CHI - YYC

$90 Find Cheap Flights from Chicago to Calgary

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 4/27. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Calgary

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Calgary, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Calgary, as well as popular online travel agencies
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$208
Typical prices: $331-$160
WestJet
Wed 5/27Sat 5/30
ORD - YYC • Non-stop
Cheapest one-way
$90
Typical prices: $110-$219
WestJet
Mon 4/27
ORD - YYC • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers extra legroom on this route.
Use the CTA Blue Line for a quick departure from ORD.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $208 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, United Airlines and WestJet. Average duration is 3h 56m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 74% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 35% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 29% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Calgary!
Flight Deals
Booking Insights
Expert advice
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

Wed, May 27 - Sat, May 30
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
$208WestJet
Mon, Apr 27 - Thu, Apr 30
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
$214WestJet
Wed, May 27 - Sat, May 30
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
$215WestJet
Wed, May 27 - Sat, May 30
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
$225WestJet
Tue, May 12 - Tue, May 19
Air Canada Logo
8:45 am - 3:59 pm
ORD
-
YYC
8h 14m
1 stop
Air Canada Logo
6:30 am - 4:59 pm
YYC
-
ORD
9h 29m
1 stop
$232Air Canada
Mon, May 25 - Sat, May 30
United Airlines Logo
7:42 pm - 10:37 pm
ORD
-
YYC
3h 55mnonstop
United Airlines Logo
8:30 am - 1:07 pm
YYC
-
ORD
3h 37mnonstop
$254United Airlines
Sat, Apr 18 - Tue, Apr 21
Delta Logo
9:46 am - 11:00 pm
MDW
-
YYC
14h 14m
2 stops
Delta Logo
7:40 am - 6:36 pm
YYC
-
MDW
9h 56m
2 stops
$294Delta
Sat, Apr 25 - Sat, May 2
Delta Logo
9:46 am - 11:00 pm
MDW
-
YYC
14h 14m
2 stops
Delta Logo
7:40 am - 10:28 pm
YYC
-
MDW
13h 48m
2 stops
$313Delta
Wed, Apr 29 - Wed, May 6
Multiple Airlines Logo
2:15 pm - 11:00 am
MDW
-
YYC
21h 45m
1 stop
Multiple Airlines Logo
7:00 am - 10:02 pm
YYC
-
MDW
14h 02m
1 stop
$329Multiple Airlines
Sat, Apr 25 - Sat, May 2
Multiple Airlines Logo
7:34 pm - 5:10 pm
MDW
-
YYC
22h 36m
1 stop
Multiple Airlines Logo
7:00 am - 10:14 pm
YYC
-
MDW
14h 14m
2 stops
$344Multiple 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 May.

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 $156 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 Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago to Calgary. For your return ticket, we recommend flying on a Sunday and avoiding Mondays 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 $212 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $394 and $370 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 $276 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 4 weeks before departure, which saves you about 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 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 seasonFebruary
Cheapest flight$90
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 16% 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 is the cheapest flight from Chicago to Calgary?

    In the last 3 days, the lowest price for a flight from Chicago to Calgary was $90 for a one-way ticket and $208 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, Air Canada, and United Airlines 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, Star Alliance, and oneworld 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 $292 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $399 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 $75 or less one-way and $278 or less round-trip.

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

Reviews of the top 5 airlines serving from Chicago to Calgary

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Calgary. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Calgary? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8370 reviews
7.8Entertainment
8.1Boarding
7.2Food
7.9Comfort
8.5Crew
Airline reviews

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

6.0 GoodJoseph, Apr 2026
MSP - RIC
Read more Delta reviews

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta. The airline did not hold the connection, and we were informed that the next available flight is not for another 24 hours. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for us as a resident of New Jersey.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

I wasn’t checked in for the third leg of my flight, my bag was checked through to Dublin but when I went to the gate in Toronto they said I wasn’t on the flight and had given my seat away. I had to wait 24 hours for another flight and instead on the one I had booked it was now 2 flights.

Flight was delayed by 3/4 of an hour. Overall flight was good.

No pre boarding kiosk to check in, baggage claim detected luggage didn’t leave the airport, poorly managed recovery of lost luggage, and blame lost tag from conveyor to TSA/security, very poor from TSA/security check to delivery, crucial if compensation will go thru and will likely wait for months unlike United,

Waited at airport from 10 am till 4 pm and no flight due to fog. Ugh.

Plane was one hour late. Hardly any space for our carry-ons. Stressful to catch connections.

Plane seating was uncomfortable, very tight fitting for someone my height, did not recline and overall un enjoyable

Overall service is good. Just thought foods need to upgrade for economy class

No communication from Kayak or West Jet. Booked extra flights, flights cancelled, no one answers calls. Will be disputing charges.

Leg room is a problem the plane was dirty and there were no movies available on the app

The gate personnel and flight attendants were all friendly and diligent. The poor attendants from London to Calgary were 2 colleagues short, as one of their team broke her leg on the way to work, and the other stayed with the invited colleague. I felt bad for the crew, but they did a great job regardless.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Our original flight was cancelled due to mechanical reasons. This cancellation caused us to miss our connection and we were not able to get another flight for 3 days and then needed to make an extra connection to get there. Air Canada did not rebook our flight for us, it took several hours of talking with staff in the airport and making phone calls to get the flights rebooked. We never received a voucher for our hotel and meals while we were waiting for our next flight and it was only after talking to several staff that we were provided some general information about how we could be reimbursed. We tried entering our ticket information in the website provided, but it did not recognize our flight information. When we asked someone on the phone about this they said we'd need to contact the customer relations department, but that it's not possible to reach them on the phone. I don't understand what company would have a customer relations department that you can't talk to. We spent about $1,000 for hotels and meals for our family while waiting for a flight home and I'm not confident we will ever get reimbursed for this. I understand that mechanical issues can happen to any airline, but this is the 4th time that this has happened to my wife and I on Air Canada and we have only flown Air Canada about 8 times, so this is not a good track record. Also, when we did finally get a flight home (which was also delayed due to mechanical problems), we were told we couldn't bring a standard carry on even though the information on our ticket clearly indicated that we could bring a carry on bag. The staff at the gate were not understanding about this situation.

We were happy with the service and cost of checking a bag

Very nice staff members are very nice and friendly helpful

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

The internet connection was perfect, and the updated entertainment systems that allow me to connect my Bluetooth earbuds was excellent

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

It was good to receive a card for my birthday

Very bad, flight was cancelled due to strike and staff was unable to rebook us

It would have been better if it wasn’t cancelled

Flying in the Dreamliner is always comfortable. Though the food options for Air Canada aren't great.

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

Information on your arrival and departure airports