CHI - YYC

$145 Find Cheap Flights from Chicago to Calgary - Compare and Save

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Everything you should know

Cheapest round-trip
$268
Typical prices: $174-$326
Air Canada
Mon 10/26Fri 10/30
ORD - YYC • 1 stop
Cheapest non-stop
$274
Typical prices: $171-$307
WestJet
Thu 10/8Sun 10/11
ORD - YYC • Non-stop
Nonstop flights
You can fly direct with American Airlines, United Airlines and WestJet. Average duration is 3h 54m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Insights
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Avoid delays
Most punctual • 75% on-time
Best time • Fewest delays
Insights
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When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 15% compared to booking last minute.
Insights
Insights
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Insights
When to travel
Cheapest • 33% price drop
Most popular
Good to know
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Booking Insights
Expert advice
Flight Deals

Cheap Flights from Chicago to Calgary (CHI-YYC)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Calgary

Mon, Oct 26 - Fri, Oct 30
Air Canada Logo
10:15 am - 6:59 pmORD  Chicago O'Hare Intl-YYC Calgary
9h 44m1 stop Toronto Pearson Intl
Air Canada Logo
9:10 pm - 9:23 amYYC  Calgary-ORD Chicago O'Hare Intl
11h 13m2 stops Edmonton Toronto Pearson Intl
$268Air Canada
Mon, Oct 26 - Fri, Oct 30
Air Canada Logo
10:15 am - 4:54 pmORD  Chicago O'Hare Intl-YYC Calgary
7h 39m1 stop Toronto Pearson Intl
Air Canada Logo
6:00 am - 3:38 pmYYC  Calgary-ORD Chicago O'Hare Intl
8h 38m1 stop Toronto Pearson Intl
$269Air Canada
Thu, Oct 8 - Sun, Oct 11
WestJet Logo
5:30 pm - 8:25 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 55mnonstop
WestJet Logo
12:00 pm - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 40mnonstop
$274WestJet
Tue, Sep 1 - Sun, Sep 6
WestJet Logo
5:30 pm - 8:25 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 55mnonstop
WestJet Logo
12:00 pm - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 40mnonstop
$275WestJet
Mon, Sep 28 - Mon, Oct 5
Multiple Airlines Logo
3:40 pm - 11:47 pmORD  Chicago O'Hare Intl-YYC Calgary
9h 07m1 stop Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
12:00 pm - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 40mnonstop
$291Multiple Airlines
Wed, Sep 23 - Fri, Sep 25
Multiple Airlines Logo
6:20 am - 5:10 pmORD  Chicago O'Hare Intl-YYC Calgary
11h 50m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:00 pm - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 40mnonstop
$292Multiple Airlines
Thu, Nov 5 - Tue, Nov 10
United Airlines Logo
8:40 am - 1:35 pmORD  Chicago O'Hare Intl-YYC Calgary
4h 55mnonstop
United Airlines Logo
1:37 pm - 4:10 pmYYC  Calgary-ORD Chicago O'Hare Intl
2h 33mnonstop
$301United Airlines
Tue, Dec 8 - Fri, Dec 11
United Airlines Logo
9:00 am - 1:54 pmORD  Chicago O'Hare Intl-YYC Calgary
4h 54mnonstop
United Airlines Logo
1:30 pm - 3:50 pmYYC  Calgary-ORD Chicago O'Hare Intl
2h 20mnonstop
$301United Airlines
Tue, Sep 22 - Tue, Sep 29
American Airlines Logo
8:30 pm - 11:29 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 59mnonstop
American Airlines Logo
7:00 am - 11:29 amYYC  Calgary-ORD Chicago O'Hare Intl
3h 29mnonstop
$312American Airlines
Fri, Sep 25 - Tue, Sep 29
American Airlines Logo
8:30 pm - 11:29 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 59mnonstop
American Airlines Logo
7:00 am - 11:29 amYYC  Calgary-ORD Chicago O'Hare Intl
3h 29mnonstop
$312American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Calgary flights

Get data-powered insights and trends into flights from Chicago to Calgary to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Calgary?

Flight prices are below average for this route right now.

Flights to Calgary from Chicago usually cost between $281 and $496 in October.
The lowest price found in the past 5 days was $268 on Air Canada (Oct 26-Oct 30).

What is the cheapest Chicago to Calgary flight route?

The cheapest return flight from Chicago to Calgary costs $233 on the route between Chicago O'Hare Intl Airport (ORD) and Calgary (YYC). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Calgary?

If your flying dates are flexible, you should consider flying to Calgary on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Wednesday is the most expensive day to fly from Chicago to Calgary. For your return ticket, we recommend flying on a Friday and avoiding Tuesdays for the best deals.

What is the cheapest month to fly from Chicago to Calgary?

The cheapest month for flights from Chicago to Calgary is January, where tickets cost $224 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $448 and $404 respectively.

Can I save money by flying with a layover from Chicago to Calgary?

No, with an average price for the route of $399, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Chicago to Calgary?

To get a below average price on the flight from Chicago to Calgary, you should book around 3 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Calgary

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on WestJet, United Airlines, Air Canada and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Kaitlyn McInnis

Kaitlyn McInnis

Expert on YYC

Kaitlyn is a guidebook author and travel writer splitting her time between Atlantic Canada and Istanbul, Türkiye. She has visited over fifty countries and all seven continents, so she is very familiar with many hotels, airports and airlines around the globe. But her favorite type of vacation is sunbathing by the sea with a good book in hand.

Good to know

Low season

February

Cheapest flight

$145
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 33% increase in price.
Flight from Chicago O'Hare Airport to Calgary

When to book flights from Chicago to Calgary

Are your dates flexible? Find out the best times to travel from Chicago to Calgary based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Calgary

  • What’s the checked bag policy on Chicago to Calgary flights?

    The amount and size of checked baggage a passenger may bring on Chicago to Calgary flights depends on the ticket class and airline. Economy passengers flying with American Airlines, WestJet, United Airlines, and Delta have the option to buy checked bags with dimensions up to 62 linear inches and a maximum weight of 50 lbs. It is typically more cost-effective to purchase checked bags when booking rather than at the airport. Extra charges are applicable for overweight bags.

  • What’s the carry-on bag policy for flights from Chicago to Calgary?

    Although carry-on baggage policies vary from airline to airline, there’s considerable overlap for flights to Calgary from Chicago. West Jet, American Airlines, and Delta permit economy ticket passengers to bring a small personal item and a larger carry-on item. The personal item must fit under the seat, while the larger carry-on should not exceed 22 lbs in weight and should have dimensions up to 45 linear inches.

  • How do I get from Calgary Airport (YYC) to downtown Calgary?

    After departing from Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW) and arriving at Calgary International Airport (YYC), you may reach Downtown Calgary by bus, shuttle bus, or taxi. Bus routes 32, 57, 100, and 300 all run from YYC to downtown on a regular basis. Alternatively, you may purchase a ticket on the Airport Shuttle Bus or hail a taxi outside the terminal exit.

  • Are unaccompanied minors allowed on flights from Chicago to Calgary?

    United Airlines, Delta, American Airlines, and Air Canada offer unaccompanied minor services on non-stop flights from Chicago to Calgary. This fee-based service involves supervision prior to departure and during the flight. Upon arrival at Calgary Airport (YYC), unaccompanied minors will be connected with their designated contact person. Generally, this service is open to minors aged 5 to 17, but it’s recommended to contact specific airlines for their exact policy.

  • What is the cheapest flight from Chicago to Calgary?

    In the last 5 days, the lowest price for a flight from Chicago to Calgary was $145 for a one-way ticket and $268 for a round-trip.

  • Do I need a passport to fly between Chicago and Calgary?

    Yes, you’ll need a passport to travel to Calgary from Chicago.

  • Which airports will I be using when flying from Chicago to Calgary?

    Chicago is served by 2 major airports and there is only 1 main airport in Calgary. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Calgary.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Calgary?

    American Airlines, WestJet, Finnair, and Qatar Airways offer inflight Wi-Fi service on the Chicago to Calgary flight route.

  • Which aircraft models fly most regularly from Chicago to Calgary?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Calgary flight route.

  • Which airline alliances offer flights from Chicago to Calgary?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Calgary, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Calgary?

    There are nonstop flights from Chicago to Calgary on a daily basis.

  • Which is the best airline for flights from Chicago to Calgary, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Calgary are Delta and United Airlines. With an average price for the route of $319 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $434 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Calgary?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Calgary.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Calgary?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Calgary from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Calgary?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Calgary with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Calgary?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Calgary from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Calgary

  • Looking for a cheap flight? 25% of our users found flights on this route for $170 or less one-way and $329 or less round-trip.
  • Calgary Airport (YYC) offers an array of facilities and services for passengers with reduced mobility. These include accessible parking, restrooms, and walkways, alongside participation in the Hidden Disabilities Sunflower Lanyard program. If you need extra assistance, it’s recommended to contact your airline a day or two before departure.
  • WestJet, Delta Airlines, and American Airlines are committed to sustainability, targeting net-zero carbon emissions by 2050. These airlines are actively incorporating sustainable aviation fuel (SAF) into their fleets as part of their ongoing efforts towards environmental responsibility.
  • Many flights from Chicago to Calgary are family-friendly. For example, American Airlines and United Airlines offer priority boarding, bassinet and child restraint devices upon request, and age-appropriate entertainment for children and teens to enjoy. In addition, they offer reduced fare and strollers in the cabin without additional cost.
  • On layover flights, stops depend on the airline. WestJet and Delta Airlines typically stop at Minneapolis St Paul Airport (MSP) while American Airlines usually stops at Dallas/Fort Worth Airport (DFW). Air Canada flights usually stop at Toronto Pearson International Airport (YYZ).
  • Generally speaking, cats, dogs, and some other pets are allowed to travel with passengers from Chicago to Calgary. They don’t need a microchip, but they do need a current rabies vaccination to enter Canada. Policies differ between airlines, so it’s recommended to contact them beforehand.

Prefer to fly direct from Chicago to Calgary?

 
Find which airlines fly direct from Chicago to Calgary Airport, which days they fly and book direct flights.

Direct departures

Chicago to Calgary

Monday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

See more direct flights

Direct returns

Calgary to Chicago

Monday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

See more direct flights

Everything you need to know for your flight from Chicago to Calgary

Information on your arrival and departure airports