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Cheap flights from Calgary to Chicago from C$ 140

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 23/1. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
WestJet Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
C$ 243WestJet
Find Deal
Fri, 30 Jan - Mon, 2 Mar
Multiple Airlines Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
Multiple Airlines Logo
1:52 p.m. - 10:46 p.m.ORD-YYC
9h 54m1 stop
C$ 288Multiple Airlines
Find Deal
Fri, 30 Jan - Sat, 28 Feb
Multiple Airlines Logo
12:37 p.m. - 5:10 p.m.YYC-ORD
3h 33mdirect
Multiple Airlines Logo
3:55 p.m. - 11:58 p.m.ORD-YYC
9h 03m1 stop
C$ 302Multiple Airlines
Find Deal
Wed, 10 Dec - Mon, 15 Dec
Air Canada Logo
5:45 a.m. - 2:55 p.m.YYC-ORD
8h 10m1 stop
Air Canada Logo
2:00 p.m. - 8:39 p.m.ORD-YYC
7h 39m1 stop
C$ 303Air Canada
Find Deal
Sat, 31 Jan - Sat, 28 Feb
Delta Logo
7:35 a.m. - 9:56 p.m.YYC-ORD
13h 21m2 stops
Delta Logo
8:50 a.m. - 1:40 p.m.ORD-YYC
5h 50m1 stop
C$ 310Delta
Find Deal
Thu, 11 Dec - Mon, 15 Dec
American Airlines Logo
1:14 p.m. - 5:45 p.m.YYC-ORD
3h 31mdirect
American Airlines Logo
9:40 a.m. - 12:37 p.m.ORD-YYC
3h 57mdirect
C$ 312American Airlines
Find Deal
Tue, 10 Mar - Tue, 31 Mar
Air Canada Logo
5:35 a.m. - 3:10 p.m.YYC-ORD
8h 35m1 stop
Air Canada Logo
2:00 p.m. - 8:39 p.m.ORD-YYC
7h 39m1 stop
C$ 313Air Canada
Find Deal
Fri, 30 Jan - Sat, 28 Feb
Delta Logo
6:30 a.m. - 5:56 p.m.YYC-ORD
10h 26m1 stop
Delta Logo
12:15 p.m. - 11:15 p.m.ORD-YYC
12h 00m2 stops
C$ 338Delta
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Thu, 29 Jan - Sat, 28 Feb
United Airlines Logo
12:37 p.m. - 5:10 p.m.YYC-ORD
3h 33mdirect
United Airlines Logo
8:45 a.m. - 11:35 a.m.ORD-YYC
3h 50mdirect
C$ 362United Airlines
Find Deal
Wed, 10 Dec - Mon, 15 Dec
United Airlines Logo
12:37 p.m. - 5:10 p.m.YYC-ORD
3h 33mdirect
United Airlines Logo
8:45 a.m. - 11:35 a.m.ORD-YYC
3h 50mdirect
C$ 391United Airlines
Find Deal
Tue, 25 Nov - Sun, 30 Nov

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
30 Jan
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
2 Mar
ORD2:20 p.m.Chicago O'Hare Intl
3h 55m
YYC5:15 p.m.Calgary
C$ 243
Find similar
WestJet
12 Dec
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
19 Dec
ORD2:20 p.m.Chicago O'Hare Intl
3h 55m
YYC5:15 p.m.Calgary
C$ 429
Find similar
WestJet
12 Dec
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
19 Dec
ORD2:20 p.m.Chicago O'Hare Intl
3h 55m
YYC5:15 p.m.Calgary
C$ 435
Find similar

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
31 Jan
YYC5:45 a.m.Calgary
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
28 Feb
ORD2:00 p.m.Chicago O'Hare Intl
7h 39m
1 stop
YYC8:39 p.m.Calgary
C$ 303
Find similar
Air Canada
30 Jan
YYC5:35 a.m.Calgary
8h 35m
1 stop
ORD3:10 p.m.Chicago O'Hare Intl
28 Feb
ORD2:00 p.m.Chicago O'Hare Intl
7h 39m
1 stop
YYC8:39 p.m.Calgary
C$ 313
Find similar
Air Canada
21 Nov
YYC9:00 a.m.Calgary
8h 55m
1 stop
ORD6:55 p.m.Chicago O'Hare Intl
24 Nov
ORD4:50 p.m.Chicago O'Hare Intl
8h 24m
1 stop
YYC12:14 a.m.Calgary
C$ 355
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 96,600 searches. Data last updated 29 October 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

Fri 30/1

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Mon 2/3

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 243

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 30/1

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Sat 28/2

1:52 p.m.-10:46 p.m.

1 stop9h 54m

C$ 288

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 10/12

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

Chicago O'Hare Intl

Mon 15/12

3:55 p.m.-11:58 p.m.

1 stop9h 03m

C$ 302

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 31/1

5:45 a.m.-2:55 p.m.

1 stop8h 10m

Chicago O'Hare Intl

Sat 28/2

2:00 p.m.-8:39 p.m.

1 stop7h 39m

C$ 303

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 11/12

7:35 a.m.-9:56 p.m.

2 stops13h 21m

Chicago O'Hare Intl

Mon 15/12

8:50 a.m.-1:40 p.m.

1 stop5h 50m

C$ 310

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 10/3

1:14 p.m.-5:45 p.m.

Nonstop3h 31m

Chicago O'Hare Intl

Tue 31/3

9:40 a.m.-12:37 p.m.

Nonstop3h 57m

C$ 312

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 30/1

5:35 a.m.-3:10 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Sat 28/2

2:00 p.m.-8:39 p.m.

1 stop7h 39m

C$ 313

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 29/1

6:30 a.m.-5:56 p.m.

1 stop10h 26m

Chicago O'Hare Intl

Sat 28/2

12:15 p.m.-11:15 p.m.

2 stops12h 00m

C$ 338

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 10/12

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

Chicago O'Hare Intl

Mon 15/12

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

C$ 362

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 25/11

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

Chicago O'Hare Intl

Sun 30/11

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

C$ 391

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

In general, May is the cheapest month to fly from Calgary to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 229. The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around C$ 257.

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 C$ 660. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Calgary to Chicago O'Hare Intl Airport for around C$ 976.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the evening is the cheapest time of day to fly from Calgary to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 490. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 1,554 on average. Flights to Chicago O'Hare Intl Airport from Calgary at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

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 C$ 376 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 C$ 225 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.

Can stopping save me money on Calgary to Chicago O'Hare Intl Airport flights?

You could potentially save up to 7% 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 October 2025, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 30% 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

C$ 328

Fastest flight time

3h 28m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Calgary in the past 72 hours is C$ 328. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 408.
The fastest flight from Calgary to Chicago O'Hare Intl Airport takes 3h 28m
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?

    There are 2223.9 km between Calgary and Chicago O'Hare Intl. 3h 31m is a normal flight duration for this route.

  • 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 were last updated today.

  • 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?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • 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 C$ 151Free CancellationRating
7.1
10,372 reviews
Search Air Canada flights
WestJetPriceFrom C$ 178Free CancellationRating
7.2
3,148 reviews
Search WestJet flights
DeltaPriceFrom C$ 186Free CancellationRating
7.9
7,992 reviews
Search Delta flights
American AirlinesPriceFrom C$ 187Free CancellationRating
7.2
11,032 reviews
Search American Airlines flights
United AirlinesPriceFrom C$ 217Free CancellationRating
7.4
8,999 reviews
Search United Airlines flights

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

    Across 2 Delta flights from Calgary to Chicago O'Hare Intl Airport this week, the average price was C$ 349, with the best Delta deals starting from C$ 186 round-trip. 7,994 users have rated Delta on momondo, with an average score of 7.9/10.

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

    The best United Airlines deal for Calgary to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was C$ 217, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at C$ 522 round-trip. United Airlines operates 6 flights out of Calgary into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 9,001 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Schaumburg
Rosemont
Hoffman Estates
Northbrook
Tinley Park
Munster
Hammond
Naperville
Glenview
Great Lakes
Wheeling
Des Plaines
Elk Grove Village
Harvard
Merrillville
Oak Brook
Elmhurst
Kenosha
Skokie
Rockford

Why use momondo?

Why should I use momondo to find a flight deal from Calgary to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Calgary to Chicago. momondo saves you time and could save you money on your trip.

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?

Yes momondo offers price alerts on flights to Chicago from Calgary. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago O'Hare Intl Airport trip

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