Cheap flights from Italy to Chicago from $306

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 10/21. 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 Italy to Chicago

Recent round-trip flight deals from Italy to Chicago

TAP AIR PORTUGAL Logo
11:50 am - 10:55 amMXP-ORD
30h 05m1 stop
TAP AIR PORTUGAL Logo
6:10 pm - 12:45 amORD-MXP
23h 35m1 stop
$440TAP AIR PORTUGAL
Find Deal
Wed, Sep 10 - Mon, Sep 22
TAP AIR PORTUGAL Logo
11:50 am - 10:55 amMXP-ORD
30h 05m1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 12:45 amORD-MXP
23h 45m1 stop
$441TAP AIR PORTUGAL
Find Deal
Wed, Sep 17 - Sun, Sep 21
United Airlines Logo
7:00 am - 2:55 pmFCO-ORD
14h 55m1 stop
United Airlines Logo
10:40 am - 9:15 amORD-FCO
15h 35m1 stop
$529United Airlines
Find Deal
Mon, Sep 1 - Mon, Sep 8
United Airlines Logo
7:10 am - 2:55 pmFCO-ORD
14h 45m1 stop
United Airlines Logo
8:40 am - 9:15 amORD-FCO
17h 35m1 stop
$530United Airlines
Find Deal
Sun, Aug 24 - Thu, Sep 11
American Airlines Logo
3:00 pm - 6:50 pmNAP-ORD
10h 50mnonstop
American Airlines Logo
10:35 pm - 10:00 pmORD-NAP
16h 25m1 stop
$539American Airlines
Find Deal
Fri, Sep 5 - Sat, Sep 13
American Airlines Logo
3:00 pm - 6:50 pmNAP-ORD
10h 50mnonstop
American Airlines Logo
10:35 pm - 7:25 pmORD-NAP
13h 50m1 stop
$540American Airlines
Find Deal
Mon, Oct 6 - Sun, Oct 12
British Airways Logo
12:00 pm - 6:50 pmNAP-ORD
13h 50m1 stop
British Airways Logo
10:35 pm - 10:00 pmORD-NAP
16h 25m1 stop
$542British Airways
Find Deal
Fri, Sep 5 - Sat, Sep 13
British Airways Logo
12:00 pm - 5:20 pmNAP-ORD
36h 20m1 stop
British Airways Logo
4:55 pm - 10:00 pmORD-NAP
22h 05m1 stop
$545British Airways
Find Deal
Mon, Aug 25 - Mon, Sep 1
Iberia Logo
11:05 am - 2:30 pmFCO-ORD
10h 25mnonstop
Iberia Logo
5:00 pm - 9:10 amORD-FCO
9h 10mnonstop
$551Iberia
Find Deal
Mon, Aug 25 - Sun, Sep 7
Iberia Logo
11:05 am - 2:30 pmFCO-ORD
10h 25mnonstop
Iberia Logo
5:00 pm - 9:10 amORD-FCO
9h 10mnonstop
$573Iberia
Find Deal
Mon, Aug 25 - Sun, Sep 7

TAP AIR PORTUGAL flights from Italy to Chicago O'Hare Intl Airport

Our best TAP AIR PORTUGAL deals on Italy to Chicago O'Hare Intl Airport flight tickets
TAP AIR PORTUGAL
Sep 10
MXP11:50 amMilan Malpensa
30h 05m
1 stop
ORD10:55 amChicago O'Hare Intl
Sep 22
ORD6:10 pmChicago O'Hare Intl
23h 35m
1 stop
MXP12:45 amMilan Malpensa
TAP AIR PORTUGAL
Sep 17
MXP11:50 amMilan Malpensa
30h 05m
1 stop
ORD10:55 amChicago O'Hare Intl
Sep 21
ORD6:00 pmChicago O'Hare Intl
23h 45m
1 stop
MXP12:45 amMilan Malpensa
TAP AIR PORTUGAL
Sep 17
MXP8:15 pmMilan Malpensa
21h 40m
1 stop
ORD10:55 amChicago O'Hare Intl
Sep 21
ORD6:00 pmChicago O'Hare Intl
18h 15m
1 stop
MXP7:15 pmMilan Malpensa

American Airlines flights from Italy to Chicago O'Hare Intl Airport

Our best American Airlines deals on Italy to Chicago O'Hare Intl Airport flight tickets
American Airlines
Sep 5
NAP3:00 pmNaples
10h 50m
ORD6:50 pmChicago O'Hare Intl
Sep 13
ORD10:35 pmChicago O'Hare Intl
16h 25m
1 stop
NAP10:00 pmNaples
American Airlines
Oct 6
NAP3:00 pmNaples
10h 50m
ORD6:50 pmChicago O'Hare Intl
Oct 12
ORD10:35 pmChicago O'Hare Intl
13h 50m
1 stop
NAP7:25 pmNaples
American Airlines
Sep 5
NAP3:00 pmNaples
10h 50m
ORD6:50 pmChicago O'Hare Intl
Sep 13
ORD8:40 pmChicago O'Hare Intl
18h 20m
1 stop
NAP10:00 pmNaples

momondo Fare Finder

 
Customize your flight search to find flights from Italy 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 August 4, 2025.
Use the filters below to find and compare flights from Italy to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 9/10

11:50 am-10:55 am

1 stop30h 05m

Chicago O'Hare Intl

Mon 9/22

6:10 pm-12:45 am

1 stop23h 35m

$440

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 9/17

11:50 am-10:55 am

1 stop30h 05m

Chicago O'Hare Intl

Sun 9/21

6:00 pm-12:45 am

1 stop23h 45m

$441

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 9/1

7:00 am-2:55 pm

1 stop14h 55m

Chicago O'Hare Intl

Mon 9/8

10:40 am-9:15 am

1 stop15h 35m

$529

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Sun 8/24

7:10 am-2:55 pm

1 stop14h 45m

Chicago O'Hare Intl

Thu 9/11

8:40 am-9:15 am

1 stop17h 35m

$530

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 9/5

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

Sat 9/13

10:35 pm-10:00 pm

1 stop16h 25m

$539

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 10/6

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

Sun 10/12

10:35 pm-7:25 pm

1 stop13h 50m

$540

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 9/5

12:00 pm-6:50 pm

1 stop13h 50m

Chicago O'Hare Intl

Sat 9/13

10:35 pm-10:00 pm

1 stop16h 25m

$542

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 8/25

12:00 pm-5:20 pm

1 stop36h 20m

Chicago O'Hare Intl

Mon 9/1

4:55 pm-10:00 pm

1 stop22h 05m

$545

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 8/25

11:05 am-2:30 pm

Nonstop10h 25m

Chicago O'Hare Intl

Sun 9/7

5:00 pm-9:10 am

Nonstop9h 10m

$551

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 8/25

11:05 am-2:30 pm

Nonstop10h 25m

Chicago O'Hare Intl

Sun 9/7

5:00 pm-9:10 am

Nonstop9h 10m

$573

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 Italy 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 month to fly to Chicago O'Hare Intl Airport?

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Italy averaging around $605.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $746. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Italy because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $923.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Italy in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $655 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $863. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Italy to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Italy when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $751 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Italy for as low as $467 on momondo.

What cabin class options are available on Italy to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Italy to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

You could potentially save up to 4% on your flight if you consider stops on a Italy to Chicago O'Hare Intl Airport flight.

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

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

Best Price Found

$306

Fastest flight time

9h 50m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Italy in the past 72 hours is $306. The best round-trip flight deal from Italy to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $440.
The fastest flight from Italy to Chicago O'Hare Intl Airport takes 9h 50m
Direct flights go from Italy to Chicago O'Hare Intl Airport every day.

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

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

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

  • How old do you have to be to fly from Italy 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 Italy 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.

  • What is the most popular plane model from Italy to Chicago O'Hare Intl Airport?


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

Compare and see reviews for airlines that fly from Italy to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
British AirwaysPriceFrom $525Free CancellationRating
6.6
7,235 reviews
Search British Airways flights
American AirlinesPriceFrom $536Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
IberiaPriceFrom $550Free CancellationRating
7.0
2,865 reviews
Search Iberia flights
United AirlinesPriceFrom $611Free CancellationRating
7.4
8,912 reviews
Search United Airlines flights
LufthansaPriceFrom $639Free CancellationRating
6.8
7,285 reviews
Search Lufthansa flights
ITA AirwaysPriceFrom $658Free CancellationRating
6.7
1,011 reviews
Search ITA Airways flights

Traveling to a place near Chicago?

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

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Italy to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo allows you to filter the results for Italy to Chicago flights to just show those with flexible booking policies.

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

Once you have performed a search for Italy to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Chicago from Italy are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


An easier way to manage your Chicago O'Hare Intl Airport 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
Sat 8/9
Sat 8/16

Find better results for your trip to Chicago