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

Delta, American Airlines, and Aer Lingus are the most popular carriers operating from Tuscany to Chicago

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

The number of flights available between Tuscany and Chicago is 84 per week as of August 2026. The most frequent departure day is Tue, with 15% of weekly flights leaving on this day.

How long does it take to fly to Chicago?

Average flight duration from Tuscany to Chicago depends on which airport you fly into and out of. Flying from Florence to Chicago O'Hare Intl Airport is 13h 45m on average, while flying from Pisa to Chicago O'Hare Intl Airport is 19h 15m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

Prices for flights from Tuscany to Chicago are refreshed on a daily basis.

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

As of August 2026, there are 3 operators available to choose from for flights from Tuscany to Chicago.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Tuscany to Chicago.

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

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$377 Cheap Flights from Tuscany to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Tuscany to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 pm - 4:10 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

29h 10m2 stops Oslo Gardermoen Kastrup Copenhagen

7:15 pm - 1:15 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

23h 00m2 stops Kastrup Copenhagen Oslo Gardermoen

$525Multiple Airlines

Thu, Oct 15 - Mon, Oct 19

3:45 pm - 9:25 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

12h 40m1 stop Reykjavik Keflavik Intl

7:25 pm - 2:35 pmORD Chicago O'Hare Intl-FCO Rome Fiumicino

12h 10m1 stop Reykjavik Keflavik Intl

$536Icelandair

Wed, Oct 7 - Sun, Oct 18

3:45 pm - 9:25 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

12h 40m1 stop Reykjavik Keflavik Intl

7:25 pm - 2:35 pmORD Chicago O'Hare Intl-FCO Rome Fiumicino

12h 10m1 stop Reykjavik Keflavik Intl

$537Icelandair

Wed, Oct 7 - Sun, Oct 18

6:25 am - 1:10 pmFLR Florence Peretola-ORD Chicago O'Hare Intl

13h 45m1 stop Rome Fiumicino

3:00 pm - 10:35 amORD Chicago O'Hare Intl-FLR Florence Peretola

12h 35m1 stop Rome Fiumicino

$559ITA Airways

Thu, Sep 17 - Tue, Sep 22

6:25 am - 1:10 pmFLR Florence Peretola-ORD Chicago O'Hare Intl

13h 45m1 stop Rome Fiumicino

3:00 pm - 10:35 amORD Chicago O'Hare Intl-FLR Florence Peretola

12h 35m1 stop Rome Fiumicino

$561ITA Airways

Thu, Sep 17 - Tue, Sep 22

7:00 pm - 1:10 pmFLR Florence Peretola-ORD Chicago O'Hare Intl

25h 10m1 stop Rome Fiumicino

3:00 pm - 2:45 pmORD Chicago O'Hare Intl-FLR Florence Peretola

16h 45m1 stop Rome Fiumicino

$571ITA Airways

Mon, Sep 21 - Sun, Sep 27

10:00 am - 1:40 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 40mnonstop

7:05 pm - 5:25 pmORD Chicago O'Hare Intl-FCO Rome Fiumicino

15h 20m1 stop London Heathrow

$671American Airlines

Thu, Oct 15 - Mon, Oct 19

7:35 am - 4:00 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

15h 25m1 stop Madrid Barajas

10:25 pm - 7:20 pmORD Chicago O'Hare Intl-FCO Rome Fiumicino

13h 55m1 stop London Heathrow

$671American Airlines

Wed, Sep 16 - Fri, Oct 2

6:50 am - 2:55 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

15h 05m1 stop Frankfurt am Main

11:00 am - 8:15 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

14h 15m2 stops New York LaGuardia Washington, D.C. Dulles Intl

$828United Airlines

Fri, Oct 9 - Tue, Oct 20

9:55 am - 3:20 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

12h 25m1 stop Frankfurt am Main

3:40 pm - 7:45 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 05mnonstop

$831United Airlines

Mon, Jan 18 - Fri, Feb 19

Cheap last minute flights

Enter your travel dates to find the best prices.

3:45 pm - 9:25 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

12h 40m1 stop Reykjavik Keflavik Intl

7:25 pm - 2:35 pmORD Chicago O'Hare Intl-FCO Rome Fiumicino

12h 10m1 stop Reykjavik Keflavik Intl

$580Icelandair

Fri, Sep 4 - Sun, Oct 4

3:45 pm - 9:25 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

12h 40m1 stop Reykjavik Keflavik Intl

10:25 pm - 2:35 pmORD Chicago O'Hare Intl-FCO Rome Fiumicino

33h 10m1 stop Reykjavik Keflavik Intl

$615Icelandair

Fri, Sep 4 - Fri, Oct 2

3:45 pm - 9:25 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

12h 40m1 stop Reykjavik Keflavik Intl

10:25 pm - 2:35 pmORD Chicago O'Hare Intl-FCO Rome Fiumicino

33h 10m1 stop Reykjavik Keflavik Intl

$636Icelandair

Fri, Sep 4 - Fri, Oct 2

9:20 am - 1:10 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 50mnonstop

3:00 pm - 7:25 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 25mnonstop

$670ITA Airways

Wed, Sep 2 - Fri, Oct 2

9:20 am - 1:10 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 50mnonstop

3:00 pm - 7:25 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 25mnonstop

$670ITA Airways

Wed, Sep 2 - Sun, Oct 4

9:20 am - 1:10 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 50mnonstop

3:00 pm - 7:25 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 25mnonstop

$670ITA Airways

Wed, Sep 2 - Tue, Sep 29

7:35 am - 2:25 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

13h 50m1 stop Madrid Barajas

5:55 pm - 3:30 pmORD Chicago O'Hare Intl-FCO Rome Fiumicino

14h 35m1 stop London Heathrow

$672American Airlines

Thu, Sep 3 - Fri, Oct 2

7:35 am - 2:25 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

13h 50m1 stop Madrid Barajas

10:30 pm - 8:05 pmORD Chicago O'Hare Intl-FCO Rome Fiumicino

14h 35m1 stop London Heathrow

$672American Airlines

Thu, Sep 3 - Tue, Oct 13

9:45 am - 1:15 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 30mnonstop

3:50 pm - 7:55 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 05mnonstop

$891United Airlines

Wed, Sep 2 - Wed, Sep 9

9:45 am - 1:15 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 30mnonstop

3:50 pm - 7:55 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 05mnonstop

$1,188United Airlines

Wed, Sep 2 - Thu, Oct 1

Cheap direct flights

Enter your travel dates to find the best prices.

9:20 am - 1:10 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 50mnonstop

3:00 pm - 7:25 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 25mnonstop

$614ITA Airways

Tue, Sep 22 - Wed, Oct 7

9:20 am - 1:10 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 50mnonstop

3:00 pm - 7:25 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 25mnonstop

$619ITA Airways

Tue, Sep 22 - Wed, Oct 7

9:20 am - 1:10 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 50mnonstop

3:00 pm - 7:25 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 25mnonstop

$619ITA Airways

Tue, Sep 15 - Wed, Sep 30

10:00 am - 1:40 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 40mnonstop

5:40 pm - 8:55 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 15mnonstop

$628Finnair

Thu, Oct 15 - Wed, Oct 28

10:00 am - 1:40 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 40mnonstop

4:45 pm - 9:10 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 25mnonstop

$630Finnair

Wed, Oct 7 - Sun, Oct 18

10:00 am - 1:40 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 40mnonstop

4:45 pm - 9:10 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 25mnonstop

$631Finnair

Wed, Oct 7 - Sun, Oct 18

10:00 am - 1:40 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 40mnonstop

4:45 pm - 9:10 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 25mnonstop

$680American Airlines

Thu, Oct 15 - Mon, Oct 19

10:00 am - 1:40 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 40mnonstop

4:45 pm - 9:10 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 25mnonstop

$682American Airlines

Thu, Oct 15 - Mon, Oct 19

9:45 am - 1:10 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 25mnonstop

3:50 pm - 7:55 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 05mnonstop

$844United Airlines

Thu, Oct 8 - Mon, Oct 12

9:45 am - 1:10 pmFCO Rome Fiumicino-ORD Chicago O'Hare Intl

10h 25mnonstop

3:40 pm - 7:45 amORD Chicago O'Hare Intl-FCO Rome Fiumicino

9h 05mnonstop

$847United Airlines

Sat, Nov 21 - Fri, Nov 27

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Icelandair flights from Tuscany to Chicago

Our best Icelandair deals on Tuscany to Chicago flight tickets

Icelandair

Oct 7

FCO3:45 pmRome Fiumicino

12h 40m

1 stop

ORD9:25 pmChicago O'Hare Intl

Oct 18

ORD7:25 pmChicago O'Hare Intl

12h 10m

1 stop

FCO2:35 pmRome Fiumicino

$536

Icelandair

Oct 7

FCO3:45 pmRome Fiumicino

12h 40m

1 stop

ORD9:25 pmChicago O'Hare Intl

Oct 18

ORD7:25 pmChicago O'Hare Intl

12h 10m

1 stop

FCO2:35 pmRome Fiumicino

$537

Icelandair

Oct 21

FCO3:45 pmRome Fiumicino

33h 30m

1 stop

ORD6:15 pmChicago O'Hare Intl

Oct 31

ORD7:30 pmChicago O'Hare Intl

12h 30m

1 stop

FCO2:00 pmRome Fiumicino

$538

Lufthansa flights from Tuscany to Chicago

Our best Lufthansa deals on Tuscany to Chicago flight tickets

Lufthansa

Jan 8

FLR2:20 pmFlorence Peretola

12h 45m

1 stop

ORD8:05 pmChicago O'Hare Intl

Apr 14

ORD9:40 pmChicago O'Hare Intl

11h 55m

1 stop

FLR4:35 pmFlorence Peretola

$776

Lufthansa

Sep 10

PSA10:40 amPisa Gal Galilei

16h 15m

1 stop

ORD7:55 pmChicago O'Hare Intl

Sep 14

ORD10:30 pmChicago O'Hare Intl

12h 30m

1 stop

PSA6:00 pmPisa Gal Galilei

$792

Lufthansa

Sep 10

PSA10:40 amPisa Gal Galilei

16h 15m

1 stop

ORD7:55 pmChicago O'Hare Intl

Sep 14

ORD10:30 pmChicago O'Hare Intl

12h 30m

1 stop

PSA6:00 pmPisa Gal Galilei

$793

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RomeChicago

FCO Rome Fiumicino - ORD Chicago O'Hare Intl

FCOORD

Rome Fiumicino

Thu 10/15

6:00 pm-4:10 pm

2 stops29h 10m

Chicago O'Hare Intl

Mon 10/19

7:15 pm-1:15 am

2 stops23h 00m

$525

RomeChicago

FCO Rome Fiumicino - ORD Chicago O'Hare Intl

FCOORD

Rome Fiumicino

Wed 10/7

3:45 pm-9:25 pm

1 stop12h 40m

Chicago O'Hare Intl

Sun 10/18

7:25 pm-2:35 pm

1 stop12h 10m

$536

RomeChicago

FCO Rome Fiumicino - ORD Chicago O'Hare Intl

FCOORD

Rome Fiumicino

Wed 10/7

3:45 pm-9:25 pm

1 stop12h 40m

Chicago O'Hare Intl

Sun 10/18

7:25 pm-2:35 pm

1 stop12h 10m

$537

FlorenceChicago

FLR Florence Peretola - ORD Chicago O'Hare Intl

FLRORD

Florence Peretola

Thu 9/17

6:25 am-1:10 pm

1 stop13h 45m

Chicago O'Hare Intl

Tue 9/22

3:00 pm-10:35 am

1 stop12h 35m

$559

FlorenceChicago

FLR Florence Peretola - ORD Chicago O'Hare Intl

FLRORD

Florence Peretola

Thu 9/17

6:25 am-1:10 pm

1 stop13h 45m

Chicago O'Hare Intl

Tue 9/22

3:00 pm-10:35 am

1 stop12h 35m

$561

FlorenceChicago

FLR Florence Peretola - ORD Chicago O'Hare Intl

FLRORD

Florence Peretola

Mon 9/21

7:00 pm-1:10 pm

1 stop25h 10m

Chicago O'Hare Intl

Sun 9/27

3:00 pm-2:45 pm

1 stop16h 45m

$571

RomeChicago

FCO Rome Fiumicino - ORD Chicago O'Hare Intl

FCOORD

Rome Fiumicino

Thu 10/15

10:00 am-1:40 pm

Nonstop10h 40m

Chicago O'Hare Intl

Mon 10/19

7:05 pm-5:25 pm

1 stop15h 20m

$671

RomeChicago

FCO Rome Fiumicino - ORD Chicago O'Hare Intl

FCOORD

Rome Fiumicino

Wed 9/16

7:35 am-4:00 pm

1 stop15h 25m

Chicago O'Hare Intl

Fri 10/2

10:25 pm-7:20 pm

1 stop13h 55m

$671

RomeChicago

FCO Rome Fiumicino - ORD Chicago O'Hare Intl

FCOORD

Rome Fiumicino

Fri 10/9

6:50 am-2:55 pm

1 stop15h 05m

Chicago O'Hare Intl

Tue 10/20

11:00 am-8:15 am

2 stops14h 15m

$828

Quickest round-trip

RomeChicago

FCO Rome Fiumicino - ORD Chicago O'Hare Intl

FCOORD

Rome Fiumicino

Mon 1/18

9:55 am-3:20 pm

1 stop12h 25m

Chicago O'Hare Intl

Fri 2/19

3:40 pm-7:45 am

Nonstop9h 05m

$831

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 Tuscany to Chicago

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 Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Tuscany, with most prices found around $648. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Tuscany to Chicago during February average around $759.

Cheap Tuscany to Chicago flight deals and tips

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

Best Price Found	$377
Fastest flight time	10h 25m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Tuscany in the past 72 hours is $377. The best round-trip flight deal from Tuscany to Chicago found on momondo in the last 72 hours is $525.

The fastest flight from Tuscany to Chicago takes 10h 25m

Direct flights go from Tuscany to Chicago every day.

There are 3 airports in Chicago. From Tuscany there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Tuscany to Chicago

When did momondo last update prices for flights from Tuscany to Chicago?
Prices for flights from Tuscany to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Tuscany to Chicago?
As of August 2026, there are 3 operators available to choose from for flights from Tuscany to Chicago.
How old do you have to be to fly from Tuscany to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Tuscany to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Tuscany to Chicago

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

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $755	Free Cancellation	Rating 7.1 12,021 reviews		Search American Airlines flights

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Porter

Crown Point

Griffith

Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Tuscany to Chicago for you.

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

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

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

momondo provides multiple filters to help you find the best flight to Chicago from Tuscany. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Tuscany and alert you when they change.

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Fly into one of these airports located in Chicago

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Cheap flights from Tuscany to Chicago from $377

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Tuscany to Chicago departing on 10/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Icelandair flights from Tuscany to Chicago

Our best Icelandair deals on Tuscany to Chicago flight tickets

Lufthansa flights from Tuscany to Chicago

Our best Lufthansa deals on Tuscany to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Tuscany to Chicago

What is the cheapest month to fly to Chicago?

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

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

How long does it take to fly to Chicago?

Cheap Tuscany to Chicago flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Tuscany to Chicago

Best airlines flying from Tuscany to Chicago

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

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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