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Cheap flights from Calgary to Chicago from C$ 183

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 26/5. 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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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 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 238WestJet
Mon, 18 May - Sun, 24 May
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 239WestJet
Wed, 20 May - Tue, 26 May
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 242WestJet
Tue, 26 May - Fri, 29 May
American Airlines Logo
6:15 a.m. - 10:45 a.m.
YYC
-
ORD
3h 30mdirect
American Airlines Logo
8:50 p.m. - 11:42 p.m.
ORD
-
YYC
3h 52mdirect
C$ 275American Airlines
Fri, 29 May - Sun, 7 Jun
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
9:54 p.m. - 1:53 p.m.
ORD
-
YYC
16h 59m
1 stop
C$ 280WestJet
Mon, 18 May - Sun, 24 May
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 291WestJet
Thu, 28 May - Thu, 4 Jun
United Airlines Logo
12:34 p.m. - 5:01 p.m.
YYC
-
ORD
3h 27mdirect
United Airlines Logo
6:00 a.m. - 9:48 p.m.
ORD
-
YYC
16h 48m
1 stop
C$ 297United Airlines
Wed, 20 May - Tue, 26 May
American Airlines Logo
7:00 a.m. - 11:35 a.m.
YYC
-
ORD
3h 35mdirect
American Airlines Logo
8:50 p.m. - 11:42 p.m.
ORD
-
YYC
3h 52mdirect
C$ 304American Airlines
Thu, 4 Jun - Sun, 7 Jun
United Airlines Logo
6:00 a.m. - 11:56 p.m.
YYC
-
ORD
16h 56m
1 stop
United Airlines Logo
6:00 a.m. - 9:48 p.m.
ORD
-
YYC
16h 48m
1 stop
C$ 305United Airlines
Wed, 20 May - Tue, 26 May
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 311WestJet
Fri, 22 May - Fri, 12 Jun

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
18 Sep
YYC6:30 a.m.Calgary
7h 25m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
22 Sep
ORD2:15 p.m.Chicago O'Hare Intl
7h 45m
1 stop
YYC9:00 p.m.Calgary
C$ 328
Air Canada
23 May
YYC6:30 a.m.Calgary
7h 25m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
9 Jun
ORD7:25 a.m.Chicago O'Hare Intl
16h 33m
1 stop
YYC10:58 p.m.Calgary
C$ 346
Air Canada
2 Jun
YYC7:15 a.m.Calgary
8h 44m
1 stop
ORD4:59 p.m.Chicago O'Hare Intl
16 Jun
ORD9:55 a.m.Chicago O'Hare Intl
14h 03m
1 stop
YYC10:58 p.m.Calgary
C$ 364

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
20 May
YYC12:34 p.m.Calgary
3h 27m
ORD5:01 p.m.Chicago O'Hare Intl
26 May
ORD6:00 a.m.Chicago O'Hare Intl
16h 48m
1 stop
YYC9:48 p.m.Calgary
C$ 297
United Airlines
20 May
YYC6:00 a.m.Calgary
16h 56m
1 stop
ORD11:56 p.m.Chicago O'Hare Intl
26 May
ORD6:00 a.m.Chicago O'Hare Intl
16h 48m
1 stop
YYC9:48 p.m.Calgary
C$ 305
United Airlines
16 Sep
YYC6:00 a.m.Calgary
14h 12m
1 stop
ORD9:12 p.m.Chicago O'Hare Intl
21 Sep
ORD7:45 p.m.Chicago O'Hare Intl
3h 51m
YYC10:36 p.m.Calgary
C$ 339

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 30 April 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

Mon 18/5

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Sun 24/5

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 238

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 20/5

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Tue 26/5

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 239

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 26/5

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Fri 29/5

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 242
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 29/5

6:15 a.m.-10:45 a.m.

Nonstop3h 30m

Chicago O'Hare Intl

Sun 7/6

8:50 p.m.-11:42 p.m.

Nonstop3h 52m

C$ 275

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 18/5

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Sun 24/5

9:54 p.m.-1:53 p.m.

1 stop16h 59m

C$ 280

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 28/5

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Thu 4/6

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 291

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 20/5

12:34 p.m.-5:01 p.m.

Nonstop3h 27m

Chicago O'Hare Intl

Tue 26/5

6:00 a.m.-9:48 p.m.

1 stop16h 48m

C$ 297

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 4/6

7:00 a.m.-11:35 a.m.

Nonstop3h 35m

Chicago O'Hare Intl

Sun 7/6

8:50 p.m.-11:42 p.m.

Nonstop3h 52m

C$ 304

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 20/5

6:00 a.m.-11:56 p.m.

1 stop16h 56m

Chicago O'Hare Intl

Tue 26/5

6:00 a.m.-9:48 p.m.

1 stop16h 48m

C$ 305

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 22/5

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Fri 12/6

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 311

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, November 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$ 311. The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around C$ 343.

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$ 606. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, 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$ 1,089.

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

In the morning 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$ 703. Flying to Chicago O'Hare Intl Airport in the morning 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$ 1,338 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 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 C$ 385 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$ 297 on momondo.

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

As of April 2026, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 17% 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$ 290

Fastest flight time

3h 25m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Calgary in the past 72 hours is C$ 290. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 455.
The fastest flight from Calgary to Chicago O'Hare Intl Airport takes 3h 25m
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?

    There are 2223.9 km between Calgary and Chicago O'Hare Intl. 3h 25m 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$ 120Free CancellationRating
7.1
10,982 reviews
Search Air Canada flights
DeltaPriceFrom C$ 147Free CancellationRating
7.9
8,463 reviews
Search Delta flights
United AirlinesPriceFrom C$ 167Free CancellationRating
7.4
9,677 reviews
Search United Airlines flights
WestJetPriceFrom C$ 183Free CancellationRating
7.2
3,328 reviews
Search WestJet flights
American AirlinesPriceFrom C$ 194Free CancellationRating
7.1
11,681 reviews
Search American 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$ 373, with the best Delta deals starting from C$ 147 round-trip. 8,463 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$ 167, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at C$ 404 round-trip. United Airlines operates 7 flights out of Calgary into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 9,677 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
Des Plaines
Merrillville
Rosemont
Northbrook
Tinley Park
Downers Grove
Skokie
Great Lakes
Wheeling
Hammond
Glenview
Harvey
Naperville
Munster
Hoffman Estates
Elmhurst
Harvard
DeKalb
Kankakee

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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