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Cheap flights from Tuscany to Chicago from $267

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 5/8. 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

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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
6:55 pm - 4:00 pm
FLR
-
ORD
28h 05m
1 stop
TAP AIR PORTUGAL Logo
6:05 pm - 5:50 pm
ORD
-
FLR
16h 45m
1 stop
$463TAP AIR PORTUGAL
Sat, Apr 18 - Sat, Apr 25
Icelandair Logo
3:45 pm - 9:25 pm
FCO
-
ORD
12h 40m
1 stop
Icelandair Logo
7:25 pm - 2:35 pm
ORD
-
FCO
12h 10m
1 stop
$482Icelandair
Mon, Aug 24 - Sun, Sep 6
TAP AIR PORTUGAL Logo
6:50 pm - 4:00 pm
FLR
-
ORD
28h 10m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 10:50 am
ORD
-
FLR
33h 50m
1 stop
$498TAP AIR PORTUGAL
Thu, Apr 16 - Wed, Apr 22
Multiple Airlines Logo
10:30 am - 5:50 pm
FCO
-
ORD
14h 20m
1 stop
Multiple Airlines Logo
10:35 pm - 7:05 pm
ORD
-
FCO
13h 30m
1 stop
$555Multiple Airlines
Tue, Aug 25 - Sat, Sep 5
Multiple Airlines Logo
10:30 am - 5:50 pm
FCO
-
ORD
14h 20m
1 stop
Multiple Airlines Logo
10:35 pm - 7:05 pm
ORD
-
FCO
13h 30m
1 stop
$558Multiple Airlines
Wed, Aug 26 - Sat, Sep 12
Scandinavian Airlines Logo
7:55 pm - 4:10 pm
FLR
-
ORD
27h 15m
1 stop
Scandinavian Airlines Logo
7:15 pm - 7:05 pm
ORD
-
FLR
16h 50m
1 stop
$562Scandinavian Airlines
Thu, Apr 16 - Wed, Apr 22
Scandinavian Airlines Logo
7:55 pm - 4:10 pm
FLR
-
ORD
27h 15m
1 stop
Scandinavian Airlines Logo
7:15 pm - 9:10 am
ORD
-
FLR
30h 55m
2 stops
$573Scandinavian Airlines
Thu, Apr 16 - Wed, Apr 22
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
American Airlines Logo
3:15 pm - 2:55 pm
PSA
-
ORD
30h 40m
1 stop
American Airlines Logo
5:48 pm - 6:55 pm
ORD
-
PSA
18h 07m
2 stops
$606American Airlines
Fri, May 8 - Tue, Jun 2
American Airlines Logo
12:50 pm - 11:54 pm
PSA
-
ORD
18h 04m
2 stops
American Airlines Logo
5:48 pm - 6:55 pm
ORD
-
PSA
18h 07m
2 stops
$616American Airlines
Fri, May 8 - Tue, Jun 2

American Airlines flights from Tuscany to Chicago

Our best American Airlines deals on Tuscany to Chicago flight tickets
American Airlines
May 8
PSA3:15 pmPisa Gal Galilei
30h 40m
1 stop
ORD2:55 pmChicago O'Hare Intl
Jun 2
ORD5:48 pmChicago O'Hare Intl
18h 07m
2 stops
PSA6:55 pmPisa Gal Galilei
$606
American Airlines
Apr 27
FCO10:00 amRome Fiumicino
10h 30m
ORD1:30 pmChicago O'Hare Intl
May 5
ORD5:55 pmChicago O'Hare Intl
12h 00m
1 stop
FCO12:55 pmRome Fiumicino
$613
American Airlines
May 8
PSA12:50 pmPisa Gal Galilei
18h 04m
2 stops
ORD11:54 pmChicago O'Hare Intl
Jun 2
ORD5:48 pmChicago O'Hare Intl
18h 07m
2 stops
PSA6:55 pmPisa Gal Galilei
$616

TAP AIR PORTUGAL flights from Tuscany to Chicago

Our best TAP AIR PORTUGAL deals on Tuscany to Chicago flight tickets
TAP AIR PORTUGAL
Apr 18
FLR6:55 pmFlorence Peretola
28h 05m
1 stop
ORD4:00 pmChicago O'Hare Intl
Apr 25
ORD6:05 pmChicago O'Hare Intl
16h 45m
1 stop
FLR5:50 pmFlorence Peretola
$463
TAP AIR PORTUGAL
Apr 16
FLR6:50 pmFlorence Peretola
28h 10m
1 stop
ORD4:00 pmChicago O'Hare Intl
Apr 22
ORD6:00 pmChicago O'Hare Intl
33h 50m
1 stop
FLR10:50 amFlorence Peretola
$498
TAP AIR PORTUGAL
Apr 16
FLR6:50 pmFlorence Peretola
28h 10m
1 stop
ORD4:00 pmChicago O'Hare Intl
Apr 22
ORD6:00 pmChicago O'Hare Intl
33h 50m
1 stop
FLR10:50 amFlorence Peretola
$500

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 February 28, 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

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sat 4/18

6:55 pm-4:00 pm

1 stop28h 05m

Chicago O'Hare Intl

Sat 4/25

6:05 pm-5:50 pm

1 stop16h 45m

$463

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 8/24

3:45 pm-9:25 pm

1 stop12h 40m

Chicago O'Hare Intl

Sun 9/6

7:25 pm-2:35 pm

1 stop12h 10m

$482

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 4/16

6:50 pm-4:00 pm

1 stop28h 10m

Chicago O'Hare Intl

Wed 4/22

6:00 pm-10:50 am

1 stop33h 50m

$498

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Tue 8/25

10:30 am-5:50 pm

1 stop14h 20m

Chicago O'Hare Intl

Sat 9/5

10:35 pm-7:05 pm

1 stop13h 30m

$555

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Wed 8/26

10:30 am-5:50 pm

1 stop14h 20m

Chicago O'Hare Intl

Sat 9/12

10:35 pm-7:05 pm

1 stop13h 30m

$558

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 4/16

7:55 pm-4:10 pm

1 stop27h 15m

Chicago O'Hare Intl

Wed 4/22

7:15 pm-7:05 pm

1 stop16h 50m

$562

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 4/16

7:55 pm-4:10 pm

1 stop27h 15m

Chicago O'Hare Intl

Wed 4/22

7:15 pm-9:10 am

2 stops30h 55m

$573

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

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Fri 5/8

3:15 pm-2:55 pm

1 stop30h 40m

Chicago O'Hare Intl

Tue 6/2

5:48 pm-6:55 pm

2 stops18h 07m

$606

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Fri 5/8

12:50 pm-11:54 pm

2 stops18h 04m

Chicago O'Hare Intl

Tue 6/2

5:48 pm-6:55 pm

2 stops18h 07m

$616

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

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 October is, on average, the cheapest month to fly to Chicago from Tuscany, with most prices found around $613. If you’re not able to fly to Chicago in October, then April is your next best option. Flight prices from Tuscany to Chicago during April average around $614.

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 20m

Direct flights

Every day

Airports in Chicago

3 airports
The fastest flight from Tuscany to Chicago takes 10h 20m
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

  • 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
7.1
11,370 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.

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport