YYC - CHI

$145 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 6/1. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$239
Typical prices: $391-$192
WestJet
Fri 5/29Sat 6/6
YYC - ORD • Non-stop
Cheapest one-way
$145
Typical prices: $141-$232
WestJet
Mon 6/1
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
Cheapest • from $239 (round-trip)
Best reviews • 7.4 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 38m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $250 (round-trip)
Shortest trip • 7h 37m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 31% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 26% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Fri, May 29 - Sat, Jun 6
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$239WestJet
Fri, Oct 16 - Mon, Oct 19
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$243WestJet
Tue, May 26 - Wed, May 27
United Airlines Logo
12:28 pm - 5:05 pm
YYC
-
ORD
3h 37mnonstop
United Airlines Logo
7:05 am - 9:48 pm
ORD
-
YYC
15h 43m
1 stop
$251United Airlines
Tue, May 26 - Wed, May 27
United Airlines Logo
1:27 pm - 12:44 am
YYC
-
ORD
10h 17m
1 stop
United Airlines Logo
7:05 am - 9:48 pm
ORD
-
YYC
15h 43m
1 stop
$257United Airlines
Tue, Sep 1 - Tue, Sep 8
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$269WestJet
Fri, May 29 - Mon, Jun 1
American Airlines Logo
6:15 am - 10:45 am
YYC
-
ORD
3h 30mnonstop
American Airlines Logo
8:55 pm - 11:43 pm
ORD
-
YYC
3h 48mnonstop
$270American Airlines
Fri, May 29 - Wed, Jun 10
Delta Logo
7:45 am - 6:50 pm
YYC
-
ORD
10h 05m
1 stop
Delta Logo
2:09 pm - 11:01 pm
ORD
-
YYC
9h 52m
1 stop
$275Delta
Fri, May 29 - Tue, Jun 9
Delta Logo
6:45 am - 5:56 pm
YYC
-
MDW
10h 11m
1 stop
Delta Logo
9:17 am - 8:38 pm
MDW
-
YYC
12h 21m
2 stops
$333Delta
Thu, Aug 13 - Tue, Aug 18
Multiple Airlines Logo
7:00 am - 10:08 pm
YYC
-
MDW
14h 08m
1 stop
Multiple Airlines Logo
12:27 pm - 9:50 pm
MDW
-
YYC
10h 23m
1 stop
$347Multiple Airlines
Thu, Aug 13 - Tue, Aug 18
Multiple Airlines Logo
7:00 am - 10:08 pm
YYC
-
MDW
14h 08m
1 stop
Multiple Airlines Logo
12:27 pm - 9:50 pm
MDW
-
YYC
10h 23m
1 stop
$380Multiple Airlines
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.

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

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

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 $146 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 Friday and avoiding Wednesdays 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 March, where tickets cost $62 (return) on average. On the other hand, the most expensive months are February and August, where the average cost of round-trip tickets is $102 and $102 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 $244, 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 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 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 Air Canada, WestJet, United Airlines 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$145
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 10% increase in price.
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 $145 for a one-way ticket and $239 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 737-800 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 $375 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 $285 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 $174 or less one-way and $229 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,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

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

Reviews of the top 3 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 9700 reviews
8.1Crew
7.3Comfort
7.1Entertainment
6.6Food
7.7Boarding
Airline reviews

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

6.0 GoodAnonymous, May 2026
DEN - ORD
Read more United Airlines reviews

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Better movie options. More diligence on the size and amount of bags people bring on board. Lady across aisle from me had a bucket style bag that would only go so far under the seat in front of her. She was not told once that the whole bag is supposed to be under the seat. Crew is very hardworking however.

I didn’t have any food but my Prosecco hit the spot. We left on time and the crew was friendly.

Flight didn’t happen because both my connections were lost and Toronto wouldn’t let me board. I was checked in to all 3 flights at the check-in fest in Dublin.

I wasn’t able to book or pay for a seat and they forgot to check me in for my third flight so I spent 24 hours in Toronto waiting for another one.

Flight was delayed for 5hours. Food vouchers just aren’t good enough

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

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 good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

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

Information on your arrival and departure airports