Cheap flights from Tuscany to Chicago from $277

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 3/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

Find the cheapest flights from Tuscany to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
TAP AIR PORTUGAL Logo
7:35 pm - 3:25 pm
FCO
-
ORD
26h 50m
1 stop
TAP AIR PORTUGAL Logo
7:10 pm - 12:05 am
ORD
-
FCO
21h 55m
1 stop
$435TAP AIR PORTUGAL
Thu, Feb 5 - Wed, Feb 18
TAP AIR PORTUGAL Logo
6:00 am - 3:00 pm
FCO
-
ORD
16h 00m
1 stop
TAP AIR PORTUGAL Logo
7:10 pm - 12:05 am
ORD
-
FCO
21h 55m
1 stop
$440TAP AIR PORTUGAL
Wed, Feb 11 - Wed, Feb 18
LOT Logo
10:45 am - 7:50 pm
FCO
-
ORD
16h 05m
1 stop
LOT Logo
9:50 pm - 6:05 pm
ORD
-
FCO
13h 15m
1 stop
$485LOT
Wed, Apr 8 - Mon, Apr 20
LOT Logo
11:50 am - 8:00 pm
FCO
-
ORD
15h 10m
1 stop
LOT Logo
9:55 pm - 6:35 pm
ORD
-
FCO
13h 40m
1 stop
$530LOT
Thu, Feb 19 - Tue, Feb 24
LOT Logo
7:35 pm - 8:00 pm
FCO
-
ORD
31h 25m
1 stop
LOT Logo
10:55 pm - 6:30 pm
ORD
-
FCO
13h 35m
1 stop
$538LOT
Mon, Feb 23 - Mon, Mar 9
LOT Logo
7:35 pm - 8:00 pm
FCO
-
ORD
31h 25m
1 stop
LOT Logo
10:55 pm - 6:30 pm
ORD
-
FCO
13h 35m
1 stop
$539LOT
Sat, Feb 28 - Mon, Mar 16
Multiple Airlines Logo
7:40 am - 2:55 pm
FCO
-
ORD
14h 15m
1 stop
Multiple Airlines Logo
10:20 pm - 5:55 pm
ORD
-
FCO
12h 35m
1 stop
$541Multiple Airlines
Tue, May 12 - Thu, May 28
Icelandair Logo
11:25 am - 5:20 pm
FCO
-
ORD
12h 55m
1 stop
Icelandair Logo
6:30 pm - 2:00 pm
ORD
-
FCO
12h 30m
1 stop
$547Icelandair
Thu, Feb 12 - Thu, Feb 19
ITA Airways Logo
11:40 am - 6:35 pm
FLR
-
ORD
36h 55m
2 stops
ITA Airways Logo
9:15 am - 6:15 pm
ORD
-
FLR
26h 00m
2 stops
$583ITA Airways
Tue, Mar 10 - Tue, Mar 31
Multiple Airlines Logo
6:25 am - 8:00 pm
CIA
-
ORD
20h 35m
2 stops
Multiple Airlines Logo
9:55 pm - 9:45 pm
ORD
-
CIA
16h 50m
2 stops
$614Multiple Airlines
Wed, Feb 11 - Wed, Feb 18

TAP AIR PORTUGAL flights from Tuscany to Chicago

Our best TAP AIR PORTUGAL deals on Tuscany to Chicago flight tickets
TAP AIR PORTUGAL
Feb 5
FCO7:35 pmRome Fiumicino
26h 50m
1 stop
ORD3:25 pmChicago O'Hare Intl
Feb 18
ORD7:10 pmChicago O'Hare Intl
21h 55m
1 stop
FCO12:05 amRome Fiumicino
$435
TAP AIR PORTUGAL
Jan 22
FLR7:15 pmFlorence Peretola
27h 10m
1 stop
ORD3:25 pmChicago O'Hare Intl
Jan 28
ORD7:10 pmChicago O'Hare Intl
16h 20m
1 stop
FLR6:30 pmFlorence Peretola
$436
TAP AIR PORTUGAL
Jan 22
FLR7:15 pmFlorence Peretola
27h 10m
1 stop
ORD3:25 pmChicago O'Hare Intl
Jan 28
ORD7:10 pmChicago O'Hare Intl
33h 25m
1 stop
FLR11:35 amFlorence Peretola
$438

LOT flights from Tuscany to Chicago

Our best LOT deals on Tuscany to Chicago flight tickets
LOT
Apr 8
FCO10:45 amRome Fiumicino
16h 05m
1 stop
ORD7:50 pmChicago O'Hare Intl
Apr 20
ORD9:50 pmChicago O'Hare Intl
13h 15m
1 stop
FCO6:05 pmRome Fiumicino
$485
LOT
Feb 19
FCO11:50 amRome Fiumicino
15h 10m
1 stop
ORD8:00 pmChicago O'Hare Intl
Feb 24
ORD9:55 pmChicago O'Hare Intl
13h 40m
1 stop
FCO6:35 pmRome Fiumicino
$530
LOT
Feb 23
FCO7:35 pmRome Fiumicino
31h 25m
1 stop
ORD8:00 pmChicago O'Hare Intl
Mar 9
ORD10:55 pmChicago O'Hare Intl
13h 35m
1 stop
FCO6:30 pmRome Fiumicino
$538

momondo Fare Finder

 
Customize your flight search to find flights from Tuscany to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated January 14, 2026.
Use the filters below to find and compare flights from Tuscany to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 2/5

7:35 pm-3:25 pm

1 stop26h 50m

Chicago O'Hare Intl

Wed 2/18

7:10 pm-12:05 am

1 stop21h 55m

$435

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Wed 2/11

6:00 am-3:00 pm

1 stop16h 00m

Chicago O'Hare Intl

Wed 2/18

7:10 pm-12:05 am

1 stop21h 55m

$440

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Wed 4/8

10:45 am-7:50 pm

1 stop16h 05m

Chicago O'Hare Intl

Mon 4/20

9:50 pm-6:05 pm

1 stop13h 15m

$485

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 2/19

11:50 am-8:00 pm

1 stop15h 10m

Chicago O'Hare Intl

Tue 2/24

9:55 pm-6:35 pm

1 stop13h 40m

$530

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 2/23

7:35 pm-8:00 pm

1 stop31h 25m

Chicago O'Hare Intl

Mon 3/9

10:55 pm-6:30 pm

1 stop13h 35m

$538

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Sat 2/28

7:35 pm-8:00 pm

1 stop31h 25m

Chicago O'Hare Intl

Mon 3/16

10:55 pm-6:30 pm

1 stop13h 35m

$539

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Tue 5/12

7:40 am-2:55 pm

1 stop14h 15m

Chicago O'Hare Intl

Thu 5/28

10:20 pm-5:55 pm

1 stop12h 35m

$541

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 2/12

11:25 am-5:20 pm

1 stop12h 55m

Chicago O'Hare Intl

Thu 2/19

6:30 pm-2:00 pm

1 stop12h 30m

$547

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Tue 3/10

11:40 am-6:35 pm

2 stops36h 55m

Chicago O'Hare Intl

Tue 3/31

9:15 am-6:15 pm

2 stops26h 00m

$583

RomeChicago

CIA - ORD

CIAORD

Rome Ciampino

Wed 2/11

6:25 am-8:00 pm

2 stops20h 35m

Chicago O'Hare Intl

Wed 2/18

9:55 pm-9:45 pm

2 stops16h 50m

$614

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

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

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Tuscany, with most prices found around $581. If you’re not able to fly to Chicago in February, then October is your next best option. Flight prices from Tuscany to Chicago during October average around $613.

Cheap Tuscany to Chicago flight deals and tips

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

Fastest flight time

10h 25m

Direct flights

Every day

Airports in Chicago

3 airports
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).
  • 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?

  • 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 AirlinesPriceFrom $755Free CancellationRating
7.2
11,119 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
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.

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.
1 adult
Fri 2/13
Fri 2/20

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