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Cheap flights from Calgary to Chicago O'Hare Intl Airport from $108

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 - 9:55 amYYC-ORD
8h 05m1 stop
9:03 am - 4:52 pmORD-YYC
8h 49m1 stop
$196Air Canada
Find Deal
Mon, Mar 31 - Tue, Apr 8
8:30 am - 6:38 pmYYC-ORD
9h 08m1 stop
2:05 pm - 9:18 pmORD-YYC
8h 13m1 stop
$215Air Canada
Find Deal
Thu, Jan 9 - Sat, Jan 18
7:00 am - 4:58 pmYYC-ORD
8h 58m1 stop
12:35 pm - 11:16 pmORD-YYC
11h 41m2 stops
$221Delta
Find Deal
Sat, Dec 7 - Tue, Dec 10
6:35 am - 8:53 pmYYC-ORD
13h 18m2 stops
6:55 am - 8:53 pmORD-YYC
14h 58m2 stops
$236Delta
Find Deal
Thu, Jan 9 - Sun, Jan 12
12:30 pm - 4:50 pmYYC-ORD
3h 20mnonstop
9:00 am - 11:54 amORD-YYC
3h 54mnonstop
$350United Airlines
Find Deal
Tue, Apr 1 - Tue, Apr 8
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
7:10 am - 9:41 pmORD-YYC
15h 31m1 stop
$369United Airlines
Find Deal
Fri, Jan 24 - Sun, Jan 26
1:20 pm - 5:45 pmYYC-ORD
3h 25mnonstop
9:45 am - 12:30 pmORD-YYC
3h 45mnonstop
$379American Airlines
Find Deal
Wed, Apr 30 - Mon, May 5
12:30 am - 10:02 amYYC-ORD
8h 32m1 stop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$421WestJet
Find Deal
Tue, Apr 29 - Mon, May 5
1:00 am - 4:47 pmYYC-ORD
14h 47m2 stops
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$423WestJet
Find Deal
Tue, Apr 29 - Mon, May 5
12:45 pm - 9:08 pmYYC-ORD
7h 23m1 stop
5:00 am - 11:59 amORD-YYC
7h 59m1 stop
$517American Airlines
Find Deal
Tue, Dec 3 - Sun, Dec 8
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$108WestJet
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Mon, Mar 3
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
$110WestJet
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Thu, May 1
8:30 am - 6:38 pmYYC-ORD
9h 08m1 stop
$118Air Canada
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Sat, Jan 18
12:50 am - 8:57 amYYC-ORD
7h 07m1 stop
$124Air Canada
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Fri, Jan 17
7:00 am - 9:12 pmYYC-ORD
13h 12m2 stops
$136Delta
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Sat, Dec 7
7:00 am - 8:28 pmYYC-ORD
12h 28m2 stops
$137Delta
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Tue, Dec 17
12:45 pm - 7:23 amYYC-ORD
17h 38m1 stop
$183American Airlines
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Tue, Dec 3
12:41 pm - 5:08 pmYYC-ORD
3h 27mnonstop
$253United Airlines
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Fri, Feb 14
1:20 pm - 5:45 pmYYC-ORD
3h 25mnonstop
$254American Airlines
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Fri, Mar 14
12:41 pm - 5:09 pmYYC-ORD
3h 28mnonstop
$273United Airlines
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Thu, Dec 5
12:41 pm - 5:09 pmYYC-ORD
3h 28mnonstop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$313United Airlines
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Thu, Nov 21 - Fri, Nov 29
2:09 pm - 11:57 pmYYC-ORD
8h 48m1 stop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$318United Airlines
Find Deal
Thu, Nov 21 - Fri, Nov 29
8:00 am - 5:58 pmYYC-ORD
8h 58m1 stop
6:17 am - 1:50 pmORD-YYC
8h 33m1 stop
$344Delta
Find Deal
Thu, Nov 21 - Fri, Nov 29
8:30 am - 6:36 pmYYC-ORD
9h 06m1 stop
7:28 am - 8:44 pmORD-YYC
14h 16m1 stop
$354Air Canada
Find Deal
Thu, Nov 21 - Sun, Nov 24
12:41 pm - 5:09 pmYYC-ORD
3h 28mnonstop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$922Air Canada
Find Deal
Thu, Nov 21 - Sun, Nov 24
7:00 am - 4:52 pmYYC-ORD
8h 52m1 stop
1:31 pm - 7:46 pmORD-YYC
31h 15m2 stops
$1,050WestJet
Find Deal
Thu, Nov 21 - Sun, Nov 24
7:00 am - 4:52 pmYYC-ORD
8h 52m2 stops
6:17 am - 7:16 pmORD-YYC
13h 59m2 stops
$1,582WestJet
Find Deal
Thu, Nov 21 - Sun, Nov 24
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$170WestJet
Find Deal
Mon, Apr 21 - Mon, Apr 28
12:30 pm - 4:50 pmYYC-ORD
3h 20mnonstop
9:00 am - 11:54 amORD-YYC
3h 54mnonstop
$350United Airlines
Find Deal
Tue, Apr 1 - Tue, Apr 8
1:20 pm - 5:45 pmYYC-ORD
3h 25mnonstop
9:45 am - 12:30 pmORD-YYC
3h 45mnonstop
$379American Airlines
Find Deal
Wed, Apr 30 - Mon, May 5
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:45 am - 11:34 amORD-YYC
3h 49mnonstop
$450United Airlines
Find Deal
Sat, Jan 25 - Mon, Jan 27
12:41 pm - 5:09 pmYYC-ORD
3h 28mnonstop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$490United Airlines
Find Deal
Thu, Dec 5 - Sat, Dec 7
1:20 pm - 5:45 pmYYC-ORD
3h 25mnonstop
9:45 am - 12:30 pmORD-YYC
3h 45mnonstop
$523American Airlines
Find Deal
Thu, May 15 - Fri, May 30
12:41 pm - 5:10 pmYYC-ORD
3h 29mnonstop
8:47 am - 11:41 amORD-YYC
3h 54mnonstop
$537Air Canada
Find Deal
Fri, Mar 7 - Tue, Mar 11
12:41 pm - 5:09 pmYYC-ORD
3h 28mnonstop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$552United Airlines
Find Deal
Fri, Dec 6 - Wed, Dec 25
12:41 pm - 5:08 pmYYC-ORD
3h 27mnonstop
8:47 am - 11:33 amORD-YYC
3h 46mnonstop
$605Air Canada
Find Deal
Thu, Feb 13 - Wed, Feb 19
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:45 am - 11:34 amORD-YYC
3h 49mnonstop
$636Air Canada
Find Deal
Tue, Jan 7 - Fri, Jan 17

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
Apr 1
YYC12:30 pmCalgary
3h 20m
ORD4:50 pmChicago O'Hare Intl
Apr 8
ORD9:00 amChicago O'Hare Intl
3h 54m
YYC11:54 amCalgary
United Airlines
Jan 24
YYC12:41 pmCalgary
3h 34m
ORD5:15 pmChicago O'Hare Intl
Jan 26
ORD7:10 amChicago O'Hare Intl
15h 31m
1 stop
YYC9:41 pmCalgary
United Airlines
Dec 5
YYC12:41 pmCalgary
3h 28m
ORD5:09 pmChicago O'Hare Intl
Dec 7
ORD8:45 amChicago O'Hare Intl
3h 54m
YYC11:39 amCalgary

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
Mar 31
YYC12:50 amCalgary
8h 05m
1 stop
ORD9:55 amChicago O'Hare Intl
Apr 8
ORD9:03 amChicago O'Hare Intl
8h 49m
1 stop
YYC4:52 pmCalgary
Air Canada
Jan 9
YYC8:30 amCalgary
9h 08m
1 stop
ORD6:38 pmChicago O'Hare Intl
Jan 18
ORD2:05 pmChicago O'Hare Intl
8h 13m
1 stop
YYC9:18 pmCalgary
Air Canada
Jan 23
YYC12:50 amCalgary
9h 04m
1 stop
ORD10:54 amChicago O'Hare Intl
Jan 26
ORD4:00 pmChicago O'Hare Intl
10h 18m
1 stop
YYC1:18 amCalgary

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 from Calgary to Chicago O'Hare Intl Airport?

January. The cheapest time of year to fly to Chicago O'Hare Intl Airport from Calgary is January. Most expensive is December

What is the cheapest day to depart Calgary for Chicago O'Hare Intl Airport?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday

When is the cheapest time to fly from Calgary to Chicago O'Hare Intl Airport?

In the morning. Calgary to Chicago O'Hare Intl Airport flights are approximately 17% more expensive at noon than in the morning

How far in advance should you book Calgary to Chicago O'Hare Intl Airport flights?

18 days before. The cheapest time to buy a flight from Calgary to Chicago O'Hare Intl Airport is approximately 18 days to departure

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 November 2024, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 18% 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

$108

Fastest flight time

3h 20m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Calgary in the past 72 hours is $108. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $196.
The fastest flight from Calgary to Chicago O'Hare Intl Airport takes 3h 20m
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 20m 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
7.3
2,810 reviews
Search WestJet flights
Air CanadaPriceFrom $213Free CancellationRating
7.0
8,238 reviews
Search Air Canada flights
American AirlinesPriceFrom $219Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
9,173 reviews
Search United Airlines 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 7 United Airlines flights for this route in a normal week, average airfare is usually $403 round-trip - but some users have found much cheaper deals with momondo.

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

    Across 8,238 Air Canada reviews on momondo, the average score is 7.0/10. Air Canada flies from Calgary to Chicago O'Hare Intl Airport about 7 times each week, with ticket deals ranging from $213 to $412. 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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