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Cheap flights from Calgary to Chicago O'Hare Intl Airport from $89

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 O'Hare Intl Airport departing on 3/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Calgary to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Calgary to Chicago.

Cheap last minute flights

Planning a quick getaway from Calgary to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Calgary to Chicago

Find recent round-trip train or bus tickets from Calgary to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
12:50 am - 10:54 amYYC-ORD
9h 04m1 stop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$144Air Canada
Find Deal
Mon, Jan 13 - Tue, Jan 21
12:50 am - 10:54 amYYC-ORD
9h 04m1 stop
2:05 pm - 10:09 pmORD-YYC
9h 04m1 stop
$155Air Canada
Find Deal
Mon, Jan 13 - Tue, Jan 21
12:50 am - 10:54 amYYC-ORD
9h 04m1 stop
5:01 pm - 1:18 amORD-YYC
9h 17m1 stop
$175Air Canada
Find Deal
Mon, Jan 27 - Wed, Feb 19
8:00 am - 9:58 pmYYC-ORD
12h 58m2 stops
1:45 pm - 11:18 pmORD-YYC
10h 33m1 stop
$217Delta
Find Deal
Tue, Jan 14 - Tue, Jan 21
8:00 am - 9:58 pmYYC-ORD
12h 58m2 stops
12:15 pm - 8:53 pmORD-YYC
9h 38m1 stop
$218Delta
Find Deal
Tue, Jan 14 - Tue, Jan 21
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$261WestJet
Find Deal
Thu, May 22 - Sun, May 25
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$343WestJet
Find Deal
Thu, May 22 - Mon, May 26
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:53 am - 11:39 amORD-YYC
3h 46mnonstop
$400United Airlines
Find Deal
Thu, Jan 30 - Wed, Feb 19
6:29 am - 2:25 pmYYC-ORD
6h 56m1 stop
1:13 pm - 9:57 pmORD-YYC
9h 44m1 stop
$476American Airlines
Find Deal
Fri, Jan 17 - Thu, Jan 23
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$484United Airlines
Find Deal
Mon, Feb 3 - Thu, Feb 6
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$89WestJet
Find Deal
Mon, Mar 3
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$90WestJet
Find Deal
Thu, Mar 27
8:30 am - 6:38 pmYYC-ORD
9h 08m1 stop
$98Air Canada
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Wed, Jan 15
6:15 am - 2:51 pmYYC-ORD
7h 36m1 stop
$103Air Canada
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Sun, Jan 19
7:20 pm - 9:33 amYYC-ORD
13h 13m1 stop
$108United Airlines
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Thu, Mar 20
1:45 pm - 12:05 amYYC-ORD
9h 20m1 stop
$118United Airlines
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Thu, May 8
6:35 am - 8:53 pmYYC-ORD
13h 18m2 stops
$134Delta
Find Deal
Wed, Jan 15
6:35 am - 8:53 pmYYC-ORD
13h 18m2 stops
$135Delta
Find Deal
Mon, Jan 13
6:29 am - 12:19 amYYC-ORD
16h 50m1 stop
$175American Airlines
Find Deal
Thu, Dec 26
6:29 am - 9:19 pmYYC-ORD
13h 50m1 stop
$180American Airlines
Find Deal
Thu, Dec 26
12:45 pm - 7:20 amYYC-ORD
17h 35m1 stop
7:09 am - 9:55 pmORD-YYC
15h 46m1 stop
$302American Airlines
Find Deal
Mon, Dec 23 - Fri, Dec 27
7:00 am - 5:09 pmYYC-ORD
9h 09m1 stop
7:30 am - 6:13 pmORD-YYC
11h 43m1 stop
$380Delta
Find Deal
Sun, Dec 22 - Wed, Dec 25
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
6:28 pm - 1:18 amORD-YYC
7h 50m1 stop
$419Air Canada
Find Deal
Thu, Dec 19 - Tue, Jan 7
1:30 pm - 11:20 pmYYC-ORD
8h 50m1 stop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$554United Airlines
Find Deal
Sun, Dec 22 - Mon, Dec 30
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
12:56 pm - 11:18 pmORD-YYC
11h 22m1 stop
$555Air Canada
Find Deal
Mon, Dec 23 - Wed, Dec 25
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$592United Airlines
Find Deal
Thu, Dec 19 - Tue, Jan 7
4:35 pm - 5:30 amYYC-ORD
11h 55m1 stop
2:25 pm - 11:50 pmORD-YYC
10h 25m1 stop
Mon, Dec 23 - Tue, Dec 24
4:35 pm - 5:30 amYYC-ORD
11h 55m1 stop
4:21 pm - 11:50 pmORD-YYC
8h 29m1 stop
Mon, Dec 23 - Thu, Dec 26
11:00 am - 9:39 pmYYC-ORD
9h 39m2 stops
6:15 am - 4:16 pmORD-YYC
11h 01m2 stops
$861WestJet
Find Deal
Thu, Dec 19 - Tue, Jan 7
6:00 am - 5:09 pmYYC-ORD
10h 09m2 stops
6:20 am - 10:30 pmORD-YYC
17h 10m2 stops
$874WestJet
Find Deal
Thu, Dec 19 - Fri, Dec 27
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$261WestJet
Find Deal
Thu, May 22 - Sun, May 25
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$343WestJet
Find Deal
Thu, May 22 - Mon, May 26
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$359United Airlines
Find Deal
Tue, Feb 4 - Thu, Feb 6
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$381United Airlines
Find Deal
Tue, Jan 14 - Tue, Jan 21
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:53 am - 11:39 amORD-YYC
3h 46mnonstop
$400United Airlines
Find Deal
Thu, Jan 30 - Wed, Feb 19
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$484United Airlines
Find Deal
Mon, Feb 3 - Thu, Feb 6
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$506Air Canada
Find Deal
Fri, Jan 31 - Fri, Feb 7
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$554Air Canada
Find Deal
Fri, Jan 17 - Fri, Jan 24
12:41 pm - 5:08 pmYYC-ORD
3h 27mnonstop
8:53 am - 11:39 amORD-YYC
3h 46mnonstop
$635Air Canada
Find Deal
Thu, Feb 13 - Wed, Feb 19
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$689Air Canada
Find Deal
Mon, Jan 13 - Mon, Jan 20

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
Jan 13
YYC12:50 amCalgary
9h 04m
1 stop
ORD10:54 amChicago O'Hare Intl
Jan 21
ORD8:50 amChicago O'Hare Intl
3h 49m
YYC11:39 amCalgary
Air Canada
Jan 13
YYC12:50 amCalgary
9h 04m
1 stop
ORD10:54 amChicago O'Hare Intl
Jan 21
ORD2:05 pmChicago O'Hare Intl
9h 04m
1 stop
YYC10:09 pmCalgary
Air Canada
Jan 27
YYC12:50 amCalgary
9h 04m
1 stop
ORD10:54 amChicago O'Hare Intl
Feb 19
ORD5:01 pmChicago O'Hare Intl
9h 17m
1 stop
YYC1:18 amCalgary

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
May 22
YYC12:15 pmCalgary
3h 29m
ORD4:44 pmChicago O'Hare Intl
May 25
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
WestJet
May 22
YYC12:15 pmCalgary
3h 29m
ORD4:44 pmChicago O'Hare Intl
May 26
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
WestJet
Dec 25
YYC7:00 amCalgary
6h 38m
1 stop
ORD2:38 pmChicago O'Hare Intl
Dec 29
ORD6:20 amChicago O'Hare Intl
13h 11m
2 stops
YYC6:31 pmCalgary

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 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 $307.

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 Saturday when prices can be found for as low as $349. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $487.

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 $368 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $443. 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 to Chicago O'Hare Intl Airport?

In general, most travelers find the cheapest time to book a flight to Chicago O'Hare Intl Airport is about 18 days prior to their departure date when tickets on average are $363. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $140.

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 10% 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 December 2024, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 10% 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

$89

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 $89. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $144.
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.

  • 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 3h 26m 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
WestJetPriceFrom $186Free CancellationRating
7.2
2,818 reviews
Search WestJet flights
Air CanadaPriceFrom $213Free CancellationRating
7.0
8,382 reviews
Search Air Canada flights
American AirlinesPriceFrom $219Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
9,055 reviews
Search United Airlines flights
DeltaPriceFrom $268Free CancellationRating
8.0
8,604 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 $226 round-trip. Over the 3 United Airlines flights for this route in a normal week, average airfare is usually $406 round-trip - but some users have found much cheaper deals with momondo.

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

    Across 8,382 Air Canada reviews on momondo, the average score is 7.0/10. Air Canada flies from Calgary to Chicago O'Hare Intl Airport about 3 times each week, with ticket deals ranging from $213 to $406. Price data is based on momondo searches in the last 72 hours.


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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