$153 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 10/11. 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
Chicagononstop$252
St. Louis
St. Louis1 stop$352
Chicago
Chicagononstop$252
St. Louis
St. Louis1 stop$352

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

Fri, Oct 30 - Mon, Nov 2
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 6:15 pm
ORD
-
YYC
4h 55mnonstop
$252WestJet
Mon, Sep 28 - Tue, Oct 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
$266WestJet
Fri, Sep 11 - Tue, Sep 15
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$271WestJet
Thu, Jul 2 - Sat, Jul 4
United Airlines Logo
12:28 pm - 5:04 pm
YYC
-
ORD
3h 36mnonstop
United Airlines Logo
7:45 pm - 10:37 pm
ORD
-
YYC
3h 52mnonstop
$278United Airlines
Mon, Sep 28 - Tue, Oct 6
Air Canada Logo
11:55 pm - 9:00 am
YYC
-
ORD
8h 05m
1 stop
Air Canada Logo
8:45 am - 3:57 pm
ORD
-
YYC
8h 12m
1 stop
$288Air Canada
Fri, Oct 30 - Mon, Nov 2
Air Canada Logo
6:00 am - 2:56 pm
YYC
-
ORD
7h 56m
1 stop
Air Canada Logo
4:00 pm - 11:24 pm
ORD
-
YYC
8h 24m
1 stop
$293Air Canada
Wed, Oct 21 - Sat, Oct 24
Delta Logo
7:45 am - 10:10 pm
YYC
-
MDW
13h 25m
2 stops
Delta Logo
12:30 pm - 11:13 pm
MDW
-
YYC
11h 43m
2 stops
$294Delta
Wed, Sep 23 - Wed, Oct 7
Delta Logo
6:45 am - 5:23 pm
YYC
-
ORD
9h 38m
1 stop
Delta Logo
1:55 pm - 11:13 pm
ORD
-
YYC
10h 18m
1 stop
$294Delta
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
12:45 pm - 11:42 pm
YYC
-
STL
9h 57m
1 stop
American Airlines Logo
3:32 pm - 9:34 pm
STL
-
YYC
7h 02m
1 stop
$376American Airlines
Tue, Sep 1 - Tue, Sep 8
United Airlines Logo
6:00 am - 8:46 pm
YYC
-
STL
13h 46m
1 stop
United Airlines Logo
5:30 pm - 10:36 pm
STL
-
YYC
6h 06m
1 stop
$380United 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 October.

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 5 days was to Chicago, at $158 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 $158.

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

The average price for all round-trip flights from Calgary to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $369 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 $877.

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 $345, 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 March, when tickets cost $62 (return) on average. On the other hand, the most expensive months are August and May, when the average cost of round-trip tickets is $133 and $108 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 Fridays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Illinois, Friday is the cheapest day to fly and Thursday 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 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$153
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly with an average 10% 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.

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 $224 one-way - $335 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.
7.8
DeltaOverall score based on 8419 reviews
7.8Comfort
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
Airline reviews

We sat on the runway for over an hour before departure. That was unwelcome.

6.0 GoodAnonymous, Jun 2026
SEA - SFO
Read more Delta reviews

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Crew helpful. Plenty of food although not great but ok. Good time.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

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.

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.

Food was not inspired but was satisfying. Same for infotainment selection. You’d think business class would come with complimentary WiFi. Crew was uniformly attentive and excellent.

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.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

I was tired enough to fall asleep soon after takeoff and slept until "we are starting our descent to Toronto" announcement. That's not bad at all.

It was great to have a vegetarian meal option, but departure was delayed because they had oversold the flight. Air Canada, you’re in charge of how many tickets are sold: don’t oversell!

The lead flight attendent was outstanding. We were delayed waiting for a connection and she kept us up-to-date with a great sense of humor. She also made sure a passenger in the back of the plane was sble to get out first to make a connection. She needs to be recognized by your company! She is awesome!

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

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.

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

Information on your arrival and departure airports