$103 Find Cheap Flights from Calgary to Illinois

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 Illinois departing on 2/20. 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 Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Calgary to Illinois, 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 Illinois, as well as popular online travel agencies
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Cheap Flights from Calgary to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$165
St. Louis
St. Louis1 stop$307
Chicago
Chicago1 stop$165
St. Louis
St. Louis1 stop$307

Book Cheap Calgary to Illinois Plane Tickets

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

Sat, Feb 28 - Sat, Mar 7
Air Canada Logo
5:30 am - 3:10 pm
YYC
-
ORD
8h 40m
1 stop
Air Canada Logo
3:55 pm - 11:59 pm
ORD
-
YYC
9h 04m
1 stop
$165Air Canada
Sat, Feb 28 - Sat, Mar 7
Air Canada Logo
5:30 am - 3:10 pm
YYC
-
ORD
8h 40m
1 stop
Air Canada Logo
3:55 pm - 11:59 pm
ORD
-
YYC
9h 04m
1 stop
$168Air Canada
Sat, May 30 - Sun, May 31
WestJet Logo
12:15 pm - 4:43 pm
YYC
-
ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pm
ORD
-
YYC
3h 49mnonstop
$175WestJet
Fri, Feb 6 - Fri, Feb 13
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 5:15 pm
ORD
-
YYC
3h 55mnonstop
$178WestJet
Sat, Feb 28 - Sat, Mar 7
Air Canada Logo
5:30 am - 3:10 pm
YYC
-
ORD
8h 40m
1 stop
Air Canada Logo
3:55 pm - 11:59 pm
ORD
-
YYC
9h 04m
1 stop
$181Air Canada
Tue, Mar 31 - Wed, Apr 8
United Airlines Logo
6:00 am - 9:17 pm
YYC
-
ORD
14h 17m
1 stop
United Airlines Logo
12:55 pm - 9:48 pm
ORD
-
YYC
9h 53m
1 stop
$185United Airlines
Thu, May 14 - Mon, May 18
WestJet Logo
12:15 pm - 4:43 pm
YYC
-
ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pm
ORD
-
YYC
3h 49mnonstop
$196WestJet
Thu, Mar 26 - Tue, Mar 31
Delta Logo
6:45 am - 1:25 pm
YYC
-
MDW
5h 40m
1 stop
Delta Logo
2:05 pm - 8:45 pm
MDW
-
YYC
7h 40m
1 stop
$228Delta
Fri, Feb 6 - Wed, Feb 11
Delta Logo
6:30 am - 1:06 pm
YYC
-
MDW
5h 36m
1 stop
Delta Logo
1:51 pm - 8:54 pm
MDW
-
YYC
8h 03m
1 stop
$243Delta
Mon, Mar 16 - Wed, Mar 18
American Airlines Logo
1:30 pm - 9:29 am
YYC
-
STL
18h 59m
1 stop
American Airlines Logo
6:38 pm - 12:50 pm
STL
-
YYC
19h 12m
1 stop
$313American Airlines
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?

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 Illinois departing in February.

What is the cheapest Calgary to Illinois flight route?

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

The cheapest ticket to Illinois from Calgary found in the last 72 hours was to Chicago, at $102 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 72 hours was $102.

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

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 $183, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Calgary to Illinois, 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 Illinois is April, when tickets cost $189 (return) on average. On the other hand, the most expensive months are July and October, when the average cost of round-trip tickets is $345 and $323 respectively.

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

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

If you are looking for a flight deal from Calgary to Illinois, look for departures on Sundays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Illinois, Thursday 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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Calgary to Illinois, 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 Illinois, you should book around 6 weeks before departure, which saves you about 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$103
Best time to beat the crowds but there is an average 7% increase in price.
Flight from Calgary to Chicago O'Hare Airport

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.

  • 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 $341 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 $793.

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 $225 one-way - $274 round-trip

Reviews of the top 5 airlines serving from Calgary to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Calgary to Illinois. 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 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.
7.9
DeltaOverall score based on 8055 reviews
7.8Entertainment
8.1Boarding
7.9Comfort
8.5Crew
7.2Food
Airline reviews

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

4.0 OkayUros, Jan 2026
MEM - ATL
Read more Delta reviews

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Inexperienced boarding crew allowed too many bags on to a full flight and delayed takeoff causing a missed connection and unplanned overnight stay. There was a hotel at the airport but Delta would not pay for it offering only to shuttle me to an area hotel. Never even offerred so much as an apology by anyone working for Delta.

Staff was great! Kind and cordial! Middle seat row 28 seat B has a hump in it. Trays were getting stuck when putting down and up. Good flight

Departure was delayed resulting in me missing my connection. Delta did not autimatically find me another flight.

The seats weren’t reclining even though it wasn’t as exit seat

It was good because we traveled without luggage, carry on only.

We departed late, and we arrived to Atlanta late for our connecting flight to Quito. I asked the flight attendant before landing to please make an announcement and let us go out of the plane first she agreed but never did the announcement. We run and arrived 3 minutes late and they closed the gate of the plane. We ended up staying one day in Atlanta for the next flight to Quito. When we arrived to Quito 2 of our 50lbs bags arrived completely broken and destroyed. I made the complaint and so far nobody in Delta wants to help.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Very bad! They kept delaying my flight and wouldn’t do anything about it

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

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

Typical Canadian airline experience. Charger and tray were broken, food was poor quality, and yet you're still paying more than flights with equal to better service than elsewhere globally.

Not enough food option. And not enough advices or information about what we are gonna eat.

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.

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.

The app was great, service was wonderful, everything was quick and easy

On the flight from Montreal to Calgary the flight attendant we had was excellent. Unfortunately I did not get her name but she made the flight very comfortable and enjoyable.

Like- beer/wine for free Dis-like- all other aspects- customer service was horrible the entire trip. No help from Air Canada after they changed flight 6+ hours later. Also they put us on standby for no reason. Then almost 2 hours to get our bags after we arrived back at airport

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

Information on your arrival and departure airports