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Cheap flights from Calgary to Chicago from $141

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 5/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:30 am - 2:55 pm
YYC
-
ORD
7h 25m
1 stop
Multiple Airlines Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$195Multiple Airlines
Thu, May 21 - Sat, May 30
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$240WestJet
Fri, Aug 21 - Tue, Aug 25
American Airlines Logo
1:40 pm - 6:25 pm
YYC
-
ORD
3h 45mnonstop
American Airlines Logo
8:55 pm - 11:43 pm
ORD
-
YYC
3h 48mnonstop
$245American Airlines
Thu, May 28 - Mon, Jun 1
United Airlines Logo
12:28 pm - 5:05 pm
YYC
-
ORD
3h 37mnonstop
United Airlines Logo
7:05 am - 9:48 pm
ORD
-
YYC
15h 43m
1 stop
$251United Airlines
Tue, May 26 - Wed, May 27
United Airlines Logo
1:27 pm - 12:44 am
YYC
-
ORD
10h 17m
1 stop
United Airlines Logo
7:05 am - 9:48 pm
ORD
-
YYC
15h 43m
1 stop
$257United Airlines
Tue, May 26 - Wed, May 27
American Airlines Logo
6:45 am - 7:32 am
YYC
-
ORD
23h 47m
1 stop
American Airlines Logo
8:55 pm - 11:43 pm
ORD
-
YYC
3h 48mnonstop
$260American Airlines
Thu, May 28 - Mon, Jun 1
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$261WestJet
Fri, Sep 11 - Mon, Sep 14
Delta Logo
7:45 am - 6:50 pm
YYC
-
ORD
10h 05m
1 stop
Delta Logo
12:30 pm - 8:30 pm
ORD
-
YYC
9h 00m
1 stop
$266Delta
Wed, May 20 - Tue, May 26
American Airlines Logo
6:15 am - 10:45 am
YYC
-
ORD
3h 30mnonstop
American Airlines Logo
8:55 pm - 11:43 pm
ORD
-
YYC
3h 48mnonstop
$267American Airlines
Fri, May 22 - Tue, Jun 2
Delta Logo
6:45 am - 5:56 pm
YYC
-
MDW
10h 11m
1 stop
Delta Logo
9:17 am - 8:38 pm
MDW
-
YYC
12h 21m
2 stops
$333Delta
Fri, May 29 - Tue, Jun 9

United Airlines flights from Calgary to Chicago

Our best United Airlines deals on Calgary to Chicago flight tickets
United Airlines
May 26
YYC12:28 pmCalgary
3h 37m
ORD5:05 pmChicago O'Hare Intl
May 27
ORD7:05 amChicago O'Hare Intl
15h 43m
1 stop
YYC9:48 pmCalgary
$251
United Airlines
May 26
YYC1:27 pmCalgary
10h 17m
1 stop
ORD12:44 amChicago O'Hare Intl
May 27
ORD7:05 amChicago O'Hare Intl
15h 43m
1 stop
YYC9:48 pmCalgary
$257
United Airlines
May 20
YYC12:34 pmCalgary
3h 27m
ORD5:01 pmChicago O'Hare Intl
May 26
ORD6:00 amChicago O'Hare Intl
16h 48m
1 stop
YYC9:48 pmCalgary
$272

Air Canada flights from Calgary to Chicago

Our best Air Canada deals on Calgary to Chicago flight tickets
Air Canada
May 21
YYC6:30 amCalgary
7h 25m
1 stop
ORD2:55 pmChicago O'Hare Intl
May 30
ORD10:41 amChicago O'Hare Intl
11h 10m
1 stop
YYC8:51 pmCalgary
$309
Air Canada
May 28
YYC7:45 pmCalgary
12h 15m
1 stop
ORD9:00 amChicago O'Hare Intl
Jun 6
ORD2:00 pmChicago O'Hare Intl
9h 58m
1 stop
YYC10:58 pmCalgary
$313
Air Canada
May 8
YYC12:50 amCalgary
8h 28m
1 stop
ORD10:18 amChicago O'Hare Intl
May 9
ORD3:50 pmChicago O'Hare Intl
8h 08m
1 stop
YYC10:58 pmCalgary
$314

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 May 7, 2026.
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

Cheapest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 5/21

6:30 am-2:55 pm

1 stop7h 25m

Chicago O'Hare Intl

Sat 5/30

5:30 pm-8:25 pm

Nonstop3h 55m

$195

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 8/21

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 8/25

5:30 pm-8:25 pm

Nonstop3h 55m

$240

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 5/28

1:40 pm-6:25 pm

Nonstop3h 45m

Chicago O'Hare Intl

Mon 6/1

8:55 pm-11:43 pm

Nonstop3h 48m

$245

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 5/26

12:28 pm-5:05 pm

Nonstop3h 37m

Chicago O'Hare Intl

Wed 5/27

7:05 am-9:48 pm

1 stop15h 43m

$251

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 5/26

1:27 pm-12:44 am

1 stop10h 17m

Chicago O'Hare Intl

Wed 5/27

7:05 am-9:48 pm

1 stop15h 43m

$257

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 5/28

6:45 am-7:32 am

1 stop23h 47m

Chicago O'Hare Intl

Mon 6/1

8:55 pm-11:43 pm

Nonstop3h 48m

$260

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 9/11

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Mon 9/14

5:30 pm-8:25 pm

Nonstop3h 55m

$261

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 5/20

7:45 am-6:50 pm

1 stop10h 05m

Chicago O'Hare Intl

Tue 5/26

12:30 pm-8:30 pm

1 stop9h 00m

$266
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/22

6:15 am-10:45 am

Nonstop3h 30m

Chicago O'Hare Intl

Tue 6/2

8:55 pm-11:43 pm

Nonstop3h 48m

$267

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 5/29

6:45 am-5:56 pm

1 stop10h 11m

Chicago Midway

Tue 6/9

9:17 am-8:38 pm

2 stops12h 21m

$333

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 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 typical price of a round-trip flight between Calgary and Chicago?

What is the cheapest month to fly to Chicago?

The month of March is, on average, the cheapest month to fly to Chicago from Calgary, with most prices found around $62. If you’re not able to fly to Chicago in March, then September is your next best option. Flight prices from Calgary to Chicago during September average around $64.

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 $292. 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 $484.

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 morning. Flights from Calgary to Chicago during this time can be as low as $358. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $876.

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 from Calgary 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 $282 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 $217 on momondo.

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 May 2026, prices for Calgary to Chicago flights are approximately 12% 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

$178

Fastest flight time

3h 25m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Calgary in the past 72 hours is $178. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is $278.
The fastest flight from Calgary to Chicago takes 3h 25m
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

Frequently asked questions about flying from Calgary to Chicago

  • 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
11,002 reviews
Search Air Canada flights
United AirlinesPriceFrom $135Free CancellationRating
7.4
9,694 reviews
Search United Airlines flights
WestJetPriceFrom $137Free CancellationRating
7.2
3,332 reviews
Search WestJet flights
American AirlinesPriceFrom $208Free CancellationRating
7.1
11,667 reviews
Search American Airlines 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 $460, but momondo users have found United Airlines deals from Calgary to Chicago from as low as $135 round-trip. United Airlines has been scored 7.4/10 in 9,694 reviews.

  • WestJet Flights From Calgary to Chicago

    Another popular option for Calgary to Chicago flights is WestJet (7.2/10, 3,332 ratings). WestJet flies from Calgary to Chicago around 2 times per week, with deals starting from $137 round-trip and rising to an average price of around $280.

Traveling to a place near Chicago?

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