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Cheap flights from Chicago to Calgary from C$ 92

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 30/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 191WestJet
Find Deal
Thu, 23 Oct - Mon, 27 Oct
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 193WestJet
Find Deal
Thu, 23 Oct - Mon, 27 Oct
United Airlines Logo
8:45 a.m. - 11:41 a.m.ORD-YYC
3h 56mdirect
United Airlines Logo
12:37 p.m. - 5:09 p.m.YYC-ORD
3h 32mdirect
C$ 221United Airlines
Find Deal
Wed, 18 Feb - Tue, 24 Feb
United Airlines Logo
8:47 a.m. - 9:53 p.m.ORD-YYC
14h 06m1 stop
United Airlines Logo
12:37 p.m. - 5:10 p.m.YYC-ORD
3h 33mdirect
C$ 235United Airlines
Find Deal
Wed, 5 Nov - Thu, 13 Nov
Multiple Airlines Logo
1:26 p.m. - 8:26 p.m.ORD-YYC
8h 00m1 stop
Multiple Airlines Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 257Multiple Airlines
Find Deal
Thu, 30 Oct - Sun, 2 Nov
American Airlines Logo
9:49 a.m. - 12:34 p.m.ORD-YYC
3h 45mdirect
American Airlines Logo
1:29 p.m. - 5:54 p.m.YYC-ORD
3h 25mdirect
C$ 263American Airlines
Find Deal
Tue, 21 Oct - Tue, 28 Oct
Multiple Airlines Logo
1:26 p.m. - 12:44 a.m.ORD-YYC
12h 18m2 stops
Multiple Airlines Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 267Multiple Airlines
Find Deal
Thu, 23 Oct - Mon, 27 Oct
American Airlines Logo
9:49 a.m. - 12:34 p.m.ORD-YYC
3h 45mdirect
American Airlines Logo
1:29 p.m. - 5:54 p.m.YYC-ORD
3h 25mdirect
C$ 270American Airlines
Find Deal
Wed, 15 Oct - Wed, 22 Oct
Air Canada Logo
3:50 p.m. - 11:22 p.m.ORD-YYC
8h 32m1 stop
Air Canada Logo
12:45 a.m. - 11:18 a.m.YYC-ORD
9h 33m1 stop
C$ 285Air Canada
Find Deal
Tue, 21 Oct - Mon, 27 Oct
Air Canada Logo
9:55 a.m. - 5:02 p.m.ORD-YYC
8h 07m1 stop
Air Canada Logo
1:10 a.m. - 9:51 a.m.YYC-ORD
7h 41m1 stop
C$ 293Air Canada
Find Deal
Sat, 18 Oct - Thu, 23 Oct

Delta flights from Chicago to Calgary

Our best Delta deals on Chicago to Calgary flight tickets
Delta
30 Sep
MDW1:43 p.m.Chicago Midway
7h 59m
1 stop
YYC8:42 p.m.Calgary
4 Oct
YYC6:40 a.m.Calgary
9h 55m
1 stop
MDW5:35 p.m.Chicago Midway
C$ 345
Find similar
Delta
30 Sep
ORD3:55 p.m.Chicago O'Hare Intl
5h 47m
1 stop
YYC8:42 p.m.Calgary
4 Oct
YYC6:40 a.m.Calgary
11h 25m
2 stops
ORD7:05 p.m.Chicago O'Hare Intl
C$ 359
Find similar
Delta
8 Nov
MDW9:20 a.m.Chicago Midway
5h 34m
1 stop
YYC1:54 p.m.Calgary
15 Nov
YYC6:20 a.m.Calgary
5h 47m
1 stop
MDW1:07 p.m.Chicago Midway
C$ 360
Find similar

WestJet flights from Chicago to Calgary

Our best WestJet deals on Chicago to Calgary flight tickets
WestJet
23 Oct
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
27 Oct
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
C$ 191
Find similar
WestJet
23 Oct
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
27 Oct
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
C$ 193
Find similar
WestJet
31 Oct
ORD2:20 p.m.Chicago O'Hare Intl
3h 55m
YYC5:15 p.m.Calgary
3 Nov
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
C$ 198
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 96,600 searches. Data last updated 17 September 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

Thu 23/10

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Mon 27/10

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

C$ 191

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 23/10

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Mon 27/10

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

C$ 193

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 18/2

8:45 a.m.-11:41 a.m.

Nonstop3h 56m

Calgary

Tue 24/2

12:37 p.m.-5:09 p.m.

Nonstop3h 32m

C$ 221

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 5/11

8:47 a.m.-9:53 p.m.

1 stop14h 06m

Calgary

Thu 13/11

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

C$ 235

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 30/10

1:26 p.m.-8:26 p.m.

1 stop8h 00m

Calgary

Sun 2/11

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

C$ 257

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 21/10

9:49 a.m.-12:34 p.m.

Nonstop3h 45m

Calgary

Tue 28/10

1:29 p.m.-5:54 p.m.

Nonstop3h 25m

C$ 263

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 23/10

1:26 p.m.-12:44 a.m.

2 stops12h 18m

Calgary

Mon 27/10

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

C$ 267

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 15/10

9:49 a.m.-12:34 p.m.

Nonstop3h 45m

Calgary

Wed 22/10

1:29 p.m.-5:54 p.m.

Nonstop3h 25m

C$ 270

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 21/10

3:50 p.m.-11:22 p.m.

1 stop8h 32m

Calgary

Mon 27/10

12:45 a.m.-11:18 a.m.

1 stop9h 33m

C$ 285

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 18/10

9:55 a.m.-5:02 p.m.

1 stop8h 07m

Calgary

Thu 23/10

1:10 a.m.-9:51 a.m.

1 stop7h 41m

C$ 293

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 cheapest month to fly to Calgary from Chicago is in May. Flight prices, which tend to average around C$ 303, are often lower during this time because this is during the off-season. 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 C$ 333.

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 Wednesday when prices can be found for as low as C$ 227. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 433.

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

Our data shows that the cheapest Chicago to Calgary flights are usually those with departure times in the evening. Our users have found flights to Calgary in the evening for as low as C$ 216. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 315 on average. Flights to Calgary from Chicago in the morning are generally more expensive because this time of day is more convenient for travellers’ 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 C$ 388 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 C$ 307 on momondo.

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

There are 3 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 September 2025, prices for Chicago to Calgary flights are approximately 42% 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

C$ 121

Fastest flight time

3h 45m

Direct flights

Every day

Airports in Calgary

1 airport
The best one-way flight to Calgary from Chicago in the past 72 hours is C$ 121. The best round-trip flight deal from Chicago to Calgary found on momondo in the last 72 hours is C$ 210.
The fastest flight from Chicago to Calgary takes 3h 45m
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?

    The distance between Chicago and Calgary is about 2249.2 km. By plane, this route typically takes 3h 45m.

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

    Prices for flights from Chicago to Calgary Airport are updated 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 for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Calgary Airport.

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

    The necessary travel and health documents for your Calgary Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • 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
United AirlinesPriceFrom C$ 141Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
WestJetPriceFrom C$ 210Free CancellationRating
7.2
3,095 reviews
Search WestJet flights

  • United Airlines Flights From Chicago to Calgary

    Across 14 United Airlines flights from Chicago to Calgary this week, the average price was C$ 267, with the best United Airlines deals starting from C$ 102 round-trip. 8,926 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • WestJet Flights From Chicago to Calgary

    WestJet is also a popular choice for this route. WestJet flight deals for Chicago to Calgary start from as low as C$ 153 round-trip, depending on your selected dates, with average WestJet deals seen on momondo around C$ 275. WestJet operates 4 flights to Calgary from Chicago in an average week. Users have rated it 7.2/10 across 3,095 reviews.

Travelling to a place near Calgary?

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

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Calgary from Chicago.

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

Yes. momondo allows you to filter the results for Chicago to Calgary flights to just show those with flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Calgary from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Chicago to Calgary flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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