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Cheap flights from Calgary to Chicago from C$ 128

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 16/3. 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

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Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
5:35 a.m. - 3:10 p.m.
YYC
-
ORD
8h 35m1 stop
Air Canada Logo
3:55 p.m. - 12:14 a.m.
ORD
-
YYC
9h 19m1 stop
C$ 213Air Canada
Wed, 28 Jan - Wed, 4 Feb
Air Canada Logo
5:35 a.m. - 3:10 p.m.
YYC
-
ORD
8h 35m1 stop
Air Canada Logo
3:55 p.m. - 12:14 a.m.
ORD
-
YYC
9h 19m1 stop
C$ 219Air Canada
Thu, 15 Jan - Wed, 21 Jan
United Airlines Logo
2:13 p.m. - 11:59 p.m.
YYC
-
ORD
8h 46m1 stop
United Airlines Logo
8:45 a.m. - 11:35 a.m.
ORD
-
YYC
3h 50mdirect
C$ 222United Airlines
Tue, 3 Feb - Wed, 4 Feb
Air Canada Logo
5:35 a.m. - 3:10 p.m.
YYC
-
ORD
8h 35m1 stop
Air Canada Logo
7:15 a.m. - 8:19 p.m.
ORD
-
YYC
14h 04m2 stops
C$ 230Air Canada
Wed, 28 Jan - Wed, 4 Feb
Air Canada Logo
8:00 a.m. - 5:48 p.m.
YYC
-
ORD
8h 48m1 stop
Air Canada Logo
3:55 p.m. - 12:14 a.m.
ORD
-
YYC
9h 19m1 stop
C$ 242Air Canada
Tue, 3 Feb - Wed, 4 Feb
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$ 249WestJet
Fri, 16 Jan - Mon, 19 Jan
United Airlines Logo
6:15 a.m. - 11:59 p.m.
YYC
-
ORD
16h 44m1 stop
United Airlines Logo
8:45 a.m. - 11:35 a.m.
ORD
-
YYC
3h 50mdirect
C$ 251United Airlines
Mon, 2 Feb - Tue, 3 Feb
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$ 252WestJet
Fri, 30 Jan - Fri, 6 Feb
United Airlines Logo
6:15 a.m. - 9:15 p.m.
YYC
-
ORD
14h 00m1 stop
United Airlines Logo
8:45 a.m. - 11:35 a.m.
ORD
-
YYC
3h 50mdirect
C$ 259United Airlines
Mon, 2 Feb - Wed, 4 Feb
WestJet Logo
12:15 p.m. - 4:43 p.m.
YYC
-
ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.
ORD
-
YYC
3h 49mdirect
C$ 275WestJet
Tue, 26 May - Sat, 30 May

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
13 Jan
YYC6:30 a.m.Calgary
9h 56m
2 stops
ORD5:26 p.m.Chicago O'Hare Intl
20 Jan
ORD12:30 p.m.Chicago O'Hare Intl
9h 24m
1 stop
YYC8:54 p.m.Calgary
C$ 308
Find similar
Delta
9 Apr
YYC7:20 a.m.Calgary
9h 40m
1 stop
ORD6:00 p.m.Chicago O'Hare Intl
13 Apr
ORD6:00 a.m.Chicago O'Hare Intl
18h 06m
2 stops
YYC11:06 p.m.Calgary
C$ 310
Find similar
Delta
26 May
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
30 May
ORD10:35 a.m.Chicago O'Hare Intl
8h 50m
1 stop
YYC6:25 p.m.Calgary
C$ 346
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
28 Jan
YYC5:35 a.m.Calgary
8h 35m
1 stop
ORD3:10 p.m.Chicago O'Hare Intl
4 Feb
ORD3:55 p.m.Chicago O'Hare Intl
9h 19m
1 stop
YYC12:14 a.m.Calgary
C$ 213
Find similar
Air Canada
15 Jan
YYC5:35 a.m.Calgary
8h 35m
1 stop
ORD3:10 p.m.Chicago O'Hare Intl
21 Jan
ORD3:55 p.m.Chicago O'Hare Intl
9h 19m
1 stop
YYC12:14 a.m.Calgary
C$ 219
Find similar
Air Canada
28 Jan
YYC5:35 a.m.Calgary
8h 35m
1 stop
ORD3:10 p.m.Chicago O'Hare Intl
4 Feb
ORD7:15 a.m.Chicago O'Hare Intl
14h 04m
2 stops
YYC8:19 p.m.Calgary
C$ 230
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 16 December 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

Wed 28/1

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

1 stop8h 35m

Chicago O'Hare Intl

Wed 4/2

3:55 p.m.-12:14 a.m.

1 stop9h 19m

C$ 213

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 15/1

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

1 stop8h 35m

Chicago O'Hare Intl

Wed 21/1

3:55 p.m.-12:14 a.m.

1 stop9h 19m

C$ 219

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 3/2

2:13 p.m.-11:59 p.m.

1 stop8h 46m

Chicago O'Hare Intl

Wed 4/2

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

Nonstop3h 50m

C$ 222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 28/1

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

1 stop8h 35m

Chicago O'Hare Intl

Wed 4/2

7:15 a.m.-8:19 p.m.

2 stops14h 04m

C$ 230

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 3/2

8:00 a.m.-5:48 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Wed 4/2

3:55 p.m.-12:14 a.m.

1 stop9h 19m

C$ 242

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 16/1

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

Nonstop3h 35m

Chicago O'Hare Intl

Mon 19/1

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

Nonstop3h 55m

C$ 249

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 2/2

6:15 a.m.-11:59 p.m.

1 stop16h 44m

Chicago O'Hare Intl

Tue 3/2

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

Nonstop3h 50m

C$ 251

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 30/1

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

Nonstop3h 35m

Chicago O'Hare Intl

Fri 6/2

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

Nonstop3h 55m

C$ 252

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 2/2

6:15 a.m.-9:15 p.m.

1 stop14h 00m

Chicago O'Hare Intl

Wed 4/2

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

Nonstop3h 50m

C$ 259

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 26/5

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Sat 30/5

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 275

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?

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$ 226. 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$ 255.

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$ 609. 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$ 996.

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$ 483. 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$ 1,486 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$ 353 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$ 227 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?

No. A direct flight is the cheapest option for a flight between Calgary to Chicago O'Hare Intl Airport.

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

C$ 161

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 C$ 161. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 362.
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?

    There are 2223.9 km between Calgary and Chicago O'Hare Intl. 3h 27m 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$ 149Free CancellationRating
7.1
10,527 reviews
Search Air Canada flights
WestJetPriceFrom C$ 176Free CancellationRating
7.2
3,202 reviews
Search WestJet flights
DeltaPriceFrom C$ 183Free CancellationRating
7.9
8,010 reviews
Search Delta flights
American AirlinesPriceFrom C$ 185Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
United AirlinesPriceFrom C$ 194Free CancellationRating
7.4
9,094 reviews
Search United Airlines flights

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

    Across 1 Delta flight from Calgary to Chicago O'Hare Intl Airport this week, the average price was C$ 344, with the best Delta deals starting from C$ 183 round-trip. 8,010 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$ 194, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at C$ 498 round-trip. United Airlines operates 3 flights out of Calgary into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 9,094 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
Skokie
Hammond
Harvey
Naperville
Glenview
Great Lakes
Wheeling
Elmhurst
Harvard
Merrillville
Elk Grove Village
Oak Brook
Kenosha

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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