$257 Find Cheap Flights from Chicago to Tuscany - Compare and Save

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1 adult, Economy, 0 bags

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Cheap Flights from Chicago to Tuscany

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Florence
Florence2 stops$654
Pisa
Pisa1 stop$769
Florence
Florence2 stops$654
Pisa
Pisa1 stop$769
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 O'Hare Intl Airport to Tuscany?

Flight prices are below average for this route right now.

Flights to Tuscany from Chicago O'Hare Intl Airport usually cost between $809 and $869 in February.
The lowest price found in the past 5 days was $654 on Multiple Airlines (Feb 10-Feb 24).

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Tuscany?

The cheapest month for flights from Chicago O'Hare Intl Airport to Tuscany is November, when tickets cost $820 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $1,482 and $1,338 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Tuscany?

To get a below average price on the flight from Chicago O'Hare Intl Airport to Tuscany, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low season

November

Cheapest flight

$257
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Chicago O'Hare Airport to Florence

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

 
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 2114 reviews
7.4Comfort
7.1Food
6.8Entertainment
7.7Boarding
8.2Crew
Airline reviews

Wonderful, i asked at front gate to change my seat up closer and they gave me a row with no one in it. Very kind of them as the flight was on the light side.

10.0 ExcellentSusan, Aug 2026
Read more SWISS reviews

Wonderful, i asked at front gate to change my seat up closer and they gave me a row with no one in it. Very kind of them as the flight was on the light side.

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

Connection times always good online, but not in reality when first leg is delayed (2 out of 2 times this trip).

It was good flight was smooth, little cold on the plane but other wise good.

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

We left 1.5 hours late due to a “maintenance” issue. Very poor communication as to when we would board & depart. The crew in First Class was uncharacteristically not friendly). Delay into Brussels cost me my connection to Rome so lost the entire first day of vacation ( had a 10:30am flight to Rome - ended up on a 6:55pm flight).

Everything was OK except the meals, that was overpriced chicken meat.

Miss My connection I had to take a flight from Indianapolis to Denver , then to san fransisco , sleep in sans fransisco en the flight to Los Cabos the next morning

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

We asked for vegetarian food. Crew’s answer was may be it is. Also when we booked there weee no food options and we need to give 72 hours of notice which also was not mentioned in booking.

Other than the toilets it was great. One was broken and another wasn’t flushing by the end of the flight

Premium economy was very comfortable with excellent service and legroom. On Kayak I was able to find a very affordable discounted fare

Overall seamless flight from SFO to FCO. I chose economy to have more money to spend while in Italy. The seats bottoms are a bit on the thin side but they give you a pillow and blanket so Inl used the blanket to thicken up the seat bottom. You have to have a physical boarding pass (at least for my flight) so that was interesting. Crew was nice, food was good and over pretty down the middle.

1 1/2 hours delayed boarding at JFK caused us to almost miss connecting flight in Rome. Only 30 minutes of time to run from one end of FCO to the other for connecting flight. Not very easy to do for older travelers.

Staff was nice but seat is not what I expected

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.

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).

The flight and staff were perfect. No notes. Amazing experience overall.

It was a safe and smooth flight. Members of the crew at the second level, business could have been more polite and engaging.

I was booked to travel from Dallas to Nairobi via Chicago and Brussels and had been issued boarding passes for all three segments of my journey. At the boarding gate in Dallas, I was required to check my carry-on luggage due to limited cabin space. Despite my attempts to explain that I was traveling internationally and would not have access to the bag during transit, my concerns were not considered. I also informed the staff that I did not have a padlock to secure the luggage, but this was disregarded. Consequently, I had to hastily transfer essential items from my carry-on into my handbag. Unfortunately, the onboard experience on the Chicago to Brussels flight further reinforced my dissatisfaction. The cabin crew appeared disengaged, indifferent, and lacking in attentiveness, resulting in a service experience that fell well below my expectations.

Flight was on time and got us to destination quicker than scheduled.

I have very bad experience with United because Vince two weeks that I did not receive my luggage yet

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.

My bags were lost. I waited in a line for 5 hours after I landed and got no resolution to the issue.

Comfortable seats, good service overall. The food could’ve been a little bit better. The boarding process was slightly chaotic and in fairness, not all of that is related to the performance of British Airways.

They gave away my business class seat. No explanation and no apology. Told me I had to take the downgrade if I wanted to get to India. Then no WiFi for 10 hours. Just ridiculous. We should not work with this company at Deloitte. They don’t know how to run a business.

It's hard to tell where to plug in electronics, and the port on my seat didn't work. Their entertainment system was down. Vegetarian food options were tasty. Friendly, helpful flight attendants.

Lady next to me was coughing profusely the entire flight, other lady moved seats because of it, 8 hours of that during an overnight flight is a bit much.

The seats are extra cramped if you are taller than 5’8! Spring for the extra legroom seats for sure if you have a long flight!

Very disappointed with British Airways. It has been over 24 hours and I still have not received my checked baggage or any proper update. Customer support has been unresponsive, making the situation even more frustrating. Poor baggage handling and lack of communication seriously impacted my travel experience.

Cancelled flight and re booked seats were a downgrade. British Airways said the upgrade was t available but when I checked it was but then they wouldn’t make it right

Flight delay of 4 1/2 hours with no reason for over 3 hours. Missed our connection in Rome & had to pay for an additional flight.

The flight was delayed for several hours. After many hours of waiting, they said it was delayed until the next day. This is completely understandable, as the staff had to wait on Boeing to approve the plane. However, the staff said hotel and meal vouchers would be issued via email (they never were). An hour after leaving the airport, our flight was cancelled.

More options for your flight from Chicago to Tuscany

Complete your trip to Tuscany with a hotel stay or car rental