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Cheap flights from Calgary to Chicago from $176

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 9/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
12:00 pm - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 55mnonstop
$231WestJet
Sun, Sep 6 - Sun, Sep 13
WestJet Logo
12:00 pm - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 55mnonstop
$234WestJet
Sat, Sep 5 - Fri, Sep 11
Air Canada Logo
6:00 am - 3:38 pmYYC  Calgary-ORD Chicago O'Hare Intl
8h 38m1 stop Toronto Pearson Intl
Air Canada Logo
10:15 am - 8:59 pmORD  Chicago O'Hare Intl-YYC Calgary
10h 44m1 stop Toronto Pearson Intl
$245Air Canada
Fri, Oct 30 - Mon, Nov 2
Air Canada Logo
7:00 am - 2:38 pmYYC  Calgary-ORD Chicago O'Hare Intl
7h 38m1 stop Toronto Pearson Intl
Air Canada Logo
10:15 am - 8:59 pmORD  Chicago O'Hare Intl-YYC Calgary
10h 44m1 stop Toronto Pearson Intl
$246Air Canada
Sun, Nov 22 - Sat, Nov 28
United Airlines Logo
12:37 pm - 5:10 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 33mnonstop
United Airlines Logo
8:40 am - 1:35 pmORD  Chicago O'Hare Intl-YYC Calgary
4h 55mnonstop
$252United Airlines
Fri, Oct 30 - Mon, Nov 2
United Airlines Logo
12:37 pm - 5:10 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 33mnonstop
United Airlines Logo
8:40 am - 1:35 pmORD  Chicago O'Hare Intl-YYC Calgary
4h 55mnonstop
$252United Airlines
Fri, Oct 30 - Thu, Nov 5
American Airlines Logo
7:00 am - 11:29 amYYC  Calgary-ORD Chicago O'Hare Intl
3h 29mnonstop
American Airlines Logo
1:46 pm - 9:44 pmORD  Chicago O'Hare Intl-YYC Calgary
8h 58m1 stop Dallas/Fort Worth
$259American Airlines
Sat, Oct 3 - Sat, Oct 24
Delta Logo
6:45 am - 3:30 pmYYC  Calgary-ORD Chicago O'Hare Intl
7h 45m1 stop Minneapolis St Paul
Delta Logo
2:05 pm - 11:06 pmORD  Chicago O'Hare Intl-YYC Calgary
10h 01m1 stop Salt Lake City
$259Delta
Sat, Sep 5 - Fri, Sep 11
Delta Logo
6:45 am - 5:41 pmYYC  Calgary-ORD Chicago O'Hare Intl
9h 56m1 stop Minneapolis St Paul
Delta Logo
2:05 pm - 11:06 pmORD  Chicago O'Hare Intl-YYC Calgary
10h 01m1 stop Salt Lake City
$260Delta
Sun, Sep 6 - Fri, Sep 11
American Airlines Logo
7:00 am - 11:29 amYYC  Calgary-ORD Chicago O'Hare Intl
3h 29mnonstop
American Airlines Logo
8:30 pm - 11:29 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 59mnonstop
$274American Airlines
Wed, Sep 23 - Sun, Sep 27

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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 30
YYC6:00 amCalgary
8h 38m
1 stop
ORD3:38 pmChicago O'Hare Intl
Nov 2
ORD10:15 amChicago O'Hare Intl
10h 44m
1 stop
YYC8:59 pmCalgary
$245
Air Canada
Oct 30
YYC6:00 amCalgary
8h 38m
1 stop
ORD3:38 pmChicago O'Hare Intl
Nov 2
ORD10:15 amChicago O'Hare Intl
10h 44m
1 stop
YYC8:59 pmCalgary
$246
Air Canada
Sep 5
YYC5:50 amCalgary
8h 05m
1 stop
ORD2:55 pmChicago O'Hare Intl
Sep 11
ORD3:45 pmChicago O'Hare Intl
8h 12m
1 stop
YYC10:57 pmCalgary
$263

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
Sep 6
YYC12:00 pmCalgary
3h 40m
ORD4:40 pmChicago O'Hare Intl
Sep 13
ORD5:30 pmChicago O'Hare Intl
3h 55m
YYC8:25 pmCalgary
$231
WestJet
Sep 5
YYC12:00 pmCalgary
3h 40m
ORD4:40 pmChicago O'Hare Intl
Sep 11
ORD5:30 pmChicago O'Hare Intl
3h 55m
YYC8:25 pmCalgary
$234
WestJet
Sep 10
YYC12:00 pmCalgary
3h 40m
ORD4:40 pmChicago O'Hare Intl
Sep 13
ORD5:30 pmChicago O'Hare Intl
3h 55m
YYC8:25 pmCalgary
$240

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 August 10, 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 Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sun 9/6

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Sun 9/13

5:30 pm-8:25 pm

Nonstop3h 55m

$231

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sat 9/5

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Fri 9/11

5:30 pm-8:25 pm

Nonstop3h 55m

$234

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 10/30

6:00 am-3:38 pm

1 stop8h 38m

Chicago O'Hare Intl

Mon 11/2

10:15 am-8:59 pm

1 stop10h 44m

$245

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sun 11/22

7:00 am-2:38 pm

1 stop7h 38m

Chicago O'Hare Intl

Sat 11/28

10:15 am-8:59 pm

1 stop10h 44m

$246

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 10/30

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Mon 11/2

8:40 am-1:35 pm

Nonstop4h 55m

$252

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 10/30

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Thu 11/5

8:40 am-1:35 pm

Nonstop4h 55m

$252

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sat 10/3

7:00 am-11:29 am

Nonstop3h 29m

Chicago O'Hare Intl

Sat 10/24

1:46 pm-9:44 pm

1 stop8h 58m

$259

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sat 9/5

6:45 am-3:30 pm

1 stop7h 45m

Chicago O'Hare Intl

Fri 9/11

2:05 pm-11:06 pm

1 stop10h 01m

$259

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sun 9/6

6:45 am-5:41 pm

1 stop9h 56m

Chicago O'Hare Intl

Fri 9/11

2:05 pm-11:06 pm

1 stop10h 01m

$260
Quickest round-trip

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Wed 9/23

7:00 am-11:29 am

Nonstop3h 29m

Chicago O'Hare Intl

Sun 9/27

8:30 pm-11:29 pm

Nonstop3h 59m

$274

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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?

Prices are currently low for flights on this route.

Typical prices usually range from $265 to $411.
The lowest price recently found on this route was $231.

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 $335. This is often the case because there is less demand to fly during this day of the week. On the other hand, Tuesday 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 $580.

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 $381 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $846. 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 $292 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 10% 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 August 2026, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 16% more expensive 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

$216

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Calgary in the past 72 hours is $216. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $329.
The fastest flight from Calgary to Chicago O'Hare Intl Airport takes 2h 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 2h 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
11,456 reviews
Search Air Canada flights
United AirlinesPriceFrom $135Free CancellationRating
7.4
10,097 reviews
Search United Airlines flights
WestJetPriceFrom $163Free CancellationRating
7.2
3,430 reviews
Search WestJet flights
American AirlinesPriceFrom $208Free CancellationRating
7.1
11,897 reviews
Search American Airlines flights
DeltaPriceFrom $253Free CancellationRating
7.8
8,497 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 $253 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 10,097 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 $398. 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
Merrillville
Rockford
South Haven
Gurnee
Rosemont
Oak Brook
Orland Park
Naperville
Joliet
New Buffalo
Kenosha
Hammond
Racine
Aurora
Janesville
Elgin
South Holland
Evanston

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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