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Cheap flights from Chicago to Calgary from $65

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 1/5. 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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WestJet Logo
2:20 pm - 5:15 pmORD-YYC
3h 55mnonstop
WestJet Logo
9:00 am - 1:35 pmYYC-ORD
3h 35mnonstop
$173WestJet
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Fri, Jan 16 - Mon, Jan 19
WestJet Logo
2:20 pm - 5:15 pmORD-YYC
3h 55mnonstop
WestJet Logo
9:00 am - 1:35 pmYYC-ORD
3h 35mnonstop
$174WestJet
Find Deal
Fri, Jan 16 - Mon, Jan 19
Air Canada Logo
10:00 am - 6:54 pmORD-YYC
9h 54m1 stop
Air Canada Logo
5:35 am - 3:10 pmYYC-ORD
8h 35m1 stop
$198Air Canada
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Fri, Nov 28 - Thu, Dec 4
United Airlines Logo
8:45 am - 11:35 amORD-YYC
3h 50mnonstop
United Airlines Logo
12:37 pm - 5:10 pmYYC-ORD
3h 33mnonstop
$215United Airlines
Find Deal
Fri, Nov 28 - Thu, Dec 4
United Airlines Logo
12:53 pm - 9:53 pmORD-YYC
10h 00m1 stop
United Airlines Logo
12:37 pm - 5:08 pmYYC-ORD
3h 31mnonstop
$217United Airlines
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Sat, Jan 10 - Sat, Jan 17
Air Canada Logo
2:00 pm - 8:39 pmORD-YYC
7h 39m1 stop
Air Canada Logo
5:35 am - 2:55 pmYYC-ORD
8h 20m1 stop
$232Air Canada
Find Deal
Wed, Nov 26 - Sat, Dec 6
American Airlines Logo
5:18 am - 11:44 amORD-YYC
7h 26m1 stop
American Airlines Logo
6:30 am - 11:26 pmYYC-ORD
15h 56m1 stop
$240American Airlines
Find Deal
Wed, Dec 3 - Sun, Dec 7
Delta Logo
1:50 pm - 8:57 pmMDW-YYC
8h 07m1 stop
Delta Logo
6:35 am - 1:10 pmYYC-MDW
5h 35m1 stop
$251Delta
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Wed, Dec 10 - Sat, Dec 13
Delta Logo
1:35 pm - 11:13 pmORD-YYC
10h 38m1 stop
Delta Logo
2:45 pm - 9:40 pmYYC-ORD
5h 55m1 stop
$251Delta
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Thu, Dec 4 - Mon, Dec 8
American Airlines Logo
5:18 am - 11:44 amORD-YYC
7h 26m1 stop
American Airlines Logo
6:30 am - 11:26 pmYYC-ORD
15h 56m1 stop
$254American Airlines
Find Deal
Wed, Dec 3 - Thu, Dec 4

American Airlines flights from Chicago to Calgary

Our best American Airlines deals on Chicago to Calgary flight tickets
American Airlines
Dec 3
ORD5:18 amChicago O'Hare Intl
7h 26m
1 stop
YYC11:44 amCalgary
Dec 7
YYC6:30 amCalgary
15h 56m
1 stop
ORD11:26 pmChicago O'Hare Intl
$240
Find similar
American Airlines
Dec 3
ORD5:18 amChicago O'Hare Intl
7h 26m
1 stop
YYC11:44 amCalgary
Dec 4
YYC6:30 amCalgary
15h 56m
1 stop
ORD11:26 pmChicago O'Hare Intl
$254
Find similar
American Airlines
Nov 12
ORD5:18 amChicago O'Hare Intl
7h 26m
1 stop
YYC11:44 amCalgary
Nov 14
YYC12:45 pmCalgary
7h 36m
1 stop
ORD9:21 pmChicago O'Hare Intl
$346
Find similar

WestJet flights from Chicago to Calgary

Our best WestJet deals on Chicago to Calgary flight tickets
WestJet
Jan 16
ORD2:20 pmChicago O'Hare Intl
3h 55m
YYC5:15 pmCalgary
Jan 19
YYC9:00 amCalgary
3h 35m
ORD1:35 pmChicago O'Hare Intl
$173
Find similar
WestJet
Jan 16
ORD2:20 pmChicago O'Hare Intl
3h 55m
YYC5:15 pmCalgary
Jan 19
YYC9:00 amCalgary
3h 35m
ORD1:35 pmChicago O'Hare Intl
$174
Find similar
WestJet
Dec 15
ORD2:20 pmChicago O'Hare Intl
3h 55m
YYC5:15 pmCalgary
Dec 26
YYC9:00 amCalgary
3h 35m
ORD1:35 pmChicago O'Hare Intl
$182
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 November 6, 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

Fri 1/16

2:20 pm-5:15 pm

Nonstop3h 55m

Calgary

Mon 1/19

9:00 am-1:35 pm

Nonstop3h 35m

$173

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 1/16

2:20 pm-5:15 pm

Nonstop3h 55m

Calgary

Mon 1/19

9:00 am-1:35 pm

Nonstop3h 35m

$174

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 11/28

10:00 am-6:54 pm

1 stop9h 54m

Calgary

Thu 12/4

5:35 am-3:10 pm

1 stop8h 35m

$198

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 11/28

8:45 am-11:35 am

Nonstop3h 50m

Calgary

Thu 12/4

12:37 pm-5:10 pm

Nonstop3h 33m

$215

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 1/10

12:53 pm-9:53 pm

1 stop10h 00m

Calgary

Sat 1/17

12:37 pm-5:08 pm

Nonstop3h 31m

$217

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 11/26

2:00 pm-8:39 pm

1 stop7h 39m

Calgary

Sat 12/6

5:35 am-2:55 pm

1 stop8h 20m

$232

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 12/3

5:18 am-11:44 am

1 stop7h 26m

Calgary

Sun 12/7

6:30 am-11:26 pm

1 stop15h 56m

$240

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 12/10

1:50 pm-8:57 pm

1 stop8h 07m

Calgary

Sat 12/13

6:35 am-1:10 pm

1 stop5h 35m

$251

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 12/4

1:35 pm-11:13 pm

1 stop10h 38m

Calgary

Mon 12/8

2:45 pm-9:40 pm

1 stop5h 55m

$251

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 12/3

5:18 am-11:44 am

1 stop7h 26m

Calgary

Thu 12/4

6:30 am-11:26 pm

1 stop15h 56m

$254

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 typical price of a round-trip flight between Chicago and Calgary?

What is the cheapest month to fly to Calgary?

The month of October is, on average, the cheapest month to fly to Calgary from Chicago, with most prices found around $213. If you aren’t able to travel during the month of October, then book flights to Calgary from Chicago during May instead. Flights to Calgary in May, while not as cheap as those in October, still average around $219.

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 $291. 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 Tuesday will generally be more expensive and average around $327. 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 $480 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 $284 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 $223 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 November 2025, prices for Chicago to Calgary flights are approximately 44% 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

$85

Fastest flight time

3h 50m

Direct flights

Every day

Airports in Calgary

1 airport
The best one-way flight to Calgary from Chicago in the past 72 hours is $85. The best round-trip flight deal from Chicago to Calgary found on momondo in the last 72 hours is $240.
The fastest flight from Chicago to Calgary takes 3h 50m
Direct flights go from Chicago to Calgary every day.
There is 1 airport near Calgary: 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 50m, 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 $91Free CancellationRating
7.1
10,416 reviews
Search Air Canada flights
United AirlinesPriceFrom $91Free CancellationRating
7.4
9,007 reviews
Search United Airlines flights
DeltaPriceFrom $109Free CancellationRating
7.9
8,001 reviews
Search Delta flights
WestJetPriceFrom $142Free CancellationRating
7.2
3,155 reviews
Search WestJet flights
American AirlinesPriceFrom $198Free CancellationRating
7.2
11,040 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 $338, with the best United Airlines deals starting from $91 round-trip. 9,007 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 $91 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around $237. Air Canada operates 7 flights to Calgary from Chicago in an average week. Users have rated it 7.1/10 across 10,416 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.

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