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Cheap flights from Calgary to Chicago from $85

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 6/2. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
12:15 pm - 4:43 pm
YYC
-
ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pm
ORD
-
YYC
3h 49mnonstop
$147WestJet
Thu, May 21 - Sat, May 30
WestJet Logo
12:15 pm - 4:43 pm
YYC
-
ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pm
ORD
-
YYC
3h 49mnonstop
$148WestJet
Sun, May 24 - Sat, May 30
United Airlines Logo
2:13 pm - 11:59 pm
YYC
-
ORD
8h 46m1 stop
United Airlines Logo
8:45 am - 11:35 am
ORD
-
YYC
3h 50mnonstop
$161United Airlines
Tue, Feb 3 - Wed, Feb 4
Air Canada Logo
8:00 am - 5:48 pm
YYC
-
ORD
8h 48m1 stop
Air Canada Logo
3:55 pm - 12:14 am
ORD
-
YYC
9h 19m1 stop
$176Air Canada
Tue, Feb 3 - Wed, Feb 4
United Airlines Logo
6:15 am - 11:59 pm
YYC
-
ORD
16h 44m1 stop
United Airlines Logo
8:45 am - 11:35 am
ORD
-
YYC
3h 50mnonstop
$182United Airlines
Mon, Feb 2 - Tue, Feb 3
Multiple Airlines Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
Multiple Airlines Logo
4:19 pm - 9:45 pm
ORD
-
YYC
30h 26m1 stop
$183Multiple Airlines
Fri, Jan 23 - Sun, Feb 1
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
$184Air Canada
Thu, Jan 22 - Mon, Feb 2
Multiple Airlines Logo
7:00 am - 5:44 pm
YYC
-
ORD
9h 44m1 stop
Multiple Airlines Logo
2:20 pm - 5:15 pm
ORD
-
YYC
3h 55mnonstop
$185Multiple Airlines
Fri, Jan 16 - Fri, Jan 23
Multiple Airlines Logo
6:30 am - 9:45 pm
YYC
-
ORD
14h 15m2 stops
Multiple Airlines Logo
2:20 pm - 5:15 pm
ORD
-
YYC
3h 55mnonstop
$187Multiple Airlines
Fri, Jan 23 - Fri, Jan 30
United Airlines Logo
6:15 am - 5:04 pm
YYC
-
ORD
9h 49m1 stop
United Airlines Logo
1:55 pm - 9:53 pm
ORD
-
YYC
8h 58m1 stop
$188United Airlines
Tue, Jan 13 - Tue, Jan 20

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
May 21
YYC12:15 pmCalgary
3h 28m
ORD4:43 pmChicago O'Hare Intl
May 30
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
$147
Find similar
WestJet
May 24
YYC12:15 pmCalgary
3h 28m
ORD4:43 pmChicago O'Hare Intl
May 30
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
$148
Find similar
WestJet
Jan 23
YYC9:00 amCalgary
3h 35m
ORD1:35 pmChicago O'Hare Intl
Feb 2
ORD2:20 pmChicago O'Hare Intl
3h 55m
YYC5:15 pmCalgary
$198
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
Feb 3
YYC2:13 pmCalgary
8h 46m
1 stop
ORD11:59 pmChicago O'Hare Intl
Feb 4
ORD8:45 amChicago O'Hare Intl
3h 50m
YYC11:35 amCalgary
$161
Find similar
United Airlines
Feb 2
YYC6:15 amCalgary
16h 44m
1 stop
ORD11:59 pmChicago O'Hare Intl
Feb 3
ORD8:45 amChicago O'Hare Intl
3h 50m
YYC11:35 amCalgary
$182
Find similar
United Airlines
Jan 13
YYC6:15 amCalgary
9h 49m
1 stop
ORD5:04 pmChicago O'Hare Intl
Jan 20
ORD1:55 pmChicago O'Hare Intl
8h 58m
1 stop
YYC9:53 pmCalgary
$188
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 December 18, 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 5/21

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sat 5/30

5:30 pm-8:19 pm

Nonstop3h 49m

$147

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 5/24

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sat 5/30

5:30 pm-8:19 pm

Nonstop3h 49m

$148

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 2/3

2:13 pm-11:59 pm

1 stop8h 46m

Chicago O'Hare Intl

Wed 2/4

8:45 am-11:35 am

Nonstop3h 50m

$161

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 2/3

8:00 am-5:48 pm

1 stop8h 48m

Chicago O'Hare Intl

Wed 2/4

3:55 pm-12:14 am

1 stop9h 19m

$176

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 2/2

6:15 am-11:59 pm

1 stop16h 44m

Chicago O'Hare Intl

Tue 2/3

8:45 am-11:35 am

Nonstop3h 50m

$182

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 1/23

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Sun 2/1

4:19 pm-9:45 pm

1 stop30h 26m

$183

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/22

5:35 am-3:10 pm

1 stop8h 35m

Chicago O'Hare Intl

Mon 2/2

3:55 pm-12:14 am

1 stop9h 19m

$184

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 1/16

7:00 am-5:44 pm

1 stop9h 44m

Chicago O'Hare Intl

Fri 1/23

2:20 pm-5:15 pm

Nonstop3h 55m

$185

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 1/23

6:30 am-9:45 pm

2 stops14h 15m

Chicago O'Hare Intl

Fri 1/30

2:20 pm-5:15 pm

Nonstop3h 55m

$187

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 1/13

6:15 am-5:04 pm

1 stop9h 49m

Chicago O'Hare Intl

Tue 1/20

1:55 pm-9:53 pm

1 stop8h 58m

$188

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 $174. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday 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 $473.

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 $340 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $781. 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 $257 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 $165 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 29% 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

$154

Fastest flight time

3h 27m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Calgary in the past 72 hours is $154. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $195.
The fastest flight from Calgary to Chicago O'Hare Intl Airport takes 3h 27m
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 27m 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
10,534 reviews
Search Air Canada flights
WestJetPriceFrom $138Free CancellationRating
7.2
3,205 reviews
Search WestJet flights
American AirlinesPriceFrom $185Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
9,095 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 $218 round-trip. Over the 6 United Airlines flights for this route in a normal week, average airfare is usually $461 round-trip - but some users have found much cheaper deals with momondo.

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

    Across 11,054 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Calgary to Chicago O'Hare Intl Airport about 1 time each week, with ticket deals ranging from $185 to $376. 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
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
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.

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