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Cheap flights from Calgary to Chicago from $156

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.
Air Canada Logo
12:50 am - 9:00 amYYC  Calgary-ORD Chicago O'Hare Intl
7h 10m1 stop Toronto Pearson Intl
Air Canada Logo
8:45 am - 3:57 pmORD  Chicago O'Hare Intl-YYC Calgary
8h 12m1 stop Montreal Pierre Elliott Trudeau Intl
$252Air Canada
Mon, Oct 12 - Tue, Oct 20
Air Canada Logo
6:00 am - 3:38 pmYYC  Calgary-ORD Chicago O'Hare Intl
8h 38m1 stop Toronto Pearson Intl
Air Canada Logo
3:45 pm - 1:50 amORD  Chicago O'Hare Intl-YYC Calgary
10h 05m1 stop Montreal Pierre Elliott Trudeau Intl
$252Air Canada
Thu, Oct 29 - Tue, Nov 3
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
$255United Airlines
Sat, Oct 31 - Sun, Nov 8
United Airlines Logo
6:00 am - 10:46 pmYYC  Calgary-ORD Chicago O'Hare Intl
15h 46m1 stop Denver Intl
United Airlines Logo
8:40 am - 11:35 amORD  Chicago O'Hare Intl-YYC Calgary
3h 55mnonstop
$256United Airlines
Thu, Oct 29 - Fri, Oct 30
American Airlines Logo
1:51 pm - 6:36 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 45mnonstop
American Airlines Logo
10:00 am - 12:51 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 51mnonstop
$257American Airlines
Wed, Oct 28 - Fri, Oct 30
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
$259WestJet
Thu, Oct 15 - Thu, Oct 22
Multiple Airlines Logo
12:00 pm - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 40mnonstop
Multiple Airlines Logo
5:46 pm - 10:43 amORD  Chicago O'Hare Intl-YYC Calgary
17h 57m1 stop Seattle/Tacoma Intl
$260Multiple Airlines
Thu, Oct 22 - Tue, Oct 27
Alaska Airlines Logo
9:07 am - 12:10 pmYYC  Calgary-ORD Chicago O'Hare Intl
27h 03m2 stops Seattle/Tacoma Intl Portland
Alaska Airlines Logo
9:00 am - 10:37 pmORD  Chicago O'Hare Intl-YYC Calgary
13h 37m1 stop Seattle/Tacoma Intl
$261Alaska Airlines
Fri, Dec 4 - Fri, Dec 11
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
$267WestJet
Sun, Oct 18 - Thu, Oct 22
American Airlines Logo
7:00 am - 11:29 amYYC  Calgary-ORD Chicago O'Hare Intl
3h 29mnonstop
American Airlines Logo
5:00 am - 11:59 amORD  Chicago O'Hare Intl-YYC Calgary
7h 59m1 stop Dallas/Fort Worth
$282American Airlines
Thu, Oct 1 - Tue, Oct 6

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Delta flights from Calgary to Chicago O'Hare Intl Airport

Our best Delta deals on Calgary to Chicago O'Hare Intl Airport flight tickets
Delta
Oct 29
YYC6:35 amCalgary
10h 35m
1 stop
ORD6:10 pmChicago O'Hare Intl
Nov 5
ORD12:30 pmChicago O'Hare Intl
12h 40m
2 stops
YYC1:10 amCalgary
$261
Delta
Oct 3
YYC6:35 amCalgary
6h 54m
1 stop
ORD2:29 pmChicago O'Hare Intl
Oct 6
ORD2:03 pmChicago O'Hare Intl
10h 07m
1 stop
YYC11:10 pmCalgary
$272
Delta
Oct 1
YYC6:35 amCalgary
9h 24m
1 stop
ORD4:59 pmChicago O'Hare Intl
Oct 5
ORD2:05 pmChicago O'Hare Intl
10h 01m
1 stop
YYC11:06 pmCalgary
$283

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
Oct 31
YYC12:37 pmCalgary
3h 33m
ORD5:10 pmChicago O'Hare Intl
Nov 8
ORD8:40 amChicago O'Hare Intl
4h 55m
YYC1:35 pmCalgary
$255
United Airlines
Oct 30
YYC12:37 pmCalgary
3h 33m
ORD5:10 pmChicago O'Hare Intl
Nov 2
ORD8:40 amChicago O'Hare Intl
4h 55m
YYC1:35 pmCalgary
$268
United Airlines
Oct 14
YYC6:00 amCalgary
15h 46m
1 stop
ORD10:46 pmChicago O'Hare Intl
Oct 21
ORD8:40 amChicago O'Hare Intl
3h 48m
YYC11:28 amCalgary
$273

momondo Fare Finder

 
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

Mon 10/12

12:50 am-9:00 am

1 stop7h 10m

Chicago O'Hare Intl

Tue 10/20

8:45 am-3:57 pm

1 stop8h 12m

$252

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 10/29

6:00 am-3:38 pm

1 stop8h 38m

Chicago O'Hare Intl

Tue 11/3

3:45 pm-1:50 am

1 stop10h 05m

$252

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sat 10/31

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Sun 11/8

8:40 am-1:35 pm

Nonstop4h 55m

$255

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 10/29

6:00 am-10:46 pm

1 stop15h 46m

Chicago O'Hare Intl

Fri 10/30

8:40 am-11:35 am

Nonstop3h 55m

$256

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Wed 10/28

1:51 pm-6:36 pm

Nonstop3h 45m

Chicago O'Hare Intl

Fri 10/30

10:00 am-12:51 pm

Nonstop3h 51m

$257
Quickest round-trip

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 10/15

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Thu 10/22

5:30 pm-8:25 pm

Nonstop3h 55m

$259

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 10/22

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 10/27

5:46 pm-10:43 am

1 stop17h 57m

$260

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 12/4

9:07 am-12:10 pm

2 stops27h 03m

Chicago O'Hare Intl

Fri 12/11

9:00 am-10:37 pm

1 stop13h 37m

$261

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sun 10/18

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Thu 10/22

5:30 pm-8:25 pm

Nonstop3h 55m

$267

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 10/1

7:00 am-11:29 am

Nonstop3h 29m

Chicago O'Hare Intl

Tue 10/6

5:00 am-11:59 am

1 stop7h 59m

$282

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?

Prices are currently low for flights on this route.

Typical prices usually range from $283 to $371.
The lowest price recently found on this route was $252.

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

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around $253.

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 $391. 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 $628.

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 $386 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $829. 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 $307 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 $221 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.

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

As of September 2026, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 11% 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

$156

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 $156. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $252.
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
United AirlinesPriceFrom $135Free CancellationRating
7.4
10,214 reviews
Search United Airlines flights
Air CanadaPriceFrom $149Free CancellationRating
7.1
11,640 reviews
Search Air Canada flights
WestJetPriceFrom $163Free CancellationRating
7.2
3,446 reviews
Search WestJet flights
American AirlinesPriceFrom $208Free CancellationRating
7.1
12,076 reviews
Search American Airlines flights
DeltaPriceFrom $253Free CancellationRating
7.8
8,579 reviews
Search Delta 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 $135 round-trip. Over the 13 United Airlines flights for this route in a normal week, average airfare is usually $355 round-trip - but some users have found much cheaper deals with momondo.

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

    Across 11,640 Air Canada reviews on momondo, the average score is 7.1/10. Air Canada flies from Calgary to Chicago O'Hare Intl Airport about 14 times each week, with ticket deals ranging from $149 to $335. 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
Rosemont
Gurnee
Oak Brook
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Evanston
Skokie

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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