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Find First Class Flights to Chicago

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Flights Deals

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

Sun, 26 Oct - Mon, 27 Oct
Delta Logo
6:00 a.m. - 9:25 a.m.YYZ-ORD
4h 25m1 stop
Delta Logo
10:35 a.m. - 5:23 p.m.ORD-YYZ
5h 48m1 stop
C$ 772Delta
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Sun, 17 Aug - Sat, 23 Aug
Delta Logo
7:00 a.m. - 4:28 p.m.YUL-ORD
10h 28m1 stop
Delta Logo
1:30 p.m. - 11:53 p.m.ORD-YUL
9h 23m1 stop
C$ 806Delta
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Sat, 19 Jul - Tue, 22 Jul
United Airlines Logo
7:00 a.m. - 7:59 a.m.YYZ-ORD
1h 59mdirect
United Airlines Logo
9:14 p.m. - 11:58 p.m.ORD-YYZ
1h 44mdirect
C$ 847United Airlines
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Mon, 17 Nov - Sun, 23 Nov
United Airlines Logo
3:00 p.m. - 11:34 p.m.YUL-ORD
9h 34m1 stop
United Airlines Logo
10:38 a.m. - 2:00 p.m.ORD-YUL
2h 22mdirect
C$ 852United Airlines
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Sun, 10 Aug - Wed, 13 Aug
United Airlines Logo
7:00 a.m. - 7:59 a.m.YYZ-ORD
1h 59mdirect
United Airlines Logo
10:50 a.m. - 1:42 p.m.ORD-YYZ
1h 52mdirect
C$ 869United Airlines
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Sat, 19 Jul - Mon, 21 Jul
United Airlines Logo
9:00 a.m. - 9:59 a.m.YYZ-ORD
1h 59mdirect
United Airlines Logo
9:14 p.m. - 11:58 p.m.ORD-YYZ
1h 44mdirect
C$ 892United Airlines
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Mon, 21 Jul - Thu, 24 Jul
United Airlines Logo
5:15 p.m. - 6:15 p.m.YYZ-ORD
2h 00mdirect
United Airlines Logo
9:14 p.m. - 11:58 p.m.ORD-YYZ
1h 44mdirect
C$ 899United Airlines
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Fri, 14 Nov - Mon, 17 Nov
United Airlines Logo
7:00 a.m. - 9:16 p.m.YUL-ORD
15h 16m1 stop
United Airlines Logo
10:38 a.m. - 2:00 p.m.ORD-YUL
2h 22mdirect
C$ 997United Airlines
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Mon, 18 Aug - Tue, 26 Aug
Delta Logo
6:00 a.m. - 12:28 p.m.YUL-MDW
7h 28m1 stop
Delta Logo
9:30 a.m. - 9:48 p.m.MDW-YUL
11h 18m2 stops
C$ 1,235Delta
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Tue, 5 Aug - Thu, 7 Aug
Alaska Airlines Logo
6:00 p.m. - 5:40 a.m.YVR-ORD
9h 40m1 stop
Alaska Airlines Logo
7:00 a.m. - 6:40 p.m.ORD-YVR
13h 40m2 stops
C$ 1,399Alaska Airlines
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Useful Info

Good to Know - First Class Flights to Chicago

Average price round-tripC$ 3,395
Good deal round-tripC$ 3,395
(avg. price over the last 2 weeks)
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 and Delta.

  • 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.

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
Alaska AirlinesOverall score based on 10000 reviews
8.5Crew
8.1Boarding
7.8Comfort
7.1Entertainment
7.1Food
Airline reviews

Flight was delayed which led to missed connection, but rebooked on a more direct flight at the last minute and arrived in Juneau on time with all our luggage. Little stressful and our family seating got split, but it all worked out in the end.

10.0 ExcellentJeffrey, Jun 2025HNL - KOA
Read more Alaska Airlines reviews

Flight was delayed which led to missed connection, but rebooked on a more direct flight at the last minute and arrived in Juneau on time with all our luggage. Little stressful and our family seating got split, but it all worked out in the end.

It was very good and comfortable, Crew was also great

The flight was delayed almost an hour. No wifi on flight.

Terrible customer service, closed check in hours before flight left, provided incorrect information

Good experience, although it was a little cramped being a tall person. Otherwise everything went smoothly and professionally though

We have always flown with Alaska when we can. As they have great customer service. This trip we had to transfer to Air LINGUS in Denver to go to Dublin. That’s where things went bad! Our checked luggage didn’t arrive. The process to make a claim was way more complicated than it should be. It took 5 days to recover our luggage. The whole time we couldn’t talk to a real person who could tell us anything. The whole time Alaska blamed Air lingus and vis a versa. No one seemed want to help us. That was the worst part.

We were delayed. We spent more time waiting on the plane than actually flying (it’s only a 37 minute flight). Other than that, it was fine.

The setting on the loudspeaker was painful and the crew member who did the talking spoke very quickly and repetitively, with extra little jokes that were distracting and mostly unfunny. I doubt that the main messages penetrated the noise.

Only offered water, no snacks provided, and it was cold on the plane, everyone was wearing sweatshirt or jacket in June. I asked for blanket, but crew said they didnt have anything and would turn the heat up, that didn't happen, so for 6 hours I remained cold.

Delay of more than 3 hours I didnt recieve neither a voucher for food Attention disaster

Great! Personable crew. I love that they pour complimentary beer and wine.

I love the 2 seats per row. More room. The crew were excellent.

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. :)

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

The way BCN airport handled boarding was a huge improvement over our trip to Spain from JFK. Instead of gate-mosquitos edging in before their zone was called, in BCN they had clearly marked lines for Zones 1-8 and people just lined up correctly. The flight itself was uneventful. The meal (curried chicken and rice) was one of the better meals we've had on Delta. Entertainment options were plentiful, power chargers were available in Main Cabin, and seats were decent. Flight staff were very friendly and positive throughout the 8 hour flight.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

The checkpoint hornets are always looking fhrough Americans' luggage keeping what they deem impassible! Grrrrr!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Boarding was organised and relaxed. Crew were fantastic! Seats were lacking padding causing butt pain and stiffness.

Klm start boarding while somw air issue in the plan

The service was great. However the lounge only gets passing grade

I appreciate that KLM was proactive in informing me of the 2 hour delay which enabled me to replan my travel. It was a bit stressful not knowing whether my connection from Montreal to Ottawa was happening. But the ground and air crew did a good job at comforting and assuring me.

Cabin crew professional, polite and friendly, boarding was seemless, but come on KLM surely you can do better than a pack of cheesy biscuits as an inflight snack

Cabin crew were excellent, very proffesional, polite and friendly, in flight snack was underwhelming, a packet of cheese biscuits, im sure KLM could run to a sandwich!

Legroom not all it could be, especially when the seat in front is reclined. Otherwise it was good, food and beverage were nice.

This portion of the flight was through Indigo. A local carrier. So all economy seating. No real service some refreshments for purchase standard economy stuff.

Transfer at Amsterdam airport is very convenient and the airport is easy to navigate. Boarding was also quick and easy. Cabin crew were excellent and the meals were good, although lacking in options.

This fight left ahead of time which meant it arrived early which was great. Staff were very professional, but as with all these Short hop Flights the food was a disappointing snack There was no entertainment on this flight, but I did not expect any

I flew premium economy and this was a good option. Although the seats didn’t recline much, I was able to get some sleep with my head propped against the window. The food was good and the entertainment was wonderful The staff were very attentive and professional

Not necessarily a Transat issue but it took 2 hours to go through immigration. Tried to reach out to Transat for resolution but was unable to reach an agent.

The flight was excellent, once it started, however we were delayed two hours when the first plane’s engines wouldn’t start. They found another identical plane and transferred us and our luggage in under two hours and made up almost an hour in the air.

Really low cost trip for the huge amount I paid…o paid 550 dollars just for the trip, one way trip, plus 95 for 1 luggage’s and the second 135 dollars…no blanket, not headphones for entertainment, food was served after 3 hours and 2 hours after, breakfast was served Bad, low cost company for high prices

The flight and crew were good. Departure and arrival were timely. Check-in was professional and helpful in Malaga on return trip (same on outbound trip from Toronto). The ad before ach program was punishing - specifically for the internet/data service with the content creator that was showed twice in each ad pod. It was so annoying I made an effort to forget the name and would not use the service. Provide an opportunity to fast forward or skip the darn ads once they have been initially viewed.

Extra attention to kids, thank you, we appreciate! Perfect landing

Over the wing seat at emergency exit only downside people using lavatory have no respect and wait in the space

Flight delayed any hour and couple of big gate changes

The pilot came out and chatted with the passengers. He explained why there was a slight delay. The crew was excellent. Very helpful. I had to buy meals for my whole family and they were in different seats, so the crew had to deal with that. They were very pleasant and accommodating and did a great job!

We were unable to land in Liberia. It was not the airline’s fault, but we had to be diverted to SJO.

We had things stolen from our luggage, we also were refused an upgrade on a flight that was not full.

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.

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