$243 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 9/22. 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

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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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Cheap Flights from Chicago to Tuscany

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Florence
Florence1 stop$677
Florence
Florence1 stop$677

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

Sun, Oct 19 - Tue, Nov 4
American Airlines Logo
10:35 pm - 11:40 amORD-PSA
30h 05m1 stop
American Airlines Logo
10:20 am - 1:50 pmPSA-ORD
34h 30m1 stop
$447American Airlines
Find Deal
Sun, Oct 19 - Tue, Nov 4
British Airways Logo
4:55 pm - 11:35 amORD-PSA
11h 40m1 stop
British Airways Logo
10:20 am - 1:50 pmPSA-ORD
34h 30m1 stop
$449British Airways
Find Deal
Tue, Nov 4 - Tue, Nov 11
United Airlines Logo
6:50 pm - 2:00 pmORD-FCO
12h 10m1 stop
United Airlines Logo
7:05 am - 5:48 pmFCO-ORD
17h 43m2 stops
$491United Airlines
Find Deal
Fri, Nov 28 - Thu, Dec 11
United Airlines Logo
12:50 pm - 8:55 amORD-FCO
13h 05m1 stop
United Airlines Logo
9:45 am - 1:10 pmFCO-ORD
10h 25mnonstop
$492United Airlines
Find Deal
Thu, Oct 30 - Wed, Nov 5
Lufthansa Logo
10:50 pm - 6:15 pmORD-FCO
13h 25m1 stop
Lufthansa Logo
12:20 pm - 6:25 pmFCO-ORD
13h 05m1 stop
$503Lufthansa
Find Deal
Fri, Nov 14 - Mon, Nov 17
SWISS Logo
3:45 pm - 7:45 amORD-FCO
9h 00mnonstop
SWISS Logo
8:15 pm - 4:20 pmFCO-ORD
27h 05m1 stop
$513SWISS
Find Deal
Sun, Nov 23 - Mon, Dec 1
Lufthansa Logo
9:50 pm - 6:15 pmORD-FCO
13h 25m1 stop
Lufthansa Logo
7:05 pm - 1:10 pmFCO-ORD
25h 05m2 stops
$515Lufthansa
Find Deal
Fri, Oct 24 - Tue, Nov 4
SWISS Logo
3:45 pm - 7:55 amORD-FCO
9h 10mnonstop
SWISS Logo
2:50 pm - 4:20 pmFCO-ORD
32h 30m1 stop
$517SWISS
Find Deal
Mon, Oct 6 - Thu, Oct 9
ITA Airways Logo
8:50 am - 2:45 pmORD-FLR
22h 55m2 stops
ITA Airways Logo
6:25 am - 6:30 pmFLR-ORD
19h 05m2 stops
$709ITA Airways
Find Deal
Tue, Sep 30 - Sun, Oct 5
ITA Airways Logo
8:50 am - 2:45 pmORD-FLR
22h 55m2 stops
ITA Airways Logo
7:00 pm - 6:30 pmFLR-ORD
30h 30m2 stops
$721ITA Airways
Find Deal
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.

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 $742 (return) on average. On the other hand, the most expensive months are June and May, when the average cost of round-trip tickets is $1,359 and $1,059 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 2 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonDecember
Cheapest flight$243
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 42% 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.

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.
7.5
SWISSOverall score based on 1730 reviews
7.4Comfort
6.8Entertainment
7.1Food
8.2Crew
7.7Boarding
Airline reviews

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

10.0 ExcellentAnonymous, Sep 2025DEN - ZRH
Read more SWISS reviews

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

At the boarding gate, passengers were offered the option of checking in their carry-on luggage, as the plane was full. However, they failed to specify that they would not be dropping it off at the exit. Instead, everyone had to wait over 30 minutes at the airport carousel, and to everyone's surprise, not even the carry-on luggage, but the checked luggage, was the first to arrive. An hour later, we finally collected our bags. Lesson learned: I will never check my carry-on luggage with Swiss Air / Helvetic Airways again.

The plan was delayed for takeoff by an hour, but we ended up making the landing on time which was a nice surprise.

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.

Delay more than hour created pressure to catch the connecting flight

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.

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.

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.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

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!

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.

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

Better consideration for families traveling with a disabled person. They insisted each person hold their own boarding pass on their own devices and gave us a hard time accepting eight boarding passes on a single device.

Two of my four flights had issues with toilets either NOT fully operational or completely out of order. Boarding was a joke because they have NOT established who is running the show. In the end, she did a terrible job. The seats 💺 were loose goose and the drinks and snacks were limiting in choices. Also, following Alitalia as an inspiration was strange since they went out of business.

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 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!!

The seating has become ridiculous… like a contest to see how narrow and short they can be made- forcing anyone over 5’1 to pay more to not be twisting oneself into a pretzel. Really insane- would have thought BA was better than this. Frankly- it cancels out a lot of the positive aspects.

flight was delayed from BWI to London - missed my connecting flight & then connecting flight (also British Air) was delayed - food is awful, TV & movie selection is great

Three major things that led to my low rating, 1. Internet wasn't available for the whole time, and 2. TV became available way into flight, after numerous system reboots, and 3. Food is not good at all.

Super tight economy class. My knees were hitting the back of seat in front of me (I'm only 5'6"). My small backpack (sized according to their required dimensions) would not fit under the seat in front of me because there is a box (is that the life jacket?) in the way. Over all, extremely uncomfortable. I forgive the tasteless food, but the tight seating was torture

Didn’t fly with them as someone had cancelled my flight

Some how my flight was canceled, neither BA or Justfly.com accepted responsibility. I only found out about this the day before when I tried to check in. I had to book another flight which due to the time ( day before) cost me $300 more. I was still receiving notifications about the flight even when I was on another flight from you. So no my flight to London was not good.

Online check-in 24 hours in advance something seems not so easy to check in to pick seats and to print a boarding pass

I like the crew, very welcoming. Food can be better. The seat arms don’t go up so. I could use the empty seat next to mine to relax better. 3hrs delay 😠

Boarding was efficient and quick, crew was very attentive, seats were comfortable.

Everything was very good! I personally struggled with the heat in the cabin for the first 2 hours

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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