YYC - CHI

$98 Find Cheap Flights from Calgary to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Calgary to Chicago departing on 5/24. 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 Chicago

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

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Everything you should know

Cheapest round-trip
$148
Typical prices: $152-$265
WestJet
Sun 5/24Fri 5/29
YYC - ORD • Non-stop
Cheapest one-way
$98
Typical prices: $127-$185
WestJet
Sun 5/24
YYC - ORD • 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 6 extra inches of legroom.
Calgary Airport provides free Wi-Fi throughout.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
WestJet
Cheapest • from $149 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines, United Airlines and WestJet. Average duration is 3h 36m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
YYC
-
ORD
Cheapest
YYC
-
ORD
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Toronto (YYZ)
Cheapest • Avg $239 (round-trip)
Toronto (YYZ)
Shortest trip • 7h 38m (one-way)
Insights
Insights
Insights
Insights
When to book
5 weeks
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 25% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
April
Cheapest • 26% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Calgary to Chicago (YYC-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Calgary to Chicago 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 Calgary to Chicago

Sun, May 24 - Fri, May 29
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$148WestJet
Wed, May 20 - Wed, May 27
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$149WestJet
Wed, May 20 - Wed, May 27
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$151WestJet
Thu, May 28 - Fri, May 29
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$159WestJet
Wed, May 20 - Wed, May 27
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$161WestJet
Mon, Apr 20 - Thu, Apr 30
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$180WestJet
Tue, May 12 - Tue, May 26
United Airlines Logo
1:27 pm - 11:57 pm
YYC
-
ORD
9h 30m
1 stop
United Airlines Logo
7:42 pm - 10:37 pm
ORD
-
YYC
3h 55mnonstop
$188United Airlines
Tue, Apr 7 - Fri, Apr 10
Delta Logo
6:30 am - 1:24 pm
YYC
-
MDW
5h 54m
1 stop
Delta Logo
9:30 am - 11:02 pm
MDW
-
YYC
14h 32m
2 stops
$281Delta
Mon, May 4 - Thu, May 7
Delta Logo
7:40 am - 10:28 pm
YYC
-
MDW
13h 48m
2 stops
Delta Logo
6:30 am - 10:57 pm
MDW
-
YYC
17h 27m
2 stops
$292Delta
Mon, May 4 - Thu, May 7
Delta Logo
7:40 am - 10:28 pm
YYC
-
MDW
13h 48m
2 stops
Delta Logo
6:30 am - 10:57 pm
MDW
-
YYC
17h 27m
2 stops
$300Delta
Booking Insights

KAYAK's insights & trends for Calgary to Chicago flights

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

What is the cheapest Calgary to Chicago flight route?

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

The cheapest return flight from Calgary to Chicago costs $144 on the route between Calgary (YYC) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Calgary to Chicago, 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 Calgary to Chicago is April, where tickets cost $188 (return) on average. On the other hand, the most expensive months are July and October, where the average cost of round-trip tickets is $345 and $323 respectively.

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

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.

No, with an average price for the route of $236, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Calgary to Chicago, 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 Calgary to Chicago, you should book around 5 weeks before departure, which saves you about 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Expert advice

Expert advice for your flight from Calgary to Chicago

 
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 seasonNovember
Cheapest flight$98
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Calgary to Chicago O'Hare Airport

When to book flights from Calgary to Chicago

Are your dates flexible? Find out the best times to travel from Calgary to Chicago 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 Calgary to Chicago

  • What is the cheapest flight from Calgary to Chicago?

    In the last 3 days, the lowest price for a flight from Calgary to Chicago was $98 for a one-way ticket and $149 for a round-trip.

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

    A passport is required to fly from Calgary to Chicago.

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

    When flying out of Calgary you will be using Calgary. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

    American Airlines, Air Canada, and WestJet offer inflight Wi-Fi service on the Calgary to Chicago flight route.

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

    The Boeing 737-700 is the aircraft model that flies most regularly on the Calgary to Chicago flight route.

  • Which airline alliances offer flights from Calgary to Chicago?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Calgary to Chicago are United Airlines and WestJet. With an average price for the route of $355 and an overall rating of 7.4, United Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of $227 and an overall rating of 7.2.

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

    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 Calgary to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Calgary 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 Calgary to Chicago?

    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 Chicago with an airline and back to Calgary with another airline.

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

    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 Chicago from Calgary 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 Calgary to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $192 or less one-way and $235 or less round-trip.

Prefer to fly direct from Calgary to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Calgary to Chicago.
Find which airlines fly direct from Calgary Airport to Chicago, which days they fly and book direct flights.

Direct departures

Calgary to Chicago

Monday

American Airlines, United Airlines, WestJet

American Airlines, United Airlines, +1 more

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

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

American Airlines, United Airlines

Sunday

American Airlines, United Airlines, WestJet

American Airlines, United Airlines, +1 more

See more direct flights

Direct returns

Chicago to Calgary

Monday

American Airlines, United Airlines, WestJet

American Airlines, United Airlines, +1 more

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

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

American Airlines, United Airlines

Sunday

American Airlines, United Airlines, WestJet

American Airlines, United Airlines, +1 more

See more direct flights

Reviews of the top 4 airlines serving from Calgary to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Calgary to Chicago. 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 Calgary to Chicago? 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.
7.4
United AirlinesOverall score based on 9342 reviews
8.1Crew
7.3Comfort
7.1Entertainment
6.6Food
7.7Boarding
Airline reviews

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

4.0 OkayConor, Feb 2026
AUA - ORD
Read more United Airlines reviews

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Flight from CHI to PVD was delayed by over 20 hours.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

No kiosk to help pre boarding unlike other airlines, still lost the luggage despite its own crew/TSA or security tagging it, poor handling of lost luggage and possibly compensation is likely poor too.

Everything was great until we had to get our bags. The bags came out in several different batches over 90 minutes after we landed maybe more we got our bags. So much for the old West Jet where they promised bags in 20 minutes. I Next time I will pack lighter and go with a carry-on.

The flight was full and good as could be expected. We arrived early which is always a good thing.

Not sure what happened, but for some reason we had to sit on the plane for an extra 10 minutes once we arrived in Abbotsford. Obviously, it was an engine issue.

It was disappointing to see the huge number of people who were allowed to board who were claiming to either be disabled or needed extra time to board who practically ran to the gate as soon as boarding opened. One of the female flight attendants in the premium economy section refused to let a lady with an infant use the toilet next to row 9 to change her baby even though the path back to the rear toilets was blocked by staff and trolleys and said she would have to carry the baby to the toilet during the descent phase when turbulence was present. The passenger refused and the baby had to wait until landing. It would have been no problem to allow this infringement of weathers petty rules. The flight was also very cold due to a cold draft throughout the flight from the bulkhead ceiling which was not controllable.

Food good . No entertainment. Need to use wifi to access your own apps. Eg Amazon Prime, YouTube. They don't tell you unless you ask.

I was seated near a "stinky" person. That's not the fault of Westjet🙁😶‍🌫️

The ceiling leaked water on me. The toilets smelled very bad in the rear cabin

When I purchased the flights I included the luggage, the luggage was not added and got charged the full price anyway. Had to pay for the luggage at check in. Initial flight was delayed, we missed our 9am connection (flew with my wife), then the airline rebooks us to the next flights, putting my wife in at 1.40pm and me at 4pm, what a crazy wait time. We managed to fix it with customer service and they put me in the 1:40pm flight too, but they left my baggage behind in the 4pm flight. When arrived to my destination, of course no luggage. It was delivered to the address thankfully late at night. The experience sucked.

Very good experience. Great cabin crew. Much better than expected

My experience was good with United too But only not so good thing was that at Calgary airport I was not given lounge access despite of flying business. Aspire lounge denied it to me, which was unfair I feel

Very bed experience never want to travel air canada anymore

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Was not sent a link to check in online. Tried to check in online using website. Site didn’t work. Called support line, was told it often didn’t work. Went to counter at airport to check bags and get boarding passes. Had to stand in a lineup. They were unable to tell me how much to pay. Had to take a paper to another counter, took a long time to be told what I owed. I fondly remember the days of checking in online, getting my boarding pass digitally, paying for my luggage on line, scanning my passport at the airport to get my luggage tags, and putting my luggage on the conveyor. Easy peasy. Air Canada has really taken a step back in time, and made what was an easy check in experience to one that seemed unduly long and frustrating.

Really out of Air Canada's control due to long delay because of mechanical issues. While doing their best, disappointed by their assumption that all passengers have smart phones. Should have communicated food voucher availability at gate area. Late arrival cost me an extra $51 because public transit was not available, Otherwise, feel Air Canada did their best dealing with their challenges. Will likely continue using them in the future.

They canceled my flight, I had to rent a car, drive 14 hours. They tell to go on line for a refund, but only offer $24 for a $210 flight and you can’t get hold of anybody by phone and no help from staff at the airport.

I wish to travel with Air Canada for my next trip

They were very attentive, polite, professional and great customer service skills.

Business class was not worth the extra charge. Overpriced for slightly larger seat. Nothing special. Small older plane.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

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

Information on your arrival and departure airports