CHI - FLR

$251 Find Cheap Flights from Chicago to Florence

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 Florence departing on 2/5. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Florence

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florence.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florence.
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Everything you should know

Cheapest round-trip
$497
Overall average: $1,020
SWISS
Mon 2/9Fri 2/20
ORD - FLR • 1 stop
Cheapest one-way
$251
Overall average: $601
Multiple Airlines
Thu 2/5
ORD - FLR • 2 stops
Top airlines
SWISS
Cheapest • from $497 (round-trip)
SWISS
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
November
Cheapest • 21% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Florence (CHI-FLR)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Florence 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 Florence

Mon, Feb 9 - Fri, Feb 20
SWISS Logo
6:50 pm - 1:45 pmORD-FLR
11h 55m1 stop
SWISS Logo
6:55 pm - 4:20 pmFLR-ORD
28h 25m1 stop
$497SWISS
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Mon, Jan 26 - Tue, Feb 3
Multiple Airlines Logo
3:35 pm - 12:35 pmORD-FLR
14h 00m2 stops
Multiple Airlines Logo
6:30 am - 2:55 pmFLR-ORD
15h 25m2 stops
$503Multiple Airlines
Find Deal
Fri, Nov 28 - Fri, Dec 5
Lufthansa Logo
9:50 pm - 4:30 pmORD-FLR
11h 40m1 stop
Lufthansa Logo
6:30 am - 1:10 pmFLR-ORD
13h 40m1 stop
$506Lufthansa
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Thu, Nov 27 - Thu, Dec 4
Multiple Airlines Logo
6:50 pm - 6:05 pmORD-FLR
16h 15m1 stop
Multiple Airlines Logo
10:25 am - 8:05 pmFLR-ORD
16h 40m1 stop
$508Multiple Airlines
Find Deal
Thu, Jan 1 - Mon, Jan 19
Lufthansa Logo
9:50 pm - 8:40 pmORD-FLR
15h 50m1 stop
Lufthansa Logo
7:10 am - 6:25 pmFLR-ORD
18h 15m1 stop
$509Lufthansa
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Wed, Mar 11 - Wed, Mar 18
ITA Airways Logo
11:00 am - 2:45 pmORD-FLR
21h 45m2 stops
ITA Airways Logo
6:30 am - 6:28 pmFLR-ORD
17h 58m2 stops
$523ITA Airways
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Thu, Nov 27 - Thu, Dec 4
United Airlines Logo
6:00 pm - 12:35 pmORD-FLR
11h 35m1 stop
United Airlines Logo
6:35 am - 2:55 pmFLR-ORD
15h 20m2 stops
$531United Airlines
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Thu, Dec 11 - Wed, Dec 24
United Airlines Logo
6:50 pm - 2:20 pmORD-FLR
12h 30m1 stop
United Airlines Logo
6:30 am - 1:10 pmFLR-ORD
13h 40m1 stop
$534United Airlines
Find Deal
Mon, Jan 12 - Sun, Jan 18
KLM Logo
11:21 am - 8:55 amMDW-FLR
14h 34m2 stops
KLM Logo
6:40 am - 5:34 pmFLR-MDW
17h 54m2 stops
$548KLM
Find Deal
Wed, Nov 5 - Tue, Nov 11
KLM Logo
1:48 pm - 11:20 amMDW-FLR
14h 32m2 stops
KLM Logo
6:40 am - 4:38 pmFLR-MDW
16h 58m2 stops
$1,733KLM
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Florence flights

Get data-powered insights and trends into flights from Chicago to Florence 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 Florence?

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 Florence departing in February.

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

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

If your flying dates are flexible, you should consider flying to Florence on a Sunday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Chicago to Florence. For your return ticket, we recommend flying on a Thursday and avoiding Mondays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Florence, 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 Florence is November, where tickets cost $741 (return) on average. On the other hand, the most expensive months are June and May, where the average cost of round-trip tickets is $1,368 and $1,031 respectively.

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

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 Florence, 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 Florence, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonDecember
Cheapest flight$251
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 45% increase in price.
Flight from Chicago O'Hare Airport to Florence

When to book flights from Chicago to Florence

Are your dates flexible? Find out the best times to travel from Chicago to Florence 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 Florence

  • Are there any lounges at the Florence Airport?

    When you land at FLR, you might want to refresh and reboot after your long flight. The Masaccio Lounge located in the Departures Terminal airside on the first floor grants pay-at-the-door access. Amenities of this lounge include air-conditioning, alcoholic and non-alcoholic drinks, internet, telephone, and more.

  • Are there any car rental agencies at FLR?

    The car rental facility at FLR is the Palagio degli Spini, a separate building that you can reach by catching a free shuttle bus at the short-term parking garage of FLR. These buses depart about every 20min. Car rental agencies here include Auto Europa, Sicily by Car, Dollar, Budget, Hertz, and many more.

  • Do the Chicago airports have facilities for nursing moms?

    Yes. ORD provides several freestanding lactation suites and mother's rooms in every terminal throughout the airport. MDW provides a lactation suite on Concourse A and a mother's room on Concourse C. All of these spaces are clean, quiet places where moms can breastfeed in private if they choose or where they can go if they need to pump.

  • Does either Chicago Airport have a USO?

    Yes. ORD has 2 USOs and MDW has one. All three of these USO lounges welcome active-duty US military members and their dependents. ORD has a USO landside in Terminal 2 and airside in Terminal 3 on the G Concourse. Midway has a USO located post-security on Concourse C. These lounges provide traveling soldiers with refreshments, comfy furniture, devices for connectivity and entertainment, and more.

  • What is the cheapest flight from Chicago to Florence?

    In the last 3 days, the lowest price for a flight from Chicago to Florence was $251 for a one-way ticket and $497 for a round-trip.

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

    Yes

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

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Florence (Florence Peretola). The cheapest flights are generally found on the Chicago O'Hare Airport to Florence Peretola flight route.

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

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Florence?

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

  • What is the most popular layover when flying to Florence from Chicago?

    Rome is the most popular layover city among KAYAK users traveling from Chicago to Florence.

  • Which is the best airline for flights from Chicago to Florence, Delta or KLM?

    The two airlines most popular with KAYAK users for flights from Chicago to Florence are Delta and KLM. With an average price for the route of $1,162 and an overall rating of 7.9, Delta is the most popular choice. KLM is also a great choice for the route, with an average price of $1,031 and an overall rating of 7.7.

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

    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 Florence.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Florence 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 Florence?

    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 Florence 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 Florence?

    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 Florence 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 Florence

  • The city of Chicago is served by two major airports - Chicago O'Hare International Airport (ORD) and Midway International Airport (MDW). ORD is a hub for United Airlines and America Airlines. MDW is a hub for Southwest Airlines and a focus city for Frontier Airlines. Florence Airport (FLR) is an international airport that serves the city of Florence in Tuscany, Italy. This airport is a hub for several international airlines such as Lufthansa and Iberia and a focus city for Air Dolomiti and Vueling.
  • When you are booking your flights from Chicago to Florence, it is unlikely that you will find a direct flight. However, one-stop flights on airline such as Iberia, Lufthansa, SWISS, and Austrian Airlines depart ORD and land at FLR. Layover cities include Madrid (MAD), Munich (MUC) Zurich (ZHR), and Vienna (VIE). Austrian Airlines, Icelandair, and Porter Airlines are among the carriers that operate two-stop flights from Chicago to Florence. These flights depart from both MDW and ORD.
  • If you need some assistance when you land at FLR, you can visit the Tourism Kiosk in the Arrivals area where you can get information about what to see, where to stay, and general inquiries. This kiosk is open every day from 9 a.m. to 7 p.m., except Sunday, when it closes at 2 p.m. The service is not available on New Year's Day or Christmas.
  • If you want to get from FLR into Florence city center on public transportation, you can take a relatively inexpensive bus. Autolinee Toscane, C.A.P., and Blubus are some of the companies that provide service along this route. A bus ride from FLR into the city takes about 15min.
  • Both airports that serve Chicago, ORD and MDW, provide travelers with an airport interfaith chapel. You can pray, contemplate, or relax in these quiet places of sanctuary. These chapels provide worship materials, prayer rugs, rosaries, and ablution facilities. In ORD, you can find the chapel in Terminal 2, and at MDW, you can find the chapel on Concourse C.

Reviews of the top 5 airlines serving from Chicago to Florence

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Florence. 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 Florence? 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 1776 reviews
8.2Crew
7.7Boarding
7.4Comfort
6.8Entertainment
7.1Food
Airline reviews

At boarding, the locations where we had to have our passports checked prior to boarding were very unclear. Occasional staff wandered around telling people, but in busy area of the terminal this was not obvious. It was also located well after the check in desk in terms of walking to the gate. The Premium Economy service was attentive and warm. The only big draw back was lack of restrooms, and no division or even curtain between PE and Economy.

8.0 ExcellentAnonymous, Oct 2025ZRH - MIA
Read more SWISS reviews

At boarding, the locations where we had to have our passports checked prior to boarding were very unclear. Occasional staff wandered around telling people, but in busy area of the terminal this was not obvious. It was also located well after the check in desk in terms of walking to the gate. The Premium Economy service was attentive and warm. The only big draw back was lack of restrooms, and no division or even curtain between PE and Economy.

Food used to be better and comfort was not attainable after 5 hours everything starts hurting.

horrible.. they cause such a problem and my daughter 14 years old was stranded in san francisco

I can’t even the whole trip was a catastrophe

Poor. Seats uncomfortable. No leg room. Hot and humid the whole trip. Food and staffs were ok.

The seats were so close together, when the man in front of me put his seat back, the screen in front of me was 9 inches from my face. There is no way to lean forward if I needed to pick something up. It was pretty uncomfortable for a ten hour flight. I was very surprised.

The food was good. Most the staff was pleasant. The flight would be drastically improved with WiFi on a long international flight.

Swiss airline do not allow online check-in before 24 hrs, this is very inconvenient to us. I tried many ways such as booking code(6 numbers) or 13 booking numbers , neither of them work, Lufthansa is better which allow us to check in even before 30 hrs, so we can assign our seats( not many people want spend extra money to assign seats on top of airfare which is already spent.)

...as stated previously, red tape should be shorted by Swiss in terms of generating refunds...

When I needed to get my bag off of the plane so that I could take a train because the connection was 4 hours later, they took 2 hours to take my bag off making me take the train and miss my flight simultaneously. The seat size on the plane is too small for an average aged woman let alone a middle-aged man. It's unacceptable and I will not fly Boeing again.

No vegetarian option was provided for the regular meal or the pre-landing snack.

The Scandinavian flight was excellent, however the second flight was partnered with TAP Portugal which was not so good. crowded gate area with no chairs, delayed flight, bad boarding process, no entertainment system onboard, and the baggage didn’t get to the carousel until well over an hour which caused our taxi that was waiting to leave. Love SAS, hate TAP.

Great logistics and timeliness as we arrived quite early. Flight smooth and fast. Excellent entertainment. Plane itself was a bit tired and the crew mostly indifferent. Baggage took forever but that’s on CPH. Would use SAS again for sure.

Will not recommend SAS for business travel. Food was so-so. Service was very good. First leg was very good. Second leg from Copenhagen to Barcelona was terrible. We paid a LOT for business class and to have seats worse than most coach seats with no entertainment and no charging available for 1/3rd of the whole trip was not acceptable. Very disappointing. I thought they were coming back in the U.S. with style, NOT YET.

I do not have a problem with the airline but both my two suitcases that were supposed to go from Hawaii to Copenhagen didn’t get on the plane in Seattle. I arrive on Monday the 21st at 10:30 in the morning. I did not get my two suitcases before Friday late afternoon that is unacceptable.

No choice of food. Needed to pay more even for a can of coke!!!

The seats were really close together and hard to get comfortable. The food was okay. The cheese was amazing! I loved the cold towels they gave us.

When my flight was changed from delays they were quick to rebook me.

I really enjoyed how clean and big the aircraft was, as well as how friendly the crew was.

Airline left me stranded in the U.S. gave me an unrequested refund of 40% of booking and canceled my trip back! When I asked why, the said “we don’t have to tell you why”. “But you can rebook”. Never again! Paid 2x and rebooked on Austrian. What a joke!

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

I liked Quiet people around me. Crew could have helped people with overhead luggage so they aren't moving other peoples bags around and causing problems for people that had there bags there first

The plane was delayed by two hours in Chicago which led to us missing the next flight. Lufthansa rebooked the flight and booked us a hotel for the night in Frankfurt. The level of customer service and getting us taken care of was superb. The flight crew and the service on the ground was superb.

Boarding and flight update was fantastic as I experienced about a 10-15 delayed for both flights. The food served onboard was great; the service of the flight attendants was excellent.

The row of seats were so cramped it was difficult to get in and out of your seat. I even upgraded. A long flight and sad accommodations 😵‍💫 the shorter flight was very comfortable and the seating was spacious

Complete mess. Our reservation was mistakenly cancelled. After almost missing the connection and walking all over the Munich airport, the Service desk got involved and we were run to our flight. Not all 4 of us in Business and not seated together as originally booked. This was the worst treatment I have ever had. And I travel a lot. 1K million miler.

I have flown with many airlines. My first time was several years ago. Now I remember why I avoided them for so long. Lufthanza is the only airline who has ever raised a size/weight issue with my modest standard size carry on. I had to repack three times to meet their carry-on weight criteria. (Apparently the rules of physics apply differently on Lufthansa flight than on other airlines.) In the meantime their staff was quite rude, repeating meaningless phrases like "Rules are Rules." And ignoring the additional fact that weight is also weight, whether it is in found in your carry on or in your suitcase. They eventually acknowledged that customer service and satisfaction is, for them, a low priority. Never choosing Lufthansa again.

They are professional. Nice crew. Still flying Boeing 747. Thank you for that. I love this airplane. Traditional.

There is more space in this economy seat. It felt like a better layout, not so cramped.

Connecting from Germany with not enough time to go thru TSA and security so many times. Kayak or whomever doesn’t leave you enough time between flights. I made it with 5 min before my zone was called. Too stressful

The seats were extremely uncomfortable. I spent €25 on internet and never gained access to it. A flight attendant told me she would file a complaint/report on my behalf but it put me in a very difficult situation.

Wonderful! Everyone very helpful and kind. Returning flight was cancelled but rebooking was easy.

Pretty normal flight was delayed due to traffic could have missed connecting flight to Venice but crew kept us well informed so we made it

Flight was on time and pretty standard. No Hiccups. I have no complaints, which is a lot to say about a 12 hour flight.

-The seats could be roomier -The entertainment in English could be more current! The moves were very old!!! -They served too many carbs! What happened to fruit and yogurt!!!!

We upgraded to premium economy and it made a difference in a 12 hr flight. I didn’t like that we had to deplane in the tarmac with our carryon luggage. Other than that, it was ok.

Everything was much better than I had expected, since I hadn’t heard of your airline before. I hope to take advantage of your excellent service again.

Staff were nice, we left on time and arrived early, food was good. Unfortunately, they lost one of our bags and have been unable to find it. So we are in Italy for a week for my husband‘s birthday and he does not have any of his clothing.

They gave us sandwiches as a meal twice. Snacks mid flight with cookies and a tuna panini. Then just the same tuna panini for dinner. That was it.

Top notch re cleanliness, comfort, operational. Attendants attentive, cheerful, courteous and professional. An unusually high-grade experience all around.

The staff was very good, the only thing was the air conditioning wasn't working during the boarding process so it was very hot inside the plane until we got airborne. The food wasn't great, the chicken was dry and hard to cut, the ravioli was ok and the little pizza pocket thing was pretty bad. Other than that is was a good flight all around

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

Information on your arrival and departure airports

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