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Cheap flights from Calgary to Chicago from $100

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 5/4. 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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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
$168WestJet
Fri, Mar 6 - Mon, Mar 9
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$190WestJet
Wed, May 20 - Tue, May 26
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$191WestJet
Wed, May 20 - Tue, May 26
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$206WestJet
Mon, May 4 - Fri, May 8
Air Canada Logo
11:40 pm - 9:10 am
YYC
-
ORD
8h 30m
1 stop
Air Canada Logo
6:40 pm - 8:28 am
ORD
-
YYC
14h 48m
1 stop
$208Air Canada
Mon, Mar 30 - Tue, Apr 7
Multiple Airlines Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
Multiple Airlines Logo
10:00 am - 6:54 pm
ORD
-
YYC
9h 54m
1 stop
$221Multiple Airlines
Mon, Feb 23 - Tue, Mar 3
Air Canada Logo
7:10 am - 3:10 pm
YYC
-
ORD
7h 00m
1 stop
Air Canada Logo
3:55 pm - 1:14 am
ORD
-
YYC
10h 19m
1 stop
$223Air Canada
Wed, Mar 4 - Wed, Mar 11
Multiple Airlines Logo
7:00 am - 5:44 pm
YYC
-
ORD
9h 44m
1 stop
Multiple Airlines Logo
2:20 pm - 5:15 pm
ORD
-
YYC
3h 55mnonstop
$225Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
United Airlines Logo
8:30 am - 1:07 pm
YYC
-
ORD
3h 37mnonstop
United Airlines Logo
7:42 pm - 10:37 pm
ORD
-
YYC
3h 55mnonstop
$229United Airlines
Fri, Jun 5 - Sun, Jun 7
Delta Logo
6:45 am - 4:52 pm
YYC
-
ORD
9h 07m
1 stop
Delta Logo
2:11 pm - 10:57 pm
ORD
-
YYC
9h 46m
1 stop
$230Delta
Fri, May 8 - Tue, May 12

Air Canada flights from Calgary to Chicago O'Hare Intl Airport

Our best Air Canada deals on Calgary to Chicago O'Hare Intl Airport flight tickets
Air Canada
Mar 30
YYC11:40 pmCalgary
8h 30m
1 stop
ORD9:10 amChicago O'Hare Intl
Apr 7
ORD6:40 pmChicago O'Hare Intl
14h 48m
1 stop
YYC8:28 amCalgary
$208
Air Canada
Mar 4
YYC7:10 amCalgary
7h 00m
1 stop
ORD3:10 pmChicago O'Hare Intl
Mar 11
ORD3:55 pmChicago O'Hare Intl
10h 19m
1 stop
YYC1:14 amCalgary
$223
Air Canada
Mar 31
YYC9:00 amCalgary
8h 53m
1 stop
ORD6:53 pmChicago O'Hare Intl
Apr 8
ORD10:43 amChicago O'Hare Intl
10h 15m
1 stop
YYC7:58 pmCalgary
$240

WestJet flights from Calgary to Chicago O'Hare Intl Airport

Our best WestJet deals on Calgary to Chicago O'Hare Intl Airport flight tickets
WestJet
May 4
YYC12:00 pmCalgary
3h 40m
ORD4:40 pmChicago O'Hare Intl
May 7
ORD5:30 pmChicago O'Hare Intl
3h 55m
YYC8:25 pmCalgary
$161
WestJet
Mar 6
YYC9:00 amCalgary
3h 35m
ORD1:35 pmChicago O'Hare Intl
Mar 9
ORD2:20 pmChicago O'Hare Intl
3h 55m
YYC5:15 pmCalgary
$168
WestJet
May 20
YYC12:00 pmCalgary
3h 40m
ORD4:40 pmChicago O'Hare Intl
May 26
ORD5:30 pmChicago O'Hare Intl
3h 55m
YYC8:25 pmCalgary
$190

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 February 3, 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

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 3/6

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Mon 3/9

2:20 pm-5:15 pm

Nonstop3h 55m

$168

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 5/20

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 5/26

5:30 pm-8:25 pm

Nonstop3h 55m

$190

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 5/20

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 5/26

5:30 pm-8:25 pm

Nonstop3h 55m

$191

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 5/4

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Fri 5/8

5:30 pm-8:25 pm

Nonstop3h 55m

$206

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 3/30

11:40 pm-9:10 am

1 stop8h 30m

Chicago O'Hare Intl

Tue 4/7

6:40 pm-8:28 am

1 stop14h 48m

$208

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 2/23

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Tue 3/3

10:00 am-6:54 pm

1 stop9h 54m

$221

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 3/4

7:10 am-3:10 pm

1 stop7h 00m

Chicago O'Hare Intl

Wed 3/11

3:55 pm-1:14 am

1 stop10h 19m

$223

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 3/6

7:00 am-5:44 pm

1 stop9h 44m

Chicago O'Hare Intl

Mon 3/9

2:20 pm-5:15 pm

Nonstop3h 55m

$225

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 6/5

8:30 am-1:07 pm

Nonstop3h 37m

Chicago O'Hare Intl

Sun 6/7

7:42 pm-10:37 pm

Nonstop3h 55m

$229

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/8

6:45 am-4:52 pm

1 stop9h 07m

Chicago O'Hare Intl

Tue 5/12

2:11 pm-10:57 pm

1 stop9h 46m

$230

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 cheapest month to fly to Chicago O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around $195.

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 $179. This is often the case because there is less demand to fly during this day of the week. On the other hand, Thursday 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 $476.

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 $347 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $799. 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 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 $256 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 $162 on momondo.

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

There are 4 cabin classes available to choose from on Calgary to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Calgary to Chicago O'Hare Intl Airport flight prices changed over time?

As of February 2026, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 15% cheaper 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

$185

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 $185. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $216.
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

  • 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 $101Free CancellationRating
7.1
10,684 reviews
Search Air Canada flights
WestJetPriceFrom $138Free CancellationRating
7.2
3,255 reviews
Search WestJet flights
United AirlinesPriceFrom $168Free CancellationRating
7.4
9,236 reviews
Search United Airlines flights
American AirlinesPriceFrom $185Free CancellationRating
7.2
11,218 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 $168 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 3,255 WestJet reviews on momondo, the average score is 7.2/10. WestJet flies from Calgary to Chicago O'Hare Intl Airport about 1 time each week, with ticket deals ranging from $138 to $237. 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
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

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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