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Cheap flights from Calgary to Chicago from C$ 148

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Calgary to Chicago departing on 7/4. 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 Calgary to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Calgary to Chicago 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 Calgary to Chicago.

Cheap last-minute flights

Planning a quick getaway from Calgary to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Calgary to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 235WestJet
Find Deal
Thu, 20 Feb - Mon, 24 Feb
12:05 a.m. - 9:55 a.m.YYC-ORD
8h 50m1 stop
9:03 a.m. - 4:52 p.m.ORD-YYC
8h 49m1 stop
C$ 274Air Canada
Find Deal
Mon, 31 Mar - Tue, 8 Apr
6:15 a.m. - 4:35 p.m.YYC-ORD
9h 20m1 stop
6:39 p.m. - 1:18 a.m.ORD-YYC
7h 39m1 stop
C$ 283Air Canada
Find Deal
Mon, 3 Mar - Mon, 3 Mar
7:00 a.m. - 2:39 p.m.YYC-ORD
6h 39m1 stop
12:35 p.m. - 11:16 p.m.ORD-YYC
11h 41m2 stops
C$ 307Delta
Find Deal
Sat, 7 Dec - Tue, 10 Dec
7:00 a.m. - 10:06 p.m.YYC-MDW
14h 06m2 stops
9:30 a.m. - 8:38 p.m.MDW-YYC
12h 08m2 stops
C$ 308Delta
Find Deal
Sat, 7 Dec - Tue, 10 Dec
8:30 a.m. - 12:49 p.m.YYC-ORD
3h 19mdirect
12:45 p.m. - 9:38 p.m.ORD-YYC
9h 53m1 stop
C$ 385United Airlines
Find Deal
Tue, 1 Apr - Tue, 8 Apr
12:30 p.m. - 4:50 p.m.YYC-ORD
3h 20mdirect
9:00 a.m. - 11:54 a.m.ORD-YYC
3h 54mdirect
C$ 490United Airlines
Find Deal
Tue, 1 Apr - Tue, 8 Apr
1:20 p.m. - 5:45 p.m.YYC-ORD
3h 25mdirect
9:45 a.m. - 12:30 p.m.ORD-YYC
3h 45mdirect
C$ 531American Airlines
Find Deal
Wed, 30 Apr - Mon, 5 May
12:30 a.m. - 10:02 a.m.YYC-ORD
8h 32m1 stop
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 589WestJet
Find Deal
Tue, 29 Apr - Mon, 5 May
1:20 p.m. - 5:45 p.m.YYC-ORD
3h 25mdirect
9:45 a.m. - 12:30 p.m.ORD-YYC
3h 45mdirect
C$ 703American Airlines
Find Deal
Sat, 5 Apr - Thu, 24 Apr
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 148WestJet
Find Deal
Mon, 7 Apr
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 151WestJet
Find Deal
Mon, 3 Mar
8:30 a.m. - 6:36 p.m.YYC-ORD
9h 06m1 stop
C$ 164Air Canada
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Sat, 7 Dec
8:30 a.m. - 6:38 p.m.YYC-ORD
9h 08m1 stop
C$ 165Air Canada
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Sat, 18 Jan
6:19 a.m. - 11:59 p.m.YYC-ORD
16h 40m1 stop
C$ 179United Airlines
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Tue, 21 Jan
1:32 p.m. - 6:03 p.m.YYC-ORD
3h 31mdirect
C$ 186American Airlines
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Wed, 19 Feb
7:00 a.m. - 9:12 p.m.YYC-ORD
13h 12m2 stops
C$ 190Delta
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Sat, 7 Dec
7:00 a.m. - 6:32 p.m.YYC-MDW
10h 32m1 stop
C$ 190Delta
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Sat, 7 Dec
12:41 p.m. - 5:08 p.m.YYC-ORD
3h 27mdirect
C$ 354United Airlines
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Fri, 14 Feb
1:20 p.m. - 5:45 p.m.YYC-ORD
3h 25mdirect
C$ 356American Airlines
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Fri, 14 Mar
12:50 a.m. - 10:05 a.m.YYC-ORD
8h 15m1 stop
2:05 p.m. - 9:18 p.m.ORD-YYC
8h 13m1 stop
C$ 315Air Canada
Find Deal
Mon, 25 Nov - Sat, 30 Nov
8:30 a.m. - 6:36 p.m.YYC-ORD
9h 06m1 stop
2:05 p.m. - 9:18 p.m.ORD-YYC
8h 13m1 stop
C$ 330Air Canada
Find Deal
Sat, 23 Nov - Sat, 30 Nov
12:50 a.m. - 8:57 a.m.YYC-ORD
7h 07m1 stop
12:52 p.m. - 9:18 p.m.ORD-YYC
9h 26m1 stop
C$ 339Air Canada
Find Deal
Fri, 22 Nov - Sat, 30 Nov
12:30 p.m. - 11:59 p.m.YYC-ORD
10h 29m2 stops
6:17 a.m. - 1:50 p.m.ORD-YYC
8h 33m1 stop
C$ 357Delta
Find Deal
Sat, 23 Nov - Sat, 30 Nov
12:41 p.m. - 5:09 p.m.YYC-ORD
3h 28mdirect
8:45 a.m. - 11:39 a.m.ORD-YYC
3h 54mdirect
C$ 438United Airlines
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Thu, 21 Nov - Fri, 29 Nov
2:09 p.m. - 11:57 p.m.YYC-ORD
8h 48m1 stop
8:45 a.m. - 11:39 a.m.ORD-YYC
3h 54mdirect
C$ 445United Airlines
Find Deal
Thu, 21 Nov - Fri, 29 Nov
8:00 a.m. - 5:58 p.m.YYC-ORD
8h 58m1 stop
6:17 a.m. - 1:50 p.m.ORD-YYC
8h 33m1 stop
C$ 482Delta
Find Deal
Thu, 21 Nov - Fri, 29 Nov
6:29 a.m. - 2:52 p.m.YYC-ORD
7h 23m1 stop
5:00 a.m. - 11:45 a.m.ORD-YYC
7h 45m1 stop
C$ 858American Airlines
Find Deal
Thu, 21 Nov - Sun, 24 Nov
3:00 p.m. - 1:37 p.m.YYC-MDW
21h 37m1 stop
9:30 a.m. - 8:35 p.m.MDW-YYC
12h 05m1 stop
C$ 1,224WestJet
Find Deal
Sat, 23 Nov - Sat, 30 Nov
8:00 a.m. - 9:58 p.m.YYC-ORD
12h 58m1 stop
6:17 a.m. - 9:06 p.m.ORD-YYC
15h 49m2 stops
C$ 1,485WestJet
Find Deal
Thu, 21 Nov - Sun, 24 Nov
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 235WestJet
Find Deal
Thu, 20 Feb - Mon, 24 Feb
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
7:45 p.m. - 10:29 p.m.ORD-YYC
3h 44mdirect
C$ 311
Find Deal
Thu, 10 Apr - Tue, 15 Apr
12:30 p.m. - 4:50 p.m.YYC-ORD
3h 20mdirect
9:00 a.m. - 11:54 a.m.ORD-YYC
3h 54mdirect
C$ 490United Airlines
Find Deal
Tue, 1 Apr - Tue, 8 Apr
1:20 p.m. - 5:45 p.m.YYC-ORD
3h 25mdirect
9:45 a.m. - 12:30 p.m.ORD-YYC
3h 45mdirect
C$ 531American Airlines
Find Deal
Wed, 30 Apr - Mon, 5 May
12:41 p.m. - 5:10 p.m.YYC-ORD
3h 29mdirect
8:47 a.m. - 11:41 a.m.ORD-YYC
3h 54mdirect
C$ 631Air Canada
Find Deal
Fri, 7 Mar - Tue, 11 Mar
1:32 p.m. - 6:03 p.m.YYC-ORD
3h 31mdirect
9:45 a.m. - 12:30 p.m.ORD-YYC
3h 45mdirect
C$ 655American Airlines
Find Deal
Sat, 1 Mar - Fri, 7 Mar
12:41 p.m. - 5:09 p.m.YYC-ORD
3h 28mdirect
8:45 a.m. - 11:39 a.m.ORD-YYC
3h 54mdirect
C$ 686United Airlines
Find Deal
Thu, 5 Dec - Sat, 7 Dec
12:41 p.m. - 5:09 p.m.YYC-ORD
3h 28mdirect
8:45 a.m. - 11:39 a.m.ORD-YYC
3h 54mdirect
C$ 697Air Canada
Find Deal
Sat, 7 Dec - Tue, 10 Dec
1:20 p.m. - 5:45 p.m.YYC-ORD
3h 25mdirect
9:45 a.m. - 12:30 p.m.ORD-YYC
3h 45mdirect
C$ 703American Airlines
Find Deal
Sat, 5 Apr - Thu, 24 Apr
12:41 p.m. - 5:10 p.m.YYC-ORD
3h 29mdirect
8:47 a.m. - 11:41 a.m.ORD-YYC
3h 54mdirect
C$ 752Air Canada
Find Deal
Fri, 7 Mar - Tue, 11 Mar

Air Canada flights from Calgary to Chicago

Our best Air Canada deals on Calgary to Chicago flight tickets
Air Canada
31 Mar
YYC12:05 a.m.Calgary
8h 50m
1 stop
ORD9:55 a.m.Chicago O'Hare Intl
8 Apr
ORD9:03 a.m.Chicago O'Hare Intl
8h 49m
1 stop
YYC4:52 p.m.Calgary
Air Canada
3 Mar
YYC6:15 a.m.Calgary
9h 20m
1 stop
ORD4:35 p.m.Chicago O'Hare Intl
3 Mar
ORD6:39 p.m.Chicago O'Hare Intl
7h 39m
1 stop
YYC1:18 a.m.Calgary
Air Canada
10 Apr
YYC8:30 a.m.Calgary
3h 19m
ORD12:49 p.m.Chicago O'Hare Intl
15 Apr
ORD9:03 a.m.Chicago O'Hare Intl
8h 49m
1 stop
YYC4:52 p.m.Calgary

Delta flights from Calgary to Chicago

Our best Delta deals on Calgary to Chicago flight tickets
Delta
7 Dec
YYC7:00 a.m.Calgary
6h 39m
1 stop
ORD2:39 p.m.Chicago O'Hare Intl
10 Dec
ORD12:35 p.m.Chicago O'Hare Intl
11h 41m
2 stops
YYC11:16 p.m.Calgary
Delta
7 Dec
YYC7:00 a.m.Calgary
14h 06m
2 stops
MDW10:06 p.m.Chicago Midway
10 Dec
MDW9:30 a.m.Chicago Midway
12h 08m
2 stops
YYC8:38 p.m.Calgary
Delta
7 Dec
YYC7:00 a.m.Calgary
8h 58m
1 stop
ORD4:58 p.m.Chicago O'Hare Intl
10 Dec
ORD12:35 p.m.Chicago O'Hare Intl
11h 41m
2 stops
YYC11:16 p.m.Calgary

See travel insights to Chicago from

How to get the cheapest flight ticket from Calgary to Chicago

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 from Calgary to Chicago?

September. The cheapest time of year to fly to Chicago from Calgary is September. The most expensive is December.

What is the cheapest day to depart Calgary for Chicago?

Friday. The cheapest day of the week is typically Friday. The most expensive is typically Monday

When is the cheapest time to fly from Calgary to Chicago?

In the afternoon. Calgary to Chicago flights are approximately 30% more expensive in the morning than in the afternoon

What is the cheapest Calgary to Chicago flight route?

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

How far in advance should you book Calgary to Chicago flights?

48 days before. The cheapest time to buy a flight from Calgary to Chicago is approximately 48 days to departure

Can stopping save me money on Calgary to Chicago flights?

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

How have Calgary to Chicago flight prices changed over time?

As of November 2024, prices for Calgary to Chicago flights are approximately 2% more expensive when compared to flights at the same time last year.

When to book flights from Calgary to Chicago

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

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

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

Best price found

C$ 148

Fastest flight time

3h 19m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Calgary in the past 72 hours is C$ 148. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is C$ 235.
The fastest flight from Calgary to Chicago takes 3h 19m
Direct flights go from Calgary to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Calgary to Chicago by plane?

    Chicago is 2249.2 km away from Calgary. Flights usually cover this in 3h 19m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Calgary Airport to Chicago are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Calgary Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

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


Best airlines flying from Calgary to Chicago

Compare and see reviews for airlines that fly from Calgary to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom C$ 198Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom C$ 234Free CancellationRating
7.3
2,811 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 284Free CancellationRating
7.0
8,237 reviews
Search Air Canada flights
DeltaPriceFrom C$ 310Free CancellationRating
8.0
8,756 reviews
Search Delta flights
United AirlinesPriceFrom C$ 322Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
WestJet EncorePriceFrom C$ 564Free CancellationRating
8.6
10 reviews
Search WestJet Encore flights
  • United Airlines Flights From Calgary to Chicago

    United Airlines operates around 7 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 431, but momondo users have found United Airlines deals from Calgary to Chicago from as low as C$ 230 round-trip. United Airlines has been scored 7.4/10 in 9,171 reviews.

  • Air Canada Flights From Calgary to Chicago

    The best Air Canada deal for Calgary to Chicago flight tickets found on momondo in the last 72 hours was C$ 203, round-trip. It should be noted that an average Air Canada flight deal for this route in this time was higher, at C$ 397 round-trip. Air Canada operates 7 flights out of Calgary into Chicago in an average week, so prices vary by time and availability. 8,237 Air Canada reviews by users on momondo have scored the airline at 7.0/10.


Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Calgary to Chicago. momondo saves you time and could save you money on your trip.

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

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

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

Once you have performed a search for Calgary to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Chicago from Calgary are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago