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Cheap flights from Calgary to Chicago from $93

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 9/11. 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
0 bags

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Cheap round-trip flights

WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$138WestJet
Find Deal
Thu, Sep 4 - Thu, Sep 11
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$143WestJet
Find Deal
Wed, Sep 17 - Fri, Sep 19
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$144WestJet
Find Deal
Wed, Sep 17 - Fri, Sep 19
Logo
1:10 am - 9:51 amYYC-ORD
7h 41m1 stop
Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$164
Find Deal
Wed, Sep 3 - Thu, Sep 11
Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
Logo
5:01 am - 1:53 pmORD-YYC
9h 52m1 stop
$165
Find Deal
Sat, Oct 11 - Sat, Oct 18
Air Canada Logo
1:10 am - 9:51 amYYC-ORD
7h 41m1 stop
Air Canada Logo
6:20 pm - 1:12 amORD-YYC
7h 52m1 stop
$174Air Canada
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Tue, Sep 16 - Fri, Sep 19
United Airlines Logo
6:15 am - 7:55 pmYYC-ORD
12h 40m1 stop
United Airlines Logo
2:53 pm - 9:48 pmORD-YYC
7h 55m1 stop
$175United Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
Air Canada Logo
1:10 am - 9:51 amYYC-ORD
7h 41m1 stop
Air Canada Logo
3:50 pm - 11:22 pmORD-YYC
8h 32m1 stop
$184Air Canada
Find Deal
Wed, Sep 3 - Thu, Sep 11
United Airlines Logo
12:30 pm - 4:50 pmYYC-ORD
3h 20mnonstop
United Airlines Logo
9:00 am - 11:54 amORD-YYC
3h 54mnonstop
$187United Airlines
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Fri, Oct 31 - Sun, Nov 2
Lufthansa Logo
6:15 am - 1:15 pmYYC-ORD
6h 00m1 stop
Lufthansa Logo
8:08 pm - 10:53 pmORD-YYC
3h 45mnonstop
$214Lufthansa
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Sun, Aug 31 - Sun, Sep 7

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
Oct 11
YYC6:15 amCalgary
12h 40m
1 stop
ORD7:55 pmChicago O'Hare Intl
Oct 18
ORD2:53 pmChicago O'Hare Intl
7h 55m
1 stop
YYC9:48 pmCalgary
$175
Find similar
United Airlines
Oct 31
YYC12:30 pmCalgary
3h 20m
ORD4:50 pmChicago O'Hare Intl
Nov 2
ORD9:00 amChicago O'Hare Intl
3h 54m
YYC11:54 amCalgary
$187
Find similar
United Airlines
Jul 11
YYC12:38 pmCalgary
3h 34m
ORD5:12 pmChicago O'Hare Intl
Jul 14
ORD8:03 pmChicago O'Hare Intl
3h 50m
YYC10:53 pmCalgary
$283
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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
Sep 4
YYC12:15 pmCalgary
3h 28m
ORD4:43 pmChicago O'Hare Intl
Sep 11
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
$138
Find similar
WestJet
Sep 17
YYC12:15 pmCalgary
3h 28m
ORD4:43 pmChicago O'Hare Intl
Sep 19
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
$143
Find similar
WestJet
Sep 17
YYC12:15 pmCalgary
3h 28m
ORD4:43 pmChicago O'Hare Intl
Sep 19
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
$144
Find similar

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 $184.

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 $173. 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 $463.

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 $350 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $466. 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 $275 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 $207 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 July 2025, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 35% 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

$93

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 $93. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $138.
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.
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  • 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
Air CanadaPriceFrom $109Free CancellationRating
7.1
9,692 reviews
Search Air Canada flights
WestJetPriceFrom $140Free CancellationRating
7.2
2,924 reviews
Search WestJet flights
American AirlinesPriceFrom $219Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $239Free CancellationRating
7.4
8,846 reviews
Search United 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 $239 round-trip. Over the 9 United Airlines flights for this route in a normal week, average airfare is usually $461 round-trip - but some users have found much cheaper deals with momondo.

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

    Across 2,924 WestJet reviews on momondo, the average score is 7.2/10. WestJet flies from Calgary to Chicago O'Hare Intl Airport about 4 times each week, with ticket deals ranging from $140 to $294. 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
Rockford
Schaumburg
South Haven
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Tinley Park
Hammond
Elgin
Aurora
Orland Park
Janesville
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.

An easier way to manage your Chicago O'Hare Intl Airport trip

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