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Cheap flights from Tuscany to Chicago from $289

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 5/3. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
TAP AIR PORTUGAL Logo
6:50 pm - 4:05 pm
FLR
-
ORD
28h 15m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 6:00 pm
ORD
-
FLR
17h 00m
1 stop
$465TAP AIR PORTUGAL
Fri, Apr 17 - Fri, Apr 24
TAP AIR PORTUGAL Logo
6:55 pm - 4:00 pm
FLR
-
ORD
28h 05m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 11:00 am
ORD
-
FLR
34h 00m
1 stop
$470TAP AIR PORTUGAL
Sat, Apr 18 - Fri, Apr 24
TAP AIR PORTUGAL Logo
6:50 pm - 4:05 pm
FLR
-
ORD
28h 15m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 11:00 am
ORD
-
FLR
34h 00m
1 stop
$473TAP AIR PORTUGAL
Fri, Apr 17 - Fri, Apr 24
Multiple Airlines Logo
7:05 pm - 11:42 am
FCO
-
ORD
23h 37m
1 stop
Multiple Airlines Logo
2:09 pm - 2:30 pm
ORD
-
FCO
17h 21m
1 stop
$517Multiple Airlines
Thu, Apr 16 - Mon, Apr 27
Icelandair Logo
11:25 am - 6:20 pm
FCO
-
ORD
12h 55m
1 stop
Icelandair Logo
10:25 pm - 2:35 pm
ORD
-
FCO
33h 10m
1 stop
$525Icelandair
Mon, Mar 16 - Fri, May 15
Icelandair Logo
3:45 pm - 9:25 pm
FCO
-
ORD
12h 40m
1 stop
Icelandair Logo
10:25 pm - 2:35 pm
ORD
-
FCO
33h 10m
1 stop
$531Icelandair
Fri, Apr 17 - Fri, Apr 24
SWISS Logo
7:45 pm - 3:55 pm
FLR
-
ORD
27h 10m
1 stop
SWISS Logo
7:05 pm - 2:10 pm
ORD
-
FLR
12h 05m
1 stop
$592SWISS
Mon, Apr 13 - Mon, Apr 20
Air Canada Logo
6:30 am - 2:55 pm
FLR
-
ORD
15h 25m
2 stops
Air Canada Logo
9:50 am - 9:30 am
ORD
-
FLR
16h 40m
2 stops
$593Air Canada
Fri, Apr 17 - Fri, Apr 24
Air Canada Logo
6:30 am - 2:55 pm
FLR
-
ORD
15h 25m
2 stops
Air Canada Logo
9:50 am - 9:30 am
ORD
-
FLR
16h 40m
2 stops
$597Air Canada
Fri, Apr 17 - Fri, Apr 24
Multiple Airlines Logo
7:25 am - 6:15 pm
CIA
-
ORD
17h 50m
3 stops
Multiple Airlines Logo
7:25 pm - 9:05 pm
ORD
-
CIA
18h 40m
2 stops
$647Multiple Airlines
Tue, Apr 21 - Sun, Apr 26

United Airlines flights from Tuscany to Chicago O'Hare Intl Airport

Our best United Airlines deals on Tuscany to Chicago O'Hare Intl Airport flight tickets
United Airlines
Apr 17
FLR6:30 amFlorence Peretola
13h 25m
1 stop
ORD12:55 pmChicago O'Hare Intl
Apr 24
ORD1:00 pmChicago O'Hare Intl
20h 35m
2 stops
FLR4:35 pmFlorence Peretola
$613
United Airlines
Apr 17
FLR6:30 amFlorence Peretola
20h 35m
2 stops
ORD8:05 pmChicago O'Hare Intl
Apr 24
ORD1:00 pmChicago O'Hare Intl
20h 35m
2 stops
FLR4:35 pmFlorence Peretola
$617
United Airlines
Apr 15
FLR6:30 amFlorence Peretola
15h 25m
2 stops
ORD2:55 pmChicago O'Hare Intl
Apr 22
ORD4:20 pmChicago O'Hare Intl
17h 15m
2 stops
FLR4:35 pmFlorence Peretola
$626

Austrian Airlines flights from Tuscany to Chicago O'Hare Intl Airport

Our best Austrian Airlines deals on Tuscany to Chicago O'Hare Intl Airport flight tickets
Austrian Airlines
Apr 18
FLR7:00 amFlorence Peretola
18h 44m
2 stops
ORD6:44 pmChicago O'Hare Intl
Apr 24
ORD4:20 pmChicago O'Hare Intl
10h 55m
1 stop
FLR10:15 amFlorence Peretola
$633
Austrian Airlines
Apr 16
FLR7:00 amFlorence Peretola
13h 20m
1 stop
ORD1:20 pmChicago O'Hare Intl
Apr 23
ORD1:00 pmChicago O'Hare Intl
26h 15m
2 stops
FLR10:15 pmFlorence Peretola
$637
Austrian Airlines
Apr 18
FLR7:00 amFlorence Peretola
18h 44m
2 stops
ORD6:44 pmChicago O'Hare Intl
Apr 24
ORD4:20 pmChicago O'Hare Intl
14h 45m
1 stop
FLR2:05 pmFlorence Peretola
$643

momondo Fare Finder

 
Customize your flight search to find flights from Tuscany to Chicago O'Hare Intl Airport 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 March 4, 2026.
Use the filters below to find and compare flights from Tuscany to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 4/17

6:50 pm-4:05 pm

1 stop28h 15m

Chicago O'Hare Intl

Fri 4/24

6:00 pm-6:00 pm

1 stop17h 00m

$465

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sat 4/18

6:55 pm-4:00 pm

1 stop28h 05m

Chicago O'Hare Intl

Fri 4/24

6:00 pm-11:00 am

1 stop34h 00m

$470

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 4/17

6:50 pm-4:05 pm

1 stop28h 15m

Chicago O'Hare Intl

Fri 4/24

6:00 pm-11:00 am

1 stop34h 00m

$473

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 4/16

7:05 pm-11:42 am

1 stop23h 37m

Chicago O'Hare Intl

Mon 4/27

2:09 pm-2:30 pm

1 stop17h 21m

$517

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 3/16

11:25 am-6:20 pm

1 stop12h 55m

Chicago O'Hare Intl

Fri 5/15

10:25 pm-2:35 pm

1 stop33h 10m

$525

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Fri 4/17

3:45 pm-9:25 pm

1 stop12h 40m

Chicago O'Hare Intl

Fri 4/24

10:25 pm-2:35 pm

1 stop33h 10m

$531

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Mon 4/13

7:45 pm-3:55 pm

1 stop27h 10m

Chicago O'Hare Intl

Mon 4/20

7:05 pm-2:10 pm

1 stop12h 05m

$592

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 4/17

6:30 am-2:55 pm

2 stops15h 25m

Chicago O'Hare Intl

Fri 4/24

9:50 am-9:30 am

2 stops16h 40m

$593

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 4/17

6:30 am-2:55 pm

2 stops15h 25m

Chicago O'Hare Intl

Fri 4/24

9:50 am-9:30 am

2 stops16h 40m

$597

RomeChicago

CIA - ORD

CIAORD

Rome Ciampino

Tue 4/21

7:25 am-6:15 pm

3 stops17h 50m

Chicago O'Hare Intl

Sun 4/26

7:25 pm-9:05 pm

2 stops18h 40m

$647

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Tuscany to Chicago O'Hare Intl Airport

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 airline that flies from Tuscany to Chicago O'Hare Intl?

Air Serbia, Icelandair, and American Airlines are the most popular carriers operating from Tuscany to Chicago O'Hare Intl

Cheap Tuscany to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Tuscany to Chicago O'Hare Intl Airport

Fastest flight time

10h 20m

Direct flights

Every day
The fastest flight from Tuscany to Chicago O'Hare Intl Airport takes 10h 20m
Direct flights go from Tuscany to Chicago O'Hare Intl Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Tuscany to Chicago O'Hare Intl Airport?

    Prices for flights from Tuscany to Chicago O'Hare Intl Airport are updated daily.

  • How many operators does momondo search for flights from Tuscany to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Tuscany to Chicago O'Hare Intl Airport?

    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 Tuscany to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Tuscany to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Tuscany to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $755Free CancellationRating
7.1
11,378 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
Elgin
South Holland

Why use momondo?

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

Finding the right flight to Chicago from Tuscany is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. All flights to Chicago from Tuscany on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo helps you find the best flight between Tuscany and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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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