CHI - YYC

$142 Find Cheap Flights from Chicago to Calgary - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Calgary departing on 9/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$261
Typical prices: $180-$320
WestJet
Thu 10/8Thu 10/15
ORD - YYC • Non-stop
Cheapest one-way
$142
Typical prices: $116-$208
WestJet
Tue 9/1
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
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Avoid delays
Most punctual • 74% 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 17% compared to booking last minute.
Insights
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Insights
When to travel
Cheapest • 33% price drop
Most popular
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+1
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Flight Deals

Cheap Flights from Chicago to Calgary (CHI-YYC)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Calgary that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Calgary

Thu, Oct 8 - Thu, Oct 15
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
$261WestJet
Mon, Oct 19 - Fri, Oct 23
WestJet Logo
3:30 pm - 8:40 pmORD  Chicago O'Hare Intl-YYC Calgary
6h 10m1 stop Minneapolis St Paul
WestJet Logo
1:40 pm - 9:36 pmYYC  Calgary-ORD Chicago O'Hare Intl
6h 56m1 stop Minneapolis St Paul
$262WestJet
Fri, Oct 16 - Wed, Oct 21
Delta Logo
2:03 pm - 11:10 pmORD  Chicago O'Hare Intl-YYC Calgary
10h 07m1 stop Salt Lake City
Delta Logo
7:45 am - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
7h 55m1 stop Minneapolis St Paul
$272Delta
Thu, Oct 1 - Tue, Oct 6
Delta Logo
2:05 pm - 11:06 pmORD  Chicago O'Hare Intl-YYC Calgary
10h 01m1 stop Salt Lake City
Delta Logo
6:35 am - 6:10 pmYYC  Calgary-ORD Chicago O'Hare Intl
10h 35m1 stop Salt Lake City
$272Delta
Fri, Oct 23 - Mon, Oct 26
American Airlines Logo
10:00 am - 12:51 pmORD  Chicago O'Hare Intl-YYC Calgary
3h 51mnonstop
American Airlines Logo
1:51 pm - 6:36 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 45mnonstop
$277American Airlines
Tue, Sep 29 - Fri, Oct 2
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
$277American Airlines
Tue, Dec 8 - Fri, Dec 11
Air Canada Logo
3:45 pm - 1:50 amORD  Chicago O'Hare Intl-YYC Calgary
10h 05m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
7:00 am - 2:38 pmYYC  Calgary-ORD Chicago O'Hare Intl
7h 38m1 stop Toronto Pearson Intl
$288Air Canada
Mon, Dec 7 - Sun, Dec 13
Air Canada Logo
3:45 pm - 1:50 amORD  Chicago O'Hare Intl-YYC Calgary
10h 05m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
7:00 am - 2:38 pmYYC  Calgary-ORD Chicago O'Hare Intl
7h 38m1 stop Toronto Pearson Intl
$288Air Canada
Fri, Oct 2 - Mon, Oct 5
Multiple Airlines Logo
2:15 pm - 10:57 pmORD  Chicago O'Hare Intl-YYC Calgary
9h 42m1 stop Toronto Pearson Intl
Multiple Airlines Logo
12:00 pm - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 40mnonstop
$294Multiple Airlines
Fri, Oct 2 - Mon, Oct 5
Multiple Airlines Logo
2:15 pm - 10:57 pmORD  Chicago O'Hare Intl-YYC Calgary
9h 42m1 stop Toronto Pearson Intl
Multiple Airlines Logo
12:00 pm - 4:40 pmYYC  Calgary-ORD Chicago O'Hare Intl
3h 40mnonstop
$297Multiple 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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Calgary departing in October.

Flight prices are below average for this route right now.

Flights to Calgary from Chicago usually cost between $282 and $487 in October.
The lowest price found in the past 5 days was $261 on WestJet (Oct 8-Oct 15).

What is the cheapest Chicago to Calgary flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Calgary costs $218 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?

The average price of all round-trip flights from Chicago to Calgary clicked on KAYAK for each day over the last 12 months.

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?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Calgary, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

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 $409 respectively.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $136 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Calgary, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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 17% 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

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
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

$142
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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

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 $142 for a one-way ticket and $261 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, Qatar Airways, Finnair, and British 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 $323 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 $433 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 $169 or less one-way and $314 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?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying 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