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Cheap flights from Chicago to Italy from $217

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Italy departing on 3/2. 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 Chicago to Italy

Cheap round-trip flights

Enter your travel dates to find the best prices.
TAP AIR PORTUGAL Logo
8:15 pm - 11:35 am
ORD
-
FLR
32h 20m1 stop
TAP AIR PORTUGAL Logo
7:15 pm - 3:25 pm
FLR
-
ORD
27h 10m1 stop
$403TAP AIR PORTUGAL
Fri, Jan 23 - Thu, Feb 5
TAP AIR PORTUGAL Logo
6:00 pm - 6:30 pm
ORD
-
FLR
17h 30m1 stop
TAP AIR PORTUGAL Logo
7:15 pm - 4:00 pm
FLR
-
ORD
27h 45m1 stop
$411TAP AIR PORTUGAL
Sun, Apr 12 - Sat, Apr 18
Scandinavian Airlines Logo
7:10 pm - 10:30 am
ORD
-
VCE
32h 20m1 stop
Scandinavian Airlines Logo
11:05 am - 4:55 pm
VCE
-
ORD
12h 50m1 stop
$450Scandinavian Airlines
Sun, Feb 1 - Sun, Feb 8
Scandinavian Airlines Logo
7:15 pm - 10:10 am
ORD
-
VCE
31h 55m1 stop
Scandinavian Airlines Logo
11:00 am - 4:10 pm
VCE
-
ORD
12h 10m1 stop
$452Scandinavian Airlines
Sat, Apr 18 - Sat, Apr 25
Lufthansa Logo
6:00 pm - 5:25 pm
ORD
-
NAP
16h 25m1 stop
Lufthansa Logo
11:20 am - 8:05 pm
NAP
-
ORD
15h 45m2 stops
$480Lufthansa
Mon, Feb 23 - Thu, Mar 5
Lufthansa Logo
6:00 pm - 12:30 pm
ORD
-
NAP
11h 30m1 stop
Lufthansa Logo
3:05 pm - 1:25 pm
NAP
-
ORD
29h 20m2 stops
$490Lufthansa
Sun, Jan 18 - Mon, Feb 2
Turkish Airlines Logo
11:25 am - 6:20 pm
ORD
-
BLQ
23h 55m1 stop
Turkish Airlines Logo
7:20 pm - 9:40 am
BLQ
-
ORD
21h 20m1 stop
$515Turkish Airlines
Tue, Apr 7 - Wed, Apr 15
British Airways Logo
9:45 pm - 9:40 pm
ORD
-
BLQ
16h 55m1 stop
British Airways Logo
7:20 am - 1:50 pm
BLQ
-
ORD
13h 30m1 stop
$516British Airways
Tue, Feb 17 - Tue, Feb 24
Turkish Airlines Logo
7:50 pm - 9:30 am
ORD
-
BLQ
30h 40m1 stop
Turkish Airlines Logo
7:20 pm - 6:15 pm
BLQ
-
ORD
29h 55m1 stop
$525Turkish Airlines
Tue, Apr 7 - Wed, Apr 15
British Airways Logo
4:01 pm - 9:40 pm
ORD
-
BLQ
22h 39m2 stops
British Airways Logo
7:20 am - 7:17 pm
BLQ
-
ORD
18h 57m2 stops
$536British Airways
Tue, Feb 17 - Tue, Feb 24

TAP AIR PORTUGAL flights from Chicago to Italy

Our best TAP AIR PORTUGAL deals on Chicago to Italy flight tickets
TAP AIR PORTUGAL
Jan 23
ORD8:15 pmChicago O'Hare Intl
32h 20m
1 stop
FLR11:35 amFlorence Peretola
Feb 5
FLR7:15 pmFlorence Peretola
27h 10m
1 stop
ORD3:25 pmChicago O'Hare Intl
$403
Find similar
TAP AIR PORTUGAL
Apr 29
ORD6:00 pmChicago O'Hare Intl
17h 25m
1 stop
NAP6:25 pmNaples
May 14
NAP7:15 pmNaples
27h 45m
1 stop
ORD4:00 pmChicago O'Hare Intl
$411
Find similar
TAP AIR PORTUGAL
May 2
ORD6:15 pmChicago O'Hare Intl
17h 00m
1 stop
VCE6:15 pmVenice Marco Polo
May 12
VCE11:40 amVenice Marco Polo
35h 20m
1 stop
ORD4:00 pmChicago O'Hare Intl
$412
Find similar

Turkish Airlines flights from Chicago to Italy

Our best Turkish Airlines deals on Chicago to Italy flight tickets
Turkish Airlines
Apr 7
ORD11:25 amChicago O'Hare Intl
23h 55m
1 stop
BLQ6:20 pmBologna Guglielmo Marconi
Apr 15
BLQ7:20 pmBologna Guglielmo Marconi
21h 20m
1 stop
ORD9:40 amChicago O'Hare Intl
$515
Find similar
Turkish Airlines
Apr 21
ORD7:50 pmChicago O'Hare Intl
29h 35m
1 stop
NAP8:25 amNaples
Apr 29
NAP3:45 pmNaples
24h 55m
1 stop
ORD9:40 amChicago O'Hare Intl
$518
Find similar
Turkish Airlines
Jan 13
ORD11:50 amChicago O'Hare Intl
27h 05m
1 stop
FCO9:55 pmRome Fiumicino
May 1
FCO7:05 amRome Fiumicino
33h 35m
1 stop
ORD9:40 amChicago O'Hare Intl
$601
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Italy 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 December 31, 2025.
Use the filters below to find and compare flights from Chicago to Italy that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Fri 1/23

8:15 pm-11:35 am

1 stop32h 20m

Florence Peretola

Thu 2/5

7:15 pm-3:25 pm

1 stop27h 10m

$403

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sun 4/12

6:00 pm-6:30 pm

1 stop17h 30m

Florence Peretola

Sat 4/18

7:15 pm-4:00 pm

1 stop27h 45m

$411

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Sun 2/1

7:10 pm-10:30 am

1 stop32h 20m

Venice Marco Polo

Sun 2/8

11:05 am-4:55 pm

1 stop12h 50m

$450

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Sat 4/18

7:15 pm-10:10 am

1 stop31h 55m

Venice Marco Polo

Sat 4/25

11:00 am-4:10 pm

1 stop12h 10m

$452

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Mon 2/23

6:00 pm-5:25 pm

1 stop16h 25m

Naples

Thu 3/5

11:20 am-8:05 pm

2 stops15h 45m

$480

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 1/18

6:00 pm-12:30 pm

1 stop11h 30m

Naples

Mon 2/2

3:05 pm-1:25 pm

2 stops29h 20m

$490

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Tue 4/7

11:25 am-6:20 pm

1 stop23h 55m

Bologna Guglielmo Marconi

Wed 4/15

7:20 pm-9:40 am

1 stop21h 20m

$515

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Tue 2/17

9:45 pm-9:40 pm

1 stop16h 55m

Bologna Guglielmo Marconi

Tue 2/24

7:20 am-1:50 pm

1 stop13h 30m

$516

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Tue 4/7

7:50 pm-9:30 am

1 stop30h 40m

Bologna Guglielmo Marconi

Wed 4/15

7:20 pm-6:15 pm

1 stop29h 55m

$525

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Tue 2/17

4:01 pm-9:40 pm

2 stops22h 39m

Bologna Guglielmo Marconi

Tue 2/24

7:20 am-7:17 pm

2 stops18h 57m

$536

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 Italy from

How to get the cheapest flight ticket from Chicago to Italy

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 Italy?

The cheapest month to fly to Italy from Chicago is in November. Flight prices, which tend to average around $570, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of November, then book flights to Italy from Chicago during January instead. Flights to Italy in January, while not as cheap as those in November, still average around $582.

What is the cheapest day to depart on your flight to Italy?

According to our data, Monday is the cheapest day to fly to Italy from Chicago. The lowest ticket price found for a Monday departure recently was $908. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Italy for around $1,022.

What is the cheapest Chicago to Italy flight route?

Fly from Chicago O'Hare Intl to Rome Fiumicino for the best Chicago - Italy flight prices

How far in advance should I book a flight to Italy?

You are more likely to see cheaper flights to Italy from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Italy for around $801 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Italy from Chicago for as low as $773 on momondo.

What cabin class options are available on Chicago to Italy flights?

There are 3 cabin classes available to choose from on Chicago to Italy flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Italy flights?

No. A direct flight is the cheapest option for a flight between Chicago to Italy.

Cheap Chicago to Italy flight deals and tips

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

Best Price Found

$563

Fastest flight time

8h 40m

Direct flights

Every day

Airports in Italy

416 airports
The best one-way flight to Italy from Chicago in the past 72 hours is $563. The best round-trip flight deal from Chicago to Italy found on momondo in the last 72 hours is $786.
The fastest flight from Chicago to Italy takes 8h 40m
Direct flights go from Chicago to Italy every day.
There are 416 airports in Italy. From Chicago there are direct flights to Rome Fiumicino (FCO), Milan Malpensa (MXP).
Search flight deals

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

    Prices for flights from Chicago to Italy refresh daily.

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

  • How old do you have to be to fly from Chicago to Italy?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Italy.

  • What documentation or ID do you need to fly to Italy?

    The travel and health documents you'll need for your trip to Italy may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Italy. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Italy?

Best airlines flying from Chicago to Italy

Compare and see reviews for airlines that fly from Chicago to Italy with momondo
Airline
Rating
Free Cancellation
Price
IberiaPriceFrom $230Free CancellationRating
7.0
3,058 reviews
Search Iberia flights
TAP AIR PORTUGALPriceFrom $337Free CancellationRating
7.1
2,102 reviews
Search TAP AIR PORTUGAL flights
Air CanadaPriceFrom $390Free CancellationRating
7.1
10,571 reviews
Search Air Canada flights
IcelandairPriceFrom $392Free CancellationRating
7.1
593 reviews
Search Icelandair flights
Scandinavian AirlinesPriceFrom $414Free CancellationRating
7.4
1,627 reviews
Search Scandinavian Airlines flights
SWISSPriceFrom $414Free CancellationRating
7.5
1,830 reviews
Search SWISS flights
KLMPriceFrom $455Free CancellationRating
7.7
1,435 reviews
Search KLM flights
Air FrancePriceFrom $458Free CancellationRating
7.4
1,514 reviews
Search Air France flights
British AirwaysPriceFrom $459Free CancellationRating
6.7
7,632 reviews
Search British Airways flights
DeltaPriceFrom $481Free CancellationRating
7.9
8,011 reviews
Search Delta flights

Why use momondo?

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

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 Italy from Chicago.

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

All flight searches from Chicago to Italy on momondo can be filtered to show those which offer flexible booking policies.

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

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

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

If you are not ready to book a flight from Chicago to Italy now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Italy and let you know when they change.

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Find better results for your trip to Italy

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