CHI - NAP

$256 Find Cheap Flights from Chicago to Naples - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Naples departing on 8/29. 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
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$574
Typical prices: $695-$1,050
Scandinavian Airlines
Sun 10/4Sat 10/10
ORD - NAP • 1 stop
Cheapest non-stop
$724
Finnair
Sun 8/9Tue 8/25
ORD - NAP • Non-stop
Top airlines
Cheapest • from $574 (round-trip)
Best reviews • 7.5 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with American Airlines. Average duration is 9h 30m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest
Most popular
Insights
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Avoid delays
Most punctual • 70% on-time
Best time • Fewest delays
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Top layover airports
Cheapest • Avg $501 (round-trip)
Shortest trip • 11h 44m (one-way)
Insights
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When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 13% compared to booking last minute.
Insights
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When to travel
Cheapest • 29% price drop
Most popular
Good to know
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Flight Deals

Cheap Flights from Chicago to Naples (CHI-NAP)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Naples 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Naples

Sun, Oct 4 - Sat, Oct 10
Scandinavian Airlines Logo
7:15 pm - 6:45 pm
ORD
-
NAP
16h 30m
1 stop
Scandinavian Airlines Logo
8:35 pm - 4:10 pm
NAP
-
ORD
26h 35m
1 stop
$574Scandinavian Airlines
Mon, Oct 5 - Sat, Oct 10
Scandinavian Airlines Logo
7:15 pm - 6:45 pm
ORD
-
NAP
16h 30m
1 stop
Scandinavian Airlines Logo
8:35 pm - 4:10 pm
NAP
-
ORD
26h 35m
1 stop
$575Scandinavian Airlines
Sun, Oct 4 - Sat, Oct 10
Scandinavian Airlines Logo
7:15 pm - 6:45 pm
ORD
-
NAP
16h 30m
1 stop
Scandinavian Airlines Logo
8:35 pm - 4:10 pm
NAP
-
ORD
26h 35m
1 stop
$578Scandinavian Airlines
Mon, Oct 5 - Sat, Oct 10
Scandinavian Airlines Logo
7:15 pm - 6:45 pm
ORD
-
NAP
16h 30m
1 stop
Scandinavian Airlines Logo
8:35 pm - 4:10 pm
NAP
-
ORD
26h 35m
1 stop
$582Scandinavian Airlines
Wed, Oct 21 - Sat, Oct 31
Scandinavian Airlines Logo
7:15 pm - 6:45 pm
ORD
-
NAP
16h 30m
1 stop
Scandinavian Airlines Logo
8:20 pm - 5:45 pm
NAP
-
ORD
27h 25m
1 stop
$588Scandinavian Airlines
Wed, Dec 2 - Wed, Dec 9
Air France Logo
1:05 pm - 3:50 pm
MDW
-
NAP
19h 45m
2 stops
Air France Logo
6:35 am - 10:10 pm
NAP
-
MDW
22h 35m
2 stops
$739Air France
Mon, Aug 3 - Wed, Aug 19
Delta Logo
5:10 pm - 7:05 am
MDW
-
NAP
30h 55m
1 stop
Delta Logo
9:05 am - 9:59 am
NAP
-
MDW
31h 54m
1 stop
$794Delta
Tue, Aug 11 - Tue, Aug 18
Air France Logo
10:54 am - 7:05 am
MDW
-
NAP
13h 11m
1 stop
Air France Logo
7:15 pm - 6:33 pm
NAP
-
MDW
30h 18m
2 stops
$804Air France
Wed, Aug 19 - Wed, Aug 26
Delta Logo
6:05 am - 8:10 am
MDW
-
NAP
19h 05m
2 stops
Delta Logo
9:05 am - 10:36 pm
NAP
-
MDW
20h 31m
1 stop
$805Delta
Mon, Aug 3 - Wed, Aug 19
Delta Logo
10:54 am - 10:35 am
MDW
-
NAP
16h 41m
2 stops
Delta Logo
9:05 am - 10:36 pm
NAP
-
MDW
20h 31m
1 stop
$809Delta
Booking Insights

KAYAK's insights & trends for Chicago to Naples flights

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

How much is a round-trip flight from Chicago to Naples?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Naples departing in October.

What is the cheapest Chicago to Naples flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Naples costs $749 on the route between Chicago O'Hare Intl Airport (ORD) and Naples (NAP). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Naples?

The average price of all round-trip flights from Chicago to Naples clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Naples, look for departures on Sundays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Naples, Saturday is the cheapest day to fly and Thursday is the most expensive.

What is the cheapest month to fly from Chicago to Naples?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Naples, 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 from Chicago to Naples is May, where tickets cost $371 (return) on average. On the other hand, the most expensive months are July and June, where the average cost of round-trip tickets is $810 and $796 respectively.

Can I save money by flying with a layover from Chicago to Naples?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $692, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Naples, 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 on the flight from Chicago to Naples, you should book around 2 weeks before departure, which saves you about 13% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$256
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 46% increase in price.
Flight from Chicago O'Hare Airport to Naples

When to book flights from Chicago to Naples

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

FAQs for booking flights from Chicago to Naples

  • Are there services for those people with reduced mobility at Naples International Airport?

    Naples International Airport is dedicated to giving the best experience to all passengers especially those with reduced mobility. The airport offers traffic lights with sound indications, paths and tactile maps for the visually impaired not forgetting platforms with accessed ramps. Passengers with reduced mobility should contact the airport 48 hours before their flight in case they need assistance and plan of taking advantage of the services to be provided.

  • Can I find nursing rooms at Chicago International Airport?

    Chicago International Airport has nursing rooms which is located in Terminal 3 Rotunda, next to the Yoga room and Urban Garden. The room has seats, sinks, an outlet, and paper towels.

  • Can I find a business center at Naples International Airport?

    Naples International Airport has multiple business centers which offer services. The Premier Executive Center located in North Naples, Florida. It offers conference rooms, money transfers, and currency exchange.

  • Where can I sleep at Chicago O’Hare International Airport?

    Should you need a place to rest before your flight, there is the Hilton Chicago O’Hare International Airport is located inside the airport and is directly across Terminals 1, 2 and 3 connected by underground walkways. The hotel offers delicacies and alcoholic and non-alcoholic drinks.

  • What is the cheapest flight from Chicago to Naples?

    In the last 5 days, the lowest price for a flight from Chicago to Naples was $255 for a one-way ticket and $574 for a round-trip.

  • Do I need a passport to fly between Chicago and Naples?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago and on arrival in Naples.

  • Which airports will I be using when flying from Chicago to Naples?

    Chicago is served by 2 major airports and there is only 1 main airport in Naples. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Naples.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Naples?

    Finnair, American Airlines, Iberia, and British Airways offer inflight Wi-Fi service on the Chicago to Naples flight route.

  • Which aircraft models fly most regularly from Chicago to Naples?

    The Boeing 787-8 Dreamliner is the aircraft model that flies most regularly on the Chicago to Naples flight route.

  • Which airline alliances offer flights from Chicago to Naples?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Naples, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Naples?

    There are nonstop flights from Chicago to Naples on a daily basis.

  • Which is the best airline for flights from Chicago to Naples, Finnair or SWISS?

    The two airlines most popular with KAYAK users for flights from Chicago to Naples are Finnair and SWISS. With an average price for the route of $1,333 and an overall rating of 7.6, Finnair is the most popular choice. SWISS is also a great choice for the route, with an average price of $890 and an overall rating of 7.5.

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

    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 from Chicago to Naples.

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

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

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

    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 Naples with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Naples?

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

KAYAK’s top tips for finding a cheap flight from Chicago to Naples

  • Looking for a cheap flight? 25% of our users found flights on this route for $552 or less one-way and $1,050 or less round-trip.
  • Naples International Airport (NAP) offers two options that one can take from the airport to reach the city center. The options consist of a taxi and a bus. Though the taxi is more expensive than the bus it’s the fastest option since one can only use less than 15 minutes to arrive at the city center. One can also use the bus since it is the cheapest method and takes only 15 minutes for one to reach their destination.
  • Chicago offers a variety of parking lots that enable passengers to arrive at terminals in a few minutes. The airport has parking lots like Baymont by Wyndham O’Hare parking, La Quinta Inn Suites ORD Airport Parking and ORD Routes Airport Parking. The lots offer both short and long-term parking where the short-term packing facility is located adjacent to the domestic terminals. Long-term parking facilities are located at Economic Lots F and these lots offer free shuttle buses operating 24 hours a day.
  • If one is planning on extending their stay in Naples, renting a car would come in handy since it will be of help as one moves around. You can find a car rental at Surface Car Rental Capodichino Airport, which is 2 miles from the city center. One can rent a car from companies like Hertz, Budget, Dollar, and Thrifty are all set up to offer a wide range of cars.
  • Chicago O’Hare International Airport (ORD) has six animal relief areas where four are outdoor areas while the other two are inside the airport security. These animal relief areas are located at the Multi-Modal Facility and on the lower levels of Terminals 1, 2, and 3. The animal relief areas have chew toys, pet carriers, plastic bags, and dog treats. The area is covered in synthetic grass, small fire hydrants and a pop-up sprinkler system that cleans and gets rid of waste.
  • You can’t get bored during your flight since Turkish Airlines offers a wide range of options when it comes to entertainment. One can choose from a selection of TV shows, movies, games and music that keeps them entertained when onboard.

Prefer to fly direct from Chicago to Naples?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Naples.
Find which airlines fly direct from Chicago to Naples Airport, which days they fly and book direct flights.

Direct departures

Chicago to Naples

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Direct returns

Naples to Chicago

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Reviews of the top 5 airlines serving from Chicago to Naples

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Naples. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Naples? 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.
7.5
SWISSOverall score based on 1985 reviews
7.1Food
7.7Boarding
8.3Crew
7.4Comfort
6.8Entertainment
Airline reviews

Made us gate check carry ons Then didn’t get them on the plane. Service they used didn’t deliver our carry ons for more than a day Total mess

2.0 MediocreAndrew, Dec 2025
ZRH - FCO
Read more SWISS reviews

Made us gate check carry ons Then didn’t get them on the plane. Service they used didn’t deliver our carry ons for more than a day Total mess

They didn't give us Nothing to eat, come on..... 1 package of chips and a glass of soda won't do anything to the company

I slept the whole flight so I can't tell you about the food and there was no entertainment offered. Crew was very nice, seats were comfortable in business, and boarding was easy.

The seats had no space at all beyond the knees. The seat in-front literally reclined on your face, very uncomfortable plane. Was nothing like the normal SWISS experience. The food was okay but could be better.

They rebooked our flight and then canceled our trip halfway through the journey without any explanation. Needed to pay by ourselves for alternative flight options without any help from Swiss.

Flight was diverted from Firenze to Pisa causing delay and inconvenience.

Easy boarding Seats were very uncomfortable no room arm rests didn't even go up all the way

Wonderful experience! The crew was outstanding and amazing from check in to gate to flight crew! Amazing. Thank you!

Carry on luggage size for economy passengers significantly smaller than other airlines, so nearly all ecomy passengers had their bags taken and checked.

Missed connecting train since flight was late into Zurich and I had to stay at airport hotel because of it as well as I had to repurchase train ticket

Istanbul to Lahore flight was less than standard for international business class cabins. Seat did not were not flat and it did not operate easily. I had to push buttons hard repeatedly to operate the seat. I was in 5A seat

My, Syed Zawar Hussein Shirazi frequently flyer membership number was not included on my boarding pass from O’Hare to Istanbul despite my reminder to the attendant at check in. Further she forgot to give me my boarding pass form Istanbul to Lahore and she needs to improve her customer service, please 🙏

Chicago to Istanbul was a much better experience than I expected since I’m more accustomed to Qatar Airways business class. The business lounge in the Istanbul airport was amazing - loved the lockers and phone charging stations, and the bathroom was a spa experience in itself. The onward leg from Istanbul to Karachi was utterly disappointing. Terrible plane, and I felt like I was in economy - the seats don’t come near to lying flat and the food was mediocre. What a sad downgrade - it isn’t as though the ticket on that leg was cheaper. So, on that front, there’s no contest with Qatar airways.

Second leg of Turkish Airline with Indigo is disaster for following reason. 1) You have to carry your cabin bags through ladder to boeing 777 because it was parked somewhere in parking lot and was not given a gate to board passengers and this seems to be people traveling to and fro from those flights and is not issue with flight itself. 2) I choose non vegetarian food on Turkish portal way ahead of checkin to entire trip, However the Indigo flight gave me random veg food saying they code veg food code from Turkish. 3) Indigo did not served any alcoholic beverages stating some weird reason which is non nonsensical. 4)Indigo have TV screens in front of you but it displays nothing except "Welcome Onboard" with annoying white black ground in dark flight. This is the most stupidest and annoying part because you are held hostage for 7 hours and only thing you could do is stare back at white screen which does not have entertainment package or even flight tracker. Such a shame.

During mid flight, try to get a flight attendant to help I couldn’t find one Otherwise, everything was perfect

The 2 agents on the check in counter were super nice , helpful and very polite. Boarding was like a 1 2 3, I would recommend Turkish airlines for your next trip.

7 stars hospitality and an excellent service by the Turkish Airline entire team. Somehow, our membership numbers for mileage points were not indicated on our boarding passes issued at O’Hare Airport by the Turkish Airlines check in desk. During transit in Istanbul, I brought to attention of customer service Turkish Airlines. Please have our mileage points posted to our membership account from O’Hare Chicago to Lahore for both my wife Kaukab Shirazi Thank you

Terrible boarding process, no proper line maintained even for business class, crews are not very attentive, business class food quality / variety / quantity have gone down, everything has become cheap.

Food quality and the overall service of the staff and significantly decreased. The flight was delayed at the Istanbul airport and the passengers were kept onboard for more than 3 hours. The staff didn’t kept the passengers informed and everyone was upset.

Turkish Airlines apparently no longer gives you 2 checked bags allowance on international flights, so that pleasure cost me $165 for my second suitcase at the airport. On top of that, they damaged that very suitcase, which happens to be a designer one and part of a set - ripped one of the four wheels right off.

I flew Aer Lingus Business class for the first time. Having flown economy a few times, I was familiar with the airline, and happy enough with economy. I’ve certainly been in nicer economy airlines before, but Aer Lingus is usually very reasonable, and I find the staff to be kind and have an Irish sense of humor and accommodation. The business experience was good, in that you got superior service to the back, lay down seats, better food and drinks, and more attentive service. However, the plane was a bit older, the WiFi was slow(not Starlink) and the pods were too close to one another for privacy, or function. When the Oder lady to the left of me fell asleep(fully reclined) there was no way for me to escape without having to wake her and put her seat all the way up. That lead to me being stuck with luggage I couldn’t put away in a cramped(for business) space, and no way to use the restroom for almost the whole 8 1/2 hour trip. I ended up trying to sleep with a large backpack blocking my feet. The food was good for plane food, but not great. The drinks were great, shame I couldn’t have had more, but I’d have peed myself. I love a window, but next time maybe an isle seat. Overall, the experience was good, not great, but an expensive good experience during which I got zero sleep. I’d do it again, but it’d have to be a deal.

OK overall. Flight was delayed Crew on flight was good

Late late late. Delayed and arrived an hour late for a 1 hour 45 minute connection. Every time. Poor record for this company. I try to fly any other carrier first.

I flew economy class. Seats were very good and the crew was excellent

Fast and sensible boarding was absolutely amazing. But extortionate wifi and seats that barely moved, making me unable to sleep, didn't do a lot of favors.

I appteciate the very courteous staff. The flight was good. Something that wasn't good was that my bag was only checked as far as Dublin and I had a connecting flight to Vienna. (That was a mistake the ORD desk made.) Fortunately the desk at DUB was able to re-tag without me having to re-check in (which initially it seemed I might have to do.)

It was excellent! The plane left Chicago early. Arrived in Dublin early. The crew was excellent! It was a great experience.

We couldn't talk to aer lingus we had issues with the flight change and aer lingus made us talk to kayak

Horrible. Garbage airline. Due to the strike we got a replacement plane/crew. I didn't get my exit row seat I paid for. Food was horrible. Plane was hot and didn't have AC vents.

Are Longus was fine. I booked thru Kayak and was unable to get my business class seat early. Sat next to galley. Crew forgot to wake me for breakfast.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

When you pay for Premium Economy and you’re promised amenities for the extra money, you expect them to work. They didn’t. USB connector wouldn’t charge continuously. 120v outlet wouldn’t hold anything you plugged into it. The adapter would just fall out. The noise canceling headphones stopped noise cancelling in the first 15 minutes for EVERYONE. No one on the plane knew how to fix it so I couldn’t listen to any movies. I just put in my AirPods and went to sleep. Very unhappy with the crappy Panasonic entertainment system. I won’t buy premium again.

30 minutes still don't have gate number, ask many people can't get answer.

The staff was very nice and helpful. Some of the best crew I have met.

Disaster. Downgraded. Zero apology. No effort or coordination between gate and crew. Awful seat blocked by door emergency slide box. Iberia is a mess. App never works. Avoid this airline.

It was extremely cold in the back of the plane. The seats are uncomfortable and space very small. Crew was excellent as usual.

It was a wonderful experience with great food, great staff, and no difficulties boarding!

I was in business class for the 8 hour flight where: 1. The WiFi did not work 2. The entertainment system did not work 3. We were told there were no hot drinks for the entire flight

Paid for “extra room” selected seat. Wasn’t a benefit. Also was in aisle and was bumped almost every time attendants walked down aisle. Should have saved the assigned seat money and let them select.

Alaska located my mother, aware that she had mobility issues and they seated her closer to the door. She and I were seated together so I felt more secure to be able to assist her. The desk attendant reviewed what steps to take when boarding. Allowed us to board first, we loved that. I was allowed time to help her board slowly, seat her, put all her things in their place before the crowds came through. These small details made me want to travel Alaska more when possible.

I bought the ticket through Iberian, but I was unable to check in using my code. American wouldn’t let me check in and Iberian counter was closed.

The comfort level was low, but the staff was nice

Everything you need to know for your flight from Chicago to Naples

Information on your arrival and departure airports