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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.

Recent first class round-trip flight deals to Chicago

KAYAK's recommended First Class round-trip deals departing in the coming months from the most popular airlines that fly to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
6:30 a.m. - 8:41 a.m.YYZ-MDW
3h 11m1 stop
Delta Logo
1:47 p.m. - 11:23 p.m.MDW-YYZ
8h 36m1 stop
C$ 655Delta
Find Deal
Sun, 8 Jun - Mon, 9 Jun
Delta Logo
3:50 p.m. - 6:37 p.m.YYZ-ORD
3h 47m1 stop
Delta Logo
7:05 a.m. - 1:40 p.m.ORD-YYZ
5h 35m1 stop
C$ 667Delta
Find Deal
Tue, 27 May - Wed, 30 Jul
Delta Logo
6:30 a.m. - 8:40 a.m.YYZ-MDW
3h 10m1 stop
Delta Logo
1:09 p.m. - 5:15 p.m.MDW-YYZ
3h 06m1 stop
C$ 796Delta
Find Deal
Sat, 7 Jun - Sun, 8 Jun
United Airlines Logo
7:47 p.m. - 11:30 p.m.YYZ-ORD
4h 43m1 stop
United Airlines Logo
7:04 a.m. - 9:58 a.m.ORD-YYZ
1h 54mdirect
C$ 842United Airlines
Find Deal
Mon, 9 Jun - Tue, 10 Jun
United Airlines Logo
1:00 p.m. - 2:01 p.m.YYZ-ORD
2h 01mdirect
United Airlines Logo
8:50 a.m. - 11:49 a.m.ORD-YYZ
1h 59mdirect
C$ 844United Airlines
Find Deal
Tue, 27 May - Wed, 30 Jul
United Airlines Logo
7:47 p.m. - 11:30 p.m.YYZ-ORD
4h 43m1 stop
United Airlines Logo
9:31 p.m. - 10:04 a.m.ORD-YYZ
11h 33m1 stop
C$ 850United Airlines
Find Deal
Sun, 8 Jun - Mon, 9 Jun
United Airlines Logo
7:47 p.m. - 11:30 p.m.YYZ-ORD
4h 43m1 stop
United Airlines Logo
11:23 a.m. - 5:09 p.m.ORD-YYZ
4h 46m1 stop
C$ 919United Airlines
Find Deal
Mon, 9 Jun - Tue, 10 Jun
Alaska Airlines Logo
3:30 p.m. - 11:59 p.m.YVR-ORD
6h 29m1 stop
Alaska Airlines Logo
6:00 a.m. - 6:17 p.m.ORD-YVR
14h 17m2 stops
C$ 1,262Alaska Airlines
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Wed, 21 May - Mon, 26 May
Alaska Airlines Logo
1:17 p.m. - 5:40 a.m.YVR-ORD
14h 23m2 stops
Alaska Airlines Logo
8:00 a.m. - 6:17 p.m.ORD-YVR
12h 17m2 stops
C$ 1,664Alaska Airlines
Find Deal
Tue, 10 Jun - Sun, 15 Jun
Alaska Airlines Logo
11:17 a.m. - 11:56 p.m.YYC-ORD
11h 39m2 stops
Alaska Airlines Logo
7:00 a.m. - 10:27 a.m.ORD-YYC
28h 27m2 stops
C$ 1,967Alaska Airlines
Find Deal
Wed, 21 May - Sun, 25 May
Useful Info

Good to Know - First Class Flights to Chicago

Average price round-tripC$ 1,657
Good deal round-tripC$ 805
Good deal one-wayC$ 1,539
(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 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.

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.
9.2
WestJet EncoreOverall score based on 5 reviews
9.6Boarding
8.4Comfort
7.6Food
7.0Entertainment
9.2Crew
Airline reviews

Great flight, comfort, and staff. Prefer tv in back of seat but watching on phone will do

10.0 ExcellentDarren, May 2023YYZ - LAX
Read more WestJet Encore reviews

Great flight, comfort, and staff. Prefer tv in back of seat but watching on phone will do

Fine except the person next to me took up her seat had raised the arm divide so she spilled into my seat. because of her size. Fortunately no one was in the seat on my right so I could use part of it.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

My youngest didn't have a assigned seat until we biard6the plane.

Booked a premium seats weeks ago and got an email the night before that id instead be seated in the cabin. Only reason I booked this overnight flight was for the better seating. All they are doing to compensate is giving a $29 coupon to use on another flight. I won’t be booking this airline again.

It was all great all around. Will travel with Alaska next trip.

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

Everything was good. However, the selections of movies and TV shows were boring and unexciting. It was disappointing.

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

There was no seating at the gate, no where to charge your devices, super crowded. Boarding in group F meant all luggage space was taken when it was time for me to board. The boarding crew was short with everyone and seemed irritated. The luggage space was insufficient, the seat was too small for me (6'4") and very uncomfortable trip. I was in a middle seat between a person snoring the whole trip and a person with very strong body odor. The flight crew was terse and unfriendly, seemed irritated and impatient. Yelled a lot at people with earbuds in, understandable. Finally, we arrived 10 minutes early, only to sit on the tarmac for 20 minutes and wait for a gate. Worst flight experience I've had in years.

I made a mistake. Read what I wrote in the flight from Dulles to SEA. The negative experience was from SEA to BOI. Total garbage. Wont do it again.

Flight 351 SEA to BOI was terrible. We got to cruising altitude and I needed to use the restroom but the fasten seatbelt sign never came off. There was no turbulence and I'd felt the plane level off so I stood up to use the restroom about 15 minutes after we leveled off. The stewardess went over the intercom and said I needed to be seated because the captain hadn't turned off the fasten seatbelt sign....Which... Fair.... But not five minutes later she went and used the bathroom. Felt very unprofessional to leave a paying customer with a burning urethra for the entire flight and bark at them to sit down and still use the bathroom yourself. They never did turn off the seatbelt sign.

For longer trips, snacks are puny, boring and don’t have ANY nutritional value.

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.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

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.

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

They only had vegetarian food left on the flight which I wasn’t happy about. I didn’t get any food to eat at all.

Overall very poor. Flight was disorganised, staff were rude and this is my second experience with KLM that I've had baggage go missing. It feels like, if you are an economy customer, KLM staff do not show you any care. I shall never fly with KLM again. Worst airline in Europe

Great boarding, great short flight but no entertainment whatsoever and no wifi. Prepare to disembark by a staircase.

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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