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Cheap First Class Flight Deals to Chicago

 
These are the cheapest deals for flights from Canada to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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 first class round-trip flight deals to Chicago

Wed, 16 Sep - Mon, 21 Sep
Delta Logo
6:00 a.m. - 12:59 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
7h 59m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:10 p.m. - 10:59 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
4h 49m1 stop Detroit Metropolitan Wayne County
C$ 602Delta
Wed, 9 Sep - Sat, 12 Sep
Delta Logo
6:00 a.m. - 9:07 a.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:37 p.m. - 10:59 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 22m1 stop Detroit Metropolitan Wayne County
C$ 603Delta
Wed, 9 Sep - Sat, 12 Sep
Delta Logo
6:00 a.m. - 10:37 a.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
5h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 p.m. - 10:59 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
3h 59m1 stop Detroit Metropolitan Wayne County
C$ 603Delta
Sat, 5 Sep - Sun, 6 Sep
United Airlines Logo
9:45 a.m. - 11:21 a.m.YUL  Montreal Pierre Elliott Trudeau Intl-ORD Chicago O'Hare Intl
2h 36mdirect
United Airlines Logo
2:01 p.m. - 5:30 p.m.ORD  Chicago O'Hare Intl-YUL Montreal Pierre Elliott Trudeau Intl
2h 29mdirect
C$ 683United Airlines
Thu, 10 Sep - Thu, 17 Sep
United Airlines Logo
1:00 p.m. - 2:05 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 05mdirect
United Airlines Logo
4:35 p.m. - 7:37 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
2h 02mdirect
C$ 964United Airlines
Mon, 7 Sep - Thu, 10 Sep
United Airlines Logo
7:00 a.m. - 8:00 a.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 00mdirect
United Airlines Logo
10:43 a.m. - 1:42 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 59mdirect
C$ 965United Airlines
Thu, 10 Sep - Sun, 13 Sep
WestJet Logo
12:20 p.m. - 9:42 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
10h 22m1 stop New York John F Kennedy Intl
WestJet Logo
7:05 a.m. - 4:18 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
8h 13m1 stop New York LaGuardia
C$ 1,197WestJet
Thu, 22 Oct - Fri, 30 Oct
Alaska Airlines Logo
3:20 p.m. - 11:59 p.m.YVR  Vancouver Intl-ORD Chicago O'Hare Intl
6h 39m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
7:16 p.m. - 11:55 p.m.ORD  Chicago O'Hare Intl-YVR Vancouver Intl
6h 39m1 stop Seattle/Tacoma Intl
C$ 1,234Alaska Airlines
Mon, 19 Oct - Mon, 9 Nov
Alaska Airlines Logo
5:25 p.m. - 5:40 a.m.YVR  Vancouver Intl-ORD Chicago O'Hare Intl
10h 15m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
6:35 p.m. - 11:38 a.m.ORD  Chicago O'Hare Intl-YVR Vancouver Intl
18h 03m1 stop Seattle/Tacoma Intl
C$ 1,300Alaska Airlines
Tue, 17 Nov - Fri, 27 Nov
Alaska Airlines Logo
8:00 a.m. - 4:37 p.m.YVR  Vancouver Intl-ORD Chicago O'Hare Intl
7h 37m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
6:07 a.m. - 2:40 p.m.ORD  Chicago O'Hare Intl-YVR Vancouver Intl
9h 33m1 stop Seattle/Tacoma Intl
C$ 1,393Alaska Airlines

Good to Know - First Class Flights to Chicago

Average price round-trip

C$ 1,858

Good deal round-trip

C$ 1,580

Good deal one-way

C$ 686
(avg. price over the last 2 weeks)
or less
or less

When to book first class flights to Chicago

Are your dates flexible? We break down the daily and monthly prices for first class flights to Chicago, so you can find the best time to fly.
Average price per month
To calculate monthly average prices, KAYAK takes all prices for each month over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all the values for each month.
Flight prices as travel date approaches
To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.

FAQs for Chicago first class flights

  • What is the most popular airline offering First Class flights to Chicago?

    Among KAYAK users, United Airlines is the most popular airline offering First Class seats on flights to Chicago.

  • Which airlines offer First Class tickets on flights to Chicago?

    Traveling to Chicago and want to offer yourself a First Class experience? Depending on the origin, the following airlines offer seats in First Class: United Airlines, Alaska Airlines, Delta and WestJet.

  • How does KAYAK find such good deals on First Class tickets to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago for economy class as well as First Class travelers.

  • What is the best airline for first class flights to Chicago?

    The highest-rated airline by KAYAK users offering first class flights to Chicago is Porter Airlines, with an overall rating of 8.0.

Top tips for finding first class flights to Chicago

  • What’s a good price for a first class ticket between Canada and Chicago? 25% of our users found flights on this route for C$ 667 or less one-way and C$ 1,536 or less round-trip.
  • Try flying direct if you’re looking to save money, as direct first class tickets are cheaper on average.

Reviews of the top 5 airlines flying to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Canada to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly first class to Chicago? 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 456 reviews
6.9Entertainment
8.0Comfort
7.5Food
8.6Crew
8.2Boarding
Airline reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

10.0 ExcellentAnonymous, Aug 2026
Read more Porter Airlines reviews

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. :)

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

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

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

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

I had requested wheelchair assistance prior to flight. The airport staff had no record of it. It was not provided at Cedar Rapids which was a small airport, so I managed on my own. At O'Hare airport the same thing happened. The staff told me they had no record of my request for a wheel chair. But they finally provided it after a delay when I insisted that I needed it.

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

Could not make the flight. No one would help us at all

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

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

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.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

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.

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 needed to catch a United flight. There wasn't enough signage or help on arrival to navigate the transfer.

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

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