Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Calgary to Chicago from C$ 124

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 24/9. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

WestJet Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 183WestJet
Find Deal
mié., 3 sep. - mar., 9 sep.
WestJet Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 193WestJet
Find Deal
mié., 3 sep. - mar., 9 sep.
Air Canada Logo
1:10 a.m. - 9:51 a.m.YYC-ORD
7h 41m1 stop
Air Canada Logo
6:20 p.m. - 1:12 a.m.ORD-YYC
7h 52m1 stop
C$ 227Air Canada
Find Deal
mar., 2 sep. - mar., 9 sep.
United Airlines Logo
6:15 a.m. - 6:26 p.m.YYC-ORD
11h 11m1 stop
United Airlines Logo
9:44 p.m. - 1:53 p.m.ORD-YYC
17h 09m1 stop
C$ 239United Airlines
Find Deal
mié., 24 sep. - jue., 23 oct.
Air Canada Logo
1:10 a.m. - 9:51 a.m.YYC-ORD
7h 41m1 stop
Air Canada Logo
8:40 a.m. - 3:50 p.m.ORD-YYC
8h 10m1 stop
C$ 245Air Canada
Find Deal
mar., 23 sep. - jue., 23 oct.
United Airlines Logo
12:37 p.m. - 5:10 p.m.YYC-ORD
3h 33mdirect
United Airlines Logo
8:45 a.m. - 11:35 a.m.ORD-YYC
3h 50mdirect
C$ 257United Airlines
Find Deal
jue., 20 nov. - mar., 25 nov.
American Airlines Logo
6:45 a.m. - 9:45 p.m.YYC-ORD
14h 00m1 stop
American Airlines Logo
8:30 p.m. - 11:19 p.m.ORD-YYC
3h 49mdirect
C$ 285American Airlines
Find Deal
jue., 4 sep. - dom., 7 sep.
American Airlines Logo
6:29 a.m. - 10:54 a.m.YYC-ORD
3h 25mdirect
American Airlines Logo
6:30 p.m. - 11:50 a.m.ORD-YYC
18h 20m1 stop
C$ 289American Airlines
Find Deal
vie., 29 ago. - jue., 4 sep.
Delta Logo
7:55 a.m. - 5:30 p.m.YYC-ORD
8h 35m1 stop
Delta Logo
1:00 p.m. - 10:57 p.m.ORD-YYC
10h 57m1 stop
C$ 308Delta
Find Deal
mié., 3 sep. - mar., 9 sep.
Delta Logo
7:55 a.m. - 5:30 p.m.YYC-ORD
8h 35m1 stop
Delta Logo
1:00 p.m. - 10:57 p.m.ORD-YYC
10h 57m1 stop
C$ 310Delta
Find Deal
mié., 3 sep. - mar., 9 sep.

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
4 Sep
YYC6:45 a.m.Calgary
14h 00m
1 stop
ORD9:45 p.m.Chicago O'Hare Intl
7 Sep
ORD8:30 p.m.Chicago O'Hare Intl
3h 49m
YYC11:19 p.m.Calgary
C$ 285
Find similar
American Airlines
29 Aug
YYC6:29 a.m.Calgary
3h 25m
ORD10:54 a.m.Chicago O'Hare Intl
4 Sep
ORD6:30 p.m.Chicago O'Hare Intl
18h 20m
1 stop
YYC11:50 a.m.Calgary
C$ 289
Find similar
American Airlines
19 Sep
YYC6:29 a.m.Calgary
3h 25m
ORD10:54 a.m.Chicago O'Hare Intl
21 Sep
ORD8:30 p.m.Chicago O'Hare Intl
3h 49m
YYC11:19 p.m.Calgary
C$ 322
Find similar

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
3 Sep
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
9 Sep
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
C$ 183
Find similar
WestJet
3 Sep
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
9 Sep
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
C$ 193
Find similar
WestJet
4 Sep
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
9 Sep
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
C$ 210
Find similar

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 96,600 searches. Data last updated 30 julio 2025.
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

mié. 3/9

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

mar. 9/9

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 183

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mié. 3/9

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

mar. 9/9

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 193

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mar. 2/9

1:10 a.m.-9:51 a.m.

1 stop7h 41m

Chicago O'Hare Intl

mar. 9/9

6:20 p.m.-1:12 a.m.

1 stop7h 52m

C$ 227

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mié. 24/9

6:15 a.m.-6:26 p.m.

1 stop11h 11m

Chicago O'Hare Intl

jue. 23/10

9:44 p.m.-1:53 p.m.

1 stop17h 09m

C$ 239

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mar. 23/9

1:10 a.m.-9:51 a.m.

1 stop7h 41m

Chicago O'Hare Intl

jue. 23/10

8:40 a.m.-3:50 p.m.

1 stop8h 10m

C$ 245

CalgaryChicago

YYC - ORD

YYCORD

Calgary

jue. 20/11

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

Chicago O'Hare Intl

mar. 25/11

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

C$ 257

CalgaryChicago

YYC - ORD

YYCORD

Calgary

jue. 4/9

6:45 a.m.-9:45 p.m.

1 stop14h 00m

Chicago O'Hare Intl

dom. 7/9

8:30 p.m.-11:19 p.m.

Nonstop3h 49m

C$ 285

CalgaryChicago

YYC - ORD

YYCORD

Calgary

vie. 29/8

6:29 a.m.-10:54 a.m.

Nonstop3h 25m

Chicago O'Hare Intl

jue. 4/9

6:30 p.m.-11:50 a.m.

1 stop18h 20m

C$ 289

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mié. 3/9

7:55 a.m.-5:30 p.m.

1 stop8h 35m

Chicago O'Hare Intl

mar. 9/9

1:00 p.m.-10:57 p.m.

1 stop10h 57m

C$ 308

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mié. 3/9

7:55 a.m.-5:30 p.m.

1 stop8h 35m

Chicago O'Hare Intl

mar. 9/9

1:00 p.m.-10:57 p.m.

1 stop10h 57m

C$ 310

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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?

In general, May is the cheapest month to fly from Calgary to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 226. The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around C$ 254.

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 C$ 669. 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 O'Hare Intl Airport for around C$ 1,009.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the evening is the cheapest time of day to fly from Calgary to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 483. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 1,462 on average. Flights to Chicago O'Hare Intl Airport from Calgary at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

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 C$ 387 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 C$ 279 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.

Can stopping save me money on Calgary to Chicago O'Hare Intl Airport flights?

You could potentially save up to 7% on your flight if you consider stops on a Calgary to Chicago O'Hare Intl Airport flight.

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 26% 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

C$ 124

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 C$ 124. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 183.
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?

    There are 2223.9 km between Calgary and Chicago O'Hare Intl. 3h 25m is a normal flight duration for this route.

  • 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 were last updated today.

  • 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?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • 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 C$ 149Free CancellationRating
7.1
9,837 reviews
Search Air Canada flights
WestJetPriceFrom C$ 177Free CancellationRating
7.2
2,975 reviews
Search WestJet flights
DeltaPriceFrom C$ 183Free CancellationRating
8.0
7,980 reviews
Search Delta flights
American AirlinesPriceFrom C$ 184Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom C$ 251Free CancellationRating
7.4
8,896 reviews
Search United Airlines flights

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

    Across 3 Delta flights from Calgary to Chicago O'Hare Intl Airport this week, the average price was C$ 250, with the best Delta deals starting from C$ 133 round-trip. 7,980 users have rated Delta on momondo, with an average score of 8.0/10.

  • United Airlines Flights From Calgary to Chicago O'Hare Intl Airport

    The best United Airlines deal for Calgary to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was C$ 183, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at C$ 409 round-trip. United Airlines operates 8 flights out of Calgary into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 8,896 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hoffman Estates
Lisle
Tinley Park
Glenview
Hammond
Naperville
Wheeling
Great Lakes
Munster
Des Plaines
Benton Harbor
Harvard
Merrillville
Schaumburg
Oak Brook
Elmhurst
Elk Grove Village
Bridgeview
Kenosha
Skokie

Why use momondo?

Why should I use momondo to find a flight deal from Calgary to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Calgary to Chicago. momondo saves you time and could save you money on your trip.

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?

Yes momondo offers price alerts on flights to Chicago from Calgary. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago O'Hare Intl Airport 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
lun. 4/8
lun. 11/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago