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R9 584 Find cheap flights to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 25/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sun 25/8
Sun 1/9

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
In the last 7 days, travellers have searched 50 552 696 times on KAYAK, and here's why:

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Cheap flight deals to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Chicago that are departing in the next months. 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 and deals for you by selecting your travel dates.
Choose your dates
20:00 - 23:14CPT-ORD
34h 14m1 stop
20:00 - 15:10ORD-CPT
36h 10m2 stops
R18 396United Airlines
Find Deal
Fri, Oct 18 - Fri, Oct 25
18:05 - 9:40JNB-ORD
22h 35m1 stop
20:30 - 9:55ORD-JNB
30h 25m1 stop
R18 911Turkish Airlines
Find Deal
Thu, Sep 5 - Fri, Sep 13
18:50 - 17:56JNB-ORD
30h 06m2 stops
6:00 - 19:00ORD-JNB
30h 00m1 stop
R19 205Delta
Find Deal
Thu, Sep 5 - Fri, Sep 13
19:50 - 14:30JNB-ORD
26h 40m1 stop
15:00 - 3:55ORD-JNB
28h 55m2 stops
R21 008Qatar Airways
Find Deal
Tue, Dec 10 - Mon, Dec 23
14:30 - 8:05JNB-ORD
24h 35m2 stops
10:15 - 13:05ORD-JNB
19h 50m1 stop
R21 063Ethiopian Air
Find Deal
Sat, Aug 31 - Fri, Sep 6
22:10 - 13:55JNB-ORD
23h 45m1 stop
22:00 - 10:20ORD-JNB
28h 20m1 stop
R21 155British Airways
Find Deal
Tue, Dec 10 - Mon, Dec 23
14:30 - 8:05JNB-ORD
24h 35m2 stops
10:15 - 0:50ORD-JNB
31h 35m2 stops
R24 301Ethiopian Air
Find Deal
Sat, Aug 31 - Fri, Sep 6
23:25 - 18:38JNB-MDW
26h 13m2 stops
14:24 - 21:20MDW-JNB
23h 56m2 stops
R48 326KLM
Find Deal
Sun, Aug 4 - Fri, Aug 23
23:15 - 14:20JNB-ORD
22h 05m1 stop
16:45 - 21:20ORD-JNB
21h 35m1 stop
R55 298KLM
Find Deal
Tue, Aug 6 - Mon, Sep 30
21:05 - 13:05JNB-ORD
23h 00m1 stop
22:25 - 9:25ORD-JNB
28h 00m1 stop
R80 537British Airways
Find Deal
Tue, Oct 15 - Tue, Oct 22

Flights to Chicago - Travel Insights & Trends

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

What is the cheapest day to fly to Chicago?

The average price of all 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 Wednesday where tickets can be as cheap as R19 975. On the other hand, the most expensive day to fly is Saturday, where prices are R23 131 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 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 February, where tickets cost R16 703 on average for one-way flights. On the other hand, the most expensive months are August and July, where the average cost of tickets from South Africa is R23 583 and R22 167 respectively. For return trips, the best month to travel is October with an average price of R17 439.

What is the cheapest time of day to fly to Chicago?

The average price for all 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 in the morning, when flights cost R19 388 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 R20 620.

How far in advance should I book a flight to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 113 days 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 O'Hare Intl Airport, with an average flight price of R13 719.

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 83% 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 Johannesburg, which takes 22h 35m, Cape Town, which takes 25h 50m, and Durban, which takes 34h 40m.

Good to know

Low season

January

High season

June

Cheapest flight

R9 584
Best time to beat the crowds (8% less expensive on average)
Most popular time to fly (8% more expensive on average)
Flight from Durban to Chicago

When to book flights to Chicago

Are your dates flexible? Find out the best times to travel to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    The distance between Chicago Midway Airport and the city centre of Chicago is 14 km, which makes it the closest of the 3 Chicago airports airports. Chicago O'Hare Airport is 26 km away from the centre and Chicago Greater Rockford is 126 km away.

  • How does KAYAK find such low prices on flights to Chicago?

    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 to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    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 to Chicago 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 to Chicago?

    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 to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airline offers the most flights to Chicago?

    Of the 15 airlines that fly to Chicago, United Airlines offers the most flights, with around 4 972 per week, followed by American Airlines with 3 631 flights per week.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly direct to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Direct departures

South Africa to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

See more direct flights

Direct returns

Chicago to South Africa

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

See more direct flights
See more direct flights

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 South Africa 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 with 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.
7,8
KLMOverall score based on 1417 reviews
7,7Comfort
7,3Food
8,4Crew
7,9Boarding
7,2Entertainment
Airline reviews

Delay, luggage didn’t arrive. Had to go the next day to collect it

2,0 MediocreEmrah, Jul 2024AMS - MUC
Read more about KLM reviews

Delay, luggage didn’t arrive. Had to go the next day to collect it

KLM is my favourite airline. Never ever let us down.Staff are first class.

The plane. Airbus A330-200. Comfortable for a 7-hour flight. Seats seemed to have more legroom. I was in row 17. Flight was operated by Delta but was better than expected.

It was operated by Delta. Boarding took a long time. How difficult can it be? Overall decent trip. Liked the Salt Lake City airport. Better option than Chicago for transfers.

Pretty bad. Food was awful. drinks were scarce, as if drinking an extra drink would ruin the airline. attendants were not very helpful. likely Dutch "directedness" (I cannot be bothered). Crammed flight. Entertainment in very minimal dosage. Almost all old movies and series with 1-3 episodes only. Very limited number of options available. Jesus!! it seems you need to bring your own entertainment these days even of flights that are 13 hrs long!! I would and I will avoid in the future!

Quick and efficient as always. Air France managed to loose and damage my luggage that never made it onto my KLM flight.

The flight was delayed for 2 hrs. Because they didn’t have a crew to fly. And it is not a first time for klm to do that. Last time they cancelled my filght and rebooked me 3 days later. Not reliable airline

We left one hour late because of technical difficulties. The economy comfort seats are great for the price. The crew was mediocre, they do not provide a pleasant experience, they just deliver food and drinks and give orders, not very amicable, no service and hospitality focus.

Seats are fair enough for medium tall people. Good food all the trip. Fight attendances are warm

The food was ok. The crew seemed like they were cranky. I had one guy get mad at me for passing in between the storage area to get to the other toilet. I can understand if it's not allowed but reprimanding me like I'm a student saying "This is the last time!" was not appropriate. During my meal time, there was a French family around me. No problems there but when we usually have meals, they are supposed to put their chair in the upright position. These people did not do it and the steward did not tell them to raise their seat in the upright position. However, I was told to do so! So, me and another person next to me had to eat with the monitor almost touching our faces. Furthermore, a lady in front of me was putting her feet up and preventing another elder passenger from putting her seat back. To make it worse, she was continuously hitting her back into her seat, shaking my monitor while I was watching a movie. A crew member did speak to her about it but then she accused me of pushing her seat forward! The crew member gave me a death stare and told me to stop pushing the seat forward. I did not even touch her seat at all, if I did, she would know it. Her boyfriend also stood up and tried to push her seat even further past the maximum decline to no avail. None of these people were reprimanded but the steward, some bald guy, was extremely friendly with them and did not even try to instruct them to do anything until it was time to land. I resisted the urge to really argue with them because I would have obviously been seen as the aggressor (I have no idea why). I hardly said anything on this flight except "more wine please" and "sorry" if I bumped into someone accidentally. Overall, it was an annoying flight and I had to resist the urge to yell at the steward and the people he was overly friendly with. The happiest moment of this flight was leaving it.

Do I need to repeat my complaints about my lost carry on bag?

Noice cancelling headphones would be better since it’s a crowded plane And kids behaviors are unavoidable

More facilities to transport to the gates......felt too much walking distance

Just happy I flew Qatar Airways awesome no wonder they are #1 in the world right now! The food was just delicious, very courteous, professional crew.

It was good no problems made it on time for the next flight overseas!

It was a really long flight from Doha to Philadelphia and it was overall a good one. The one area that I would comment on is that there is a lot of single-use plastic and disposables in the meal service for American Airlines. It would be great to see more circular options in the meal service to reduce the amount of waste.

Suddenly Flight has been change by Qatar and there’s no information is there of us from Bom to Doha and counter person is behaving like Qatar owner next I will not buy Qatar and I will not suggest anyone to fly in Qatar

The crew was fantastic and the over flight was perfect as well.

They shld provide food. Between food they are giving 10 hours gap which is toooo much

The crew was great and the food and liquor offerings were good. Seats were a bit cramped. Flight arrived early at destination. That's a plus.

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

The new Airbus A231neo has neat tech but the economy seats are so tight together that I always had my shoulders against one passenger or the other. I was very miffed that Basic Economy REQUIRES check-in of bags other than your personal carry-on; if you want to offer low-cost airline prices and then add services for a fee, just let me carry on my duffel. Hell, I could have put my carry on IN the duffel and called it a day but the gate agent would not let me; I ended up paying $40 for the risk of losing my bag. Not the worst flight, but far from the best.

My flight was delayed by a whole day, so I lost a day of my vacation.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

Lost our bags. They didn’t make it to Lilongwe

Business and economy lines were common for most of the journey including check in and security control in Addis Abbeba. Food choice was fine, however there was a hair in my rice

Again, entertainment system didn't work. 50% of aircraft don't seem to have a functional entertainment system and the crew is absolutely uninterested in fixing. They just say Addis needs to fix it. Well, Addis had better get off it's butt and fix their aircraft.

Bathrooms were absolutely atrocious. Absolutely third world. Unusable. From non-flushing toilets to poor maintenance - missing toilet paper, dirty with mess, etc. Horrifying. Does Ethiopian Airways expect customers to clean the bathroom before use. For sure inconsiderate passengers don't do anything to clear/clean after use.

Boarding was mayhem. Entertainment system wasn't operational. Food was poor. It was like flying in the 1990's. For the price of the ticket, this was not value for money. It felt much more like an extreme discount airline.

My entertainment screen wasn't working and they couldn't fix it.

The gate was changed at the very last moment and no one informed us. The flight was one hour late and the screen broken, the remote control not working. One toilet was out of order . the other toilets were also not totally functioning, because the washbasin was plugged and the water couldn't flow away.

It is just ok, the sits are very uncomfortable, the temperature too low and there weren’t blankets. The food is mediocre and there are no screens to watch movies.

Flight was smooth but unnecessary long because we had to refuel at FCO Rome. Air hostesses service and response to call light could be better. Both planes were old with broken seat arms and toilets. Why Africans had to be given the farthest Gates is what baffles me and why we have to pay for Aisle seats I found really strange. Is there ever an end to ripping people off even after paying over $2300 for one seat.

it was a nice tripe but they need to work on the serving of soda,they should be abled to serve cain soda not on cup.At least each passenger should be entitled to one cain of soda not serving on cup.thanks.

Entertainment was good. Food was OK. Cab crew was great.

Overall flight experience was good. Unfortunately our process getting to our flight was a hit or miss. Our flight was delayed perhaps for the best as getting from terminal to terminal is very long and security had problems with the machines that delayed us getting to our flight. Heathrow security could care-less that you have a flight you are about to miss!

Access to movies was nice, food not bad, and landing was smooth. Cramming us in like sardines is not fun. A little more space to bend down to get a bag or not touch my neighbors arm because we’re so close would be better for a 9 hour flight. Whomever designed the seating and you, who bought these planes, clearly are NOT interested in customers’ comfort. So stop pretending you do. Also, if you want traveler’s to check their bags so there is space to store carry one, don’t charge so much to check baggage. Seriously?!

Horrible. Crew is not helpful. Lounge is sub standard and overcrowded. Getting to your plane is underwhelming “via a bus”. Worst experience I have had.

I had to wait for 10 hours at the airport and no hotel accommodation was provided. That sucks big time.

They can't seem to deliver a delayed bag in less than a week. Is this the 19th century?

We're waiting an BA flight being operated from London to Raleigh

Could be better in all aspects. Poor communication. Rude staff

The seats are comfortable enough, but the layout in business is wacky. The boarding process is disorganized. The flight attendants are friendly enough, but the food and snacks are sub par.

Crew was great. Food definitely top 10% for airline food. Seat was comfortable and legroom was good, BUT the seats were too close together and I was touching arms with the guy next to me the entire flight. Also, I had an aisle seat, and although my arm was pulled right up to my side, I was bumped by passengers and crew at least 6x. I'm looking into business class next time. One last note: the whole British-AA airlines partnership thing was confusing. In 2024 this should be seamless, and passengers shouldn't need this # for BA and that # for AA. There should be a single unified way of messaging from the airlines and checking things for the passengers.

Book Cheap Chicago Plane Tickets

Recent return flight deals

 
These are the cheapest return flights to Chicago found on KAYAK in the last 72 hours.
18/10Fri
1 stopUnited Airlines
34h 14mCPT-ORD
25/10Fri
2 stopsUnited Airlines
36h 10mORD-CPT
R18 396
5/9Thu
1 stopTurkish Airlines
22h 35mJNB-ORD
13/9Fri
1 stopTurkish Airlines
30h 25mORD-JNB
R18 911
5/9Thu
2 stopsDelta
30h 06mJNB-ORD
13/9Fri
1 stopDelta
30h 00mORD-JNB
R19 205
10/12Tue
1 stopQatar Airways
26h 40mJNB-ORD
23/12Mon
2 stopsQatar Airways
28h 55mORD-JNB
R21 008
31/8Sat
2 stopsEthiopian Air
24h 35mJNB-ORD
6/9Fri
1 stopEthiopian Air
19h 50mORD-JNB
R21 063
10/12Tue
1 stopBritish Airways
23h 45mJNB-ORD
23/12Mon
1 stopBritish Airways
28h 20mORD-JNB
R21 155
31/8Sat
2 stopsEthiopian Air
24h 35mJNB-ORD
6/9Fri
2 stopsEthiopian Air
31h 35mORD-JNB
R24 301
4/8Sun
2 stopsKLM
26h 13mJNB-MDW
23/8Fri
2 stopsKLM
23h 56mMDW-JNB
R48 326
6/8Tue
1 stopKLM
22h 05mJNB-ORD
30/9Mon
1 stopKLM
21h 35mORD-JNB
R55 298
15/10Tue
1 stopBritish Airways
23h 00mJNB-ORD
22/10Tue
1 stopBritish Airways
28h 00mORD-JNB
R80 537

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
25/10Fri
2 stopsTurkish Airlines
25h 35mDUR-ORD
R9 584
18/12Wed
2 stopsRwandAir
29h 50mJNB-ORD
R11 277
21/10Mon
2 stopsEthiopian Air
24h 35mJNB-ORD
R12 803
15/12Sun
1 stopEthiopian Air
25h 10mJNB-ORD
R13 024
22/9Sun
1 stopKLM
22h 20mCPT-ORD
R16 207
15/12Sun
2 stopsKLM
26h 10mJNB-MDW
R17 623
10/8Sat
1 stopUnited Airlines
19h 45mCPT-ORD
R19 076
10/8Sat
2 stopsUnited Airlines
24h 20mCPT-ORD
R19 168
12/8Mon
2 stopsBritish Airways
29h 24mJNB-ORD
R20 806
10/8Sat
1 stopBritish Airways
27h 30mJNB-ORD
R27 998

Search by stops

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Search by price

Recent domestic flight deals

17/8Sat
directSpirit Airlines
4h 07mLAX-ORD
27/8Tue
directSpirit Airlines
4h 20mORD-LAX
R1 803
7/9Sat
directSpirit Airlines
2h 52mBOS-ORD
9/9Mon
multi-stopSpirit Airlines
23h 45mORD-BOS
R1 876
31/8Sat
directJetBlue
2h 50mBOS-ORD
3/9Tue
directJetBlue
2h 26mORD-BOS
R2 152
1/9Sun
multi-stopJetBlue
8h 43mBOS-ORD
6/9Fri
directJetBlue
2h 32mORD-BOS
R2 171
27/8Tue
directDelta
3h 01mBOS-ORD
3/9Tue
directDelta
2h 36mORD-BOS
R2 336
20/8Tue
directDelta
2h 29mLGA-ORD
21/8Wed
directDelta
2h 09mORD-LGA
R2 520
8/10Tue
directAmerican Airlines
2h 36mDFW-ORD
9/10Wed
directAmerican Airlines
2h 33mORD-DFW
R3 845
6/10Sun
directAmerican Airlines
2h 41mJFK-ORD
19/10Sat
directAmerican Airlines
2h 24mORD-JFK
R4 121
15/8Thu
multi-stopUnited Airlines
5h 14mEWR-ORD
17/8Sat
directUnited Airlines
2h 22mORD-EWR
R4 213
15/8Thu
directUnited Airlines
2h 37mLGA-ORD
17/8Sat
multi-stopUnited Airlines
6h 30mORD-LGA
R4 360

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Flights to Chicago

Return flight deals:

Chicago - South Africa

Cabin classes: