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Cheap flights from Calgary to Chicago from $100

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 3/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 5:15 pm
ORD
-
YYC
3h 55mnonstop
$162WestJet
vie., feb. 6 - lun., feb. 9
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 5:15 pm
ORD
-
YYC
3h 55mnonstop
$169WestJet
vie., feb. 6 - vie., feb. 13
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
8:41 am - 11:31 am
ORD
-
YYC
3h 50mnonstop
$177WestJet
lun., feb. 23 - mar., mar. 3
Multiple Airlines Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
Multiple Airlines Logo
3:55 pm - 11:59 pm
ORD
-
YYC
9h 04m1 stop
$178Multiple Airlines
lun., feb. 23 - mar., mar. 3
WestJet Logo
12:15 pm - 4:43 pm
YYC
-
ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pm
ORD
-
YYC
3h 49mnonstop
$179WestJet
jue., may. 14 - lun., may. 18
Air Canada Logo
5:35 am - 3:10 pm
YYC
-
ORD
8h 35m1 stop
Air Canada Logo
2:00 pm - 8:59 pm
ORD
-
YYC
7h 59m1 stop
$183Air Canada
mié., ene. 21 - sáb., ene. 24
Air Canada Logo
5:35 am - 3:10 pm
YYC
-
ORD
8h 35m1 stop
Air Canada Logo
2:00 pm - 8:59 pm
ORD
-
YYC
7h 59m1 stop
$203Air Canada
mié., ene. 21 - vie., ene. 23
Delta Logo
6:30 am - 4:16 pm
YYC
-
MDW
8h 46m1 stop
Delta Logo
1:51 pm - 8:54 pm
MDW
-
YYC
8h 03m1 stop
$228Delta
sáb., ene. 31 - lun., feb. 2
Multiple Airlines Logo
9:45 pm - 11:45 am
YYC
-
MDW
13h 00m2 stops
Multiple Airlines Logo
5:01 pm - 7:09 pm
MDW
-
YYC
27h 08m1 stop
$233Multiple Airlines
mié., ene. 21 - vie., ene. 23
Delta Logo
6:30 am - 10:22 pm
YYC
-
MDW
14h 52m2 stops
Delta Logo
1:26 pm - 8:54 pm
MDW
-
YYC
8h 28m2 stops
$278Delta
sáb., ene. 31 - lun., feb. 2

WestJet flights from Calgary to Chicago

Our best WestJet deals on Calgary to Chicago flight tickets
WestJet
Feb 6
YYC9:00 amCalgary
3h 35m
ORD1:35 pmChicago O'Hare Intl
Feb 13
ORD2:20 pmChicago O'Hare Intl
3h 55m
YYC5:15 pmCalgary
$169
WestJet
Feb 23
YYC9:00 amCalgary
3h 35m
ORD1:35 pmChicago O'Hare Intl
Mar 3
ORD8:41 amChicago O'Hare Intl
3h 50m
YYC11:31 amCalgary
$177
WestJet
May 14
YYC12:15 pmCalgary
3h 28m
ORD4:43 pmChicago O'Hare Intl
May 18
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
$179

Delta flights from Calgary to Chicago

Our best Delta deals on Calgary to Chicago flight tickets
Delta
Jan 21
YYC6:30 amCalgary
13h 35m
2 stops
ORD9:05 pmChicago O'Hare Intl
Jan 24
ORD7:05 amChicago O'Hare Intl
14h 49m
2 stops
YYC8:54 pmCalgary
$228
Delta
Feb 3
YYC6:30 amCalgary
10h 25m
1 stop
ORD5:55 pmChicago O'Hare Intl
Feb 10
ORD1:58 pmChicago O'Hare Intl
10h 04m
2 stops
YYC11:02 pmCalgary
$229
Delta
Apr 20
YYC7:55 amCalgary
9h 09m
1 stop
ORD6:04 pmChicago O'Hare Intl
Apr 24
ORD1:22 pmChicago O'Hare Intl
10h 38m
1 stop
YYC11:00 pmCalgary
$230

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 enero 8, 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

CalgaryChicago

YYC - ORD

YYCORD

Calgary

vie. 2/6

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

lun. 2/9

2:20 pm-5:15 pm

Nonstop3h 55m

$162

CalgaryChicago

YYC - ORD

YYCORD

Calgary

vie. 2/6

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

vie. 2/13

2:20 pm-5:15 pm

Nonstop3h 55m

$169

CalgaryChicago

YYC - ORD

YYCORD

Calgary

lun. 2/23

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

mar. 3/3

8:41 am-11:31 am

Nonstop3h 50m

$177

CalgaryChicago

YYC - ORD

YYCORD

Calgary

lun. 2/23

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

mar. 3/3

3:55 pm-11:59 pm

1 stop9h 04m

$178

CalgaryChicago

YYC - ORD

YYCORD

Calgary

jue. 5/14

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

lun. 5/18

5:30 pm-8:19 pm

Nonstop3h 49m

$179

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mié. 1/21

5:35 am-3:10 pm

1 stop8h 35m

Chicago O'Hare Intl

sáb. 1/24

2:00 pm-8:59 pm

1 stop7h 59m

$183

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mié. 1/21

5:35 am-3:10 pm

1 stop8h 35m

Chicago O'Hare Intl

vie. 1/23

2:00 pm-8:59 pm

1 stop7h 59m

$203

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

sáb. 1/31

6:30 am-4:16 pm

1 stop8h 46m

Chicago Midway

lun. 2/2

1:51 pm-8:54 pm

1 stop8h 03m

$228

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

mié. 1/21

9:45 pm-11:45 am

2 stops13h 00m

Chicago Midway

vie. 1/23

5:01 pm-7:09 pm

1 stop27h 08m

$233

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

sáb. 1/31

6:30 am-10:22 pm

2 stops14h 52m

Chicago Midway

lun. 2/2

1:26 pm-8:54 pm

2 stops8h 28m

$278

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 April is, on average, the cheapest month to fly to Chicago from Calgary, with most prices found around $189. If you’re not able to fly to Chicago in April, then January is your next best option. Flight prices from Calgary to Chicago during January average around $207.

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 $173. 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 $456.

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 $340. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $785.

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 $257 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 $162 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 January 2026, prices for Calgary to Chicago flights are approximately 3% 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

$225

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 $225. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is $274.
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 1397.6 mi away from Calgary. In terms of flight time, this usually takes a little over 3h 27m.

  • 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 $101Free CancellationRating
7.1
10,603 reviews
Search Air Canada flights
WestJetPriceFrom $137Free CancellationRating
7.2
3,235 reviews
Search WestJet flights
American AirlinesPriceFrom $185Free CancellationRating
7.2
11,095 reviews
Search American Airlines flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
9,141 reviews
Search United 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 $459, but momondo users have found United Airlines deals from Calgary to Chicago from as low as $218 round-trip. United Airlines has been scored 7.4/10 in 9,141 reviews.

  • American Airlines Flights From Calgary to Chicago

    Another popular option for Calgary to Chicago flights is American Airlines (7.2/10, 11,095 ratings). American Airlines flies from Calgary to Chicago around 7 times per week, with deals starting from $185 round-trip and rising to an average price of around $376.

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
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
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.
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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