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Cheap flights from Calgary to Chicago 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 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 - 6:14 pmYYC-MDW
10h 39m2 stops
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
$221Delta
Find Deal
Wed, Jan 8 - 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
Find Deal
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
Find Deal
Fri, Jan 17
7:00 am - 9:12 pmYYC-ORD
13h 12m2 stops
$136Delta
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Sat, Dec 7
6:35 am - 12:46 pmYYC-MDW
5h 11m1 stop
$136Delta
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Wed, Jan 8
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
Find Deal
Thu, Dec 5
12:41 pm - 5:09 pmYYC-ORD
3h 28mnonstop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$313United Airlines
Find Deal
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 - 6:32 pmYYC-MDW
10h 32m1 stop
7:17 pm - 1:50 pmMDW-YYC
19h 33m1 stop
$1,067WestJet
Find Deal
Fri, Nov 22 - Mon, Nov 25
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

Our best United Airlines deals on Calgary to Chicago 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

Our best Air Canada deals on Calgary to Chicago 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

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?

September. The cheapest time of year to fly to Chicago from Calgary is September. Most expensive is December

What is the cheapest day to depart Calgary for Chicago?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Thursday

When is the cheapest time to fly from Calgary to Chicago?

In the evening. Calgary to Chicago flights are approximately 43% more expensive at noon than in the evening

What is the cheapest Calgary to Chicago flight route?

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

How far in advance should you book Calgary to Chicago flights?

48 days before. The cheapest time to buy a flight from Calgary to Chicago is approximately 48 days to departure

Can stopping save me money on Calgary to Chicago flights?

No. A direct flight is the cheapest option for a flight between Calgary to Chicago.

How have Calgary to Chicago flight prices changed over time?

As of November 2024, prices for Calgary to Chicago flights are approximately 2% more expensive 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

$108

Fastest flight time

3h 20m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Calgary in the past 72 hours is $108. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is $196.
The fastest flight from Calgary to Chicago takes 3h 20m
Direct flights go from Calgary to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Calgary to Chicago by plane?

    Chicago is 1397.6 mi away from Calgary. In terms of flight time, this usually takes a little over 3h 20m.

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

    Prices for flights from Calgary Airport to Chicago were last updated today.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to 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?

  • What is the most popular airline 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
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

    United Airlines operates around 7 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been $403, but momondo users have found United Airlines deals from Calgary to Chicago from as low as $226 round-trip. United Airlines has been scored 7.4/10 in 9,172 reviews.

  • Air Canada Flights From Calgary to Chicago

    Another popular option for Calgary to Chicago flights is Air Canada (7.0/10, 8,238 ratings). Air Canada flies from Calgary to Chicago around 7 times per week, with deals starting from $213 round-trip and rising to an average price of around $412.


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. momondo allows you to filter the results for Calgary to Chicago flights to just show those with flexible booking policies.

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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Calgary and alert you when they change.


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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 78.5 mi from Chicago