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Cheap flights from Calgary to Chicago O'Hare Intl Airport from C$ 138

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 O'Hare Intl Airport departing on 20/2. 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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Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Calgary to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Calgary to Chicago.

Cheap last-minute flights

Planning a quick getaway from Calgary to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Calgary to Chicago

Find recent round-trip train or bus tickets from Calgary to Chicago.

All round-trip flight deals from Calgary to Chicago

The cheapest plane tickets from Calgary to Chicago found on KAYAK recently.
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 196WestJet
Find Deal
Thu, 20 Feb - Thu, 27 Feb
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 217WestJet
Find Deal
Thu, 17 Apr - Sun, 20 Apr
7:20 p.m. - 9:33 a.m.YYC-ORD
13h 13m1 stop
1:05 p.m. - 9:41 p.m.ORD-YYC
9h 36m1 stop
C$ 276United Airlines
Find Deal
Mon, 17 Mar - Tue, 18 Mar
8:30 a.m. - 6:38 p.m.YYC-ORD
9h 08m1 stop
4:51 p.m. - 1:18 a.m.ORD-YYC
9h 27m1 stop
C$ 292Air Canada
Find Deal
Mon, 3 Feb - Tue, 11 Feb
12:05 a.m. - 10:10 a.m.YYC-ORD
9h 05m1 stop
6:28 p.m. - 1:18 a.m.ORD-YYC
7h 50m1 stop
C$ 302Air Canada
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Sun, 2 Feb - Tue, 11 Feb
6:35 a.m. - 8:53 p.m.YYC-ORD
13h 18m2 stops
12:15 p.m. - 8:53 p.m.ORD-YYC
9h 38m1 stop
C$ 311Delta
Find Deal
Thu, 20 Feb - Wed, 26 Feb
6:35 a.m. - 5:29 p.m.YYC-ORD
9h 54m1 stop
12:15 p.m. - 11:15 p.m.ORD-YYC
12h 00m2 stops
C$ 312Delta
Find Deal
Mon, 3 Feb - Tue, 11 Feb
12:45 p.m. - 11:56 p.m.YYC-ORD
10h 11m1 stop
8:35 p.m. - 11:50 a.m.ORD-YYC
16h 15m1 stop
C$ 429American Airlines
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Sat, 22 Feb - Mon, 24 Feb
1:32 p.m. - 6:03 p.m.YYC-ORD
3h 31mdirect
8:35 p.m. - 11:50 a.m.ORD-YYC
16h 15m1 stop
C$ 448American Airlines
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Fri, 21 Feb - Mon, 24 Feb
2:09 p.m. - 12:23 a.m.YYC-ORD
9h 14m1 stop
8:47 a.m. - 11:39 a.m.ORD-YYC
3h 52mdirect
C$ 449United Airlines
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Tue, 18 Mar - Wed, 19 Mar
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 138WestJet
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Thu, 20 Feb
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 144WestJet
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Mon, 31 Mar
1:30 p.m. - 12:35 a.m.YYC-ORD
10h 05m1 stop
C$ 171United Airlines
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Wed, 23 Apr
11:55 p.m. - 9:59 a.m.YYC-ORD
9h 04m1 stop
C$ 173Air Canada
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Fri, 23 May
8:30 a.m. - 6:41 p.m.YYC-ORD
9h 11m1 stop
C$ 174Air Canada
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Thu, 27 Mar
6:35 a.m. - 8:53 p.m.YYC-ORD
13h 18m2 stops
C$ 193Delta
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Tue, 18 Feb
6:35 a.m. - 8:53 p.m.YYC-ORD
13h 18m2 stops
C$ 194Delta
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Thu, 20 Feb
1:22 p.m. - 5:53 p.m.YYC-ORD
3h 31mdirect
C$ 213American Airlines
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Thu, 27 Mar
1:32 p.m. - 6:03 p.m.YYC-ORD
3h 31mdirect
C$ 269American Airlines
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Fri, 21 Feb
8:30 a.m. - 12:49 p.m.YYC-ORD
3h 19mdirect
C$ 292United Airlines
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Thu, 3 Jul
12:50 a.m. - 8:57 a.m.YYC-ORD
7h 07m1 stop
6:28 p.m. - 1:18 a.m.ORD-YYC
7h 50m1 stop
C$ 409Air Canada
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Thu, 23 Jan - Mon, 27 Jan
12:50 a.m. - 10:10 a.m.YYC-ORD
8h 20m1 stop
12:56 p.m. - 11:18 p.m.ORD-YYC
11h 22m1 stop
C$ 413Air Canada
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Sun, 26 Jan - Thu, 30 Jan
12:50 a.m. - 10:10 a.m.YYC-ORD
8h 20m1 stop
8:50 a.m. - 11:39 a.m.ORD-YYC
3h 49mdirect
C$ 596Air Canada
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Thu, 23 Jan - Mon, 27 Jan
7:30 a.m. - 12:39 a.m.YYC-ORD
16h 09m1 stop
6:06 p.m. - 7:46 p.m.ORD-YYC
26h 40m2 stops
C$ 633
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Fri, 24 Jan - Mon, 27 Jan
4:35 p.m. - 2:23 p.m.YYC-ORD
20h 48m2 stops
10:29 a.m. - 10:55 p.m.ORD-YYC
13h 26m2 stops
C$ 662
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Fri, 24 Jan - Mon, 27 Jan
4:35 p.m. - 5:55 a.m.YYC-ORD
36h 20m3 stops
7:26 a.m. - 10:55 p.m.ORD-YYC
16h 29m2 stops
C$ 717
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Fri, 24 Jan - Mon, 27 Jan
12:41 p.m. - 5:15 p.m.YYC-ORD
3h 34mdirect
8:50 a.m. - 11:39 a.m.ORD-YYC
3h 49mdirect
C$ 891United Airlines
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Fri, 24 Jan - Mon, 27 Jan
12:30 a.m. - 2:47 p.m.YYC-ORD
13h 17m1 stop
7:26 a.m. - 10:55 p.m.ORD-YYC
16h 29m2 stops
C$ 943
Find Deal
Thu, 23 Jan - Mon, 27 Jan
12:20 a.m. - 4:13 p.m.YYC-ORD
14h 53m2 stops
6:15 a.m. - 7:08 p.m.ORD-YYC
13h 53m2 stops
C$ 1,098WestJet
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Thu, 23 Jan - Mon, 27 Jan
12:50 a.m. - 10:10 a.m.YYC-ORD
8h 20m1 stop
8:50 a.m. - 11:39 a.m.ORD-YYC
3h 49mdirect
C$ 1,228Air Canada
Find Deal
Sun, 26 Jan - Thu, 30 Jan
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 196WestJet
Find Deal
Thu, 20 Feb - Thu, 27 Feb
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 217WestJet
Find Deal
Thu, 17 Apr - Sun, 20 Apr
12:15 p.m. - 4:44 p.m.YYC-ORD
3h 29mdirect
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 364Delta
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Fri, 2 May - Mon, 5 May
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 415Delta
Find Deal
Sun, 16 Mar - Thu, 27 Mar
6:29 a.m. - 10:53 a.m.YYC-ORD
3h 24mdirect
8:20 p.m. - 11:20 p.m.ORD-YYC
4h 00mdirect
C$ 495American Airlines
Find Deal
Tue, 10 Jun - Tue, 17 Jun
12:41 p.m. - 5:10 p.m.YYC-ORD
3h 29mdirect
8:47 a.m. - 11:39 a.m.ORD-YYC
3h 52mdirect
C$ 622United Airlines
Find Deal
Tue, 18 Mar - Wed, 19 Mar
1:17 p.m. - 5:49 p.m.YYC-ORD
3h 32mdirect
9:50 a.m. - 12:32 p.m.ORD-YYC
3h 42mdirect
C$ 659American Airlines
Find Deal
Fri, 25 Apr - Mon, 28 Apr
12:41 p.m. - 5:10 p.m.YYC-ORD
3h 29mdirect
8:47 a.m. - 11:39 a.m.ORD-YYC
3h 52mdirect
C$ 667United Airlines
Find Deal
Tue, 18 Mar - Thu, 20 Mar
12:41 p.m. - 5:15 p.m.YYC-ORD
3h 34mdirect
8:50 a.m. - 11:39 a.m.ORD-YYC
3h 49mdirect
C$ 1,312Air Canada
Find Deal
Sat, 1 Feb - Fri, 7 Feb
12:41 p.m. - 5:08 p.m.YYC-ORD
3h 27mdirect
8:53 a.m. - 11:39 a.m.ORD-YYC
3h 46mdirect
C$ 1,496Air Canada
Find Deal
Sun, 23 Feb - Wed, 26 Feb

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
17 Mar
YYC7:20 p.m.Calgary
13h 13m
1 stop
ORD9:33 a.m.Chicago O'Hare Intl
18 Mar
ORD1:05 p.m.Chicago O'Hare Intl
9h 36m
1 stop
YYC9:41 p.m.Calgary
United Airlines
18 Mar
YYC2:09 p.m.Calgary
9h 14m
1 stop
ORD12:23 a.m.Chicago O'Hare Intl
19 Mar
ORD8:47 a.m.Chicago O'Hare Intl
3h 52m
YYC11:39 a.m.Calgary
United Airlines
7 Mar
YYC7:20 p.m.Calgary
13h 13m
1 stop
ORD9:33 a.m.Chicago O'Hare Intl
11 Mar
ORD8:47 a.m.Chicago O'Hare Intl
3h 52m
YYC11:39 a.m.Calgary

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
20 Feb
YYC6:35 a.m.Calgary
13h 18m
2 stops
ORD8:53 p.m.Chicago O'Hare Intl
26 Feb
ORD12:15 p.m.Chicago O'Hare Intl
9h 38m
1 stop
YYC8:53 p.m.Calgary
Delta
3 Feb
YYC6:35 a.m.Calgary
9h 54m
1 stop
ORD5:29 p.m.Chicago O'Hare Intl
11 Feb
ORD12:15 p.m.Chicago O'Hare Intl
12h 00m
2 stops
YYC11:15 p.m.Calgary
Delta
23 Feb
YYC6:35 a.m.Calgary
9h 54m
1 stop
ORD5:29 p.m.Chicago O'Hare Intl
25 Feb
ORD12:15 p.m.Chicago O'Hare Intl
9h 38m
1 stop
YYC8:53 p.m.Calgary

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?

In general, September 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$ 383. The month of June is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around C$ 412.

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 Monday when prices can be found for as low as C$ 392. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, 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$ 548.

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

In the morning 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$ 505. Flying to Chicago O'Hare Intl Airport in the morning 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$ 581 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 23 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 509 when searching 23 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$ 380 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 January 2025, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 28% 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$ 138

Fastest flight time

3h 19m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Calgary in the past 72 hours is C$ 138. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 196.
The fastest flight from Calgary to Chicago O'Hare Intl Airport takes 3h 19m
Direct flights go from Calgary to Chicago O'Hare Intl Airport every day.

  • How far is Calgary to Chicago O'Hare Intl by plane?

    There are 2223.9 km between Calgary and Chicago O'Hare Intl. 3h 24m 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
American AirlinesPriceFrom C$ 204Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom C$ 238Free CancellationRating
7.2
2,829 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 270Free CancellationRating
7.0
8,633 reviews
Search Air Canada flights
DeltaPriceFrom C$ 319Free CancellationRating
8.0
8,521 reviews
Search Delta flights
United AirlinesPriceFrom C$ 339Free CancellationRating
7.4
8,984 reviews
Search United Airlines flights
WestJet EncorePriceFrom C$ 580Free CancellationRating
8.9
9 reviews
Search WestJet Encore flights
  • United Airlines Flights From Calgary to Chicago O'Hare Intl Airport

    Across 6 United Airlines flights from Calgary to Chicago O'Hare Intl Airport this week, the average price was C$ 438, with the best United Airlines deals starting from C$ 236 round-trip. 8,985 users have rated United Airlines on momondo, with an average score of 7.4/10.

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

    The best Air Canada deal for Calgary to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was C$ 188, round-trip. It should be noted that an average Air Canada flight deal for this route in this time was higher, at C$ 372 round-trip. Air Canada operates 6 flights out of Calgary into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 8,635 Air Canada reviews by users on momondo have scored the airline at 7.0/10.


Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lisle
Naperville
Elk Grove Village
Wheeling
Skokie
Rosemont
Glenview
Great Lakes
Des Plaines
Benton Harbor
Elmhurst
Merrillville
Harvard
Oak Brook
Schaumburg
Bridgeview
Rockford

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.


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