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Cheap flights from Calgary to Chicago from $113

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 10/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Calgary to Chicago (YYC-ORD)

Cheap round-trip flights

Logo
1:10 am - 9:09 amYYC-ORD
6h 59m1 stop
Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$159
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Thu, Oct 16 - Fri, Oct 24
Air Canada Logo
1:10 am - 9:09 amYYC-ORD
6h 59m1 stop
Air Canada Logo
3:50 pm - 11:22 pmORD-YYC
8h 32m1 stop
$163Air Canada
Find Deal
Thu, Oct 16 - Fri, Oct 24
WestJet Logo
9:30 pm - 12:39 pmYYC-ORD
14h 09m1 stop
WestJet Logo
2:20 pm - 5:15 pmORD-YYC
3h 55mnonstop
$169WestJet
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Fri, Oct 17 - Sun, Oct 26
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$174WestJet
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Fri, Oct 17 - Sun, Oct 19
United Airlines Logo
12:37 pm - 5:10 pmYYC-ORD
3h 33mnonstop
United Airlines Logo
1:55 pm - 9:53 pmORD-YYC
8h 58m1 stop
$189United Airlines
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Tue, Oct 28 - Fri, Oct 31
United Airlines Logo
12:37 pm - 5:10 pmYYC-ORD
3h 33mnonstop
United Airlines Logo
7:10 am - 9:53 pmORD-YYC
15h 43m1 stop
$190United Airlines
Find Deal
Fri, Oct 31 - Tue, Nov 4
American Airlines Logo
12:54 pm - 12:30 pmYYC-ORD
22h 36m1 stop
American Airlines Logo
9:49 am - 12:34 pmORD-YYC
3h 45mnonstop
$208American Airlines
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Fri, Oct 10 - Wed, Oct 15
American Airlines Logo
6:45 am - 7:15 pmYYC-ORD
11h 30m1 stop
American Airlines Logo
2:55 pm - 9:54 pmORD-YYC
7h 59m1 stop
$212American Airlines
Find Deal
Tue, Sep 30 - Tue, Oct 7
Delta Logo
2:59 pm - 9:19 pmYYC-ORD
5h 20m1 stop
Delta Logo
6:08 am - 1:54 pmORD-YYC
8h 46m1 stop
$224Delta
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Fri, Oct 17 - Fri, Oct 24
Delta Logo
2:59 pm - 9:19 pmYYC-ORD
5h 20m1 stop
Delta Logo
8:57 am - 11:02 pmORD-YYC
15h 05m2 stops
$225Delta
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Sat, Nov 1 - Tue, Nov 4

Air Canada flights from Calgary to Chicago O'Hare Intl Airport

Our best Air Canada deals on Calgary to Chicago O'Hare Intl Airport flight tickets
Air Canada
Oct 16
YYC1:10 amCalgary
6h 59m
1 stop
ORD9:09 amChicago O'Hare Intl
Oct 24
ORD3:50 pmChicago O'Hare Intl
8h 32m
1 stop
YYC11:22 pmCalgary
$163
Find similar
Air Canada
Oct 15
YYC1:10 amCalgary
7h 41m
1 stop
ORD9:51 amChicago O'Hare Intl
Oct 23
ORD8:40 amChicago O'Hare Intl
8h 10m
1 stop
YYC3:50 pmCalgary
$178
Find similar
Air Canada
Oct 16
YYC1:10 amCalgary
6h 59m
1 stop
ORD9:09 amChicago O'Hare Intl
Oct 24
ORD3:35 pmChicago O'Hare Intl
8h 41m
1 stop
YYC11:16 pmCalgary
$185
Find similar

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
Oct 17
YYC9:30 pmCalgary
14h 09m
1 stop
ORD12:39 pmChicago O'Hare Intl
Oct 26
ORD2:20 pmChicago O'Hare Intl
3h 55m
YYC5:15 pmCalgary
$169
Find similar
WestJet
Oct 17
YYC12:15 pmCalgary
3h 28m
ORD4:43 pmChicago O'Hare Intl
Oct 19
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
$174
Find similar
WestJet
Oct 17
YYC8:15 pmCalgary
15h 24m
1 stop
ORD12:39 pmChicago O'Hare Intl
Oct 19
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
$175
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 September 3, 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

Thu 10/16

1:10 am-9:09 am

1 stop6h 59m

Chicago O'Hare Intl

Fri 10/24

5:30 pm-8:19 pm

Nonstop3h 49m

$159

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 10/16

1:10 am-9:09 am

1 stop6h 59m

Chicago O'Hare Intl

Fri 10/24

3:50 pm-11:22 pm

1 stop8h 32m

$163

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/17

9:30 pm-12:39 pm

1 stop14h 09m

Chicago O'Hare Intl

Sun 10/26

2:20 pm-5:15 pm

Nonstop3h 55m

$169

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

$174

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 10/28

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Fri 10/31

1:55 pm-9:53 pm

1 stop8h 58m

$189

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/31

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Tue 11/4

7:10 am-9:53 pm

1 stop15h 43m

$190

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/10

12:54 pm-12:30 pm

1 stop22h 36m

Chicago O'Hare Intl

Wed 10/15

9:49 am-12:34 pm

Nonstop3h 45m

$208

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 9/30

6:45 am-7:15 pm

1 stop11h 30m

Chicago O'Hare Intl

Tue 10/7

2:55 pm-9:54 pm

1 stop7h 59m

$212

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/17

2:59 pm-9:19 pm

1 stop5h 20m

Chicago O'Hare Intl

Fri 10/24

6:08 am-1:54 pm

1 stop8h 46m

$224

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 11/1

2:59 pm-9:19 pm

1 stop5h 20m

Chicago O'Hare Intl

Tue 11/4

8:57 am-11:02 pm

2 stops15h 05m

$225

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 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 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 $169. 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 $478.

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 $348 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $688. 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 $277 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 $204 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 September 2025, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 23% 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

$219

Fastest flight time

3h 25m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Calgary in the past 72 hours is $219. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $235.
The fastest flight from Calgary to Chicago O'Hare Intl Airport takes 3h 25m
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 25m 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 $109Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
WestJetPriceFrom $138Free CancellationRating
7.2
3,082 reviews
Search WestJet flights
United AirlinesPriceFrom $239Free CancellationRating
7.4
8,937 reviews
Search United Airlines flights
American AirlinesPriceFrom $250Free CancellationRating
7.2
10,000 reviews
Search American 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 $239 round-trip. Over the 10 United Airlines flights for this route in a normal week, average airfare is usually $468 round-trip - but some users have found much cheaper deals with momondo.

  • WestJet Flights From Calgary to Chicago O'Hare Intl Airport

    Across 3,082 WestJet reviews on momondo, the average score is 7.2/10. WestJet flies from Calgary to Chicago O'Hare Intl Airport about 3 times each week, with ticket deals ranging from $138 to $236. 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
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
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.

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