
Cheap Flights from Canada to Chicago
Recent round-trip flight deals from Canada to Chicago
Recent one-way flight deals from Canada to Chicago
Recent last minute flight deals from Canada to Chicago
Recent direct flight deals from Canada to Chicago
KAYAK's insights & trends for flights to Chicago
Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.
What is the cheapest flight to Chicago?
These are the best round-trip prices found by users searching on KAYAK in the last 5 days.In the last 5 days, the cheapest flight deal to Chicago was found on the route from Toronto, at $227 return. The most popular connection is from Montreal to Chicago and KAYAK users have found round-trip deals for as low as $283 in the last 5 days.
How much is a flight to Chicago?
The average and cheapest price for all round-trip flights to Chicago from each origin found by users searching on KAYAK in the last month.A flight to Chicago costs $436 on average. The cheapest price found on KAYAK in the last 2 weeks cost $129 and departed from Toronto Pearson Intl Airport. The most popular routes on KAYAK are Toronto to Chicago which costs $578 on average, and Vancouver to Chicago, which costs $498 on average.
What is the cheapest day to fly to Chicago?
The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.Based on KAYAK data, the cheapest day to fly to Chicago is Friday where round-trip tickets can be as cheap as $487. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $643 on average.
What is the cheapest month to fly to Chicago?
To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights 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 to Chicago is January, where tickets cost $284 on average for return flights. On the other hand, the most expensive months are December and August, where the average cost of tickets from Canada is $364 and $362 respectively. For one-way flights, the best month to travel is May with an average price of $202.
What is the cheapest time of day to fly to Chicago?
The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.The cheapest time of day to fly to Chicago is generally at night, when round-trip flights cost $409 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $810.
What is a good deal for flights to Chicago?
If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Toronto Island Airport $219 round-trip, from Montreal Pierre Elliott Trudeau Intl Airport $330 round-trip, from Calgary $338 round-trip.
How far in advance should I book a flight to Chicago?
To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights 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, you should book around 3 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.
Which is the cheapest airport to fly into in Chicago?
Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $173.
What are the most popular airlines flying to Chicago?
The most popular airline among KAYAK users flying to Chicago is Air Canada, followed by United Airlines and American Airlines.
Which airline offers the most flights to Chicago?
Of the 5 airlines that fly to Chicago, United Airlines offers the most flights, with around 180 per week, followed by Air Canada with 106 flights per week.
How many airports are there in Chicago?
There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 95% of all flights arriving there.
How long is the flight to Chicago?
The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Toronto, which takes 2h 02m, Calgary, which takes 2h 20m, Montreal, which takes 2h 36m, and Vancouver, which takes 3h 09m.
How many direct flights to Chicago are there each day?
There are around 5,048 direct flights from within Canada to Chicago every day. Most flights depart in the morning, with 50% of flights departing in the morning.
How many direct flights to Chicago are there each week?
Each week there are around 35,330 direct flights from within Canada to Chicago. The most common day for departures is Sunday, with 18% of flights taking off on this day.
How many long-haul flights are there to Chicago each week?
Each week, there are 78 medium-haul flights (3-6 hour flight duration) and 1,218 short-haul flights (up to 3 hour flight duration) to Chicago. There aren't any long-haul flights (6-12 hour flight duration).
How many cities have direct flights to Chicago?
From Canada, there are direct flights to Chicago from 8 cities. The city with the most direct flights is Toronto, with 645 direct flights each week.
Good to know
Low season | January |
|---|---|
High season | August |
Cheapest flight | $157 |
Flights from Canada to Chicago: the best tips from KAYAK users
FAQs - booking Chicago flights
Top tips for finding cheap flights to Chicago
Reviews of the top 5 airlines serving from Canada to Chicago
A very comfortable flight, an additional wash room could have made it almost perfect.
A very comfortable flight, an additional wash room could have made it almost perfect.
Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.
I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.
It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.
Organization and the adjusted times but the snacks could be of a bigger portion
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.
All good the seats a little tight and no I pad screen
Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.
was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....
It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)
Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.
Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok
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
Reliable, nice crew, I fly often on that flight and I like it all.
Efficient all round, very good crew. Short flight so the food, of course, was just snacks
My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.
So far so good but food and entertainment are not available for this flight
It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.
lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.
They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad
Always a pleasure to fly with WestJet. I am however frustrated about the rising costs. We have started to resort to Ultra Basic fares to afford but really missing the extra bag but too costly.
The crew were all helpful, kind, and effective. There could have been more space under the seats.
Horrible, delayed 3 hours due to a mechanical issue where the plane is deemed unsafe so we had to deplane after an hour on the tarmac. No credit was given even though plenty of passengers missed their connecting flights and then the baggage claim info showed that no flight was being loaded on the carousel whilst the bags were being dropped, so no one knew if it was the right flight or not since the arrivals screen didn’t show anything.
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.
Maybe glass of wine would be nice at no charge
We traveled with a 7 year old that has autism and he is significantly cognitively delayed. Your site makes it known there are no wagons allowed even if they fold down flat and many autistic children cannot travel without one because they are unable to follow directions or cooperate with walking through the airport and are too big for a stroller. Please consider making exceptions for our special needs children. Also it would be very thoughtful if you’d allow seat selection for no fee for special needs families. The autistic child we traveled with must sit behind another adult in our family because he continuously kicks the seat in front of him and is unable to understand why that is disruptive. We had to pay quite a bit extra to have our 4 seats situated with 2 in row 19 and 2 in row 20 directly behind.
Our itinerary included a 1 hour and 30 minute layover, which should have been sufficient under normal circumstances. However, our original flight was delayed. Before we even deplaned, we were instructed to collect our checked bags from baggage claim, clear immigration and customs, and then recheck our bags for the connecting flight. The airline knew—or should have known—that this was impossible. Checked baggage acceptance closes one hour before departure, meaning there was no realistic way for passengers from the delayed flight to recheck their bags in time. Despite this, the airline gave us misleading instructions instead of informing us that we would likely miss our connection. We completed immigration and customs in approximately 10 minutes, but our checked bags did not arrive at the carousel for more than 30 minutes. After collecting them, we had another 10-minute walk to the baggage drop area, only to find that no airline attendant was present. We then went to another airline counter, where an employee told us this had happened before and that there was nothing they could do because the baggage acceptance window had already closed. At that point, there were still 40 minutes remaining before our flight's departure, yet no one was willing to assist or offer a practical solution. When we asked to be rebooked, we were simply told to call the airline's 800 number ourselves. There was no accountability or customer support at the airport, leaving us stranded in a foreign country with no immediate assistance. After finally reaching an agent on the 800 number, we were rebooked on a flight for the following day. However, we were initially told that the airline would not provide any hotel accommodation and that we would have to arrange and pay for it ourselves. Only after making multiple calls and speaking with several different agents did one representative finally issue a hotel voucher. The entire experience was an exhausting and frustrating ordeal. What should have been a 20-hour journey ultimately became more than 30 hours due to the airline's poor planning, misleading instructions, lack of accountability, and inadequate customer service. The unnecessary delays, confusion, and absence of meaningful assistance caused significant physical exhaustion and severe mental stress. This experience fell far below the level of service passengers should reasonably expect.
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.
I loved the fact it was on time and it was a smooth flight to my destination.
Service was okay except attendant over served alcohol to passenger and passenger got tipsy and made me uncomfortable
Snacks and drinks should be served together and air hostess was not supportive with no smile which was kind of disappointing.
After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.
It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.
Bad service as well. Another 3hr delayed flight from chicago to Charlotte.
Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…
flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working
Minimal food offered (crackers). Had to clean the seat with a wet wipe because of dried food.
They charge 5 dollars for plastic headphones for a flight of 1 hour! Seats are awful. Service is terrible.
Everything was seamless. I would have appreciated knowing there would not be any real food available for purchase in advance. Otherwise a great experience. Thank you!
I was mostly pleased. My greatest disappointment was with respect to the timely update to the estimated departure and arrival times. It was especially sad that the arrival time was not updated online once we were in flight so as to allow my wife to arrive on time to the airport. She was not happy.
I was truly shocked at how poor this flight went. The crew was not friendly during the checking process. The asked for people to gate check and were rude about it. They didn't handle my luggage with care. When I got to my seat I noticed a large section of the ceiling vent area was, no joke, TAPED TOGETHER WITH CLEAR PACKING TAPE! To add insult to injury, the back rest button was disabled on my seat and all the seats I could see. The wifi, never connected for me, despite troubleshooting it for a while. I did everything from restarting my wifi/phone to forgetting the network and restarting the app. But that didn't stop the mandatory 2 ads from playing every single time. Even the bags took over 45 mins to arrive at the carousel. Everything about this flight was a flop and I am beginning to notice that some of these events are becoming a trend. Perhaps it's time I switch loyalty programs.
Horrible airline, will never buy another ticket with the airline or Kayak. They close the gate 2 hours early in Kenya, I had to buy a new ticket and get a hotel room
It would be helpful to be able to download an eticket from either American airlines or Cathay Pacific; not just Cathay Pacific.
Another American Airlines flight, another significant delay. At least this one wasn't canceled like many others have been. This time we sat on the runway at LaGuardia for 2.5 hours. By my count that is 7 American flights the last three months that have been delayed 2 hours or more or canceled entirely.
There was no clear update on the flight until last minute and made it an hour delay. No clear flight aircraft or incoming flight which we will be boarding. We would plan accordingly for our connecting flight. This is one one the worst service, I also had to buy an another ticket with different ai carrier. American airline was not letting me plan my trip, made us just waiting. Not a good service at all.
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.