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Cheap flights from Calgary to Chicago from $176

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.
Alaska Airlines Logo
9:07 am - 4:31 pmYYC  Calgary-ORD Chicago O'Hare Intl
7h 24m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
6:00 am - 9:37 pmORD  Chicago O'Hare Intl-YYC Calgary
15h 37m1 stop Seattle/Tacoma Intl
$302Alaska Airlines
Fri, Dec 11 - Sun, Dec 13
Alaska Airlines Logo
9:07 am - 5:49 pmYYC  Calgary-ORD Chicago O'Hare Intl
8h 42m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
6:47 pm - 9:37 pmORD  Chicago O'Hare Intl-YYC Calgary
26h 50m1 stop Seattle/Tacoma Intl
$302Alaska Airlines
Fri, Dec 4 - Mon, Dec 7
Delta Logo
7:15 am - 6:09 pmYYC  Calgary-ORD Chicago O'Hare Intl
10h 54m1 stop Salt Lake City
Delta Logo
6:00 am - 8:43 pmORD  Chicago O'Hare Intl-YYC Calgary
14h 43m2 stops Minneapolis St Paul Salt Lake City
$304Delta
Fri, Jan 15 - Sun, Jan 17
Delta Logo
7:45 am - 4:49 pmYYC  Calgary-ORD Chicago O'Hare Intl
8h 04m1 stop Minneapolis St Paul
Delta Logo
1:55 pm - 11:13 pmORD  Chicago O'Hare Intl-YYC Calgary
10h 18m1 stop Salt Lake City
$304Delta
Wed, Apr 7 - Mon, Apr 12
United Airlines Logo
1:37 pm - 5:10 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 33mnonstop
United Airlines Logo
12:29 pm - 10:53 pmORD  Chicago O'Hare Intl-YYC Calgary
10h 24m1 stop Denver Intl
$319United Airlines
Thu, Dec 3 - Tue, Dec 8
United Airlines Logo
1:37 pm - 5:10 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 33mnonstop
United Airlines Logo
7:00 am - 10:53 pmORD  Chicago O'Hare Intl-YYC Calgary
15h 53m1 stop Denver Intl
$330United Airlines
Thu, Dec 10 - Sat, Dec 12
Air Canada Logo
7:00 am - 3:38 pmYYC  Calgary-ORD Chicago O'Hare Intl
8h 38m1 stop Toronto Pearson Intl
Air Canada Logo
3:50 pm - 12:50 amORD  Chicago O'Hare Intl-YYC Calgary
9h 00m1 stop Montreal Pierre Elliott Trudeau Intl
$331Air Canada
Fri, Nov 20 - Mon, Nov 23
Air Canada Logo
1:20 am - 9:23 amYYC  Calgary-ORD Chicago O'Hare Intl
8h 03m1 stop Toronto Pearson Intl
Air Canada Logo
4:30 pm - 12:06 amORD  Chicago O'Hare Intl-YYC Calgary
7h 36m1 stop Toronto Pearson Intl
$336Air Canada
Wed, Nov 25 - Mon, Nov 30
American Airlines Logo
3:29 pm - 7:25 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 56mnonstop
American Airlines Logo
10:51 am - 2:44 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 53mnonstop
$410American Airlines
Thu, Feb 25 - Sun, Feb 28
American Airlines Logo
2:52 pm - 6:39 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 47mnonstop
American Airlines Logo
9:50 am - 1:54 pmORD  Chicago O'Hare Intl-YYC Calgary
4h 04mnonstop
$420American Airlines
Fri, Jan 22 - Sun, Jan 24

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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
Dec 3
YYC1:37 pmCalgary
3h 33m
ORD5:10 pmChicago O'Hare Intl
Dec 8
ORD12:29 pmChicago O'Hare Intl
10h 24m
1 stop
YYC10:53 pmCalgary
$319
United Airlines
Dec 11
YYC1:37 pmCalgary
3h 33m
ORD5:10 pmChicago O'Hare Intl
Dec 13
ORD7:00 amChicago O'Hare Intl
15h 53m
1 stop
YYC10:53 pmCalgary
$331
United Airlines
Dec 3
YYC1:37 pmCalgary
3h 33m
ORD5:10 pmChicago O'Hare Intl
Dec 8
ORD12:29 pmChicago O'Hare Intl
10h 24m
1 stop
YYC10:53 pmCalgary
$342

Alaska Airlines flights from Calgary to Chicago O'Hare Intl Airport

Our best Alaska Airlines deals on Calgary to Chicago O'Hare Intl Airport flight tickets
Alaska Airlines
Dec 4
YYC9:07 amCalgary
8h 42m
1 stop
ORD5:49 pmChicago O'Hare Intl
Dec 7
ORD6:47 pmChicago O'Hare Intl
26h 50m
1 stop
YYC9:37 pmCalgary
$302
Alaska Airlines
Nov 16
YYC9:09 amCalgary
28h 00m
2 stops
ORD1:09 pmChicago O'Hare Intl
Nov 18
ORD7:00 amChicago O'Hare Intl
14h 39m
1 stop
YYC9:39 pmCalgary
$311
Alaska Airlines
Dec 2
YYC9:07 amCalgary
7h 24m
1 stop
ORD4:31 pmChicago O'Hare Intl
Dec 11
ORD6:47 pmChicago O'Hare Intl
26h 50m
1 stop
YYC9:37 pmCalgary
$314

momondo Fare Finder

 
Use the filters below to find and compare flights from Calgary to Chicago O'Hare Intl Airport 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

Fri 12/11

9:07 am-4:31 pm

1 stop7h 24m

Chicago O'Hare Intl

Sun 12/13

6:00 am-9:37 pm

1 stop15h 37m

$302

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 12/4

9:07 am-5:49 pm

1 stop8h 42m

Chicago O'Hare Intl

Mon 12/7

6:47 pm-9:37 pm

1 stop26h 50m

$302

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 1/15

7:15 am-6:09 pm

1 stop10h 54m

Chicago O'Hare Intl

Sun 1/17

6:00 am-8:43 pm

2 stops14h 43m

$304

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Wed 4/7

7:45 am-4:49 pm

1 stop8h 04m

Chicago O'Hare Intl

Mon 4/12

1:55 pm-11:13 pm

1 stop10h 18m

$304

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 12/3

1:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Tue 12/8

12:29 pm-10:53 pm

1 stop10h 24m

$319

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 12/10

1:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Sat 12/12

7:00 am-10:53 pm

1 stop15h 53m

$330

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 11/20

7:00 am-3:38 pm

1 stop8h 38m

Chicago O'Hare Intl

Mon 11/23

3:50 pm-12:50 am

1 stop9h 00m

$331

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Wed 11/25

1:20 am-9:23 am

1 stop8h 03m

Chicago O'Hare Intl

Mon 11/30

4:30 pm-12:06 am

1 stop7h 36m

$336
Quickest round-trip

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 2/25

3:29 pm-7:25 pm

Nonstop3h 56m

Chicago O'Hare Intl

Sun 2/28

10:51 am-2:44 pm

Nonstop3h 53m

$410

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 1/22

2:52 pm-6:39 pm

Nonstop3h 47m

Chicago O'Hare Intl

Sun 1/24

9:50 am-1:54 pm

Nonstop4h 04m

$420

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 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?

Prices are currently typical for flights on this route.

Typical prices usually range from $268 to $500.
The lowest price recently found on this route was $302.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around $279.

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 Friday when prices can be found for as low as $424. This is often the case because there is less demand to fly during this day of the week. On the other hand, Tuesday 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 $627.

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 $383 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $726. 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 from Calgary to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Calgary when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $342 when searching 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 $224 on momondo.

What cabin class options are available on Calgary to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Calgary to Chicago O'Hare Intl Airport 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 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 2026, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 5% more expensive 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

$176

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 $176. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $302.
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.
Search flight deals

Frequently asked questions about flying from Calgary to Chicago O'Hare Intl Airport

  • 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
United AirlinesPriceFrom $135Free CancellationRating
7.3
10,460 reviews
Search United Airlines flights
Air CanadaPriceFrom $149Free CancellationRating
7.1
11,854 reviews
Search Air Canada flights
WestJetPriceFrom $163Free CancellationRating
7.2
3,441 reviews
Search WestJet flights
American AirlinesPriceFrom $244Free CancellationRating
7.0
12,230 reviews
Search American Airlines flights
DeltaPriceFrom $253Free CancellationRating
7.8
8,697 reviews
Search Delta 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 $135 round-trip. Over the 4 United Airlines flights for this route in a normal week, average airfare is usually $339 round-trip - but some users have found much cheaper deals with momondo.

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

    Across 11,854 Air Canada reviews on momondo, the average score is 7.1/10. Air Canada flies from Calgary to Chicago O'Hare Intl Airport about 6 times each week, with ticket deals ranging from $149 to $366. 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
Lake Geneva
Schaumburg
Merrillville
Rockford
South Haven
Oak Brook
Rosemont
Gurnee
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Skokie
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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