What airlines fly to Tuscany?

ITA Airways, British Airways and Delta are the top three most popular airlines that fly to Tuscany from Chicago according to our data. ITA Airways is the first choice among our users, with 32% of people opting to fly with this airline when traveling to Tuscany. Keep in mind that there are 10 different airlines that fly to Tuscany on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago to Tuscany on average per week?

As of August 2025, 93 flights take off from Chicago and land in Tuscany each week. The most common flight departure day for this route is Sat, with 16% of weekly flights taking off on this day.

What is the cheapest airline that flies from Chicago to Tuscany?

TAP AIR PORTUGAL, ITA Airways, and Turkish Airlines are the most popular carriers operating from Chicago to Tuscany

When did momondo last update prices for flights from Chicago to Tuscany?

Prices for flights from Chicago to Tuscany were last updated today.

How many operators does momondo search for flights from Chicago to Tuscany?

As of August 2025, there are 17 operators available to choose from for flights from Chicago to Tuscany.

How old do you have to be to fly from Chicago to Tuscany?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Tuscany.

What documentation or ID do you need to fly to Tuscany?

The required travel and health documents for your Tuscany trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Tuscany. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$180 Cheap Flights from Chicago to Tuscany in 2025

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Find the cheapest flights from Chicago to Tuscany

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:25 pm - 12:05 amORD-FCO

20h 40m1 stop

7:35 pm - 3:15 pmFCO-ORD

26h 40m1 stop

$332TAP AIR PORTUGAL

Find Deal

Sun, Nov 9 - Thu, Nov 20

6:15 pm - 7:00 pmORD-FCO

17h 45m1 stop

8:00 pm - 12:35 pmFCO-ORD

23h 35m1 stop

$333TAP AIR PORTUGAL

Find Deal

Sat, Oct 11 - Wed, Oct 22

3:45 pm - 7:45 amORD-FCO

9h 00mnonstop

12:45 pm - 2:25 pmFCO-ORD

32h 40m2 stops

$378United Airlines

Find Deal

Sun, Dec 7 - Tue, Dec 16

3:45 pm - 7:45 amORD-FCO

9h 00mnonstop

9:45 am - 1:10 pmFCO-ORD

10h 25mnonstop

$384United Airlines

Find Deal

Tue, Nov 25 - Fri, Dec 5

10:35 am - 9:45 amORD-FCO

16h 10m1 stop

12:00 pm - 10:37 pmFCO-ORD

17h 37m1 stop

$398Delta

Find Deal

Sun, Nov 9 - Fri, Nov 21

10:35 am - 7:55 amMDW-FCO

14h 20m1 stop

12:40 pm - 9:44 pmFCO-MDW

16h 04m1 stop

$398Delta

Find Deal

Wed, Dec 3 - Wed, Dec 10

9:45 pm - 9:30 amORD-PSA

28h 45m1 stop

11:00 am - 1:50 pmPSA-ORD

33h 50m1 stop

$590British Airways

Find Deal

Sun, Nov 9 - Sat, Nov 15

5:10 pm - 9:30 amORD-PSA

33h 20m1 stop

11:00 am - 1:50 pmPSA-ORD

33h 50m1 stop

$591British Airways

Find Deal

Sun, Nov 9 - Sat, Nov 15

10:30 pm - 5:35 pmORD-PSA

12h 05m1 stop

10:30 am - 12:55 pmPSA-ORD

33h 25m1 stop

$782Lufthansa

Find Deal

Sun, Sep 28 - Mon, Oct 6

3:35 pm - 5:35 pmORD-PSA

19h 00m2 stops

6:15 pm - 12:55 pmPSA-ORD

25h 40m1 stop

$810Lufthansa

Find Deal

Sun, Sep 28 - Mon, Oct 6

Air Canada flights from Chicago to Tuscany

Our best Air Canada deals on Chicago to Tuscany flight tickets

Air Canada

Nov 11

ORD9:08 pmChicago O'Hare Intl

28h 47m

2 stops

FCO8:55 amRome Fiumicino

Nov 21

FCO1:15 pmRome Fiumicino

32h 25m

2 stops

ORD2:40 pmChicago O'Hare Intl

$376

Find similar

Air Canada

Nov 26

ORD12:50 pmChicago O'Hare Intl

13h 05m

1 stop

FCO8:55 amRome Fiumicino

Dec 11

FCO10:55 amRome Fiumicino

15h 35m

1 stop

ORD7:30 pmChicago O'Hare Intl

$391

Find similar

Air Canada

Dec 3

ORD8:45 amChicago O'Hare Intl

17h 40m

2 stops

FCO9:25 amRome Fiumicino

Dec 11

FCO10:55 amRome Fiumicino

19h 37m

2 stops

ORD11:32 pmChicago O'Hare Intl

$396

Find similar

United Airlines flights from Chicago to Tuscany

Our best United Airlines deals on Chicago to Tuscany flight tickets

United Airlines

Dec 7

ORD3:45 pmChicago O'Hare Intl

9h 00m

FCO7:45 amRome Fiumicino

Dec 16

FCO12:45 pmRome Fiumicino

32h 40m

2 stops

ORD2:25 pmChicago O'Hare Intl

$378

Find similar

United Airlines

Nov 25

ORD3:45 pmChicago O'Hare Intl

9h 00m

FCO7:45 amRome Fiumicino

Dec 5

FCO9:45 amRome Fiumicino

10h 25m

ORD1:10 pmChicago O'Hare Intl

$384

Find similar

United Airlines

Nov 5

ORD6:00 amChicago O'Hare Intl

19h 55m

2 stops

FCO8:55 amRome Fiumicino

Nov 18

FCO9:45 amRome Fiumicino

10h 25m

ORD1:10 pmChicago O'Hare Intl

$388

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 11/9

8:25 pm-12:05 am

1 stop20h 40m

Rome Fiumicino

Thu 11/20

7:35 pm-3:15 pm

1 stop26h 40m

$332

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sat 10/11

6:15 pm-7:00 pm

1 stop17h 45m

Rome Fiumicino

Wed 10/22

8:00 pm-12:35 pm

1 stop23h 35m

$333

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 12/7

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Tue 12/16

12:45 pm-2:25 pm

2 stops32h 40m

$378

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 11/25

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Fri 12/5

9:45 am-1:10 pm

Nonstop10h 25m

$384

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 11/9

10:35 am-9:45 am

1 stop16h 10m

Rome Fiumicino

Fri 11/21

12:00 pm-10:37 pm

1 stop17h 37m

$398

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 12/3

10:35 am-7:55 am

1 stop14h 20m

Rome Fiumicino

Wed 12/10

12:40 pm-9:44 pm

1 stop16h 04m

$398

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Sun 11/9

9:45 pm-9:30 am

1 stop28h 45m

Pisa Gal Galilei

Sat 11/15

11:00 am-1:50 pm

1 stop33h 50m

$590

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Sun 11/9

5:10 pm-9:30 am

1 stop33h 20m

Pisa Gal Galilei

Sat 11/15

11:00 am-1:50 pm

1 stop33h 50m

$591

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Sun 9/28

10:30 pm-5:35 pm

1 stop12h 05m

Pisa Gal Galilei

Mon 10/6

10:30 am-12:55 pm

1 stop33h 25m

$782

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Sun 9/28

3:35 pm-5:35 pm

2 stops19h 00m

Pisa Gal Galilei

Mon 10/6

6:15 pm-12:55 pm

1 stop25h 40m

$810

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Tuscany

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Tuscany?

The month of November is, on average, the cheapest month to fly to Tuscany from Chicago, with most prices found around $742. If you’re not able to fly to Tuscany in November, then October is your next best option. Flight prices from Chicago to Tuscany during October average around $798.

What is the cheapest day to depart on your flight to Tuscany?

On average, the least expensive day to fly to Tuscany from Chicago is on a Sunday. momondo users have found tickets for Sunday departures for as low as $984. However, this price may fluctuate depending on the airline, the season, and holidays. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $1,399. These prices are subject to change though, so be sure to set up a Price Alert for flights to Tuscany.

What is the cheapest time of day to depart on your flight to Tuscany?

Our data shows that the cheapest Chicago to Tuscany flights are usually those with departure times in the morning. Our users have found flights to Tuscany in the morning for as low as $900. At noon is when there is more demand to fly to Tuscany, so prices are often more expensive at around $1,583 per ticket.

How far in advance should I book a flight to Tuscany?

You are more likely to see cheaper flights to Tuscany from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Tuscany for around $1,044 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Tuscany from Chicago for as low as $874 on momondo.

Can stopping save me money on Chicago to Tuscany flights?

You could potentially save up to 58% on your flight if you consider stops on a Chicago to Tuscany flight.

Cheap Chicago to Tuscany flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Tuscany

Best Price Found	$180
Fastest flight time	9h 00m
Direct flights	Every day
Airports in Tuscany	4 airports

The best one-way flight to Tuscany from Chicago in the past 72 hours is $180. The best round-trip flight deal from Chicago to Tuscany found on momondo in the last 72 hours is $332.

The fastest flight from Chicago to Tuscany takes 9h 00m

Direct flights go from Chicago to Tuscany every day.

There are 4 airports near Tuscany: Rome Fiumicino (FCO), Rome Ciampino (CIA), Florence Peretola (FLR), Pisa Gal Galilei (PSA)

Search flight deals

When did momondo last update prices for flights from Chicago to Tuscany?
Prices for flights from Chicago to Tuscany were last updated today.
How many operators does momondo search for flights from Chicago to Tuscany?
As of August 2025, there are 17 operators available to choose from for flights from Chicago to Tuscany.
How old do you have to be to fly from Chicago to Tuscany?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Tuscany.
What documentation or ID do you need to fly to Tuscany?
The required travel and health documents for your Tuscany trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Tuscany. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Chicago to Tuscany

Compare and see reviews for airlines that fly from Chicago to Tuscany with momondo

Airline	Rating	Free Cancellation	Price
Scandinavian Airlines	PriceFrom $470	Free Cancellation	Rating 7.3 1,457 reviews	Search Scandinavian Airlines flights
KLM	PriceFrom $491	Free Cancellation	Rating 7.8 1,383 reviews	Search KLM flights
Air France	PriceFrom $594	Free Cancellation	Rating 7.5 1,466 reviews	Search Air France flights
British Airways	PriceFrom $600	Free Cancellation	Rating 6.6 7,230 reviews	Search British Airways flights
Lufthansa	PriceFrom $630	Free Cancellation	Rating 6.8 7,280 reviews	Search Lufthansa flights
Delta	PriceFrom $699	Free Cancellation	Rating 8.0 7,985 reviews	Search Delta flights
SWISS	PriceFrom $708	Free Cancellation	Rating 7.5 1,686 reviews	Search SWISS flights
United Airlines	PriceFrom $728	Free Cancellation	Rating 7.4 8,905 reviews	Search United Airlines flights
ITA Airways	PriceFrom $752	Free Cancellation	Rating 6.7 1,011 reviews	Search ITA Airways flights
Iberia	PriceFrom $777	Free Cancellation	Rating 7.0 2,864 reviews	Search Iberia flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Tuscany?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Tuscany from Chicago.

Can I find flights from Chicago to Tuscany with flexible booking policies on momondo?

momondo does allow users to show only those flights to Tuscany from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Tuscany?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Tuscany.

I’m not ready to book a flight from Chicago to Tuscany right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Tuscany from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.