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Cheap flights from Calgary to Chicago from C$ 128

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 11/10. 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

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Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

WestJet Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 199WestJet
Find Deal
jue., 25 sep. - lun., 29 sep.
WestJet Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 208WestJet
Find Deal
mié., 17 sep. - vie., 19 sep.
United Airlines Logo
12:30 p.m. - 4:50 p.m.YYC-ORD
3h 20mdirect
United Airlines Logo
9:00 a.m. - 11:54 a.m.ORD-YYC
3h 54mdirect
C$ 232United Airlines
Find Deal
sáb., 22 nov. - dom., 23 nov.
United Airlines Logo
6:15 a.m. - 7:55 p.m.YYC-ORD
12h 40m1 stop
United Airlines Logo
2:53 p.m. - 9:48 p.m.ORD-YYC
7h 55m1 stop
C$ 239United Airlines
Find Deal
sáb., 11 oct. - sáb., 18 oct.
Air Canada Logo
1:10 a.m. - 9:51 a.m.YYC-ORD
7h 41m1 stop
Air Canada Logo
6:20 p.m. - 1:12 a.m.ORD-YYC
7h 52m1 stop
C$ 284Air Canada
Find Deal
mar., 16 sep. - vie., 19 sep.
Air Canada Logo
1:05 a.m. - 9:52 a.m.YYC-ORD
7h 47m1 stop
Air Canada Logo
3:50 p.m. - 12:10 a.m.ORD-YYC
9h 20m1 stop
C$ 289Air Canada
Find Deal
mar., 19 ago. - mié., 27 ago.
American Airlines Logo
6:45 a.m. - 11:59 p.m.YYC-ORD
16h 14m1 stop
American Airlines Logo
8:30 p.m. - 11:19 p.m.ORD-YYC
3h 49mdirect
C$ 311American Airlines
Find Deal
mié., 17 sep. - vie., 19 sep.
Delta Logo
6:40 a.m. - 4:45 p.m.YYC-ORD
9h 05m1 stop
Delta Logo
2:15 p.m. - 10:57 p.m.ORD-YYC
9h 42m1 stop
C$ 313Delta
Find Deal
mar., 12 ago. - mié., 20 ago.
Delta Logo
6:45 a.m. - 5:39 p.m.YYC-MDW
9h 54m1 stop
Delta Logo
9:15 a.m. - 10:57 p.m.MDW-YYC
14h 42m2 stops
C$ 313Delta
Find Deal
mié., 6 ago. - mar., 12 ago.
American Airlines Logo
6:29 a.m. - 10:54 a.m.YYC-ORD
3h 25mdirect
American Airlines Logo
5:00 a.m. - 11:52 a.m.ORD-YYC
7h 52m1 stop
C$ 332American Airlines
Find Deal
lun., 6 oct. - mié., 8 oct.

WestJet flights from Calgary to Chicago

Our best WestJet deals on Calgary to Chicago flight tickets
WestJet
25 Sep
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
29 Sep
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
WestJet
17 Sep
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
19 Sep
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
WestJet
29 Aug
YYC12:15 p.m.Calgary
3h 29m
ORD4:44 p.m.Chicago O'Hare Intl
7 Sep
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary

United Airlines flights from Calgary to Chicago

Our best United Airlines deals on Calgary to Chicago flight tickets
United Airlines
22 Nov
YYC12:30 p.m.Calgary
3h 20m
ORD4:50 p.m.Chicago O'Hare Intl
23 Nov
ORD9:00 a.m.Chicago O'Hare Intl
3h 54m
YYC11:54 a.m.Calgary
United Airlines
11 Oct
YYC6:15 a.m.Calgary
12h 40m
1 stop
ORD7:55 p.m.Chicago O'Hare Intl
18 Oct
ORD2:53 p.m.Chicago O'Hare Intl
7h 55m
1 stop
YYC9:48 p.m.Calgary
United Airlines
6 Oct
YYC1:30 p.m.Calgary
9h 29m
1 stop
ORD11:59 p.m.Chicago O'Hare Intl
7 Oct
ORD8:47 a.m.Chicago O'Hare Intl
3h 51m
YYC11:38 a.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 to Chicago?

The month of February is another great option to travel to Chicago, with average flight prices from Calgary averaging around C$ 273.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 666. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,005. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

In the afternoon is the cheapest time of day to fly from Calgary to Chicago when you can find flight prices for as low as C$ 361. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,431 per ticket.

What is the cheapest Calgary to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Calgary when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 375 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Calgary for as low as C$ 283 on momondo.

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

There are 4 cabin classes available to choose from on Calgary to Chicago 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 Calgary to Chicago flights?

You could potentially save up to 2% on your flight if you consider stops on a Calgary to Chicago flight.

How have Calgary to Chicago flight prices changed over time?

As of July 2025, prices for Calgary to Chicago flights are approximately 10% cheaper 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$ 128

Fastest flight time

3h 20m

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$ 128. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is C$ 199.
The fastest flight from Calgary to Chicago takes 3h 20m
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 20m, 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
Air CanadaPriceFrom C$ 148Free CancellationRating
7.1
9,683 reviews
Search Air Canada flights
American AirlinesPriceFrom C$ 169Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom C$ 175Free CancellationRating
7.2
2,920 reviews
Search WestJet flights
DeltaPriceFrom C$ 184Free CancellationRating
8.0
7,958 reviews
Search Delta flights
United AirlinesPriceFrom C$ 249Free CancellationRating
7.4
8,844 reviews
Search United Airlines flights
  • Delta Flights From Calgary to Chicago

    Delta operates around 3 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 268, but momondo users have found Delta deals from Calgary to Chicago from as low as C$ 135 round-trip. Delta has been scored 8.0/10 in 7,962 reviews.

  • United Airlines Flights From Calgary to Chicago

    The best United Airlines deal for Calgary to Chicago flight tickets found on momondo in the last 72 hours was C$ 183, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at C$ 401 round-trip. United Airlines operates 10 flights out of Calgary into Chicago in an average week, so prices vary by time and availability. 8,844 United Airlines reviews by users on momondo have scored the airline at 7.4/10.


Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hammond
Munster
Benton Harbor
Merrillville

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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1 adult
dom. 13/7
dom. 20/7

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago