$100 Find Cheap Flights from Canada to Illinois

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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 for flights to Illinois
These are the airlines KAYAK users have selected most often from within our search results for flights to Illinois
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Booking Insights

KAYAK's insights & trends for flights to Illinois

Get data-powered insights and trends for flights to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Illinois?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

The cheapest ticket to Illinois from Canada found in the last 72 hours was to Chicago O'Hare Intl Airport, at $110 round-trip. The most popular route is Edmonton (YEG) to Chicago O'Hare Intl Airport (ORD) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $110.

How much is a flight to Illinois?

The average and cheapest price for all round-trip flights to Illinois from each origin found by users searching on KAYAK in the last month.

A flight to Illinois costs $470 on average. The cheapest price found on KAYAK in the last 2 weeks was $108 for the route Calgary (YYC) to Chicago O'Hare Intl Airport (ORD). The most popular routes on KAYAK are Montreal to Chicago which costs $631 on average, and Toronto to Chicago, which costs $695 on average.

See prices from:

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Canada 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 Canada to Illinois is September, when tickets cost $155 (return) on average. On the other hand, the most expensive months are October and July, when the average cost of round-trip tickets is $448 and $383 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights 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 Canada to Illinois, you should book around 4 weeks before departure, which saves you about 46% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Which is the cheapest airport to fly into in Illinois?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago Midway Airport (MDW), with an average flight price of $189.

Good to know

Low seasonJanuary
Cheapest flight$100
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Halifax to Chicago O'Hare Airport

Flights from Canada to Illinois: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Canada to Illinois 
LisaFlew with United AirlinesYWG-ORDDec 2024
Turn on your data or the wifi in case gates change.
Verified travelerFlew with WestJetYYC-ORDJun 2024
checkin luggage online as they jack up the price 100% at airport
Verified travelerFlew with United AirlinesYUL-ORDApr 2024
Come prepared with your own entertainment as the flight did not offer in flight entertainment
Verified travelerFlew with United AirlinesYYZ-ORDMar 2024
Carry-on baggage sizing for United US bound flights appears to be much smaller than for Canadian flights, which forced me to check my bag at the last minute. So check online ahead of time

FAQs for booking flights from Canada to Illinois

  • How does KAYAK find such low prices on flights from Canada 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 Canada to Illinois.

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

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

    Based on KAYAK data, the cheapest day to fly to Illinois is Friday where round-trip tickets can be as cheap as $451. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $631 on average.

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

    The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $394 on average. Morning departures are around 19% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the evening, which is peak travel time and where the average cost of a ticket is $617.

Reviews of the top 5 airlines serving from Canada to Illinois

 
See real verified KAYAK customer reviews for airlines flying to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Canada to Illinois. 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 Canada 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.
8.0
Porter AirlinesOverall score based on 359 reviews
7.6Food
8.0Comfort
8.2Boarding
7.0Entertainment
8.6Crew
Airline reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

2.0 MediocreAnonymous, Sep 2025YDF - YHZ
Read more Porter Airlines reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

The flight was fine see earlier note for the problem

Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

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.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

A little better seat cushions would be appreciated. Crews were all good.

The process and flight were both smooth and trouble free

Flight delayed 3 hours, missed my connection in Atlanta. Instead of getting to Savannah at 6PM arrived after 10:00PM Middle seat, couldn't get isle or window, couldn't book my seats in advance, had to book at the gate. That's a 1st for me and I used to travel a lot

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.

We were happy with our experience. The price for tickets was much less than Delta and we actually took off and landed a little ahead of scheduled times.

Seat back entertainment monitors would be nice. We did enjoy the In-Flight WiFi.

I swear airplane seats keep getting smaller and smaller but everything else was great. Smooth sailing and we got in early.

No food to provide, they forgot that, in some cases, people stay at the airport for hours without food. Now, to provide them with food, they have to ask them to pay, because some don't have money. That way, they can't eat.

After a long flight from Tokyo, our connecting flight home was canceled due to “maintenance” while we were on our layover in Toronto. Very frustrating to close out our honeymoon, although I’m sure others had it even worse during last week’s strike. Air Canada staff at Pearson Airport are the one thing that kept me remotely at peace during this — they were very helpful and deserve a lot of props. But I would not fly Air Canada again.

I had wonderful wheelchair assistance through the Montreal airport onto the flight. Air Canada was excellent in this both at the Fredericton airport and the Montreal one where an attendant helped us through customs as well as transport and baggage security.

Horrible flight cancelled had to buy another very expensive ticket

Flight was cancelled last minute due to Air Canada strike leaving us stranded and having to stressfully find a way home that cost hundreds of dollars in excess cost added to the trip. Having just experienced our mother's funeral service, this was not a good way to end our trip.

Air Canada marooned me in Canada with no way back home during my summer vacation. I had to buy a last minute flight ticket for over $500 to make it back home. I have their credit card and have flown them for years. Never again.

Flight was cancelled last minute. Had to scramble and purchase a $2000 flight through a separate airlines. Stuck in Toronto two extra days. Missed my first two days on a new job. Had to rent a car for an additional two days. Scrambled to fins a place to live those extra two days. Spent a ton of extra money and lost a lot of money, as well as made a poor impression at work. Difficult difficult difficult

Terrible, return flight was cancelled a night before the flight was scheduled to depart and I was notified by an email and an automated message on their phone line. I’ll never book Air Canada again

Could not understand what the attendant was saying during his announcements.

Everything you need to know for your flight to Illinois

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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