$286 Find Cheap Flights from Chicago to Tuscany - Compare and Save

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 8/5. 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.
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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, Sep 6 - Tue, Sep 22
Turkish Airlines Logo
8:10 pm - 6:30 pm
ORD
-
FCO
15h 20m
1 stop
Turkish Airlines Logo
8:05 pm - 9:40 am
FCO
-
ORD
20h 35m
1 stop
$674Turkish Airlines
Wed, Sep 23 - Wed, Oct 14
Turkish Airlines Logo
8:10 pm - 6:30 pm
ORD
-
FCO
15h 20m
1 stop
Turkish Airlines Logo
3:35 pm - 9:40 am
FCO
-
ORD
25h 05m
1 stop
$674Turkish Airlines
Tue, Dec 1 - Tue, Dec 8
British Airways Logo
8:45 pm - 11:35 am
ORD
-
PSA
31h 50m
2 stops
British Airways Logo
10:20 am - 6:45 pm
PSA
-
ORD
15h 25m
1 stop
$675British Airways
Sun, Sep 6 - Wed, Sep 16
TAP AIR PORTUGAL Logo
6:00 pm - 7:05 pm
ORD
-
FCO
18h 05m
1 stop
TAP AIR PORTUGAL Logo
1:35 pm - 12:40 pm
FCO
-
ORD
30h 05m
1 stop
$678TAP AIR PORTUGAL
Sun, Oct 18 - Wed, Oct 28
TAP AIR PORTUGAL Logo
6:00 pm - 4:40 pm
ORD
-
FCO
15h 40m
1 stop
TAP AIR PORTUGAL Logo
5:55 am - 4:30 pm
FCO
-
ORD
16h 35m
1 stop
$678TAP AIR PORTUGAL
Sun, Aug 16 - Tue, Aug 25
Etihad Airways Logo
3:00 pm - 7:25 am
ORD
-
FCO
9h 25mnonstop
Etihad Airways Logo
9:20 am - 1:10 pm
FCO
-
ORD
10h 50mnonstop
$679Etihad Airways
Sun, Aug 16 - Wed, Aug 26
Multiple Airlines Logo
3:00 pm - 7:25 am
ORD
-
FCO
9h 25mnonstop
Multiple Airlines Logo
9:20 am - 1:10 pm
FCO
-
ORD
10h 50mnonstop
$679Multiple Airlines
Sun, Aug 16 - Thu, Sep 3
ITA Airways Logo
3:00 pm - 7:25 am
ORD
-
FCO
9h 25mnonstop
ITA Airways Logo
9:20 am - 1:10 pm
FCO
-
ORD
10h 50mnonstop
$685ITA Airways
Sun, Aug 16 - Wed, Sep 2
ITA Airways Logo
3:00 pm - 7:25 am
ORD
-
FCO
9h 25mnonstop
ITA Airways Logo
9:20 am - 1:10 pm
FCO
-
ORD
10h 50mnonstop
$685ITA Airways
Tue, Dec 1 - Tue, Dec 8
British Airways Logo
8:45 pm - 11:35 am
ORD
-
PSA
31h 50m
2 stops
British Airways Logo
10:20 am - 9:00 pm
PSA
-
ORD
17h 40m
2 stops
$685British Airways
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.

How much is a round-trip flight from Chicago to Tuscany?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Tuscany departing in September.

Flight prices are typical for this route right now.

Flights to Tuscany from Chicago usually cost between $771 and $1,102 in September.
The lowest price found in the past 5 days was $801 on ITA Airways (Sep 6-Oct 22).

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 $869 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $1,451 and $1,319 respectively.

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 21 weeks before departure.

Good to know

Low season

November

Cheapest flight

$286
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 16% lower on average.
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.

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 2019 reviews
7.4Comfort
6.8Entertainment
8.3Crew
7.1Food
7.7Boarding
Airline reviews

Made us gate check carry ons Then didn’t get them on the plane. Service they used didn’t deliver our carry ons for more than a day Total mess

2.0 MediocreAndrew, Dec 2025
ZRH - FCO
Read more SWISS reviews

Made us gate check carry ons Then didn’t get them on the plane. Service they used didn’t deliver our carry ons for more than a day Total mess

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

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.

The seats had no space at all beyond the knees. The seat in-front literally reclined on your face, very uncomfortable plane. Was nothing like the normal SWISS experience. The food was okay but could be better.

They rebooked our flight and then canceled our trip halfway through the journey without any explanation. Needed to pay by ourselves for alternative flight options without any help from Swiss.

Flight was diverted from Firenze to Pisa causing delay and inconvenience.

Easy boarding Seats were very uncomfortable no room arm rests didn't even go up all the way

Wonderful experience! The crew was outstanding and amazing from check in to gate to flight crew! Amazing. Thank you!

Carry on luggage size for economy passengers significantly smaller than other airlines, so nearly all ecomy passengers had their bags taken and checked.

Missed connecting train since flight was late into Zurich and I had to stay at airport hotel because of it as well as I had to repurchase train ticket

The crew was amazing. Our seats was not very clean and even that was not a full flight but our seats was right beside the WC which did not let us to have a moment of rest.

Excellent service, and came on time! Thank you for your dinner that was chicken with salat/, and 🍰 it was good quality food , the breakfast was very good with good cheese , butter,etc and the tea was very good quality. The space where I was seat was nice so I could stretch my legs. I dit not have the bread as I am in a keto died. Have great time everyone in Scandinavia airline.

They lost my luggage and can’t find it. My trip is ruined. Online tracking of lost luggage doesn’t work

Seat was lumpier than I’ve ever remembered it to be although comfortable when tilted back. I don’t recall being that hungry after being served food from SAS before. Flight attendant on the second flight to Aalborg seemed to be having a bad day.

They charge for bottles of water which is crazy period we hit turbulent weather and it's in a good job period

On this shorter leg and with an older plane, just mediocre. On the connecting long haul (Chicago to Copenhagen) everything was great.

My outbound flight was incredible... Milan to Chicago. The crew worked so well together. Each passenger felt spoiled and incredibly valued. The crew on this flight was fine. Nothing to complain specifically about but could not give top rating only because of the superior crew, hospitality, warmth we felt on the first flight. Unfortunately. You managed to lose my luggage ..my only piece checked in. Lost in Copenhagen so I had the added stress, time wasted to file the report. To make things worse, Italian rail decided to strike that Sunday so I could not take the train as planned back to Switzerland. Horrible waiting time and poor communication for boarding substitution bus. The substition bus to the town of Stabio did not run on time and was late about 40 minutes.

Other than a delay that had nothing to do with the staff, it was a very pleasant experience.

The flight was cancelled early on and messed up the whole vacation and hard to get a refund from Kayak as they owned the ticket and of course they did not believe that SAS cancelled the ticket. Definite bad side to third party. SAS had rescheduled but overlapped the connecting flights. That did not work. Flight was cancelled long ago but Kayak still has it. Like it was taken? Bad IT ? Or all assumptions and no follow up which is the whole IT world. It needs to wake up and be more efficient. Especially as the world is going, there will be no freedom to do anything. And we will be living like the Middle Ages. Yeah, go read up on that while you still can.

Boarding the plane outside in the rain was a pain. Very safe flight

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

It was okay. Mothers with rowdy children should be invited to sit in front of them.

Good food, overall very comfy. The flight was full so obviously not optimal, but it is what it is.

Flight was delayed by several hours and then cancelled due to weather. But Staff was very helpful getting me on a different flight. United should offer food coupons and tooth brush and paste for stranded passengers

I had a good comfortable seat. There was nearly an hour delay. There was an accident with the champagne, but I was well compensated. These things happen sometimes.

We missed our flight. There was not enough time built into the layover to get through immigration, customs, bagclaim, bag rechecking, and the long trip to another terminal and gate. Kayak really screwed up. We took the bus up to Wisconsin and then were picked up in Brookfield by private car. It was lucky we didnt miss the last bus out.

I tried both on line and by calling the Customer Service line to arrange for a special meal as i have food intolerances. I was under the impression from your service representative that I was successful. I was not. I cannot eat spicy foods and get very ill if i eat bell peppers. I could not eat either menu choice and no special meal was actually ordered. ( your representative tried to order it for a flight that did not have meal service!!! - found this out later). Your wonderful cabin crew managed to put together a fruit, salad, roll and cheese tray for me so I had something to eat. WHY WOULD YOU SERVE SPICY FOOD, WITH NO MILDER OPTION,ON AN INTERNATIONAL FLIGHT???

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.

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

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.

Flew Premium Economy. The seats were comfortable and tilted back far enough to sleep. Food was okay and service friendly and efficient. We bought tickets through Kayak partner Underpricer and the price was good.

ITA has these new Airbus A330 Neo that hates economy class passengers. The seats have absolutely no cushion to a point where it hits your spine constantly and reminds you to fork out for premium economy or don’t travel next time. The food was absolutely horrible, ETA mentioned 3 meals for 12 hour flight but it was mostly 1 meal and 2 light snacks. I am vegetarian, so my 2’d food was 1 slice of tomato, 1 cucumber on a dry cold bun. The other 2 meals were disgusting. My young one threw up the entire time. Flight attendants were the cherry on top - plain bad. They would skip servicing drinks to some passengers completely and if you call for an attendant, they will come and stop the button on top without even asking you what you need. I would avoid ITA by all means - there are plenty of options including SAS for same routes with better seats and humane treatment.

Nice flight. Uneventful, very good crew, comfortable seats. Pleasant experience.

ITA cancelled fligh rebooked with Lufthansa. Flight good, but 2hour connection in Frankfurt was HORRIBLE, took 1.9 hours to get through scanner, customs, another security, got to gate after running all the way, so caught it but stressful and terrible start to trip.

The boarding process was organized and efficient, and the crew was friendly and attentive throughout the flight. Food and drinks were typical economy class, but good. The aircraft was old, and the restroom was not very clean. However, we arrived on time, so overall the experience was good.

In Prem Econ, safe and timely flight, good amount of space, mostly comfortable seats. Little irritants: When lying down, seat kept shifting on me...as a short person w/light weight, my seat often reverted to semi-upright. Footrest was broken. TV screen didn't work, after I asked a few times a FA rebooted it to work again. And food was marginal. I don't expect much from airplane food...surprisingly, ITA didn't even meet expectations.

Flight was canceled. Rebooked on Lufthansa Also Canceled. Had to pay 3000 more per person and fly Alaska to EWR and fly emirates to Athens.

This was a typical hour-long flight. Not much leg room, no entertainment and no food.

It was fine. I wish there were more or better selections for entertainment.

The worst part about the trip was the seat. It looked old, with a sagging cushion and crumbs on it before I sat down. When I sat down I saw that the back of the seat was broken and it would only stay in one (reclined) position. I had purposefully paid extra ($65) for that seat because a) I can only sleep on translatlantic flights if I am next to the window and b) I wanted to be close to the front because I had a tight connecting flight in Rome. One flight attendant didn't care about the problem while another offered me a middle seat in the back of the plane. Of course he did not mention a refund for the fee I had paid for this seat. The food was mediocre, not even close to the good food in Alitalia, back in the day. The entertainment system did not work when I tried to "follow the flight". English of announcements was often impossible to understand (spoke poorly and too fast).

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.