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Cheap flights from Calgary to Chicago O'Hare Intl Airport from $96

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 2/20. 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 from Calgary to Chicago

The cheapest plane tickets from Calgary to Chicago found on KAYAK recently.
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
$136WestJet
Find Deal
Thu, Feb 20 - Thu, Feb 27
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
$151WestJet
Find Deal
Thu, Apr 17 - Sun, Apr 20
7:20 pm - 9:33 amYYC-ORD
13h 13m1 stop
1:05 pm - 9:41 pmORD-YYC
9h 36m1 stop
$192United Airlines
Find Deal
Mon, Mar 17 - Tue, Mar 18
8:30 am - 6:38 pmYYC-ORD
9h 08m1 stop
4:51 pm - 1:18 amORD-YYC
9h 27m1 stop
$203Air Canada
Find Deal
Mon, Feb 3 - Tue, Feb 11
12:05 am - 10:10 amYYC-ORD
9h 05m1 stop
6:28 pm - 1:18 amORD-YYC
7h 50m1 stop
$210Air Canada
Find Deal
Sun, Feb 2 - Tue, Feb 11
6:35 am - 5:29 pmYYC-ORD
9h 54m1 stop
1:40 pm - 11:15 pmORD-YYC
10h 35m1 stop
$216Delta
Find Deal
Thu, Feb 20 - Fri, Feb 28
6:35 am - 5:29 pmYYC-ORD
9h 54m1 stop
12:15 pm - 11:15 pmORD-YYC
12h 00m2 stops
$217Delta
Find Deal
Mon, Feb 3 - Tue, Feb 11
12:45 pm - 11:56 pmYYC-ORD
10h 11m1 stop
8:35 pm - 11:50 amORD-YYC
16h 15m1 stop
$298American Airlines
Find Deal
Sat, Feb 22 - Mon, Feb 24
1:32 pm - 6:03 pmYYC-ORD
3h 31mnonstop
8:35 pm - 11:50 amORD-YYC
16h 15m1 stop
$311American Airlines
Find Deal
Fri, Feb 21 - Mon, Feb 24
2:09 pm - 12:23 amYYC-ORD
9h 14m1 stop
8:47 am - 11:39 amORD-YYC
3h 52mnonstop
$312United Airlines
Find Deal
Tue, Mar 18 - Wed, Mar 19
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$96WestJet
Find Deal
Thu, Feb 20
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$100WestJet
Find Deal
Mon, Mar 31
1:30 pm - 12:35 amYYC-ORD
10h 05m1 stop
$119United Airlines
Find Deal
Wed, Apr 23
11:55 pm - 9:59 amYYC-ORD
9h 04m1 stop
$120Air Canada
Find Deal
Fri, May 23
8:30 am - 6:41 pmYYC-ORD
9h 11m1 stop
$121Air Canada
Find Deal
Thu, Mar 27
6:35 am - 8:53 pmYYC-ORD
13h 18m2 stops
$134Delta
Find Deal
Tue, Feb 18
6:35 am - 8:53 pmYYC-ORD
13h 18m2 stops
$135Delta
Find Deal
Thu, Feb 20
1:22 pm - 5:53 pmYYC-ORD
3h 31mnonstop
$148American Airlines
Find Deal
Thu, Mar 27
1:32 pm - 6:03 pmYYC-ORD
3h 31mnonstop
$187American Airlines
Find Deal
Fri, Feb 21
8:30 am - 12:49 pmYYC-ORD
3h 19mnonstop
$203United Airlines
Find Deal
Thu, Jul 3
12:50 am - 8:57 amYYC-ORD
7h 07m1 stop
6:28 pm - 1:18 amORD-YYC
7h 50m1 stop
$284Air Canada
Find Deal
Thu, Jan 23 - Mon, Jan 27
12:50 am - 10:10 amYYC-ORD
8h 20m1 stop
12:56 pm - 11:18 pmORD-YYC
11h 22m1 stop
$287Air Canada
Find Deal
Sun, Jan 26 - Thu, Jan 30
12:50 am - 10:10 amYYC-ORD
8h 20m1 stop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$414Air Canada
Find Deal
Thu, Jan 23 - Mon, Jan 27
7:30 am - 12:39 amYYC-ORD
16h 09m1 stop
6:06 pm - 7:46 pmORD-YYC
26h 40m2 stops
Fri, Jan 24 - Mon, Jan 27
4:35 pm - 2:23 pmYYC-ORD
20h 48m2 stops
10:29 am - 10:55 pmORD-YYC
13h 26m2 stops
Fri, Jan 24 - Mon, Jan 27
4:35 pm - 5:55 amYYC-ORD
36h 20m3 stops
7:26 am - 10:55 pmORD-YYC
16h 29m2 stops
Fri, Jan 24 - Mon, Jan 27
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$619United Airlines
Find Deal
Fri, Jan 24 - Mon, Jan 27
12:30 am - 2:47 pmYYC-ORD
13h 17m1 stop
7:26 am - 10:55 pmORD-YYC
16h 29m2 stops
Thu, Jan 23 - Mon, Jan 27
12:20 am - 4:13 pmYYC-ORD
14h 53m2 stops
6:15 am - 7:08 pmORD-YYC
13h 53m2 stops
$763WestJet
Find Deal
Thu, Jan 23 - Mon, Jan 27
12:50 am - 10:10 amYYC-ORD
8h 20m1 stop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$853Air Canada
Find Deal
Sun, Jan 26 - Thu, Jan 30
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
$136WestJet
Find Deal
Thu, Feb 20 - Thu, Feb 27
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
$151WestJet
Find Deal
Thu, Apr 17 - Sun, Apr 20
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$253Delta
Find Deal
Fri, May 2 - Mon, May 5
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
$288Delta
Find Deal
Sun, Mar 16 - Thu, Mar 27
6:29 am - 10:53 amYYC-ORD
3h 24mnonstop
8:20 pm - 11:20 pmORD-YYC
4h 00mnonstop
$344American Airlines
Find Deal
Tue, Jun 10 - Tue, Jun 17
12:41 pm - 5:10 pmYYC-ORD
3h 29mnonstop
8:47 am - 11:39 amORD-YYC
3h 52mnonstop
$432United Airlines
Find Deal
Tue, Mar 18 - Wed, Mar 19
1:17 pm - 5:49 pmYYC-ORD
3h 32mnonstop
9:50 am - 12:32 pmORD-YYC
3h 42mnonstop
$458American Airlines
Find Deal
Fri, Apr 25 - Mon, Apr 28
12:41 pm - 5:10 pmYYC-ORD
3h 29mnonstop
8:47 am - 11:39 amORD-YYC
3h 52mnonstop
$463United Airlines
Find Deal
Tue, Mar 18 - Thu, Mar 20
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$911Air Canada
Find Deal
Sat, Feb 1 - Fri, Feb 7
12:41 pm - 5:08 pmYYC-ORD
3h 27mnonstop
8:53 am - 11:39 amORD-YYC
3h 46mnonstop
$1,039Air Canada
Find Deal
Sun, Feb 23 - Wed, Feb 26

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
Mar 17
YYC7:20 pmCalgary
13h 13m
1 stop
ORD9:33 amChicago O'Hare Intl
Mar 18
ORD1:05 pmChicago O'Hare Intl
9h 36m
1 stop
YYC9:41 pmCalgary
United Airlines
Jan 23
YYC12:41 pmCalgary
3h 34m
ORD5:15 pmChicago O'Hare Intl
Jan 24
ORD2:39 pmChicago O'Hare Intl
8h 02m
1 stop
YYC9:41 pmCalgary
United Airlines
Jan 22
YYC6:19 amCalgary
7h 36m
1 stop
ORD2:55 pmChicago O'Hare Intl
Jan 23
ORD8:50 amChicago O'Hare Intl
3h 49m
YYC11:39 amCalgary

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
Feb 20
YYC6:35 amCalgary
9h 54m
1 stop
ORD5:29 pmChicago O'Hare Intl
Feb 28
ORD1:40 pmChicago O'Hare Intl
10h 35m
1 stop
YYC11:15 pmCalgary
Delta
Feb 3
YYC6:35 amCalgary
9h 54m
1 stop
ORD5:29 pmChicago O'Hare Intl
Feb 11
ORD12:15 pmChicago O'Hare Intl
12h 00m
2 stops
YYC11:15 pmCalgary
Delta
Feb 23
YYC6:35 amCalgary
9h 54m
1 stop
ORD5:29 pmChicago O'Hare Intl
Feb 28
ORD1:40 pmChicago O'Hare Intl
10h 35m
1 stop
YYC11:15 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 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?

The month of June is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around $286.

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?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Calgary when booking 23 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $354 when searching 23 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 $264 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.

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

As of January 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

$96

Fastest flight time

3h 19m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Calgary in the past 72 hours is $96. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $136.
The fastest flight from Calgary to Chicago O'Hare Intl Airport takes 3h 19m
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 24m 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 $149Free CancellationRating
7.2
2,829 reviews
Search WestJet flights
Air CanadaPriceFrom $183Free CancellationRating
7.0
8,633 reviews
Search Air Canada flights
American AirlinesPriceFrom $219Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $268Free CancellationRating
8.0
8,521 reviews
Search Delta flights
United AirlinesPriceFrom $280Free CancellationRating
7.4
8,984 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 $280 round-trip. Over the 6 United Airlines flights for this route in a normal week, average airfare is usually $473 round-trip - but some users have found much cheaper deals with momondo.

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

    Across 8,633 Air Canada reviews on momondo, the average score is 7.0/10. Air Canada flies from Calgary to Chicago O'Hare Intl Airport about 6 times each week, with ticket deals ranging from $183 to $464. Price data is based on momondo searches in the last 72 hours.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Rockford
Lake Geneva
Schaumburg
Merrillville
Rosemont
Gurnee
Naperville
Kenosha
Joliet
South Haven
Racine
Hammond
Oak Brook
South Holland
Tinley Park
New Buffalo
Elk Grove Village
Aurora
Elgin
Waukegan

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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