Which layover airport offers the lowest fares from Calgary to Chicago?

Flights via Denver (DEN) offer the lowest average round-trip price of C$ 266.

Which layover airport has the shortest travel time from Calgary to Chicago?

Flights connecting via Denver (DEN) have the shortest average one-way travel time: 7h 35m.

Which layover airport has the shortest connection time from Calgary to Chicago?

Toronto (YYZ) has the shortest average layover time for this route: 2h 17m.

Which airlines fly to Chicago?

WestJet, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Calgary according to our data. WestJet is the first choice among our users, with 51% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Calgary to Chicago on average per day?

As of May 2026, there are 11 flights per day flying from Calgary to Chicago. The most common time of day flights depart is 12:00p.m., with 70% of flights taking off in the afternoon.

What is the cheapest airline that flies from Calgary to Chicago?

United Airlines and Delta are the most popular carriers operating from Calgary to Chicago

Which airport is the most popular layover for flights between Calgary and Chicago?

Toronto (YYZ) was the most common stop: 43% of momondo users choosing one-stop flights on this route connected there.

How many flights depart from Calgary to Chicago on average per week?

78 flights are operational weekly from Calgary to Chicago as of May 2026. The most popular departure day for this route is Wed, with 18% of flights per week taking off on this day.

When did momondo last update prices for flights from Calgary Airport to Chicago?

Prices for flights from Calgary Airport to Chicago are updated daily.

How many operators does momondo search for flights from Calgary Airport to Chicago?

As of May 2026, there are 5 operators available to choose from for flights from Calgary Airport to Chicago.

How old do you have to be to fly from Calgary Airport to Chicago?

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.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

C$ 205 Cheap Flights from Calgary to Chicago in 2026

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Find the cheapest flights from Calgary to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:30 a.m. - 1:07 p.m.

YYC

ORD

3h 37mdirect

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

ORD

YYC

16h 48m

1 stop

C$ 353United Airlines

Mon, 8 Jun - Sun, 14 Jun

6:45 a.m. - 5:04 p.m.

YYC

ORD

9h 19m

1 stop

12:29 p.m. - 8:35 p.m.

ORD

YYC

9h 06m

1 stop

C$ 365Delta

Fri, 4 Sep - Sun, 6 Sep

8:30 a.m. - 1:07 p.m.

YYC

ORD

3h 37mdirect

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

ORD

YYC

16h 48m

1 stop

C$ 373United Airlines

Thu, 11 Jun - Sun, 14 Jun

6:45 a.m. - 1:07 p.m.

YYC

MDW

5h 22m

1 stop

1:47 p.m. - 8:32 p.m.

MDW

YYC

7h 45m

1 stop

C$ 375Delta

Tue, 15 Sep - Wed, 23 Sep

6:00 a.m. - 8:30 p.m.

YYC

ORD

13h 30m

1 stop

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

ORD

YYC

16h 48m

1 stop

C$ 375United Airlines

Mon, 8 Jun - Mon, 15 Jun

11:55 p.m. - 9:00 a.m.

YYC

ORD

8h 05m

1 stop

2:15 p.m. - 10:57 p.m.

ORD

YYC

9h 42m

1 stop

C$ 376Air Canada

Wed, 16 Sep - Wed, 23 Sep

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

YYC

ORD

3h 35mdirect

9:40 a.m. - 9:43 p.m.

ORD

YYC

13h 03m

1 stop

C$ 380American Airlines

Tue, 16 Jun - Tue, 23 Jun

7:45 a.m. - 9:45 p.m.

YYC

MDW

13h 00m

2 stops

9:30 a.m. - 8:54 p.m.

MDW

YYC

12h 24m

2 stops

C$ 382Delta

Tue, 27 Oct - Sat, 31 Oct

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

YYC

ORD

3h 35mdirect

8:46 p.m. - 11:42 p.m.

ORD

YYC

3h 56mdirect

C$ 390American Airlines

Sat, 5 Sep - Mon, 7 Sep

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

YYC

ORD

3h 35mdirect

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

ORD

YYC

3h 55mdirect

C$ 391WestJet

Mon, 2 Nov - Fri, 13 Nov

United Airlines flights from Calgary to Chicago

Our best United Airlines deals on Calgary to Chicago flight tickets

United Airlines

8 Jun

YYC8:30 a.m.Calgary

3h 37m

ORD1:07 p.m.Chicago O'Hare Intl

14 Jun

ORD6:00 a.m.Chicago O'Hare Intl

16h 48m

1 stop

YYC9:48 p.m.Calgary

C$ 353

United Airlines

11 Jun

YYC8:30 a.m.Calgary

3h 37m

ORD1:07 p.m.Chicago O'Hare Intl

14 Jun

ORD6:00 a.m.Chicago O'Hare Intl

16h 48m

1 stop

YYC9:48 p.m.Calgary

C$ 373

United Airlines

8 Jun

YYC6:00 a.m.Calgary

13h 30m

1 stop

ORD8:30 p.m.Chicago O'Hare Intl

15 Jun

ORD6:00 a.m.Chicago O'Hare Intl

16h 48m

1 stop

YYC9:48 p.m.Calgary

C$ 375

American Airlines flights from Calgary to Chicago

Our best American Airlines deals on Calgary to Chicago flight tickets

American Airlines

16 Jun

YYC7:00 a.m.Calgary

3h 35m

ORD11:35 a.m.Chicago O'Hare Intl

23 Jun

ORD9:40 a.m.Chicago O'Hare Intl

13h 03m

1 stop

YYC9:43 p.m.Calgary

C$ 380

American Airlines

5 Sep

YYC7:00 a.m.Calgary

3h 35m

ORD11:35 a.m.Chicago O'Hare Intl

7 Sep

ORD8:46 p.m.Chicago O'Hare Intl

3h 56m

YYC11:42 p.m.Calgary

C$ 390

American Airlines

4 Sep

YYC7:00 a.m.Calgary

3h 35m

ORD11:35 a.m.Chicago O'Hare Intl

6 Sep

ORD8:46 p.m.Chicago O'Hare Intl

3h 56m

YYC11:42 p.m.Calgary

C$ 408

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 8/6

8:30 a.m.-1:07 p.m.

Nonstop3h 37m

Chicago O'Hare Intl

Sun 14/6

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

1 stop16h 48m

C$ 353

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 4/9

6:45 a.m.-5:04 p.m.

1 stop9h 19m

Chicago O'Hare Intl

Sun 6/9

12:29 p.m.-8:35 p.m.

1 stop9h 06m

C$ 365

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 11/6

8:30 a.m.-1:07 p.m.

Nonstop3h 37m

Chicago O'Hare Intl

Sun 14/6

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

1 stop16h 48m

C$ 373

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 15/9

6:45 a.m.-1:07 p.m.

1 stop5h 22m

Chicago Midway

Wed 23/9

1:47 p.m.-8:32 p.m.

1 stop7h 45m

C$ 375

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 8/6

6:00 a.m.-8:30 p.m.

1 stop13h 30m

Chicago O'Hare Intl

Mon 15/6

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

1 stop16h 48m

C$ 375

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 16/9

11:55 p.m.-9:00 a.m.

1 stop8h 05m

Chicago O'Hare Intl

Wed 23/9

2:15 p.m.-10:57 p.m.

1 stop9h 42m

C$ 376

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 16/6

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

Nonstop3h 35m

Chicago O'Hare Intl

Tue 23/6

9:40 a.m.-9:43 p.m.

1 stop13h 03m

C$ 380

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 27/10

7:45 a.m.-9:45 p.m.

2 stops13h 00m

Chicago Midway

Sat 31/10

9:30 a.m.-8:54 p.m.

2 stops12h 24m

C$ 382

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/9

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

Nonstop3h 35m

Chicago O'Hare Intl

Mon 7/9

8:46 p.m.-11:42 p.m.

Nonstop3h 56m

C$ 390

Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 2/11

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

Nonstop3h 35m

Chicago O'Hare Intl

Fri 13/11

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

Nonstop3h 55m

C$ 391

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Calgary to Chicago

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

Prices

Airlines

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Other information

What is the typical price of a round-trip flight between Calgary and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is another great option to travel to Chicago, with average flight prices from Calgary averaging around C$ 88.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 569. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 1,103. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the morning is the cheapest time of day to fly from Calgary to Chicago when you can find flight prices for as low as C$ 702. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,328 per ticket.

What is the cheapest Calgary to Chicago flight route?

Fly from Calgary to Chicago O'Hare Intl for the best Calgary - Chicago flight prices

How far in advance should I book a flight from Calgary to Chicago?

You are more likely to see cheaper flights to Chicago from Calgary when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 393 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Calgary for as low as C$ 256 on momondo.

What cabin class options are available on Calgary to Chicago flights?

There are 4 cabin classes available to choose from on Calgary to Chicago 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 flight prices changed over time?

As of May 2026, prices for Calgary to Chicago flights are approximately 9% cheaper when compared to flights at the same time last year.

When to book flights from Calgary to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Calgary to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Calgary to Chicago (YYC to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Calgary to Chicago

Best price found	C$ 281
Fastest flight time	3h 20m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Calgary in the past 72 hours is C$ 281. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is C$ 489.

The fastest flight from Calgary to Chicago takes 3h 20m

Direct flights go from Calgary to Chicago every day.

There are 3 airports in Chicago. From Calgary there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Calgary to Chicago

How far is Calgary to Chicago by plane?
Chicago is 2249.2 km away from Calgary. Flights usually cover this in 3h 20m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Calgary Airport to Chicago?
Prices for flights from Calgary Airport to Chicago are updated daily.
How many operators does momondo search for flights from Calgary Airport to Chicago?
As of May 2026, there are 5 operators available to choose from for flights from Calgary Airport to Chicago.
How old do you have to be to fly from Calgary Airport to Chicago?
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.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Calgary to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Calgary to Chicago is Boeing 737-800 (31.17% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (19.60%), Boeing 737-700 (11.08%), and Airbus A320-100/200 (9.25%).
What is the most popular airline from Calgary to Chicago?
Based on momondo bookings for flights between Calgary and Chicago, the leading airline is WestJet, making up 56% of the total bookings. Other popular airlines include Air Canada with 14%, American Airlines with 14%, and United Airlines with 13%.

Best airlines flying from Calgary to Chicago

Compare and see reviews for airlines that fly from Calgary to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom C$ 112	Free Cancellation	Rating 7.1 11,095 reviews	Search Air Canada flights
Delta	PriceFrom C$ 148	Free Cancellation	Rating 7.9 8,423 reviews	Search Delta flights
WestJet	PriceFrom C$ 185	Free Cancellation	Rating 7.2 3,347 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 187	Free Cancellation	Rating 7.4 9,751 reviews	Search United Airlines flights
American Airlines	PriceFrom C$ 196	Free Cancellation	Rating 7.1 11,639 reviews	Search American Airlines flights

Delta Flights From Calgary to Chicago
Delta operates around 4 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 377, but momondo users have found Delta deals from Calgary to Chicago from as low as C$ 148 round-trip. Delta has been scored 7.9/10 in 8,422 reviews.
United Airlines Flights From Calgary to Chicago
The best United Airlines deal for Calgary to Chicago flight tickets found on momondo in the last 72 hours was C$ 187, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at C$ 515 round-trip. United Airlines operates 9 flights out of Calgary into Chicago in an average week, so prices vary by time and availability. 9,754 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Merrillville

Hammond

Munster

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 for Calgary to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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.

An easier way to manage your Chicago trip

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Fly into one of these airports located in Chicago

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Cheap flights from Calgary to Chicago from C$ 205

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 23/11. 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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How to get the cheapest flight ticket from Calgary to Chicago

What is the typical price of a round-trip flight between Calgary and Chicago?

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Calgary to Chicago flight route?

How far in advance should I book a flight from Calgary to Chicago?

What cabin class options are available on Calgary to Chicago flights?

How have Calgary to Chicago flight prices changed over time?

What is the cheapest airline that flies from Calgary to Chicago?

Which airlines fly to Chicago?

Which airport is the most popular layover for flights between Calgary and Chicago?

Which layover airport offers the lowest fares from Calgary to Chicago?

Which layover airport has the shortest travel time from Calgary to Chicago?

Which layover airport has the shortest connection time from Calgary to Chicago?

How many flights depart from Calgary to Chicago on average per day?

How many flights depart from Calgary to Chicago on average per week?

When to book flights from Calgary to Chicago

Cheap Calgary to Chicago (YYC to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Calgary to Chicago

Best price found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Calgary to Chicago

Best airlines flying from Calgary to Chicago

Compare and see reviews for airlines that fly from Calgary to Chicago with momondo

Delta Flights From Calgary to Chicago

United Airlines Flights From Calgary to Chicago

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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