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Cheap flights from Calgary to Chicago from $145

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 6/1. 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
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$239WestJet
Fri, May 29 - Sat, Jun 6
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$243WestJet
Fri, Oct 16 - Mon, Oct 19
United Airlines Logo
12:28 pm - 5:05 pm
YYC
-
ORD
3h 37mnonstop
United Airlines Logo
7:05 am - 9:48 pm
ORD
-
YYC
15h 43m
1 stop
$255United Airlines
Sat, May 23 - Sat, May 30
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$269WestJet
Tue, Sep 1 - Tue, Sep 8
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$270WestJet
Thu, Sep 3 - Tue, Sep 8
United Airlines Logo
1:27 pm - 9:39 pm
YYC
-
ORD
7h 12m
1 stop
United Airlines Logo
7:05 am - 9:48 pm
ORD
-
YYC
15h 43m
1 stop
$271United Airlines
Sat, May 23 - Sat, May 30
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
2:20 pm - 5:15 pm
ORD
-
YYC
3h 55mnonstop
$272WestJet
Fri, Oct 23 - Sun, Oct 25
Air Canada Logo
6:30 am - 2:55 pm
YYC
-
ORD
7h 25m
1 stop
Air Canada Logo
3:45 pm - 10:57 pm
ORD
-
YYC
8h 12m
1 stop
$274Air Canada
Sat, Oct 3 - Sun, Oct 11
Delta Logo
6:45 am - 4:51 pm
YYC
-
ORD
9h 06m
1 stop
Delta Logo
12:30 pm - 8:30 pm
ORD
-
YYC
9h 00m
1 stop
$276Delta
Sun, May 24 - Thu, May 28
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$277WestJet
Fri, Aug 21 - Tue, Aug 25

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
May 24
YYC6:45 amCalgary
9h 06m
1 stop
ORD4:51 pmChicago O'Hare Intl
May 28
ORD12:30 pmChicago O'Hare Intl
9h 00m
1 stop
YYC8:30 pmCalgary
$276
Delta
Sep 15
YYC7:15 amCalgary
9h 46m
1 stop
ORD6:01 pmChicago O'Hare Intl
Sep 17
ORD1:55 pmChicago O'Hare Intl
10h 11m
1 stop
YYC11:06 pmCalgary
$285
Delta
Oct 17
YYC7:15 amCalgary
13h 19m
2 stops
ORD9:34 pmChicago O'Hare Intl
Oct 20
ORD1:55 pmChicago O'Hare Intl
10h 18m
1 stop
YYC11:13 pmCalgary
$288

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

Our best American Airlines deals on Calgary to Chicago O'Hare Intl Airport flight tickets
American Airlines
May 20
YYC1:40 pmCalgary
3h 35m
ORD6:15 pmChicago O'Hare Intl
May 26
ORD8:55 pmChicago O'Hare Intl
3h 48m
YYC11:43 pmCalgary
$270
American Airlines
May 28
YYC6:15 amCalgary
3h 30m
ORD10:45 amChicago O'Hare Intl
Jun 1
ORD8:55 pmChicago O'Hare Intl
3h 48m
YYC11:43 pmCalgary
$279
American Airlines
Jun 4
YYC7:00 amCalgary
3h 35m
ORD11:35 amChicago O'Hare Intl
Jun 8
ORD8:50 pmChicago O'Hare Intl
3h 52m
YYC11:42 pmCalgary
$282

momondo Fare Finder

 
Customize your flight search to find flights from Calgary to Chicago O'Hare Intl Airport 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 May 13, 2026.
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
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/29

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Sat 6/6

5:30 pm-8:25 pm

Nonstop3h 55m

$239

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/16

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Mon 10/19

5:30 pm-8:25 pm

Nonstop3h 55m

$243

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/23

12:28 pm-5:05 pm

Nonstop3h 37m

Chicago O'Hare Intl

Sat 5/30

7:05 am-9:48 pm

1 stop15h 43m

$255

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 9/1

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 9/8

5:30 pm-8:25 pm

Nonstop3h 55m

$269

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 9/3

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 9/8

5:30 pm-8:25 pm

Nonstop3h 55m

$270

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/23

1:27 pm-9:39 pm

1 stop7h 12m

Chicago O'Hare Intl

Sat 5/30

7:05 am-9:48 pm

1 stop15h 43m

$271

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/23

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Sun 10/25

2:20 pm-5:15 pm

Nonstop3h 55m

$272

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 10/3

6:30 am-2:55 pm

1 stop7h 25m

Chicago O'Hare Intl

Sun 10/11

3:45 pm-10:57 pm

1 stop8h 12m

$274

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 5/24

6:45 am-4:51 pm

1 stop9h 06m

Chicago O'Hare Intl

Thu 5/28

12:30 pm-8:30 pm

1 stop9h 00m

$276

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 8/21

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 8/25

5:30 pm-8:25 pm

Nonstop3h 55m

$277

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?

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

The month of March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around $251.

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 Sunday when prices can be found for as low as $317. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $485.

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 $359 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $868. 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 $282 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 $185 on momondo.

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 May 2026, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 12% 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

$174

Fastest flight time

3h 25m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Calgary in the past 72 hours is $174. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $229.
The fastest flight from Calgary to Chicago O'Hare Intl Airport takes 3h 25m
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 25m 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
Air CanadaPriceFrom $109Free CancellationRating
7.1
11,022 reviews
Search Air Canada flights
United AirlinesPriceFrom $135Free CancellationRating
7.4
9,702 reviews
Search United Airlines flights
WestJetPriceFrom $137Free CancellationRating
7.2
3,334 reviews
Search WestJet flights
American AirlinesPriceFrom $208Free CancellationRating
7.1
11,665 reviews
Search American 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 $135 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $460 round-trip - but some users have found much cheaper deals with momondo.

  • WestJet Flights From Calgary to Chicago O'Hare Intl Airport

    Across 3,334 WestJet reviews on momondo, the average score is 7.2/10. WestJet flies from Calgary to Chicago O'Hare Intl Airport about 2 times each week, with ticket deals ranging from $137 to $277. 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
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Rosemont
Naperville
Orland Park
New Buffalo
Oak Brook
Kenosha
Joliet
Aurora
Racine
Janesville
Hammond
Evanston
Elgin
Tinley Park

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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