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Cheap flights from Calgary to Chicago from $99

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 5/27. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 5:15 pm
ORD
-
YYC
3h 55mnonstop
$158WestJet
Fri, Apr 17 - Fri, Apr 24
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$164WestJet
Thu, Apr 30 - Thu, May 7
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$165WestJet
Fri, May 1 - Mon, May 4
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$166WestJet
Fri, May 29 - Sun, May 31
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$169WestJet
Thu, Apr 30 - Thu, May 7
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$173WestJet
Thu, Aug 13 - Mon, Aug 17
Delta Logo
6:40 am - 5:58 pm
YYC
-
MDW
10h 18m
2 stops
Delta Logo
9:23 am - 10:57 pm
MDW
-
YYC
14h 34m
2 stops
$230Delta
Mon, May 4 - Thu, May 7
Delta Logo
6:40 am - 5:58 pm
YYC
-
MDW
10h 18m
2 stops
Delta Logo
6:23 am - 10:57 pm
MDW
-
YYC
17h 34m
2 stops
$245Delta
Mon, May 4 - Thu, May 7
Delta Logo
6:30 am - 1:25 pm
YYC
-
MDW
5h 55m
1 stop
Delta Logo
2:05 pm - 8:45 pm
MDW
-
YYC
7h 40m
1 stop
$246Delta
Tue, Mar 31 - Tue, Apr 7
Multiple Airlines Logo
7:00 am - 7:31 pm
YYC
-
MDW
11h 31m
1 stop
Multiple Airlines Logo
6:00 am - 5:10 pm
MDW
-
YYC
12h 10m
1 stop
$274Multiple Airlines
Tue, May 5 - Tue, May 12

WestJet flights from Calgary to Chicago

Our best WestJet deals on Calgary to Chicago flight tickets
WestJet
Apr 17
YYC9:00 amCalgary
3h 35m
ORD1:35 pmChicago O'Hare Intl
Apr 24
ORD2:20 pmChicago O'Hare Intl
3h 55m
YYC5:15 pmCalgary
$158
WestJet
Apr 30
YYC12:00 pmCalgary
3h 40m
ORD4:40 pmChicago O'Hare Intl
May 7
ORD5:30 pmChicago O'Hare Intl
3h 55m
YYC8:25 pmCalgary
$164
WestJet
May 1
YYC12:00 pmCalgary
3h 40m
ORD4:40 pmChicago O'Hare Intl
May 4
ORD5:30 pmChicago O'Hare Intl
3h 55m
YYC8:25 pmCalgary
$165

United Airlines flights from Calgary to Chicago

Our best United Airlines deals on Calgary to Chicago flight tickets
United Airlines
Apr 7
YYC6:00 amCalgary
14h 20m
1 stop
ORD9:20 pmChicago O'Hare Intl
Apr 13
ORD11:03 pmChicago O'Hare Intl
15h 50m
1 stop
YYC1:53 pmCalgary
$217
United Airlines
Mar 26
YYC6:15 amCalgary
9h 45m
1 stop
ORD5:00 pmChicago O'Hare Intl
Jul 13
ORD6:00 amChicago O'Hare Intl
13h 13m
1 stop
YYC6:13 pmCalgary
$220
United Airlines
Apr 10
YYC6:00 amCalgary
15h 54m
1 stop
ORD10:54 pmChicago O'Hare Intl
Apr 13
ORD11:03 pmChicago O'Hare Intl
15h 50m
1 stop
YYC1:53 pmCalgary
$229

momondo Fare Finder

 
Customize your flight search to find flights from Calgary to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 7, 2026.
Use the filters below to find and compare flights from Calgary to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 4/17

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Fri 4/24

2:20 pm-5:15 pm

Nonstop3h 55m

$158

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 4/30

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Thu 5/7

5:30 pm-8:25 pm

Nonstop3h 55m

$164

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/1

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Mon 5/4

5:30 pm-8:25 pm

Nonstop3h 55m

$165

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/29

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Sun 5/31

5:30 pm-8:25 pm

Nonstop3h 55m

$166

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 4/30

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Thu 5/7

5:30 pm-8:25 pm

Nonstop3h 55m

$169

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 8/13

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Mon 8/17

5:30 pm-8:25 pm

Nonstop3h 55m

$173

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 5/4

6:40 am-5:58 pm

2 stops10h 18m

Chicago Midway

Thu 5/7

9:23 am-10:57 pm

2 stops14h 34m

$230

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 5/4

6:40 am-5:58 pm

2 stops10h 18m

Chicago Midway

Thu 5/7

6:23 am-10:57 pm

2 stops17h 34m

$245

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 3/31

6:30 am-1:25 pm

1 stop5h 55m

Chicago Midway

Tue 4/7

2:05 pm-8:45 pm

1 stop7h 40m

$246

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 5/5

7:00 am-7:31 pm

1 stop11h 31m

Chicago Midway

Tue 5/12

6:00 am-5:10 pm

1 stop12h 10m

$274

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Calgary and Chicago?

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Calgary, with most prices found around $189. If you’re not able to fly to Chicago in November, then January is your next best option. Flight prices from Calgary to Chicago during January average around $192.

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 Sunday when prices can be found for as low as $183. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Calgary to Chicago for around $483.

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Calgary to Chicago during this time can be as low as $341. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $838.

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 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 $266 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 $214 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.

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 March 2026, prices for Calgary to Chicago flights are approximately 5% 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

$207

Fastest flight time

3h 27m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Calgary in the past 72 hours is $207. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is $194.
The fastest flight from Calgary to Chicago takes 3h 27m
Direct flights go from Calgary to Chicago on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Calgary there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • 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 27m.

  • 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
Air CanadaPriceFrom $101Free CancellationRating
7.1
10,789 reviews
Search Air Canada flights
WestJetPriceFrom $138Free CancellationRating
7.2
3,283 reviews
Search WestJet flights
United AirlinesPriceFrom $168Free CancellationRating
7.4
9,405 reviews
Search United Airlines flights
American AirlinesPriceFrom $185Free CancellationRating
7.1
11,399 reviews
Search American Airlines flights

  • United Airlines Flights From Calgary to Chicago

    United Airlines operates around 1 flight from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been $457, but momondo users have found United Airlines deals from Calgary to Chicago from as low as $168 round-trip. United Airlines has been scored 7.4/10 in 9,405 reviews.

  • Air Canada Flights From Calgary to Chicago

    Another popular option for Calgary to Chicago flights is Air Canada (7.1/10, 10,789 ratings). Air Canada flies from Calgary to Chicago around 1 time per week, with deals starting from $101 round-trip and rising to an average price of around $335.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

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.

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.
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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport