Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Calgary to Chicago from $109

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 3/16. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? 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

WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$151WestJet
Find Deal
Fri, Oct 17 - Sun, Oct 19
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$154WestJet
Find Deal
Fri, Oct 17 - Sun, Oct 19
United Airlines Logo
12:35 pm - 5:10 pmYYC-ORD
3h 35mnonstop
United Airlines Logo
7:10 am - 9:53 pmORD-YYC
15h 43m1 stop
$172United Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
Air Canada Logo
5:35 am - 3:10 pmYYC-ORD
8h 35m1 stop
Air Canada Logo
2:00 pm - 8:39 pmORD-YYC
7h 39m1 stop
$175Air Canada
Find Deal
Sat, Nov 1 - Sat, Nov 8
United Airlines Logo
6:15 am - 11:59 pmYYC-ORD
16h 44m1 stop
United Airlines Logo
7:10 am - 9:53 pmORD-YYC
15h 43m1 stop
$178United Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
Air Canada Logo
12:45 am - 11:18 amYYC-ORD
9h 33m1 stop
Air Canada Logo
7:15 am - 6:54 pmORD-YYC
12h 39m2 stops
$179Air Canada
Find Deal
Fri, Oct 31 - Sat, Nov 8
American Airlines Logo
12:54 pm - 9:49 amYYC-ORD
19h 55m1 stop
American Airlines Logo
5:00 am - 11:59 amORD-YYC
7h 59m1 stop
$196American Airlines
Find Deal
Fri, Oct 24 - Wed, Oct 29
American Airlines Logo
1:29 pm - 5:54 pmYYC-ORD
3h 25mnonstop
American Airlines Logo
9:49 am - 12:34 pmORD-YYC
3h 45mnonstop
$198American Airlines
Find Deal
Sun, Oct 26 - Sat, Nov 1
Delta Logo
7:45 am - 6:41 pmYYC-ORD
9h 56m1 stop
Delta Logo
6:45 am - 8:47 pmORD-YYC
15h 02m2 stops
$223Delta
Find Deal
Tue, Oct 21 - Thu, Oct 23
Delta Logo
6:45 am - 3:00 pmYYC-ORD
7h 15m1 stop
Delta Logo
8:57 am - 1:54 pmORD-YYC
5h 57m1 stop
$224Delta
Find Deal
Sat, Oct 18 - Thu, Oct 23

Air Canada flights from Calgary to Chicago

Our best Air Canada deals on Calgary to Chicago flight tickets
Air Canada
Nov 1
YYC5:35 amCalgary
8h 35m
1 stop
ORD3:10 pmChicago O'Hare Intl
Nov 8
ORD2:00 pmChicago O'Hare Intl
7h 39m
1 stop
YYC8:39 pmCalgary
$175
Find similar
Air Canada
Oct 31
YYC12:45 amCalgary
9h 33m
1 stop
ORD11:18 amChicago O'Hare Intl
Nov 8
ORD7:15 amChicago O'Hare Intl
12h 39m
2 stops
YYC6:54 pmCalgary
$179
Find similar
Air Canada
Oct 26
YYC9:00 amCalgary
8h 55m
1 stop
ORD6:55 pmChicago O'Hare Intl
Nov 1
ORD3:55 pmChicago O'Hare Intl
9h 19m
1 stop
YYC12:14 amCalgary
$207
Find similar

American Airlines flights from Calgary to Chicago

Our best American Airlines deals on Calgary to Chicago flight tickets
American Airlines
Oct 24
YYC12:54 pmCalgary
19h 55m
1 stop
ORD9:49 amChicago O'Hare Intl
Oct 29
ORD5:00 amChicago O'Hare Intl
7h 59m
1 stop
YYC11:59 amCalgary
$196
Find similar
American Airlines
Oct 26
YYC1:29 pmCalgary
3h 25m
ORD5:54 pmChicago O'Hare Intl
Nov 1
ORD9:49 amChicago O'Hare Intl
3h 45m
YYC12:34 pmCalgary
$198
Find similar
American Airlines
Oct 11
YYC6:45 amCalgary
13h 29m
1 stop
ORD9:14 pmChicago O'Hare Intl
Oct 18
ORD9:49 amChicago O'Hare Intl
3h 45m
YYC12:34 pmCalgary
$229
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 832,500 searches. Data last updated September 17, 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

Fri 10/17

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-8:19 pm

Nonstop3h 49m

$151

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/17

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-8:19 pm

Nonstop3h 49m

$154

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 12/11

12:35 pm-5:10 pm

Nonstop3h 35m

Chicago O'Hare Intl

Mon 12/15

7:10 am-9:53 pm

1 stop15h 43m

$172

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 11/1

5:35 am-3:10 pm

1 stop8h 35m

Chicago O'Hare Intl

Sat 11/8

2:00 pm-8:39 pm

1 stop7h 39m

$175

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 12/11

6:15 am-11:59 pm

1 stop16h 44m

Chicago O'Hare Intl

Mon 12/15

7:10 am-9:53 pm

1 stop15h 43m

$178

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/31

12:45 am-11:18 am

1 stop9h 33m

Chicago O'Hare Intl

Sat 11/8

7:15 am-6:54 pm

2 stops12h 39m

$179

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/24

12:54 pm-9:49 am

1 stop19h 55m

Chicago O'Hare Intl

Wed 10/29

5:00 am-11:59 am

1 stop7h 59m

$196

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 10/26

1:29 pm-5:54 pm

Nonstop3h 25m

Chicago O'Hare Intl

Sat 11/1

9:49 am-12:34 pm

Nonstop3h 45m

$198

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 10/21

7:45 am-6:41 pm

1 stop9h 56m

Chicago O'Hare Intl

Thu 10/23

6:45 am-8:47 pm

2 stops15h 02m

$223

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 10/18

6:45 am-3:00 pm

1 stop7h 15m

Chicago O'Hare Intl

Thu 10/23

8:57 am-1:54 pm

1 stop5h 57m

$224

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 April is, on average, the cheapest month to fly to Chicago from Calgary, with most prices found around $191. If you’re not able to fly to Chicago in April, then February is your next best option. Flight prices from Calgary to Chicago during February average around $195.

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 Sunday when prices can be found for as low as $171. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Calgary to Chicago for around $478.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Calgary to Chicago during this time can be as low as $215. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $727.

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 $273 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 $199 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 September 2025, prices for Calgary to Chicago flights are approximately 17% 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

$208

Fastest flight time

3h 25m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Calgary in the past 72 hours is $208. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is $235.
The fastest flight from Calgary to Chicago takes 3h 25m
Direct flights go from Calgary to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • How far is Calgary to Chicago by plane?

    Chicago is 1397.6 mi away from Calgary. In terms of flight time, this usually takes a little over 3h 25m.

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

    Prices for flights from Calgary Airport to Chicago were last updated today.

  • 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 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 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 $109Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
WestJetPriceFrom $138Free CancellationRating
7.2
3,095 reviews
Search WestJet flights
American AirlinesPriceFrom $208Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $239Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights

  • United Airlines Flights From Calgary to Chicago

    United Airlines operates around 10 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been $469, but momondo users have found United Airlines deals from Calgary to Chicago from as low as $239 round-trip. United Airlines has been scored 7.4/10 in 8,926 reviews.

  • WestJet Flights From Calgary to Chicago

    Another popular option for Calgary to Chicago flights is WestJet (7.2/10, 3,095 ratings). WestJet flies from Calgary to Chicago around 1 time per week, with deals starting from $138 round-trip and rising to an average price of around $233.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Calgary to Chicago for you.

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

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

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Calgary.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Calgary and alert you when they change.

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
Fri 10/17
Fri 10/24
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 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport