Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Calgary to Chicago from $93

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 2/2. 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

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
$152WestJet
vie., ene. 23 - vie., feb. 13
Air Canada Logo
5:35 am - 2:55 pm
YYC
-
ORD
8h 20m1 stop
Air Canada Logo
2:00 pm - 8:59 pm
ORD
-
YYC
7h 59m1 stop
$160Air Canada
sáb., ene. 17 - sáb., ene. 24
Air Canada Logo
5:35 am - 2:55 pm
YYC
-
ORD
8h 20m1 stop
Air Canada Logo
7:15 am - 8:59 pm
ORD
-
YYC
14h 44m2 stops
$168Air Canada
sáb., ene. 17 - sáb., ene. 24
Air Canada Logo
5:35 am - 2:55 pm
YYC
-
ORD
8h 20m1 stop
Air Canada Logo
2:00 pm - 8:59 pm
ORD
-
YYC
7h 59m1 stop
$179Air Canada
sáb., ene. 17 - sáb., ene. 24
Air Canada Logo
5:35 am - 3:10 pm
YYC
-
ORD
8h 35m1 stop
Air Canada Logo
3:55 pm - 12:14 am
ORD
-
YYC
9h 19m1 stop
$182Air Canada
jue., ene. 8 - lun., ene. 12
United Airlines Logo
12:37 pm - 5:08 pm
YYC
-
ORD
3h 31mnonstop
United Airlines Logo
8:45 am - 11:35 am
ORD
-
YYC
3h 50mnonstop
$188United Airlines
mié., ene. 21 - mar., feb. 10
Multiple Airlines Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
Multiple Airlines Logo
1:45 pm - 10:46 pm
ORD
-
YYC
10h 01m1 stop
$193Multiple Airlines
vie., ene. 23 - mié., feb. 11
Multiple Airlines Logo
7:35 pm - 4:51 pm
YYC
-
ORD
20h 16m1 stop
Multiple Airlines Logo
2:20 pm - 5:15 pm
ORD
-
YYC
3h 55mnonstop
$194Multiple Airlines
vie., ene. 23 - lun., feb. 9
Air Canada Logo
5:35 am - 8:10 pm
YYC
-
ORD
13h 35m2 stops
Air Canada Logo
7:15 am - 8:59 pm
ORD
-
YYC
14h 44m2 stops
$198Air Canada
sáb., ene. 17 - sáb., ene. 24
Multiple Airlines Logo
12:30 am - 6:27 pm
YYC
-
ORD
16h 57m1 stop
Multiple Airlines Logo
2:20 pm - 5:15 pm
ORD
-
YYC
3h 55mnonstop
$199Multiple Airlines
mar., ene. 20 - vie., feb. 13

WestJet flights from Calgary to Chicago O'Hare Intl Airport

Our best WestJet deals on Calgary to Chicago O'Hare Intl Airport flight tickets
WestJet
Jan 23
YYC9:00 amCalgary
3h 35m
ORD1:35 pmChicago O'Hare Intl
Feb 13
ORD2:20 pmChicago O'Hare Intl
3h 55m
YYC5:15 pmCalgary
$152
Find similar
WestJet
May 26
YYC12:15 pmCalgary
3h 28m
ORD4:43 pmChicago O'Hare Intl
May 30
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
$200
Find similar
WestJet
May 26
YYC12:15 pmCalgary
3h 28m
ORD4:43 pmChicago O'Hare Intl
May 30
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
$205
Find similar

United Airlines flights from Calgary to Chicago O'Hare Intl Airport

Our best United Airlines deals on Calgary to Chicago O'Hare Intl Airport flight tickets
United Airlines
May 26
YYC8:30 amCalgary
3h 20m
ORD12:50 pmChicago O'Hare Intl
May 30
ORD7:15 amChicago O'Hare Intl
15h 23m
1 stop
YYC9:38 pmCalgary
$188
Find similar
United Airlines
Apr 8
YYC12:40 pmCalgary
3h 27m
ORD5:07 pmChicago O'Hare Intl
Apr 13
ORD8:46 amChicago O'Hare Intl
3h 51m
YYC11:37 amCalgary
$239
Find similar
United Airlines
Dec 11
YYC12:37 pmCalgary
3h 33m
ORD5:10 pmChicago O'Hare Intl
Dec 17
ORD8:45 amChicago O'Hare Intl
3h 50m
YYC11:35 amCalgary
$506
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Calgary to Chicago O'Hare Intl Airport 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 diciembre 4, 2025.
Use the filters below to find and compare flights from Calgary to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

vie. 1/23

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

vie. 2/13

2:20 pm-5:15 pm

Nonstop3h 55m

$152

CalgaryChicago

YYC - ORD

YYCORD

Calgary

sáb. 1/17

5:35 am-2:55 pm

1 stop8h 20m

Chicago O'Hare Intl

sáb. 1/24

2:00 pm-8:59 pm

1 stop7h 59m

$160

CalgaryChicago

YYC - ORD

YYCORD

Calgary

sáb. 1/17

5:35 am-2:55 pm

1 stop8h 20m

Chicago O'Hare Intl

sáb. 1/24

7:15 am-8:59 pm

2 stops14h 44m

$168

CalgaryChicago

YYC - ORD

YYCORD

Calgary

sáb. 1/17

5:35 am-2:55 pm

1 stop8h 20m

Chicago O'Hare Intl

sáb. 1/24

2:00 pm-8:59 pm

1 stop7h 59m

$179

CalgaryChicago

YYC - ORD

YYCORD

Calgary

jue. 1/8

5:35 am-3:10 pm

1 stop8h 35m

Chicago O'Hare Intl

lun. 1/12

3:55 pm-12:14 am

1 stop9h 19m

$182

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mié. 1/21

12:37 pm-5:08 pm

Nonstop3h 31m

Chicago O'Hare Intl

mar. 2/10

8:45 am-11:35 am

Nonstop3h 50m

$188

CalgaryChicago

YYC - ORD

YYCORD

Calgary

vie. 1/23

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

mié. 2/11

1:45 pm-10:46 pm

1 stop10h 01m

$193

CalgaryChicago

YYC - ORD

YYCORD

Calgary

vie. 1/23

7:35 pm-4:51 pm

1 stop20h 16m

Chicago O'Hare Intl

lun. 2/9

2:20 pm-5:15 pm

Nonstop3h 55m

$194

CalgaryChicago

YYC - ORD

YYCORD

Calgary

sáb. 1/17

5:35 am-8:10 pm

2 stops13h 35m

Chicago O'Hare Intl

sáb. 1/24

7:15 am-8:59 pm

2 stops14h 44m

$198

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mar. 1/20

12:30 am-6:27 pm

1 stop16h 57m

Chicago O'Hare Intl

vie. 2/13

2:20 pm-5:15 pm

Nonstop3h 55m

$199

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around $185.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Sunday when prices can be found for as low as $182. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Calgary because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $471.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Calgary in the morning is the least expensive time of day to depart. momondo users have found prices as low as $342 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $782. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Calgary to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Calgary when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $255 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Calgary for as low as $161 on momondo.

What cabin class options are available on Calgary to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Calgary to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Calgary to Chicago O'Hare Intl Airport flight prices changed over time?

As of December 2025, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 28% cheaper when compared to flights at the same time last year.

When to book flights from Calgary to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Calgary to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Calgary to Chicago O'Hare Intl Airport (YYC to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Calgary to Chicago O'Hare Intl Airport

Best Price Found

$179

Fastest flight time

3h 20m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Calgary in the past 72 hours is $179. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $171.
The fastest flight from Calgary to Chicago O'Hare Intl Airport takes 3h 20m
Direct flights go from Calgary to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is Calgary to Chicago O'Hare Intl by plane?

    The distance between Calgary and Chicago O'Hare Intl is about 1381.9 mi. Typically, this will take 3h 20m by plane in normal conditions.

  • When did momondo last update prices for flights from Calgary Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Calgary Airport to Chicago O'Hare Intl Airport are updated daily.

  • How many operators does momondo search for flights from Calgary Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Calgary Airport to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Calgary Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Calgary to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Calgary to Chicago O'Hare Intl Airport?

Best airlines flying from Calgary to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Calgary to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $101Free CancellationRating
7.1
10,500 reviews
Search Air Canada flights
WestJetPriceFrom $138Free CancellationRating
7.2
3,191 reviews
Search WestJet flights
American AirlinesPriceFrom $185Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
United AirlinesPriceFrom $232Free CancellationRating
7.4
9,063 reviews
Search United Airlines flights

  • United Airlines Flights From Calgary to Chicago O'Hare Intl Airport

    United Airlines flight deals from Calgary to Chicago O'Hare Intl Airport start from $232 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $464 round-trip - but some users have found much cheaper deals with momondo.

  • Air Canada Flights From Calgary to Chicago O'Hare Intl Airport

    Across 10,500 Air Canada reviews on momondo, the average score is 7.1/10. Air Canada flies from Calgary to Chicago O'Hare Intl Airport about 7 times each week, with ticket deals ranging from $101 to $338. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
Benton Harbor

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. 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 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?

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 O'Hare Intl Airport 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
sáb. 1/3
sáb. 1/10
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago