$342 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 2/14. 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

Wed, Jan 14 - Tue, Jan 20
TAP AIR PORTUGAL Logo
7:10 pm - 3:50 pm
ORD
-
FCO
13h 40m1 stop
TAP AIR PORTUGAL Logo
4:40 pm - 3:00 pm
FCO
-
ORD
29h 20m1 stop
$407TAP AIR PORTUGAL
Wed, Jan 14 - Tue, Jan 20
TAP AIR PORTUGAL Logo
7:10 pm - 3:50 pm
ORD
-
FCO
13h 40m1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 3:00 pm
FCO
-
ORD
26h 25m1 stop
$413TAP AIR PORTUGAL
Wed, Apr 15 - Thu, Apr 23
Scandinavian Airlines Logo
7:15 pm - 11:30 am
ORD
-
FLR
33h 15m1 stop
Scandinavian Airlines Logo
7:55 pm - 4:10 pm
FLR
-
ORD
27h 15m1 stop
$449Scandinavian Airlines
Mon, Apr 20 - Fri, May 1
Scandinavian Airlines Logo
7:15 pm - 7:05 pm
ORD
-
FLR
16h 50m1 stop
Scandinavian Airlines Logo
7:55 pm - 4:10 pm
FLR
-
ORD
27h 15m1 stop
$479Scandinavian Airlines
Mon, Feb 16 - Thu, Feb 26
Delta Logo
12:46 pm - 10:30 am
MDW
-
FCO
14h 44m1 stop
Delta Logo
12:40 pm - 10:42 pm
FCO
-
MDW
17h 02m1 stop
$537Delta
Wed, Feb 18 - Tue, Mar 3
Delta Logo
10:53 am - 10:30 am
MDW
-
FCO
16h 37m1 stop
Delta Logo
6:10 am - 5:45 pm
FCO
-
MDW
18h 35m2 stops
$538Delta
Thu, Jan 29 - Thu, Feb 5
British Airways Logo
5:10 pm - 10:10 am
ORD
-
PSA
34h 00m1 stop
British Airways Logo
12:30 pm - 1:50 pm
PSA
-
ORD
32h 20m1 stop
$563British Airways
Sun, Mar 1 - Wed, Mar 11
KLM Logo
10:53 am - 10:30 am
MDW
-
FCO
16h 37m1 stop
KLM Logo
11:40 am - 10:29 pm
FCO
-
MDW
16h 49m1 stop
$572KLM
Thu, Jan 15 - Thu, Jan 22
British Airways Logo
9:45 pm - 10:10 am
ORD
-
PSA
29h 25m1 stop
British Airways Logo
12:30 pm - 5:44 pm
PSA
-
ORD
36h 14m2 stops
$586British Airways
Sat, May 9 - Tue, May 19
KLM Logo
5:59 pm - 2:40 pm
MDW
-
PSA
37h 41m2 stops
KLM Logo
3:00 pm - 4:25 pm
PSA
-
MDW
32h 25m2 stops
$1,135KLM
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 $723 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $1,393 and $1,366 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 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$342
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 43% 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 1814 reviews
7.7Boarding
7.4Comfort
6.8Entertainment
8.3Crew
7.1Food
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 2025
ZRH - 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.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

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

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.

The check in process is chaotic. It says partially checked-in. Never heard of such a thing. Then lost our reserved seats when we finally checked in at the airport. The seats don’t recline. Then we had to get mew boarding passes at the connection. Last, my companion lost her baggage and up to now there’s no update. We’re already half-way through our vacation and still no news what happened to the luggage.

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.

Check in was was and the agent was very friendly and helpful The lounge was nice...boarding was straight from the lounge Everything worked at our seats, and video entertainment was good ..food was mediocre

The flight was excellent in World Travellor plus. Well worth the extra money. Boarding at Phoenix was the usual poorly organized event. Very stressful.

Although business class, the seating was really cramped. The food was so so.

Smooth trip no turbulence which is always a bonus for me lol! In cattle class so an element of being a bit squished (but not as bad as other shorter haul airlines) smaller plane than the one we flew out on and entertainment system wasn’t as modern but still definitely passed the time. Lovely crew x

I was attacked in the Miami airport and the staff did nothing. On my flight from London to Miami one of the flight attendants screamed at me and demanded I keep my seat in the upright position at all times during the fight so the man behind me was comfortable for the flight. I will never in my life use British airways again

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

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

The space is tight. Either you sit straight up the whole time, but the minute you relax, your knees hit the back of the seat in front of you. My seat would not recline so I was quite uncomfortable. Didn’t use my tray table bc it was stained and sticky and nasty. I was also seating in one of the last rows and one crew member and people going to the bathroom kept hitting my elbow resting on the armrest.

Had a nice little suite although I couldn’t close the door (but I didn’t ask anyone to help). 5K is a nice seat and very private (you look in on first class). Enjoyable flight and nice crew.

The plane was known to be late in advance of takeoff. My guess is that it was known to be late at 11am or 5 hours before scheduled takeoff time. We were late to leave and with a wheelchair and the a cart, we only made it to gate. We raced! Inside plane, all was great

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.