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Cheap flights from Italy to Chicago from $247

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Italy to Chicago departing on 10/4. 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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Find the cheapest flights from Italy to Chicago

Recent round-trip flight deals from Italy to Chicago

TAP AIR PORTUGAL Logo
7:10 pm - 4:30 pmVCE-ORD
28h 20m1 stop
TAP AIR PORTUGAL Logo
6:15 pm - 10:45 amORD-VCE
33h 30m1 stop
$477TAP AIR PORTUGAL
Find Deal
Thu, Sep 18 - Sat, Oct 4
Scandinavian Airlines Logo
11:20 am - 4:45 pmVCE-ORD
12h 25m1 stop
Scandinavian Airlines Logo
7:20 pm - 10:30 amORD-VCE
32h 10m1 stop
$489Scandinavian Airlines
Find Deal
Fri, Nov 21 - Sun, Nov 23
United Airlines Logo
6:40 am - 2:55 pmNAP-ORD
15h 15m1 stop
United Airlines Logo
2:20 pm - 11:40 amORD-NAP
14h 20m1 stop
$521United Airlines
Find Deal
Fri, Sep 12 - Tue, Sep 16
United Airlines Logo
6:40 am - 7:55 pmNAP-ORD
20h 15m1 stop
United Airlines Logo
5:20 pm - 1:50 pmORD-NAP
14h 30m1 stop
$522United Airlines
Find Deal
Wed, Oct 22 - Mon, Oct 27
British Airways Logo
7:40 am - 3:55 pmNAP-ORD
15h 15m1 stop
British Airways Logo
1:43 pm - 12:00 pmORD-NAP
15h 17m2 stops
$550British Airways
Find Deal
Thu, Oct 2 - Mon, Oct 6
British Airways Logo
7:40 am - 3:55 pmNAP-ORD
15h 15m1 stop
British Airways Logo
4:55 pm - 10:00 pmORD-NAP
22h 05m1 stop
$554British Airways
Find Deal
Thu, Oct 2 - Mon, Oct 6
ITA Airways Logo
7:00 am - 1:10 pmLIN-ORD
13h 10m1 stop
ITA Airways Logo
3:00 pm - 5:10 pmORD-LIN
19h 10m1 stop
$584ITA Airways
Find Deal
Mon, Sep 15 - Sun, Sep 28
Lufthansa Logo
9:45 am - 1:15 pmFCO-ORD
10h 30mnonstop
Lufthansa Logo
3:45 pm - 7:55 amORD-FCO
9h 10mnonstop
$585Lufthansa
Find Deal
Sat, Sep 13 - Sat, Oct 18
Lufthansa Logo
6:15 am - 2:55 pmMXP-ORD
15h 40m1 stop
Lufthansa Logo
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$585Lufthansa
Find Deal
Mon, Sep 15 - Sun, Sep 28
ITA Airways Logo
7:00 am - 1:10 pmLIN-ORD
13h 10m1 stop
ITA Airways Logo
3:00 pm - 11:40 amORD-LIN
13h 40m1 stop
$587ITA Airways
Find Deal
Fri, Sep 26 - Mon, Sep 29

TAP AIR PORTUGAL flights from Italy to Chicago

Our best TAP AIR PORTUGAL deals on Italy to Chicago flight tickets
TAP AIR PORTUGAL
Sep 18
VCE7:10 pmVenice Marco Polo
28h 20m
1 stop
ORD4:30 pmChicago O'Hare Intl
Oct 4
ORD6:15 pmChicago O'Hare Intl
33h 30m
1 stop
VCE10:45 amVenice Marco Polo
$477
Find similar
TAP AIR PORTUGAL
Sep 11
VCE7:10 pmVenice Marco Polo
28h 00m
1 stop
ORD4:10 pmChicago O'Hare Intl
Sep 27
ORD6:15 pmChicago O'Hare Intl
33h 30m
1 stop
VCE10:45 amVenice Marco Polo
$496
Find similar
TAP AIR PORTUGAL
Oct 22
VCE11:40 amVenice Marco Polo
31h 55m
1 stop
ORD12:35 pmChicago O'Hare Intl
Oct 26
ORD9:25 pmChicago O'Hare Intl
13h 35m
1 stop
VCE5:00 pmVenice Marco Polo
$498
Find similar

British Airways flights from Italy to Chicago

Our best British Airways deals on Italy to Chicago flight tickets
British Airways
Oct 2
NAP7:40 amNaples
15h 15m
1 stop
ORD3:55 pmChicago O'Hare Intl
Oct 6
ORD1:43 pmChicago O'Hare Intl
15h 17m
2 stops
NAP12:00 pmNaples
$550
Find similar
British Airways
Sep 5
NAP12:00 pmNaples
13h 50m
1 stop
ORD6:50 pmChicago O'Hare Intl
Sep 13
ORD10:35 pmChicago O'Hare Intl
16h 25m
1 stop
NAP10:00 pmNaples
$552
Find similar
British Airways
Oct 2
NAP7:40 amNaples
15h 15m
1 stop
ORD3:55 pmChicago O'Hare Intl
Oct 6
ORD4:55 pmChicago O'Hare Intl
22h 05m
1 stop
NAP10:00 pmNaples
$554
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Italy 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 August 28, 2025.
Use the filters below to find and compare flights from Italy to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Thu 9/18

7:10 pm-4:30 pm

1 stop28h 20m

Chicago O'Hare Intl

Sat 10/4

6:15 pm-10:45 am

1 stop33h 30m

$477

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Fri 11/21

11:20 am-4:45 pm

1 stop12h 25m

Chicago O'Hare Intl

Sun 11/23

7:20 pm-10:30 am

1 stop32h 10m

$489

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 9/12

6:40 am-2:55 pm

1 stop15h 15m

Chicago O'Hare Intl

Tue 9/16

2:20 pm-11:40 am

1 stop14h 20m

$521

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 10/22

6:40 am-7:55 pm

1 stop20h 15m

Chicago O'Hare Intl

Mon 10/27

5:20 pm-1:50 pm

1 stop14h 30m

$522

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 10/2

7:40 am-3:55 pm

1 stop15h 15m

Chicago O'Hare Intl

Mon 10/6

1:43 pm-12:00 pm

2 stops15h 17m

$550

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 10/2

7:40 am-3:55 pm

1 stop15h 15m

Chicago O'Hare Intl

Mon 10/6

4:55 pm-10:00 pm

1 stop22h 05m

$554

MilanChicago

LIN - ORD

LINORD

Milan Linate

Mon 9/15

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Sun 9/28

3:00 pm-5:10 pm

1 stop19h 10m

$584

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Sat 9/13

9:45 am-1:15 pm

Nonstop10h 30m

Chicago O'Hare Intl

Sat 10/18

3:45 pm-7:55 am

Nonstop9h 10m

$585

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 9/15

6:15 am-2:55 pm

1 stop15h 40m

Chicago O'Hare Intl

Sun 9/28

9:35 pm-1:20 pm

Nonstop8h 45m

$585

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 9/26

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Mon 9/29

3:00 pm-11:40 am

1 stop13h 40m

$587

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 Italy 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 Italy, with most prices found around $594. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Italy to Chicago during April average around $611.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $740. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Italy to Chicago for around $864.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Italy to Chicago during this time can be as low as $748. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $777.

What is the cheapest Italy to Chicago flight route?

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

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

You are more likely to see cheaper flights to Chicago from Italy when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $743 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Italy for as low as $467 on momondo.

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

There are 4 cabin classes available to choose from on Italy to Chicago 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 Italy to Chicago flights?

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

Cheap Italy to Chicago flight deals and tips

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

Best Price Found

$715

Fastest flight time

9h 50m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Italy in the past 72 hours is $715. The best round-trip flight deal from Italy to Chicago found on momondo in the last 72 hours is $683.
The fastest flight from Italy to Chicago takes 9h 50m
Direct flights go from Italy to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

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

    Prices for flights from Italy to Chicago are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Italy to Chicago.

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

    The travel and health documents you'll need for your trip to Chicago 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 Chicago. 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 Italy to Chicago?

Best airlines flying from Italy to Chicago

Compare and see reviews for airlines that fly from Italy to Chicago with momondo
Airline
Rating
Free Cancellation
Price
British AirwaysPriceFrom $525Free CancellationRating
6.7
7,316 reviews
Search British Airways flights
American AirlinesPriceFrom $536Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
IberiaPriceFrom $550Free CancellationRating
7.0
2,892 reviews
Search Iberia flights
United AirlinesPriceFrom $611Free CancellationRating
7.4
8,944 reviews
Search United Airlines flights
ITA AirwaysPriceFrom $658Free CancellationRating
6.7
1,024 reviews
Search ITA Airways 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

Finding the right flight to Chicago from Italy 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 Italy to Chicago with flexible booking policies on momondo?

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

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

Once all potential Italy to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes momondo offers price alerts on flights to Chicago from Italy. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices 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