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Cheap flights from Calgary to Chicago from $172

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 9/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:55 pm - 9:00 amYYC  Calgary-ORD Chicago O'Hare Intl
8h 05m1 stop Toronto Pearson Intl
Multiple Airlines Logo
5:30 pm - 8:25 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 55mnonstop
$245Multiple Airlines
Mon, Sep 28 - Mon, Oct 5
United Airlines Logo
1:30 pm - 3:50 pmYYC  Calgary-ORD Chicago O'Hare Intl
2h 20mnonstop
United Airlines Logo
9:00 am - 1:54 pmORD  Chicago O'Hare Intl-YYC Calgary
4h 54mnonstop
$246United Airlines
Fri, Dec 4 - Sun, Dec 6
WestJet Logo
12:00 pm - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 55mnonstop
$246WestJet
Thu, Sep 10 - Tue, Sep 15
United Airlines Logo
1:30 pm - 3:50 pmYYC  Calgary-ORD Chicago O'Hare Intl
2h 20mnonstop
United Airlines Logo
9:00 am - 1:54 pmORD  Chicago O'Hare Intl-YYC Calgary
4h 54mnonstop
$246United Airlines
Fri, Dec 4 - Tue, Dec 8
WestJet Logo
12:00 pm - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 55mnonstop
$248WestJet
Sat, Aug 29 - Tue, Sep 1
Air Canada Logo
6:00 am - 3:38 pmYYC  Calgary-ORD Chicago O'Hare Intl
8h 38m1 stop Toronto Pearson Intl
Air Canada Logo
10:15 am - 8:59 pmORD  Chicago O'Hare Intl-YYC Calgary
10h 44m1 stop Toronto Pearson Intl
$248Air Canada
Fri, Oct 30 - Mon, Nov 2
Air Canada Logo
6:00 am - 3:38 pmYYC  Calgary-ORD Chicago O'Hare Intl
8h 38m1 stop Toronto Pearson Intl
Air Canada Logo
10:15 am - 8:59 pmORD  Chicago O'Hare Intl-YYC Calgary
10h 44m1 stop Toronto Pearson Intl
$255Air Canada
Fri, Oct 30 - Mon, Nov 2
Multiple Airlines Logo
1:30 pm - 3:50 pmYYC  Calgary-ORD Chicago O'Hare Intl
2h 20mnonstop
Multiple Airlines Logo
4:30 pm - 1:24 amORD  Chicago O'Hare Intl-YYC Calgary
8h 54m1 stop Toronto Pearson Intl
$259Multiple Airlines
Thu, Dec 3 - Mon, Dec 7
Delta Logo
2:30 pm - 6:39 pmYYC  Calgary-ORD Chicago O'Hare Intl
4h 09m1 stop Minneapolis St Paul
Delta Logo
2:03 pm - 1:17 amORD  Chicago O'Hare Intl-YYC Calgary
11h 14m1 stop Salt Lake City
$271Delta
Fri, Dec 4 - Sun, Dec 6
Delta Logo
12:35 pm - 8:47 pmYYC  Calgary-ORD Chicago O'Hare Intl
8h 12m1 stop Salt Lake City
Delta Logo
2:03 pm - 1:17 amORD  Chicago O'Hare Intl-YYC Calgary
11h 14m1 stop Salt Lake City
$271Delta
Thu, Dec 3 - Sun, Dec 6

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WestJet flights from Calgary to Chicago

Our best WestJet deals on Calgary to Chicago flight tickets
WestJet
Aug 28
YYC12:00 pmCalgary
3h 40m
ORD4:40 pmChicago O'Hare Intl
Sep 6
ORD5:30 pmChicago O'Hare Intl
3h 55m
YYC8:25 pmCalgary
$249
WestJet
Sep 10
YYC12:00 pmCalgary
3h 40m
ORD4:40 pmChicago O'Hare Intl
Sep 15
ORD5:30 pmChicago O'Hare Intl
3h 55m
YYC8:25 pmCalgary
$252
WestJet
Sep 15
YYC12:00 pmCalgary
3h 40m
ORD4:40 pmChicago O'Hare Intl
Sep 20
ORD5:30 pmChicago O'Hare Intl
3h 55m
YYC8:25 pmCalgary
$253

Delta flights from Calgary to Chicago

Our best Delta deals on Calgary to Chicago flight tickets
Delta
Oct 28
YYC1:40 pmCalgary
9h 12m
2 stops
ORD11:52 pmChicago O'Hare Intl
Oct 30
ORD12:29 pmChicago O'Hare Intl
9h 11m
1 stop
YYC8:40 pmCalgary
$277
Delta
Dec 14
YYC8:45 amCalgary
6h 54m
1 stop
MDW3:39 pmChicago Midway
Dec 16
MDW6:00 amChicago Midway
19h 17m
2 stops
YYC1:17 amCalgary
$278
Delta
Dec 14
YYC7:25 amCalgary
9h 40m
1 stop
ORD5:05 pmChicago O'Hare Intl
Dec 16
ORD2:03 pmChicago O'Hare Intl
11h 14m
1 stop
YYC1:17 amCalgary
$279

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 August 18, 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

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Mon 9/28

11:55 pm-9:00 am

1 stop8h 05m

Chicago O'Hare Intl

Mon 10/5

5:30 pm-8:25 pm

Nonstop3h 55m

$245
Quickest round-trip

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 12/4

1:30 pm-3:50 pm

Nonstop2h 20m

Chicago O'Hare Intl

Sun 12/6

9:00 am-1:54 pm

Nonstop4h 54m

$246

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 9/10

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 9/15

5:30 pm-8:25 pm

Nonstop3h 55m

$246

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 12/4

1:30 pm-3:50 pm

Nonstop2h 20m

Chicago O'Hare Intl

Tue 12/8

9:00 am-1:54 pm

Nonstop4h 54m

$246

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sat 8/29

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 9/1

5:30 pm-8:25 pm

Nonstop3h 55m

$248

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 10/30

6:00 am-3:38 pm

1 stop8h 38m

Chicago O'Hare Intl

Mon 11/2

10:15 am-8:59 pm

1 stop10h 44m

$248

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 10/30

6:00 am-3:38 pm

1 stop8h 38m

Chicago O'Hare Intl

Mon 11/2

10:15 am-8:59 pm

1 stop10h 44m

$255

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 12/3

1:30 pm-3:50 pm

Nonstop2h 20m

Chicago O'Hare Intl

Mon 12/7

4:30 pm-1:24 am

1 stop8h 54m

$259

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 12/4

2:30 pm-6:39 pm

1 stop4h 09m

Chicago O'Hare Intl

Sun 12/6

2:03 pm-1:17 am

1 stop11h 14m

$271

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 12/3

12:35 pm-8:47 pm

1 stop8h 12m

Chicago O'Hare Intl

Sun 12/6

2:03 pm-1:17 am

1 stop11h 14m

$271

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?

Prices are currently low for flights on this route.

Typical prices usually range from $247 to $405.
The lowest price recently found on this route was $245.

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Calgary, with most prices found around $239. If you’re not able to fly to Chicago in January, then November is your next best option. Flight prices from Calgary to Chicago during November average around $245.

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 Friday when prices can be found for as low as $369. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Calgary to Chicago for around $606.

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 $395. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $861.

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 from Calgary 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 $295 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 $221 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?

You could potentially save up to 9% on your flight if you consider stops on a Calgary to Chicago flight.

How have Calgary to Chicago flight prices changed over time?

As of August 2026, prices for Calgary to Chicago flights are approximately 44% cheaper 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

$172

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Calgary in the past 72 hours is $172. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is $245.
The fastest flight from Calgary to Chicago takes 2h 20m
Direct flights go from Calgary to Chicago every day.
There are 3 airports in Chicago. From Calgary there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Calgary to Chicago

  • 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 2h 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
United AirlinesPriceFrom $135Free CancellationRating
7.4
10,103 reviews
Search United Airlines flights
Air CanadaPriceFrom $149Free CancellationRating
7.1
11,489 reviews
Search Air Canada flights
WestJetPriceFrom $163Free CancellationRating
7.2
3,430 reviews
Search WestJet flights
American AirlinesPriceFrom $208Free CancellationRating
7.1
11,954 reviews
Search American Airlines flights
DeltaPriceFrom $253Free CancellationRating
7.8
8,503 reviews
Search Delta flights

  • Delta Flights From Calgary to Chicago

    Delta operates around 2 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been $371, but momondo users have found Delta deals from Calgary to Chicago from as low as $253 round-trip. Delta has been scored 7.8/10 in 8,499 reviews.

  • United Airlines Flights From Calgary to Chicago

    Another popular option for Calgary to Chicago flights is United Airlines (7.4/10, 10,102 ratings). United Airlines flies from Calgary to Chicago around 13 times per week, with deals starting from $135 round-trip and rising to an average price of around $391.

Traveling to a place near Chicago?

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