$177 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 11/16. 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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

Wed, Apr 29 - Tue, May 5
TAP AIR PORTUGAL Logo
6:00 pm - 12:15 amORD-FCO
23h 15m1 stop
TAP AIR PORTUGAL Logo
8:00 pm - 4:00 pmFCO-ORD
27h 00m1 stop
$408TAP AIR PORTUGAL
Find Deal
Wed, Dec 10 - Tue, Dec 23
TAP AIR PORTUGAL Logo
7:10 pm - 11:25 amORD-FCO
33h 15m1 stop
TAP AIR PORTUGAL Logo
4:40 pm - 3:00 pmFCO-ORD
29h 20m1 stop
$412TAP AIR PORTUGAL
Find Deal
Sun, Apr 5 - Sun, Apr 12
TAP AIR PORTUGAL Logo
6:00 pm - 7:05 pmORD-FCO
18h 05m1 stop
TAP AIR PORTUGAL Logo
5:55 am - 4:00 pmFCO-ORD
17h 05m1 stop
$423TAP AIR PORTUGAL
Find Deal
Tue, Dec 2 - Tue, Dec 16
Lufthansa Logo
9:50 pm - 6:15 pmORD-FCO
13h 25m1 stop
Lufthansa Logo
7:05 am - 1:10 pmFCO-ORD
13h 05m1 stop
$482Lufthansa
Find Deal
Mon, Jan 12 - Mon, Jan 19
SWISS Logo
6:50 pm - 2:00 pmORD-FCO
12h 10m1 stop
SWISS Logo
2:50 pm - 4:20 pmFCO-ORD
32h 30m1 stop
$492SWISS
Find Deal
Tue, Mar 3 - Tue, Mar 10
ITA Airways Logo
8:50 am - 7:15 amORD-FCO
15h 25m1 stop
ITA Airways Logo
10:20 am - 6:45 pmFCO-ORD
14h 25m1 stop
$499ITA Airways
Find Deal
Mon, Dec 1 - Wed, Dec 10
Lufthansa Logo
9:50 pm - 4:30 pmORD-FLR
11h 40m1 stop
Lufthansa Logo
10:20 am - 9:08 pmFLR-ORD
17h 48m2 stops
$579Lufthansa
Find Deal
Fri, Jan 9 - Thu, Jan 15
SWISS Logo
6:50 pm - 6:05 pmORD-FLR
16h 15m1 stop
SWISS Logo
2:40 pm - 4:20 pmFLR-ORD
32h 40m1 stop
$599SWISS
Find Deal
Thu, Jan 8 - Thu, Jan 15
United Airlines Logo
6:50 pm - 2:20 pmORD-FLR
12h 30m1 stop
United Airlines Logo
6:35 am - 3:20 pmFLR-ORD
15h 45m1 stop
$634United Airlines
Find Deal
Fri, Jan 9 - Thu, Jan 15
United Airlines Logo
2:35 pm - 2:05 pmORD-FLR
16h 30m2 stops
United Airlines Logo
6:35 am - 3:20 pmFLR-ORD
15h 45m1 stop
$638United Airlines
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 $741 (return) on average. On the other hand, the most expensive months are June and May, when the average cost of round-trip tickets is $1,368 and $1,031 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonDecember
Cheapest flight$177
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 45% 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 1775 reviews
7.4Comfort
7.1Food
6.8Entertainment
7.6Boarding
8.2Crew
Airline reviews

Everything was fairly easy just hard when you get to Heathrow not know your Gate number until an hour before but otherwise really everything great. Did not get my texts in time though to do me any good but that is why I still like everything the old fashioned way and print everything out.

10.0 ExcellentAnonymous, Oct 2025ZRH - LHR
Read more SWISS reviews

Everything was fairly easy just hard when you get to Heathrow not know your Gate number until an hour before but otherwise really everything great. Did not get my texts in time though to do me any good but that is why I still like everything the old fashioned way and print everything out.

We flew an Air Bus 330 airliner from Zurich to Boston. Our seats were terrible. I am 6'5" with long legs. I tend to refuse paying extra for extra seat room, usually it's tolerable. We were side by side in row 40, with my wife in the window and me in the aisle. The internal arm rest only rose to 45 degrees, I thought it was broken. I ended up standing by our seats in the aisle for an hour. A stewardess finally approached me and asked if I was feeling sick. I told her that it was the worst seat comfort I had ever encountered. She left and shortly came back telling me that there were center row seats two up from us where only one passenger was sitting out of the 4 seats. I took her advice and sat there most of the flight. I put m legs sideways in the adjoining empty seat. But the arm rests there as well only rose to 45 degrees, so it's a feature, not a defect. The arm rest position really limits our position. It's a horrible seating design, what are the air craft designers thinking?

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 cabin was warm and few used the blankets. I should’ve upgraded.

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.

The food was good. Most the staff was pleasant. The flight would be drastically improved with WiFi on a long international flight.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

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.

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.

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.

Staff were nice, we left on time and arrived early, food was good. Unfortunately, they lost one of our bags and have been unable to find it. So we are in Italy for a week for my husband‘s birthday and he does not have any of his clothing.

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

Airlines have to stop assuming passengers bring entertainment. Provide it like you used to in business class and above!! N

I don't know about the others but the flight attendant that took care of us had the absolute wrong approach "how do we dare asking for water or anything else for that matter"

Flying on the Boeing 787 from Seattle to London was everything that I expected. Every thing was great.

Not my definition of first class. No leg room and barely any recline. The food was good. The crew was great. The comfort for the price I paid for London to Cairo was highway robbery. The Wi-Fi didn't work for me either.

Seat pitch is not enough to eat comfortably. When seat in front is reclined, your screen comes closer to your face. Ryanair seats are actually more comfortable.

The leg from Portland to Heathrow was great for a business class ticket. The BA leg from Heathrow to Lisbon was terrible. Basically coach seating with an empty seat between you and next passenger. Absolutely no leg room. Should not have been charged for business class and it was a 3 hour flight.

The flat beds. Other than that, the place was not clean.

Moved me away from my family and refused to fix it.

I have always been pleased with their service. Would not change a thing

Seating and food was the worst we have experienced in 35 years of traveling for both personal and busines .

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.