$174 Find Cheap Flights from Chicago to Tuscany

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Tuscany departing on 11/23. 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

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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Best Tuscany Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Florence
Florence1 stop$445
Florence
Florence1 stop$445

Cheap Flights from Chicago to Tuscany

 
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

Sun, Nov 23 - Fri, Dec 5
SWISS Logo
7:05 pm - 2:00 pmORD-FCO
11h 55m1 stop
SWISS Logo
9:35 am - 4:15 pmFCO-ORD
13h 40m1 stop
$174SWISS
Find Deal
Sun, Nov 2 - Sun, Nov 9
SWISS Logo
7:05 pm - 7:25 pmORD-FCO
17h 20m1 stop
SWISS Logo
9:35 am - 4:15 pmFCO-ORD
13h 40m1 stop
$224SWISS
Find Deal
Fri, Oct 17 - Sun, Oct 26
Lufthansa Logo
9:40 pm - 6:05 pmORD-FCO
13h 25m1 stop
Lufthansa Logo
6:55 am - 7:25 pmFCO-ORD
18h 30m1 stop
$408Lufthansa
Find Deal
Thu, Sep 4 - Tue, Sep 16
Lufthansa Logo
9:40 pm - 6:05 pmORD-FCO
13h 25m1 stop
Lufthansa Logo
7:00 am - 12:55 pmFCO-ORD
12h 55m1 stop
$483Lufthansa
Find Deal
Tue, Nov 11 - Fri, Nov 21
United Airlines Logo
3:45 pm - 7:45 amORD-FCO
9h 00mnonstop
United Airlines Logo
1:15 pm - 8:00 amFCO-ORD
25h 45m1 stop
$503United Airlines
Find Deal
Sun, Nov 23 - Thu, Dec 4
British Airways Logo
9:45 pm - 7:50 pmORD-FCO
15h 05m1 stop
British Airways Logo
1:10 pm - 8:04 pmFCO-ORD
13h 54m1 stop
$504British Airways
Find Deal
Wed, Oct 29 - Fri, Nov 7
British Airways Logo
5:25 pm - 7:25 pmORD-FCO
20h 00m2 stops
British Airways Logo
1:10 pm - 8:05 pmFCO-ORD
13h 55m1 stop
$506British Airways
Find Deal
Tue, Nov 4 - Tue, Nov 11
United Airlines Logo
2:00 pm - 11:05 amORD-FCO
14h 05m1 stop
United Airlines Logo
1:30 pm - 8:05 pmFCO-ORD
13h 35m1 stop
$513United Airlines
Find Deal
Wed, Aug 13 - Wed, Aug 20
ITA Airways Logo
3:00 pm - 10:35 amORD-FLR
12h 35m1 stop
ITA Airways Logo
6:25 am - 1:10 pmFLR-ORD
13h 45m1 stop
$677ITA Airways
Find Deal
Wed, Aug 13 - Tue, Aug 19
ITA Airways Logo
3:00 pm - 10:35 amORD-FLR
12h 35m1 stop
ITA Airways Logo
3:15 pm - 1:10 pmFLR-ORD
28h 55m1 stop
$678ITA Airways
Find Deal
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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.

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 November, when tickets cost $756 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $1,356 and $1,084 respectively.

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

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

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

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 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.


Good to know

Low seasonDecember
High seasonJune
Cheapest flight$174
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 39% increase in price.
Flight from Chicago O'Hare Airport to Rome Fiumicino Airport

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.

  • What is the cheapest time of day to fly to Tuscany?

    The cheapest time of day to fly to Tuscany is generally in the morning, when round-trip flights cost $900 on average. Morning departures are around 20% cheaper than evening flights, on average. The most expensive time of day to fly to Tuscany is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $1,583.

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.
7.5
SWISSOverall score based on 1623 reviews
8.2Crew
7.0Food
7.4Comfort
6.7Entertainment
7.6Boarding
Airline reviews

The meal was wonderful and strawberry ice cream was a plus.

8.0 ExcellentAnonymous, Jun 2025ZRH - ORD
Read more SWISS reviews

The meal was wonderful and strawberry ice cream was a plus.

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.

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

The cushion of the seats are old and very thin. The food can be more tasty or come with salt packages

The biggest let down was with booking experience through Kayak. I booked a flight with checked bags on Kayak. Right away I got a message from travel agency that the flight is not confirmed and to call them. I called them and they said the flight I have booked is no longer available with the price I have booked it for and I can book it with about $100 more. I already had other options I could book with cheaper price so I asked them to cancel my booking. Then they said I can have the ticket with the same price but a date change which was not working for me as I had to be there for a seminar. So again I said no then they said they will cover the charges and confirm my flight. When comes time for check-in I see I have no checked bag option which means the travel agency deceived me saying I can have my booking as I had booked it. And at that point I ended up paying $155 for my checked bag going back and forth. I am extremely angry and unhappy with this experience

PLEASE DONT TAKE FORCEFULLY(SIZE APPROPRIATE) CARRY ONS FROM PASSENGERS WHO FOR SOME REASON NEED TO KEEP IT

It was great. My seat was comfortable. The bathrooms were clean . The service was superb . I travel a lot and I have been in 64 counties. I wish I could fly first class, even though I could , but I prefer to budget my yearly travelling expense on actual visiting , not on flight. Anyway, my point is that your economy was far much better than other airlines as good as Air France. The flight attendants and all crew were polite and very helpful and respectful. Thank you for making my long trip tolerable.

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.

I took this flight to be able to fly with Swiss instead of Air Canada from Geneva.. The AC planes have a better outfit in Business class than Swiss, but the service aboard Swiss is really best, first-class, as is the food and beverages. Though using the same plane model (A330-300), the interior setup of the cabin starts to show its age, but IMO the planes are better serviced by Swiss than AC. I had in my recent trips with AC way too many technical problems that led to delays or even complete cancellation of my flight.. Their fleet is aging (average 20+ years) and the maintenance has taken a toll compared to years ago. Cutting costs in every corner has to be paid sometime by someone, and it's the travelers at the end that pays for it. Unfortunately for me, flying directly to Zurich puts a much longer after-fly trip on me than Geneva.. so I might go back to direct flight YUL-GVA, even if I don't like flying with AC.

We are flying with Swiss for a long time but this time was terrible do to are flight cancellations we are in some bad hotel with out normal food

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

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.

The staff was not at pleasant as those on the first leg of our trip.

Boarding was easy and well organized, Breakfast was not very good.

We had a 3 hour delay and then a long taxi to take off. It would have been helpful for the pilot to have communicated more about what was going on. There was no A/C during the wait, and the cabin must have been more than 85 to 90 degrees. The crew gave water to the people in the front but by the time they go to the back of the plane they stopped giving out water. Eventually I went back and asked for some in the rear of the plane (for a second time). The food was close to inedible. I thought on an Italian flight that the pasta would be better than the chick, but honestly, a Swanson's TV dinner would have been better. I had a bite or two to keep my blood sugar up, but basically I couldn't eat it.

Boarding was chaotic. Service was poor. Attendant was slow and rude. In business class, I was not offered a drink until 1.5 hrs,after takeoff. Food was inedible.

Terrible. They canceled 2 flights and then sent everyone by BUS from Rome. They should make amends by offering some sort of compensation.

We ordered a gluten free meal and never got it!

The seats are horribly uncomfortable. We were in premium economy and paid a premium price yet, the seats were the worst! You could feel every structural bar in the seat, there was no padding, no amenities kit, and the leg rests were broken. Duct tape was holding another seat together. When we arrived at our final destination, Venice, my suitcase was ripped open, and my clothes were about to fall out of the bag. I would’ve been more comfortable if I flew a paper airplane across the Atlantic.

The company tries shamelessly to squeeze every dollar)Euro out of its passengers. During the check-in the force you to go through the seat selection, you can skip it. They will assign you the worst seat available, then show you the other available seats on the map, for a fee. But they won't show you the fee until you click on it. And once you do click, there's no way to unselect it!! You will get stuck and forced to pay for that seat. Cheaters!!

Seats weren’t comfortable. Both of our seat backs were either almost straight vertical or laying back into the laps of the people behind us, which is a weird angle to try to get some sleep even on a plane. No in between. Also, neither seat would spring forward like they should.

There wasn't a time for neither food morning entertainment in a short one hour hop over.

Flight on time, flight assistants super nice, business class very comfortable. The whole experience was very good.

It is the worst ever airline. All employees I spoke with over the phone were pompous asses.

The payment system was not working so was unable to connect wifi the entire flight

everything to do with KAYAK was terrible. Your customer facing departments are utterly useless, timewasting and unhelpful.

I ordered short ribs for main course. It tasted sweet, really sweet. Horrible.

charging port did not work, no entertainment system. Other than that the flight was good and safe.

Our luggage didn’t arrive with us, that puts a damper on the whole trip.

The screen didn’t work and I didn’t get the seat upgrade I paid $300 for. They were no help with that,

Paid $180 for seat selection, and selection essnt honored. Have to call for a refund.

Was 3 hrs delayed and my poor friend I met in Barcelona was waiting at airport for 3 hrs. Dallas airport was awful

The internet was horrible. Plus they charged me $25 for service that didn't work which should have been free since I'm Concierge Key. The flight attendant Rick Young was excellent. Greeted me by name and very attentive.

Not good. First time flying AA in years and won’t be doing so again. We departed late and missed our connecting flight to Barcelona. As a result we missed the first two days of a Mediterranean cruise. No reason given for the delay. Got rerouted from JFK to Heathrow and then to Barcelona. Flight to Heathrow was delayed causing us to miss the flight to Barcelona again. Routed then to Palmero where we had to purchase transportation and a 2 night hotel stay to pick up the cruise there. Probably cost us $2k plus.

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.

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