ORD2:55 pmChicago O'Hare Intl
$209
Find similar
Air Canada
Feb 4
ORD3:55 pmChicago O'Hare Intl
9h 19m
1 stop
YYC12:14 amCalgary
Feb 9
YYC11:40 pmCalgary
17h 08m
1 stop
ORD5:48 pmChicago O'Hare Intl
$222
Find similar

United Airlines flights from Chicago to Calgary

Our best United Airlines deals on Chicago to Calgary flight tickets
United Airlines
Feb 3
ORD5:40 amChicago O'Hare Intl
8h 28m
1 stop
YYC1:08 pmCalgary
Feb 12
YYC12:33 pmCalgary
3h 32m
ORD5:05 pmChicago O'Hare Intl
$180
Find similar
United Airlines
Apr 10
ORD8:46 amChicago O'Hare Intl
3h 51m
YYC11:37 amCalgary
Apr 16
YYC12:40 pmCalgary
3h 27m
ORD5:07 pmChicago O'Hare Intl
$186
Find similar
United Airlines
May 9
ORD12:45 pmChicago O'Hare Intl
9h 53m
1 stop
YYC9:38 pmCalgary
May 11
YYC12:30 pmCalgary
3h 20m
ORD4:50 pmChicago O'Hare Intl
$195
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Calgary 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, momondo users made 832,500 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Chicago to Calgary that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 5/17

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Tue 6/2

12:15 pm-4:43 pm

Nonstop3h 28m

$159

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 5/17

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Sat 5/30

12:15 pm-4:43 pm

Nonstop3h 28m

$160

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 5/22

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Mon 6/1

12:15 pm-4:43 pm

Nonstop3h 28m

$161

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 5/23

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Sun 5/31

12:15 pm-4:43 pm

Nonstop3h 28m

$162

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 5/23

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Sat 5/30

12:15 pm-4:43 pm

Nonstop3h 28m

$163

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 1/21

8:45 am-11:35 am

Nonstop3h 50m

Calgary

Wed 1/21

2:13 pm-11:59 pm

1 stop8h 46m

$164

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 1/19

2:20 pm-5:15 pm

Nonstop3h 55m

Calgary

Wed 1/28

5:35 am-3:10 pm

1 stop8h 35m

$165

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 1/31

11:45 am-8:54 pm

1 stop10h 09m

Calgary

Tue 2/3

6:30 am-1:06 pm

1 stop5h 36m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sun 2/8

11:45 am-8:54 pm

1 stop10h 09m

Calgary

Sat 2/14

6:30 am-4:14 pm

1 stop8h 44m

$252

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 1/21

1:20 pm-4:15 pm

2 stops27h 55m

Calgary

Sat 1/24

12:30 am-11:45 am

1 stop10h 15m

$281

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 May is, on average, the cheapest month to fly to Calgary from Chicago, with most prices found around $211. If you aren’t able to travel during the month of May, then book flights to Calgary from Chicago during October instead. Flights to Calgary in October, while not as cheap as those in May, still average around $213.

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 $290. 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 Wednesday will generally be more expensive and average around $322. 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 in the afternoon when flights can be purchased for as low as $263. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $452 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 weeks ahead of your departure date. In general, you can expect to find flights to Calgary for around $270 when searching 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 $227 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.

Can stopping save me money on Chicago to Calgary flights?

No. A direct flight is the cheapest option for a flight between Chicago to Calgary.

How have Chicago to Calgary flight prices changed over time?

As of December 2025, prices for Chicago to Calgary flights are approximately 17% 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

$95

Fastest flight time

3h 49m

Direct flights

Every day

Airports in Calgary

1 airport
The best one-way flight to Calgary from Chicago in the past 72 hours is $95. The best round-trip flight deal from Chicago to Calgary found on momondo in the last 72 hours is $213.
The fastest flight from Chicago to Calgary takes 3h 49m
Direct flights go from Chicago to Calgary every day.
There is 1 airport in Calgary. From Chicago there are direct flights to Calgary (YYC).
Search flight deals

  • 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 $86Free CancellationRating
7.1
10,534 reviews
Search Air Canada flights
United AirlinesPriceFrom $90Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights
DeltaPriceFrom $109Free CancellationRating
7.9
8,005 reviews
Search Delta flights
WestJetPriceFrom $142Free CancellationRating
7.2
3,204 reviews
Search WestJet flights
American AirlinesPriceFrom $195Free CancellationRating
7.2
11,055 reviews
Search American Airlines flights

  • United Airlines Flights From Chicago to Calgary

    Across 7 United Airlines flights from Chicago to Calgary this week, the average price was $317, with the best United Airlines deals starting from $90 round-trip. 9,093 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Chicago to Calgary

    American Airlines is also a popular choice for this route. American Airlines flight deals for Chicago to Calgary start from as low as $195 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $410. American Airlines operates 1 flight to Calgary from Chicago in an average week. Users have rated it 7.2/10 across 11,055 reviews.

Traveling to a place near Calgary?

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

An easier way to manage your Calgary trip

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