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$178 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 9/10. 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
0 bags
Fri 7/12
Fri 7/19

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Best Tuscany Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Florence
Florence2 stops$551

Good to know

Low season

January

High season

September

Cheapest flight

$178
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly with an average 3% 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 to Tuscany from Chicago 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 to Tuscany with an airline and back to Chicago 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 to Tuscany from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Tuscany

  • Morning departure is around 10% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
7.8
Cathay PacificOverall score based on 1026 reviews
7.5Food
8.0Boarding
8.2Crew
7.8Comfort
8.0Entertainment
Airline reviews

There is very little in the title" Premium" in the Economy experience with Cathay, Melbourne to Hong Kong. The seats are uncomfortable and the cabin with outdated 1990's decor and trim. The food service was sloppy and the leg room providing little to no advantage over regular economy seating. Infact, the Sunday flight was not fill occupancy and I would have done better saving the significant additional costs for the PREMIUM ticket and taken advantage of the seating. If you are a regular premium economy traveler of EMIRATES expecting the same experience on CATHAY, you will be disappointed. Emirates far superior.

2.0 MediocreSam, Jun 2024HKG - MEL
Read more about Cathay Pacific reviews

There is very little in the title" Premium" in the Economy experience with Cathay, Melbourne to Hong Kong. The seats are uncomfortable and the cabin with outdated 1990's decor and trim. The food service was sloppy and the leg room providing little to no advantage over regular economy seating. Infact, the Sunday flight was not fill occupancy and I would have done better saving the significant additional costs for the PREMIUM ticket and taken advantage of the seating. If you are a regular premium economy traveler of EMIRATES expecting the same experience on CATHAY, you will be disappointed. Emirates far superior.

My biggest complaint is the comfort and no good movies to choose from. My headphones didn't work either. 😔

The flight was cancelled. I wasn't informed where to check in, how and when. It wasn't easy to get in contact with Cathay service representative, and they were not very helpful... The staff on the airport - Air Canada (I assume) were the most helpful, kind efficient, patient... Thank you for all your help and care, for your patience, for your professionalism!!!

Great, the flight attendants were very friendly and the food was also good.

The first economy rows have remote space in the seat which eats in the seating space. The seats are also smaller compared to other airlines.

The overall flight went well and the aircrew was pleasant.

Cathay Pacific seems to be an airline in trouble and on its way out. Lots of broken or poorly functioning things like entertainment screens, seats, and enough well trained staff to handle a full flight. Sad...

The flight crew was exceptionally good. Personal needs were well met. The food choices were very nice.

Excellent. Planes are a little older and could get some refurbishment, but besides that everything was excellent.

I cancelled the flights in good time but could only get a partial refund. I was not warned of this.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Original flight delayed several times and finally canceled at 2:30 in the morning. Staff at the gate was not very helpful in resolving problems or communicating why there were delays. I spent 34 hours at the airport before I could leave, they couldn't book me on another early flight even after canceling my original flight. Next flight available after my original flight was canceled was 22 hours later. I will never fly American Airlines again.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Poor response to delay, getting on plane, off plane and back on again

My flight was uncomfortable and crammed. There were no pockets to store things, I couldn’t move my seat back slightly. Beverages including soda cost extra. My husband flew on another spirit airline flight, which was delayed a total of 48 hours, only to be canceled.

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Terrible leg room, seats don’t recline, delayed flight, and even water isn’t free onboard

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

I did not enjoy the trip home on Frontier for several reasons: there is too much cost besides the flight, which was more than I would normally pay, then having to pay for luggage, and carry-on, seat (if you want to reserve when booking) then you must pay over $3 for a can of soda, and $4 for a snack. A cup of water is free.

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

Book cheap flights from Chicago to Tuscany

Recent round-trip flight deals

10/16Wed
2 stopsScandinavian Airlines
30h 50mORD-FLR
10/23Wed
1 stopScandinavian Airlines
12h 35mFLR-ORD
$551
8/19Mon
1 stopScandinavian Airlines
32h 45mORD-FLR
8/28Wed
1 stopScandinavian Airlines
12h 35mFLR-ORD
$556
11/25Mon
2 stopsDelta
15h 40mMDW-FLR
12/2Mon
2 stopsDelta
17h 38mFLR-MDW
$684
11/25Mon
2 stopsDelta
17h 50mORD-FLR
12/2Mon
2 stopsDelta
19h 15mFLR-ORD
$684
8/15Thu
2 stopsAir Canada
15h 35mORD-FCO
8/24Sat
2 stopsAir Canada
17h 44mFCO-ORD
$711
8/5Mon
2 stopsAir Canada
17h 35mORD-FCO
8/21Wed
2 stopsAir Canada
18h 13mFCO-ORD
$716
8/9Fri
1 stopUnited Airlines
27h 47mORD-FCO
8/19Mon
2 stopsUnited Airlines
20h 28mFCO-ORD
$726
8/17Sat
1 stopUnited Airlines
31h 19mORD-FCO
8/25Sun
2 stopsUnited Airlines
22h 09mFCO-ORD
$731
9/9Mon
nonstopAmerican Airlines
9h 00mORD-FCO
9/19Thu
1 stopAmerican Airlines
15h 00mFCO-ORD
$746
8/12Mon
2 stopsAmerican Airlines
21h 20mORD-FCO
8/20Tue
2 stopsAmerican Airlines
31h 25mFCO-ORD
$787

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Recent one-way flight deals

9/10Tue
1 stop
14h 21mORD-FCO
$178
9/10Tue
1 stop
20h 26mORD-FCO
$189
8/10Sat
1 stop
14h 48mORD-FCO
$196
8/4Sun
1 stopKLM
12h 20mMDW-FCO
$507
8/2Fri
1 stopDelta
19h 20mMDW-FCO
$582
8/27Tue
2 stopsDelta
15h 20mMDW-FLR
$724
7/10Wed
1 stopKLM
12h 45mMDW-FCO
$772
6/28Fri
2 stopsTurkish Airlines
20h 15mORD-FLR
$938
8/27Tue
1 stopLufthansa
12h 15mORD-PSA
$976
8/28Wed
2 stopsLufthansa
29h 20mORD-PSA
$992

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Last minute flights from Chicago to Tuscany

Last minute flight, train and bus deals

6/13Thu
multi-stop
13h 05mORD-FCO
6/17Mon
nonstop
10h 50mFCO-ORD
$838
6/13Thu
multi-stop
13h 05mORD-FCO
6/17Mon
multi-stop
14h 26mFCO-ORD
$848
6/16Sun
multi-stopTAP AIR PORTUGAL
15h 45mORD-FCO
6/22Sat
multi-stopTAP AIR PORTUGAL
15h 15mFCO-ORD
$862
6/17Mon
multi-stopUnited Airlines
13h 30mORD-FCO
6/26Wed
nonstopUnited Airlines
10h 15mFCO-ORD
$909
6/17Mon
multi-stopDelta
18h 35mORD-FCO
6/27Thu
multi-stopDelta
16h 00mFCO-ORD
$939
6/17Mon
multi-stopDelta
18h 45mORD-FCO
6/27Thu
multi-stopDelta
18h 46mFCO-ORD
$948
6/17Mon
nonstopUnited Airlines
9h 05mORD-FCO
6/26Wed
nonstopUnited Airlines
10h 15mFCO-ORD
$968
6/17Mon
multi-stopAir France
15h 30mORD-FCO
7/23Tue
multi-stopAir France
27h 17mFCO-ORD
$994
6/17Mon
multi-stopAir France
16h 11mMDW-FCO
7/23Tue
multi-stopAir France
29h 24mFCO-MDW
$994
6/17Mon
multi-stopSWISS
12h 00mORD-FCO
6/23Sun
multi-stopSWISS
22h 55mFCO-ORD
$1,095

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Flights to Tuscany

Return flight deals:

Tuscany - Chicago

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