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Cheap flights from Calgary to Chicago from $152

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 7/9. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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 - 6:15 pm
ORD
-
YYC
4h 55mnonstop
$236WestJet
Fri, Oct 30 - Mon, Nov 2
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 6:15 pm
ORD
-
YYC
4h 55mnonstop
$237WestJet
Fri, Oct 30 - Mon, Nov 2
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 6:15 pm
ORD
-
YYC
4h 55mnonstop
$251WestJet
Fri, Oct 30 - Mon, Nov 2
Air Canada Logo
7:30 am - 5:43 pm
YYC
-
ORD
9h 13m
1 stop
Air Canada Logo
4:30 pm - 11:24 pm
ORD
-
YYC
7h 54m
1 stop
$253Air Canada
Tue, Nov 3 - Fri, Nov 6
American Airlines Logo
7:00 am - 11:29 am
YYC
-
ORD
3h 29mnonstop
American Airlines Logo
10:02 am - 12:58 pm
ORD
-
YYC
3h 56mnonstop
$254American Airlines
Sun, Jul 12 - Wed, Jul 15
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 18 - Sun, Sep 20
United Airlines Logo
12:28 pm - 5:04 pm
YYC
-
ORD
3h 36mnonstop
United Airlines Logo
6:00 am - 9:48 pm
ORD
-
YYC
16h 48m
1 stop
$264United Airlines
Thu, Jul 9 - Sun, Jul 12
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$267WestJet
Mon, Sep 21 - Mon, Sep 28
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$268WestJet
Tue, Sep 8 - Fri, Sep 11
Air Canada Logo
6:30 am - 2:55 pm
YYC
-
ORD
7h 25m
1 stop
Air Canada Logo
5:35 pm - 1:17 am
ORD
-
YYC
8h 42m
1 stop
$269Air Canada
Mon, Sep 21 - Mon, Sep 28

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

Our best American Airlines deals on Calgary to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jul 12
YYC7:00 amCalgary
3h 29m
ORD11:29 amChicago O'Hare Intl
Jul 15
ORD10:02 amChicago O'Hare Intl
3h 56m
YYC12:58 pmCalgary
$254
American Airlines
Jul 12
YYC6:45 amCalgary
15h 54m
1 stop
ORD11:39 pmChicago O'Hare Intl
Jul 15
ORD6:04 amChicago O'Hare Intl
16h 39m
1 stop
YYC9:43 pmCalgary
$279
American Airlines
Dec 24
YYC1:31 pmCalgary
3h 40m
ORD6:11 pmChicago O'Hare Intl
Dec 31
ORD9:50 amChicago O'Hare Intl
3h 58m
YYC12:48 pmCalgary
$319

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
Jul 9
YYC12:28 pmCalgary
3h 36m
ORD5:04 pmChicago O'Hare Intl
Jul 12
ORD6:00 amChicago O'Hare Intl
16h 48m
1 stop
YYC9:48 pmCalgary
$264
United Airlines
Jul 15
YYC6:00 amCalgary
14h 39m
1 stop
ORD9:39 pmChicago O'Hare Intl
Jul 19
ORD6:00 amChicago O'Hare Intl
16h 48m
1 stop
YYC9:48 pmCalgary
$278
United Airlines
Oct 30
YYC12:37 pmCalgary
3h 33m
ORD5:10 pmChicago O'Hare Intl
Nov 2
ORD9:47 pmChicago O'Hare Intl
17h 09m
1 stop
YYC1:56 pmCalgary
$281

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 June 29, 2026.
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

Cheapest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/30

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Mon 11/2

2:20 pm-6:15 pm

Nonstop4h 55m

$236

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/30

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Mon 11/2

2:20 pm-6:15 pm

Nonstop4h 55m

$237

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/30

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Mon 11/2

2:20 pm-6:15 pm

Nonstop4h 55m

$251

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 11/3

7:30 am-5:43 pm

1 stop9h 13m

Chicago O'Hare Intl

Fri 11/6

4:30 pm-11:24 pm

1 stop7h 54m

$253
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 7/12

7:00 am-11:29 am

Nonstop3h 29m

Chicago O'Hare Intl

Wed 7/15

10:02 am-12:58 pm

Nonstop3h 56m

$254

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 9/18

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Sun 9/20

5:30 pm-8:25 pm

Nonstop3h 55m

$261

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 7/9

12:28 pm-5:04 pm

Nonstop3h 36m

Chicago O'Hare Intl

Sun 7/12

6:00 am-9:48 pm

1 stop16h 48m

$264

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 9/21

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Mon 9/28

5:30 pm-8:25 pm

Nonstop3h 55m

$267

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 9/8

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Fri 9/11

5:30 pm-8:25 pm

Nonstop3h 55m

$268

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 9/21

6:30 am-2:55 pm

1 stop7h 25m

Chicago O'Hare Intl

Mon 9/28

5:35 pm-1:17 am

1 stop8h 42m

$269

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 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 May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around $252.

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 Friday when prices can be found for as low as $308. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday 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 $490.

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 $368 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $895. 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 from Calgary 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 $294 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 $217 on momondo.

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

There are 4 cabin classes available to choose from on Calgary to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

You could potentially save up to 12% on your flight if you consider stops on a Calgary to Chicago O'Hare Intl Airport flight.

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

As of June 2026, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 1% 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

$227

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 $227. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $367.
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

Frequently asked questions about flying from Calgary to Chicago O'Hare Intl Airport

  • 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 $135Free CancellationRating
7.1
11,269 reviews
Search Air Canada flights
United AirlinesPriceFrom $135Free CancellationRating
7.4
9,895 reviews
Search United Airlines flights
WestJetPriceFrom $138Free CancellationRating
7.2
3,385 reviews
Search WestJet flights
American AirlinesPriceFrom $208Free CancellationRating
7.1
11,771 reviews
Search American Airlines flights
DeltaPriceFrom $241Free CancellationRating
7.8
8,454 reviews
Search Delta flights

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

    Delta flight deals from Calgary to Chicago O'Hare Intl Airport start from $241 round-trip. Over the 4 Delta flights for this route in a normal week, average airfare is usually $371 round-trip - but some users have found much cheaper deals with momondo.

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

    Across 9,895 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Calgary to Chicago O'Hare Intl Airport about 5 times each week, with ticket deals ranging from $135 to $399. 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
Rosemont
Naperville
Orland Park
Oak Brook
New Buffalo
Joliet
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
South Holland

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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