Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Calgary to Chicago from C$ 117

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 2/6. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
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$ 203WestJet
Thu, 21 May - Sat, 30 May
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$ 204WestJet
Sun, 24 May - Sat, 30 May
United Airlines Logo
2:13 p.m. - 11:59 p.m.
YYC
-
ORD
8h 46m1 stop
United Airlines Logo
8:45 a.m. - 11:35 a.m.
ORD
-
YYC
3h 50mdirect
C$ 222United Airlines
Tue, 3 Feb - Wed, 4 Feb
Air Canada Logo
8:00 a.m. - 5:48 p.m.
YYC
-
ORD
8h 48m1 stop
Air Canada Logo
3:55 p.m. - 12:14 a.m.
ORD
-
YYC
9h 19m1 stop
C$ 242Air Canada
Tue, 3 Feb - Wed, 4 Feb
United Airlines Logo
6:15 a.m. - 11:59 p.m.
YYC
-
ORD
16h 44m1 stop
United Airlines Logo
8:45 a.m. - 11:35 a.m.
ORD
-
YYC
3h 50mdirect
C$ 251United Airlines
Mon, 2 Feb - Tue, 3 Feb
Multiple Airlines Logo
9:00 a.m. - 1:35 p.m.
YYC
-
ORD
3h 35mdirect
Multiple Airlines Logo
4:19 p.m. - 9:45 p.m.
ORD
-
YYC
30h 26m1 stop
C$ 252Multiple Airlines
Fri, 23 Jan - Sun, 1 Feb
Air Canada Logo
5:35 a.m. - 3:10 p.m.
YYC
-
ORD
8h 35m1 stop
Air Canada Logo
3:55 p.m. - 12:14 a.m.
ORD
-
YYC
9h 19m1 stop
C$ 254Air Canada
Thu, 22 Jan - Mon, 2 Feb
Multiple Airlines Logo
7:00 a.m. - 5:44 p.m.
YYC
-
ORD
9h 44m1 stop
Multiple Airlines Logo
2:20 p.m. - 5:15 p.m.
ORD
-
YYC
3h 55mdirect
C$ 255Multiple Airlines
Fri, 16 Jan - Fri, 23 Jan
Delta Logo
6:30 a.m. - 4:16 p.m.
YYC
-
MDW
8h 46m1 stop
Delta Logo
11:45 a.m. - 8:54 p.m.
MDW
-
YYC
10h 09m1 stop
C$ 309Delta
Sat, 31 Jan - Sat, 7 Feb
Delta Logo
6:30 a.m. - 1:09 p.m.
YYC
-
MDW
5h 39m1 stop
Delta Logo
1:51 p.m. - 8:54 p.m.
MDW
-
YYC
8h 03m1 stop
C$ 336Delta
Fri, 30 Jan - Fri, 6 Feb

Air Canada flights from Calgary to Chicago

Our best Air Canada deals on Calgary to Chicago flight tickets
Air Canada
3 Feb
YYC8:00 a.m.Calgary
8h 48m
1 stop
ORD5:48 p.m.Chicago O'Hare Intl
4 Feb
ORD3:55 p.m.Chicago O'Hare Intl
9h 19m
1 stop
YYC12:14 a.m.Calgary
C$ 242
Find similar
Air Canada
22 Jan
YYC5:35 a.m.Calgary
8h 35m
1 stop
ORD3:10 p.m.Chicago O'Hare Intl
2 Feb
ORD3:55 p.m.Chicago O'Hare Intl
9h 19m
1 stop
YYC12:14 a.m.Calgary
C$ 254
Find similar
Air Canada
20 May
YYC8:00 a.m.Calgary
7h 59m
1 stop
ORD4:59 p.m.Chicago O'Hare Intl
30 May
ORD8:45 a.m.Chicago O'Hare Intl
16h 02m
1 stop
YYC11:47 p.m.Calgary
C$ 278
Find similar

WestJet flights from Calgary to Chicago

Our best WestJet deals on Calgary to Chicago flight tickets
WestJet
21 May
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
30 May
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
C$ 203
Find similar
WestJet
24 May
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
30 May
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
C$ 204
Find similar
WestJet
23 Jan
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
2 Feb
ORD2:20 p.m.Chicago O'Hare Intl
3h 55m
YYC5:15 p.m.Calgary
C$ 273
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Calgary to Chicago 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 18 December 2025.
Use the filters below to find and compare flights from Calgary to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 21/5

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Sat 30/5

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

Nonstop3h 49m

C$ 203

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 24/5

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Sat 30/5

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

Nonstop3h 49m

C$ 204

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 3/2

2:13 p.m.-11:59 p.m.

1 stop8h 46m

Chicago O'Hare Intl

Wed 4/2

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

C$ 222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 3/2

8:00 a.m.-5:48 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Wed 4/2

3:55 p.m.-12:14 a.m.

1 stop9h 19m

C$ 242

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 2/2

6:15 a.m.-11:59 p.m.

1 stop16h 44m

Chicago O'Hare Intl

Tue 3/2

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

C$ 251

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 23/1

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

Nonstop3h 35m

Chicago O'Hare Intl

Sun 1/2

4:19 p.m.-9:45 p.m.

1 stop30h 26m

C$ 252

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 22/1

5:35 a.m.-3:10 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Mon 2/2

3:55 p.m.-12:14 a.m.

1 stop9h 19m

C$ 254

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 16/1

7:00 a.m.-5:44 p.m.

1 stop9h 44m

Chicago O'Hare Intl

Fri 23/1

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 255

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 31/1

6:30 a.m.-4:16 p.m.

1 stop8h 46m

Chicago Midway

Sat 7/2

11:45 a.m.-8:54 p.m.

1 stop10h 09m

C$ 309

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 30/1

6:30 a.m.-1:09 p.m.

1 stop5h 39m

Chicago Midway

Fri 6/2

1:51 p.m.-8:54 p.m.

1 stop8h 03m

C$ 336

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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$ 280.

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$ 609. 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$ 997. 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$ 364. 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$ 1,487 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$ 354 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$ 227 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?

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 December 2025, prices for Calgary to Chicago flights are approximately 5% 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$ 162

Fastest flight time

3h 27m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Calgary in the past 72 hours is C$ 162. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is C$ 363.
The fastest flight from Calgary to Chicago takes 3h 27m
Direct flights go from Calgary to Chicago every day.
There are 3 airports in Chicago. From Calgary there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • How far is Calgary to Chicago by plane?

    Chicago is 2249.2 km away from Calgary. Flights usually cover this in 3h 27m, 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$ 149Free CancellationRating
7.1
10,534 reviews
Search Air Canada flights
WestJetPriceFrom C$ 176Free CancellationRating
7.2
3,204 reviews
Search WestJet flights
DeltaPriceFrom C$ 184Free CancellationRating
7.9
8,005 reviews
Search Delta flights
American AirlinesPriceFrom C$ 185Free CancellationRating
7.2
11,055 reviews
Search American Airlines flights
United AirlinesPriceFrom C$ 194Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights

  • United Airlines Flights From Calgary to Chicago

    United Airlines operates around 6 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 499, but momondo users have found United Airlines deals from Calgary to Chicago from as low as C$ 194 round-trip. United Airlines has been scored 7.4/10 in 9,093 reviews.

  • American Airlines Flights From Calgary to Chicago

    The best American Airlines deal for Calgary to Chicago flight tickets found on momondo in the last 72 hours was C$ 185, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at C$ 423 round-trip. American Airlines operates 1 flight out of Calgary into Chicago in an average week, so prices vary by time and availability. 11,055 American Airlines reviews by users on momondo have scored the airline at 7.2/10.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 17/1
Sat 24/1
By creating a price alert you accept our terms of use and privacy policy.

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
Chicago Midway Airport
Chicago O'Hare Intl Airport