CHI - FLR

$255 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 4/20. 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
$381
Overall average: $879
TAP AIR PORTUGAL
Fri 4/10Fri 4/24
ORD - FLR • 1 stop
Cheapest one-way
$255
Typical prices: $614-$723
Multiple Airlines
Mon 4/20
ORD - FLR • 2 stops
Top airlines
TAP AIR PORTUGAL
Cheapest • from $381 (round-trip)
SWISS
Best reviews • 7.6 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 19% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 23% 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

Fri, Apr 10 - Fri, Apr 24
TAP AIR PORTUGAL Logo
6:00 pm - 6:00 pm
ORD
-
FLR
17h 00m
1 stop
TAP AIR PORTUGAL Logo
6:45 pm - 4:15 pm
FLR
-
ORD
28h 30m
1 stop
$381TAP AIR PORTUGAL
Wed, Apr 22 - Thu, Apr 30
TAP AIR PORTUGAL Logo
6:00 pm - 6:05 pm
ORD
-
FLR
17h 05m
1 stop
TAP AIR PORTUGAL Logo
6:50 pm - 4:00 pm
FLR
-
ORD
28h 10m
1 stop
$382TAP AIR PORTUGAL
Wed, Apr 22 - Thu, Apr 30
TAP AIR PORTUGAL Logo
6:00 pm - 10:50 am
ORD
-
FLR
33h 50m
1 stop
TAP AIR PORTUGAL Logo
6:50 pm - 4:00 pm
FLR
-
ORD
28h 10m
1 stop
$386TAP AIR PORTUGAL
Wed, Apr 15 - Fri, Apr 24
TAP AIR PORTUGAL Logo
6:00 pm - 6:05 pm
ORD
-
FLR
17h 05m
1 stop
TAP AIR PORTUGAL Logo
6:45 pm - 4:15 pm
FLR
-
ORD
28h 30m
1 stop
$388TAP AIR PORTUGAL
Wed, Apr 15 - Tue, Apr 28
TAP AIR PORTUGAL Logo
6:00 pm - 6:05 pm
ORD
-
FLR
17h 05m
1 stop
TAP AIR PORTUGAL Logo
11:50 am - 4:00 pm
FLR
-
ORD
35h 10m
1 stop
$389TAP AIR PORTUGAL
Mon, Apr 6 - Tue, Apr 14
Scandinavian Airlines Logo
7:15 pm - 11:30 am
ORD
-
FLR
33h 15m
1 stop
Scandinavian Airlines Logo
7:55 pm - 4:10 pm
FLR
-
ORD
27h 15m
1 stop
$426Scandinavian Airlines
Wed, Apr 22 - Thu, Apr 30
Scandinavian Airlines Logo
7:15 pm - 9:10 am
ORD
-
FLR
30h 55m
2 stops
Scandinavian Airlines Logo
12:20 pm - 4:10 pm
FLR
-
ORD
34h 50m
1 stop
$457Scandinavian Airlines
Mon, Mar 9 - Thu, Mar 19
Delta Logo
10:45 am - 8:55 am
MDW
-
FLR
16h 10m
2 stops
Delta Logo
6:40 am - 5:22 pm
FLR
-
MDW
16h 42m
2 stops
$909Delta
Mon, Mar 9 - Thu, Mar 19
Delta Logo
1:10 pm - 11:25 am
MDW
-
FLR
16h 15m
2 stops
Delta Logo
6:40 am - 5:54 pm
FLR
-
MDW
17h 14m
2 stops
$910Delta
Fri, Mar 27 - Mon, Apr 6
Multiple Airlines Logo
11:00 am - 11:15 pm
MDW
-
FLR
30h 15m
3 stops
Multiple Airlines Logo
7:00 am - 10:05 am
FLR
-
MDW
34h 05m
3 stops
$1,035Multiple Airlines
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.

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 $731 (return) on average. On the other hand, the most expensive months are June and December, where the average cost of round-trip tickets is $1,393 and $1,258 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 2 weeks before departure, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$255
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 46% 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 $255 for a one-way ticket and $381 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 $1,143 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.
7.6
SWISSOverall score based on 1863 reviews
7.7Boarding
6.8Entertainment
7.1Food
8.3Crew
7.4Comfort
Airline reviews

Bad experience overall. Crew did not provide food for our 2 year old (even though we specifically bought a child infant seat for her and literally bought another full price flight), which was unacceptable. And we had to pay $310 each way to carry our ski equipment even though they advertise it as something that is free. Tickets were purchased the same way as usual, but they told us we had Economy Light tickets (I never elected to have such seats). Just plain manipulation and false advertisment. Very disappointed overall about this airline.

2.0 MediocreAnonymous, Jan 2026
JFK - GVA
Read more SWISS reviews

Bad experience overall. Crew did not provide food for our 2 year old (even though we specifically bought a child infant seat for her and literally bought another full price flight), which was unacceptable. And we had to pay $310 each way to carry our ski equipment even though they advertise it as something that is free. Tickets were purchased the same way as usual, but they told us we had Economy Light tickets (I never elected to have such seats). Just plain manipulation and false advertisment. Very disappointed overall about this airline.

The trip was great until my luggage was lost on transfer from United to Swiss. It took Swiss 3 days to get my luggage to me though it was located almost immediately.

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

Horrible!! The WiFi was not working, the food was awful

We’ve never been more uncomfortable on a flight than we have on this particular one. The seats in front of us reclined so far back that when the person reclined their seat of broccoli, it almost hit me in the face and left me with literally no room to move that said I had to recline my seed in which made the person behind me upset. It seemed like the seats also would recline without even pressing the button in the armrest and would unrecline as well for that same reason, and it also seemed that some seats reclined more than others. The bottom cushions of the seat were so thin that even after one hour of an 11 hour flight, our tailbones were so sore. It seemed like an overall old airplane. It also didn’t have individual air vents and it was extremely hot the entire flight. Several passengers were commenting on how hot it was. The breakfast was some kind of flavorless triangle, puffy egg, laying in a watery bed of steamed peppers and onions and spinach. It was not appetizing at all. The flight crew was extremely nice so that was a nice thing this flight attendant. They let us try different types of Swiss sodas, which was really nice and the dinner was actually delicious but still overall given the other considerations. It was pretty much a miserable flight without basic seat comfort.

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.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Fantastic. The only thing - out of my six luggage one was lost in Copenhagen, however it was delivered Home 3 Days later so all great..

The crew was friendly, the flight was pleasant. Thank you for your service!

Our trip plan from Kayak stated we were flying SAS. That was not true. The first leg was a Delta flight. We wasted 25 minutes before finding out to check in with the correct airline. Then our SAS flight for the second leg arrived 25 minutes late, and our third leg flight with SAS closed the gate knowing the flight delay was SAS’s fault, and that this flight would only be backed up 5 minutes. The final kicker was that between Delta and SAS, they lost all our checked luggage.

Flight was completely full January 9th? I problem i had the stewardess was bumping into me constantly walking by? very annoying.. on Austrian air I dint have this issue at all...

Amazing! Everyone was so nice and the food was so good!!

Terrible customer service. The flight attendants were rude. We experienced significant turbulence for a large portion of the flight and there was very little check in from the flight deck. The space was extremely limited to the point where it felt like torture. Never again

I was surprised how good an American airline can be - I was really impressed.

Excellent service throughout. Airport process is quick and easy. Very courteous staff. Great service in the plane! Just outstanding punctuality and service overall!!

I have paid for extra legroom on my flight. My seat was broken and did not recline. The crew could not fix it and refused to provide me with another seat

Over all experience was good. However the connection time was too short at CPG. We missed our connecting flight to AMS as the passport control line was too long and by the time we got our passport control done it was too late I wish there were some SAS staff to help us out at the passport control center Though they put us in a KLM flight from CPG to AMS, That flight was also delayed by over two hours

We missed our flight. There was not enough time built into the layover to get through immigration, customs, bagclaim, bag rechecking, and the long trip to another terminal and gate. Kayak really screwed up. We took the bus up to Wisconsin and then were picked up in Brookfield by private car. It was lucky we didnt miss the last bus out.

I tried both on line and by calling the Customer Service line to arrange for a special meal as i have food intolerances. I was under the impression from your service representative that I was successful. I was not. I cannot eat spicy foods and get very ill if i eat bell peppers. I could not eat either menu choice and no special meal was actually ordered. ( your representative tried to order it for a flight that did not have meal service!!! - found this out later). Your wonderful cabin crew managed to put together a fruit, salad, roll and cheese tray for me so I had something to eat. WHY WOULD YOU SERVE SPICY FOOD, WITH NO MILDER OPTION,ON AN INTERNATIONAL FLIGHT???

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.

My seat was broken and ducted taped and my monitor did not work the entire time over 8 hrs sitting. And I had no books or anything with me

my flight from Rome to Boston was on a very old plane. My video and audio did not work.

Good with timing of flights. The crew was exceptionally unfriendly. I heard more than one person say this. And even with the aisle, it seemed more uncomfortable than usual. The movie selection was old and poor, but the dinner was great - the lasagna and tiramisu.

The check in process is chaotic. It says partially checked-in. Never heard of such a thing. Then lost our reserved seats when we finally checked in at the airport. The seats don’t recline. Then we had to get mew boarding passes at the connection. Last, my companion lost her baggage and up to now there’s no update. We’re already half-way through our vacation and still no news what happened to the luggage.

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.

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

Information on your arrival and departure airports