$166 Find Cheap Flights from Calgary to Illinois - Compare and Save

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Cheap Flights from Calgary to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Chicago
Chicagononstop$247
St. Louis
St. Louis1 stop$278
Chicago
Chicagononstop$247
St. Louis
St. Louis1 stop$278
Booking Insights

KAYAK's insights & trends for Calgary to Illinois flights

Get data-powered insights and trends into flights from Calgary to Illinois 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 Illinois?

Flight prices are below average for this route right now.

Flights to Illinois from Calgary usually cost between $258 and $381 in November.
The lowest price found in the past 5 days was $247 on United Airlines (Nov 22-Nov 28).

What is the cheapest Calgary to Illinois flight route?

The cheapest ticket to Illinois from Calgary found in the last 5 days was to Chicago, at $151 round-trip. The most popular route is from Calgary (YYC) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 5 days was $151.

What is the cheapest time of day to fly to Illinois?

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $395 on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $861.

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

No, with an average price for the route of $289, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Calgary to Illinois is January, when tickets cost $239 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $362 and $350 respectively.

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

If you are looking for a flight deal from Calgary to Illinois, look for departures on Fridays and avoid leaving on a Tuesday, as it's usually the priciest day. When flying back from Illinois, Friday is the cheapest day to fly and Wednesday is the most expensive.

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

To get a below average price on the flight from Calgary to Illinois, you should book around 7 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low season

February

Cheapest flight

$166
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Calgary to St. Louis

FAQs - booking Illinois flights

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

    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 Illinois.

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

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

    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 from Calgary to Illinois with an airline and back with another airline.

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

    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 from Calgary to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Calgary to the following destinations at these prices or less: Chicago $242 one-way - $370 round-trip

Reviews of the top 5 airlines serving from Calgary to Illinois

 
Need help choosing which airline to fly with from Calgary to Illinois? 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.
7.8
DeltaOverall score based on 8519 reviews
7.8Comfort
8.1Boarding
8.5Crew
7.2Food
7.8Entertainment
Airline reviews

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

4.0 OkayEdith, Aug 2026
Read more Delta reviews

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

It was as good as it could be. Flying is not a pleasant experience these days.

The plane was very warm the entire time, despite my vents being open. Additionally, we didn't have internet on our personal devices

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Cramped seating for me. Luckily it wasn’t a long flight

It was beautiful easy and smooth experience. Thank you. Will definitely get Delta for my next travel.

Ran out of my choice of main course in BClass. Kind of weird combo for substitute.

They were fast and I like how they used to entertainment system to play video about the safety.

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Plane 3 hours late. Missed connection. No help from gate staff. App horrible. Lost connection repeatedly. No service desk. Finally got help from young girl driving cart.

Horrible; seating was atrocious - inadequate leg room and seat width tight even for a small individual. Profits shouldn’t be everything!

I flew basic economy, so it was what I expected. Crew was nice though, and flight was quick. Would recommend for flights under 6 hours, otherwise would upgrade to something with more leg room.

Airline staff was good the checkin process was ok but the plane itself was very bad the comfort was worst it was worst and the most stiff 5 hours of my life i felt claustrophobic

Calgary desperately needs a star alliance lounge in the transborder area for United.

Leg room was lacking. Legs crammed into seat in front.

Flight was delayed but reasonable notice and communication was always there for the passengers.

I think it would have been better to get a heads up to download the app before getting on the plane as I only had wifi in the airport and didn’t realize the plane was an older one. Maybe a little more communication before hand would be lovely. The seats as always were crammed and uncomfortable and trying to convince people to spend an extra 150 so that we have an extra foot of leg room was less then ideal.

I'm so frustrated my flight was canceled they give flight on August 5 which is not sure. Its was big mistake I booked my ticket from kayak.

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

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

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

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

Staff was nice, helpful, and did all they could. I understand economy seats are bottom of the barrel, but we're crammed in there with others in our row.

Crew was friendly. Lost our luggage and told us it’d be in later in the evening of the day we returned. It was not. Still after 5 days have not received it.

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Missed connection from delays and times changing multiple times and then involuntarily booked on another airline next day

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Incompetent crew at the boarding counter. Never flying AA again.

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

Pros: The airplane was new and had in-flight entertainment (tablet behind seats) with new movies instead of watching on personal devices. Cons: the flight time was changed without informing us. When I booked the flight, the time was 13:30pm (also in the email confirmation). However, when I reached the airport, the time was conveniently changed to 14:55pm. When I asked at the counter, they said the flight always took off at this time. The booking was made by Air Canada, but the flight was operated by United.

United did not permit online check-in from home as document scans were not getting uploaded. This should be fixed their app

Flights delayed over 4 hours with no compensation. No agents at counters to assist with re-booking.

It took 5 hour to get a crew to D Ice the plan. We had to sit on the runway for 5 hrs. in Calgary. It snows most of the winter. No proactive plan. In addition, after 3 calls to customer service they couldn't figure out how to have my wife and myself sit together on her birthday weekend. Everybody kept passing the buck. No decision from customer service, luggage drop off or check in team. The experience was a complete mess! I don't think we'll ever fly on this airline again.

The wifi I paid for did not work. The seats are tight.

There were no free snacks…little pretzel bag or cookies like we had on our flight out.

We culd not check in ovr the inrnt since e did not have the unied airlns boing efence Tis is alays a issue when boing coe shae flits witstr allince

They could have served at least some cookies with coffee or tea or juice.

The flight was on time, boarding was smooth. The crew was did an excellent job traffic controlling as people boarded.

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

Information on your arrival and departure airports