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

TAP AIR PORTUGAL and Icelandair are the most popular carriers operating from Chicago to Tuscany

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

As of November 2025, 40 flights take off from Chicago and land in Tuscany each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.

What airlines fly to Tuscany?

ITA Airways, British Airways and Lufthansa 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 29% 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.

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 November 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.

$273 Cheap Flights from Chicago to Tuscany in 2025/26

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Find the cheapest flights from Chicago to Tuscany

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:10 am - 11:30 amORD-FLR

18h 20m2 stops

7:55 pm - 4:10 pmFLR-ORD

27h 15m1 stop

$398Scandinavian Airlines

Find Deal

Tue, Apr 7 - Tue, Apr 14

6:30 pm - 2:00 pmORD-FCO

12h 30m1 stop

11:25 am - 5:20 pmFCO-ORD

12h 55m1 stop

$404Icelandair

Find Deal

Thu, Feb 5 - Thu, Feb 12

6:30 pm - 2:00 pmORD-FCO

12h 30m1 stop

11:25 am - 5:20 pmFCO-ORD

12h 55m1 stop

$406Icelandair

Find Deal

Fri, Dec 5 - Wed, Dec 10

1:14 pm - 7:55 amMDW-FCO

11h 41m1 stop

10:05 am - 6:00 pmFCO-MDW

14h 55m1 stop

$527KLM

Find Deal

Tue, Dec 2 - Thu, Dec 11

1:14 pm - 7:55 amMDW-FCO

11h 41m1 stop

10:05 am - 6:00 pmFCO-MDW

14h 55m1 stop

$536KLM

Find Deal

Tue, Dec 2 - Thu, Dec 11

6:10 pm - 9:30 amORD-PSA

33h 20m1 stop

8:40 pm - 6:15 pmPSA-ORD

28h 35m1 stop

$537British Airways

Find Deal

Sun, Mar 22 - Mon, Mar 30

9:34 am - 7:55 amMDW-FCO

15h 21m1 stop

6:10 am - 4:34 pmFCO-MDW

17h 24m2 stops

$537Delta

Find Deal

Tue, Dec 2 - Wed, Dec 10

6:17 pm - 3:15 pmMDW-FCO

13h 58m2 stops

9:05 am - 6:34 pmFCO-MDW

15h 29m1 stop

$540Delta

Find Deal

Sun, Mar 1 - Thu, Mar 12

5:40 pm - 9:30 amORD-PSA

32h 50m2 stops

10:20 am - 1:50 pmPSA-ORD

34h 30m1 stop

$565British Airways

Find Deal

Sun, Dec 7 - Tue, Dec 23

12:46 pm - 10:30 amMDW-FCO

14h 44m1 stop

12:40 pm - 10:44 pmFCO-MDW

17h 04m1 stop

$571Air France

Find Deal

Wed, Feb 18 - Wed, Mar 4

Icelandair flights from Chicago to Tuscany

Our best Icelandair deals on Chicago to Tuscany flight tickets

Icelandair

Feb 5

ORD6:30 pmChicago O'Hare Intl

12h 30m

1 stop

FCO2:00 pmRome Fiumicino

Feb 12

FCO11:25 amRome Fiumicino

12h 55m

1 stop

ORD5:20 pmChicago O'Hare Intl

$404

Find similar

Icelandair

Dec 5

ORD6:30 pmChicago O'Hare Intl

12h 30m

1 stop

FCO2:00 pmRome Fiumicino

Dec 10

FCO11:25 amRome Fiumicino

12h 55m

1 stop

ORD5:20 pmChicago O'Hare Intl

$406

Find similar

Icelandair

Dec 5

ORD6:30 pmChicago O'Hare Intl

12h 30m

1 stop

FCO2:00 pmRome Fiumicino

Dec 11

FCO11:25 amRome Fiumicino

12h 55m

1 stop

ORD5:20 pmChicago O'Hare Intl

$419

Find similar

TAP AIR PORTUGAL flights from Chicago to Tuscany

Our best TAP AIR PORTUGAL deals on Chicago to Tuscany flight tickets

TAP AIR PORTUGAL

Dec 7

ORD8:25 pmChicago O'Hare Intl

15h 20m

1 stop

FCO6:45 pmRome Fiumicino

Dec 14

FCO5:45 amRome Fiumicino

16h 00m

1 stop

ORD2:45 pmChicago O'Hare Intl

$410

Find similar

TAP AIR PORTUGAL

Dec 10

ORD7:10 pmChicago O'Hare Intl

33h 15m

1 stop

FCO11:25 amRome Fiumicino

Dec 23

FCO4:40 pmRome Fiumicino

29h 20m

1 stop

ORD3:00 pmChicago O'Hare Intl

$414

Find similar

TAP AIR PORTUGAL

Nov 30

ORD8:25 pmChicago O'Hare Intl

20h 40m

1 stop

FCO12:05 amRome Fiumicino

Dec 12

FCO6:00 amRome Fiumicino

16h 25m

1 stop

ORD3:25 pmChicago O'Hare Intl

$417

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Tue 4/7

10:10 am-11:30 am

2 stops18h 20m

Florence Peretola

Tue 4/14

7:55 pm-4:10 pm

1 stop27h 15m

$398

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Thu 2/5

6:30 pm-2:00 pm

1 stop12h 30m

Rome Fiumicino

Thu 2/12

11:25 am-5:20 pm

1 stop12h 55m

$404

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Fri 12/5

6:30 pm-2:00 pm

1 stop12h 30m

Rome Fiumicino

Wed 12/10

11:25 am-5:20 pm

1 stop12h 55m

$406

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 12/2

1:14 pm-7:55 am

1 stop11h 41m

Rome Fiumicino

Thu 12/11

10:05 am-6:00 pm

1 stop14h 55m

$527

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 12/2

1:14 pm-7:55 am

1 stop11h 41m

Rome Fiumicino

Thu 12/11

10:05 am-6:00 pm

1 stop14h 55m

$536

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Sun 3/22

6:10 pm-9:30 am

1 stop33h 20m

Pisa Gal Galilei

Mon 3/30

8:40 pm-6:15 pm

1 stop28h 35m

$537

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 12/2

9:34 am-7:55 am

1 stop15h 21m

Rome Fiumicino

Wed 12/10

6:10 am-4:34 pm

2 stops17h 24m

$537

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 3/1

6:17 pm-3:15 pm

2 stops13h 58m

Rome Fiumicino

Thu 3/12

9:05 am-6:34 pm

1 stop15h 29m

$540

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Sun 12/7

5:40 pm-9:30 am

2 stops32h 50m

Pisa Gal Galilei

Tue 12/23

10:20 am-1:50 pm

1 stop34h 30m

$565

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 2/18

12:46 pm-10:30 am

1 stop14h 44m

Rome Fiumicino

Wed 3/4

12:40 pm-10:44 pm

1 stop17h 04m

$571

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 $739. 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 $794.

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 $990 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 $855 on momondo.

Can stopping save me money on Chicago to Tuscany flights?

You could potentially save up to 19% 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

Fastest flight time	9h 00m
Direct flights	Every day
Airports in Tuscany	1 airport

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

Direct flights go from Chicago to Tuscany every day.

There is 1 airport near Tuscany: Rome Fiumicino (FCO)

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 November 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 7.4 1,580 reviews	Search Scandinavian Airlines flights
KLM	PriceFrom $491	Free Cancellation	Rating 7.7 1,411 reviews	Search KLM flights
British Airways	PriceFrom $556	Free Cancellation	Rating 6.7 7,528 reviews	Search British Airways flights
Air France	PriceFrom $588	Free Cancellation	Rating 7.4 1,493 reviews	Search Air France flights
SWISS	PriceFrom $595	Free Cancellation	Rating 7.5 1,788 reviews	Search SWISS flights
Lufthansa	PriceFrom $630	Free Cancellation	Rating 6.8 7,576 reviews	Search Lufthansa flights
United Airlines	PriceFrom $669	Free Cancellation	Rating 7.4 9,014 reviews	Search United Airlines flights
Delta	PriceFrom $732	Free Cancellation	Rating 7.9 8,009 reviews	Search Delta flights
Iberia	PriceFrom $741	Free Cancellation	Rating 7.0 3,020 reviews	Search Iberia flights
ITA Airways	PriceFrom $752	Free Cancellation	Rating 6.7 1,083 reviews	Search ITA Airways 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.