$352 Find Cheap Flights from Chicago to Tuscany

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 Tuscany departing on 8/9. 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 Tuscany

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Tuscany.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Tuscany.
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Flight Deals

Book Cheap Chicago to Tuscany Plane Tickets

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

Mon, Oct 19 - Wed, Oct 28
Turkish Airlines Logo
11:25 am - 9:20 am
ORD
-
FCO
14h 55m
1 stop
Turkish Airlines Logo
6:45 am - 7:25 pm
FCO
-
ORD
18h 40m
1 stop
$728Turkish Airlines
Wed, Sep 16 - Fri, Sep 25
Turkish Airlines Logo
11:25 am - 11:35 pm
ORD
-
FCO
29h 10m
1 stop
Turkish Airlines Logo
10:45 am - 9:40 am
FCO
-
ORD
29h 55m
1 stop
$729Turkish Airlines
Sun, Aug 16 - Tue, Aug 25
Multiple Airlines Logo
2:00 pm - 11:45 am
ORD
-
FCO
14h 45m
2 stops
Multiple Airlines Logo
9:35 am - 3:55 pm
FCO
-
ORD
13h 20m
1 stop
$732Multiple Airlines
Sat, Sep 19 - Wed, Sep 30
Scandinavian Airlines Logo
7:15 pm - 6:35 pm
ORD
-
FCO
16h 20m
1 stop
Scandinavian Airlines Logo
7:25 pm - 4:10 pm
FCO
-
ORD
27h 45m
1 stop
$734Scandinavian Airlines
Sat, Sep 19 - Fri, Oct 2
Scandinavian Airlines Logo
7:15 pm - 6:35 pm
ORD
-
FCO
16h 20m
1 stop
Scandinavian Airlines Logo
9:40 am - 4:10 pm
FCO
-
ORD
13h 30m
1 stop
$735Scandinavian Airlines
Wed, Aug 12 - Fri, Aug 21
Delta Logo
1:05 pm - 10:50 am
MDW
-
FCO
14h 45m
1 stop
Delta Logo
6:30 am - 4:27 pm
FCO
-
MDW
16h 57m
2 stops
$758Delta
Sat, Aug 15 - Wed, Aug 26
KLM Logo
10:35 am - 7:35 am
MDW
-
FCO
14h 00m
1 stop
KLM Logo
9:00 am - 6:31 pm
FCO
-
MDW
16h 31m
1 stop
$808KLM
Mon, Aug 17 - Thu, Aug 20
KLM Logo
1:05 pm - 10:50 am
MDW
-
FCO
14h 45m
1 stop
KLM Logo
9:00 am - 6:31 pm
FCO
-
MDW
16h 31m
1 stop
$827KLM
Mon, Oct 19 - Tue, Oct 27
Delta Logo
12:30 pm - 12:40 pm
MDW
-
FCO
17h 10m
1 stop
Delta Logo
10:00 am - 6:37 pm
FCO
-
MDW
14h 37m
1 stop
$848Delta
Wed, Aug 5 - Sat, Aug 29
Lufthansa Logo
9:40 pm - 8:15 pm
ORD
-
FLR
15h 35m
1 stop
Lufthansa Logo
9:50 am - 8:19 pm
FLR
-
ORD
17h 29m
2 stops
$851Lufthansa
Booking Insights

KAYAK's insights & trends for Chicago to Tuscany flights

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

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 Tuscany departing in August.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Tuscany, 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 Tuscany is October, when tickets cost $419 (return) on average. On the other hand, the most expensive months are February and March, when the average cost of round-trip tickets is $577 and $577 respectively.

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

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 Tuscany, 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 Tuscany, 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 seasonFebruary
Cheapest flight$353
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Chicago O'Hare Airport to Florence

FAQs - booking Tuscany flights

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

    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 Tuscany.

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

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

    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 from Chicago to Tuscany 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 from Chicago to Tuscany?

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

Reviews of the top 5 airlines serving from Chicago to Tuscany

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Tuscany. 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 Tuscany? 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 1926 reviews
7.7Boarding
6.8Entertainment
8.3Crew
7.4Comfort
7.1Food
Airline reviews

plenty of legspace, snacks, no pull face from flight attendants when asking for a wine. Also fast transfer ability at ZRH.

10.0 ExcellentIstvan, Apr 2026
SFO - ZRH
Read more SWISS reviews

plenty of legspace, snacks, no pull face from flight attendants when asking for a wine. Also fast transfer ability at ZRH.

The flight itself was fine, but due to a snow delay my connection to Lisbon was delayed by six hours. Despite this, Swiss Air still managed to lose my luggage. Not acceptable. Someone else on the flight also lost their luggage.

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.

No food was served on this short flight and we had no entertainment. Please add a box to check. We were served delicious Swiss chocolate though! The boarding process was fast and the crew very friendly.

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

The stewardess was incredibly rude. The gave you only one drink with dinner.

Cancelled flight, wasn't refunded paid selected seats. Poor customer service. Called airline and they didn't realize the flight was cancelled until several hours after the email notice was sent.

The worst with the trip was the space in economy, my knees are still hurting. There was no way to control personal air by turning a knob above you, it was way to hot on both rides. During the night flight they allowed 2 people from across the aile which was narrow to sit and talk for 7 hours while also using tablets and the flashlight from their phones pointing into the row where I sat at times. They allowed people with way too large baggage to bring onboard. I paid way too much for the ticket ($1,364} for economy. Kayak misinformed me to get cancellation insurance that was only valid for a very short time (less than 12 hours) and was over one hundred dollars. Hotel booking was incorrect, I had the room booked myself at the hotel, only double or larger rooms available which I paid over 400 dollars for. I will never fly with SAS again unless there is no other alternative.

Crew members were excellent. The seat wasn’t the best as well as a food options.

5 of my 7 pieces of luggage are missing and they cant call to find out where it is. I have to fill out a form and wait for them to mail it to me in several days (if they find it). That does not work for my travel itinerary. I need my full ticket cost refunded please.

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!!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

Flight was delayed by several hours and then cancelled due to weather. But Staff was very helpful getting me on a different flight. United should offer food coupons and tooth brush and paste for stranded passengers

I had a good comfortable seat. There was nearly an hour delay. There was an accident with the champagne, but I was well compensated. These things happen sometimes.

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.

Boarding was orderly, pilot and flight attendants were nice, entertainment options were good, and low sodium meals were quite tasty.

The whole experience was excellent, O can say out from Miami the best airline to travel with for any European destination. Since the ground staff to the inflight crew attention was great, service on board 10 of 10. Finally the 380 is very confortable and nice to travel.

All crew except 1 were excellent. When I asked assistance with business class seat conversion to a bed (not being familiar as never used before but have numerous times with other airlines) crew member helped very reluctantly. I should have told her that business class seat conversion is totally different in each airline such as Delta, New Zealand Air and United. Sorry it was my 1st time with America Airlines. Now I know, I won't bother asking assistance in future.

1st class seats NOT REALLY 1st class or business class but like premier economy. Should be listed as such or named something else. I have flown 1st class with other airlines and they are nothing like it at all.

The seats in Premier Economy were very comfortable. The food was better than average. The way British Airways handled our seating was atrocious.

Worst airline in the world. They downgraded me from business class to economy with no compensation.

Overall ok. Best part has always been the sundae dessert.

Very good staff members with sincere passion and responsibility in their job.

It is an airline that has the service that used to be in the old times as a standard and now is rare. Very good.

I was unable to board this flight because of visa changes that I was not alerted about and I’ve been unable to contact Kayak to obtain a refund / credit anything.

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

Cabin class types available on flights to Tuscany

Cabin classes available on flights to Tuscany. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.