$181 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 9/28. 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$440
Florence
Florence1 stop$440

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

Wed, Dec 3 - Thu, Dec 11
TAP AIR PORTUGAL Logo
7:10 pm - 6:45 pmORD-FCO
16h 35m1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 3:15 pmFCO-ORD
26h 40m1 stop
$332TAP AIR PORTUGAL
Find Deal
Sat, Oct 11 - Wed, Oct 22
TAP AIR PORTUGAL Logo
6:15 pm - 7:00 pmORD-FCO
17h 45m1 stop
TAP AIR PORTUGAL Logo
8:00 pm - 12:35 pmFCO-ORD
23h 35m1 stop
$333TAP AIR PORTUGAL
Find Deal
Wed, Dec 3 - Thu, Dec 11
TAP AIR PORTUGAL Logo
7:10 pm - 12:05 amORD-FCO
21h 55m1 stop
TAP AIR PORTUGAL Logo
4:40 pm - 3:15 pmFCO-ORD
29h 35m1 stop
$334TAP AIR PORTUGAL
Find Deal
Sun, Nov 30 - Tue, Dec 16
United Airlines Logo
7:15 am - 8:55 amORD-FCO
18h 40m1 stop
United Airlines Logo
9:45 am - 1:10 pmFCO-ORD
10h 25mnonstop
$362United Airlines
Find Deal
Sun, Nov 30 - Tue, Dec 16
United Airlines Logo
3:45 pm - 7:45 amORD-FCO
9h 00mnonstop
United Airlines Logo
9:45 am - 1:10 pmFCO-ORD
10h 25mnonstop
$366United Airlines
Find Deal
Sun, Nov 9 - Sat, Nov 15
British Airways Logo
5:10 pm - 9:30 amORD-PSA
33h 20m1 stop
British Airways Logo
11:00 am - 1:50 pmPSA-ORD
33h 50m1 stop
$591British Airways
Find Deal
Sun, Nov 9 - Sat, Nov 15
British Airways Logo
9:45 pm - 9:30 amORD-PSA
28h 45m1 stop
British Airways Logo
11:00 am - 1:50 pmPSA-ORD
33h 50m1 stop
$592British Airways
Find Deal
Wed, Dec 3 - Sun, Dec 7
SWISS Logo
6:50 pm - 1:50 pmORD-FLR
12h 00m1 stop
SWISS Logo
9:35 am - 4:20 pmFLR-ORD
13h 45m1 stop
$642SWISS
Find Deal
Sun, Sep 28 - Mon, Oct 6
Lufthansa Logo
3:35 pm - 5:35 pmORD-PSA
19h 00m2 stops
Lufthansa Logo
6:15 pm - 12:55 pmPSA-ORD
25h 40m1 stop
$810Lufthansa
Find Deal
Sun, Sep 28 - Mon, Oct 6
Lufthansa Logo
3:35 pm - 5:35 pmORD-PSA
19h 00m2 stops
Lufthansa Logo
6:15 pm - 12:30 pmPSA-ORD
25h 15m2 stops
$841Lufthansa
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 $1,360 and $1,062 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, which saves you about 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.


Good to know

Low seasonDecember
Cheapest flight$181
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 40% 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 1686 reviews
7.1Food
6.8Entertainment
7.7Boarding
7.4Comfort
8.2Crew
Airline reviews

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

8.0 ExcellentScott, Jul 2025ZRH - BOS
Read more SWISS reviews

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.

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

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!

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.

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.

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!!

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.

Flight was delayed. Though I checked in with BA live chat three times, our special meals were not provided.

My experience with British Airways is excellent, thanks for all 🫶🏻✈️

Old tired plane, Uncomfortable business class seat. Breakfast dreadful and meagre. At least flight was on time!

Boarding market okay just because of the delay we had, but not related to the crew in any way…

Safe arrival. Improvement on Time efficiency Effective Communication will be great.

The crew is very friendly and helpful. The food is good for airplane food. The flight is long and hard to sleep. The leg space is great. The plane arrived in plenty of time.

A good flight back to Tampa and thankfully although we had a 90 minute delay because of thunder storms from Charlotte to bottom iof Florida, it was a prudent to avoid these for a comfortable flight as opposed to being tossed around with turbulence.

They removed our booking without telling us. Cost us thousands to book last minute

Enjoyable flight, helpful crew everything was organized to accommodate passengers.

Captain sick. Unable to get replacement so delayed me 30 hours, many others delayed 54 hours. TOTALLY DESTROYED ALL MY PLANS, including lost my rental car which would now cost over 5 times what I paid so stuck with buses n trains... lost hotel reservations.... HORRIBLE!!!

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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