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$198+ Cheap flights from Chicago (CHI) to Italy

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Oct 26 — Nov 21
Sun 10/26
Sun 11/2
1 adult, Economy
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Cheap flight deals from Chicago to Italy

Keep the following information in mind while searching for Chicago to Italy flight deals. Data was last updated September 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$438
(oojo)

One-way from

$198
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$849

Good round-trip deal

$665 or less

Good one-way deal

$468 or less
Provider with most accurate pricing for Chicago (CHI)-Rome (ROM) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Rome (ROM) flights.
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From Chicago (CHI) to Italy
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One-way flight from Chicago (CHI) to Italy
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Highest demand for flights based on searches. 22% potential increase in price ($224 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Italy.
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Price to beat on a one-way flight from Chicago (CHI) to Italy.
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Find flight deals from Chicago to Italy

Cheapest flights from Chicago to Italy
Explore the most affordable flight options available from Chicago to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 26, 2025.

This oojo deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/57:10 pmORD - FCO
1 stop21h 55mTAP AIR PORTUGAL
Fri 11/146:00 amFCO - ORD
1 stop16h 15mTAP AIR PORTUGAL
Deal found 9/25$440
This Trip.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:40 amORD - FCO
1 stop24h 50mMultiple Airlines
Mon 11/177:10 pmFCO - ORD
1 stop24h 35mMultiple Airlines
Deal found 9/26$441
This oojo deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:30 pmORD - FCO
1 stop12h 30mIcelandair
Sat 11/1511:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 9/26$443
This FlightHub deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:30 pmORD - FCO
1 stop12h 30mIcelandair
Thu 11/1311:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 9/25$446
This oojo deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/168:25 pmORD - FCO
1 stop15h 20mTAP AIR PORTUGAL
Thu 11/207:35 pmFCO - ORD
1 stop26h 40mTAP AIR PORTUGAL
Deal found 9/26$448
This FlightHub deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/28:25 pmORD - FCO
1 stop20h 40mTAP AIR PORTUGAL
Sat 11/87:35 pmFCO - ORD
1 stop26h 10mTAP AIR PORTUGAL
Deal found 9/25$450
This Icelandair deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:30 pmORD - FCO
1 stop12h 30mIcelandair
Wed 12/1711:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 9/24$454
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:40 amORD - FCO
1 stop24h 50mMultiple Airlines
Thu 11/137:10 pmFCO - ORD
1 stop24h 35mMultiple Airlines
Deal found 9/25$459
This oojo deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:30 pmORD - FCO
1 stop12h 30mIcelandair
Wed 11/511:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 9/23$460
This oojo deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:10 pmORD - FCO
1 stop33h 15mTAP AIR PORTUGAL
Tue 12/237:35 pmFCO - ORD
1 stop26h 25mTAP AIR PORTUGAL
Deal found 9/24$461
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/84:23 pmMDW - FCO
1 stop35h 07mDelta
Fri 11/2110:05 amFCO - MDW
1 stop30h 46mDelta
Deal found 9/25$480
This Air France deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/141:08 pmMDW - FCO
1 stop13h 12mMultiple Airlines
Thu 11/1310:05 amFCO - MDW
1 stop15h 03mMultiple Airlines
Deal found 9/24$482

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated September 26, 2025.
Use the filters below to find and compare flights from Chicago to Italy that are best for you.

Fly from

Chicago

Fly to

Italy

Route

Depart

Return

Price

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 11/23

2:50 pm-9:00 am

1 stop11h 10m

Rome Fiumicino

Fri 12/5

11:00 am-10:54 pm

1 stop18h 54m

$490

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 12/3

9:34 am-10:30 am

2 stops17h 56m

Rome Fiumicino

Thu 12/11

12:40 pm-11:32 pm

1 stop17h 52m

$495

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 12/10

6:00 am-7:05 am

2 stops18h 05m

Rome Fiumicino

Tue 12/23

10:05 am-5:20 pm

1 stop14h 15m

$495

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Tue 11/18

3:50 pm-10:45 am

1 stop11h 55m

Bergamo Orio Al Serio

Tue 11/25

5:45 am-2:00 pm

1 stop15h 15m

$498

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 10/27

1:25 pm-8:45 am

2 stops13h 20m

Rome Fiumicino

Tue 11/4

9:55 am-3:10 pm

1 stop12h 15m

$507

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 11/5

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Fri 11/14

7:05 am-3:20 pm

1 stop15h 15m

$512

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 11/11

10:47 am-10:30 am

1 stop16h 43m

Rome Fiumicino

Wed 11/19

6:00 am-6:08 pm

2 stops19h 08m

$512

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 12/2

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Thu 12/11

9:45 am-1:10 pm

Nonstop10h 25m

$516

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 10/15

12:55 pm-8:15 am

1 stop12h 20m

Rome Fiumicino

Tue 11/11

9:45 am-9:16 pm

2 stops18h 31m

$526

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 12/10

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Mon 12/22

8:15 pm-4:20 pm

1 stop27h 05m

$527

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Italy

Have a flexible travel schedule? Discover the best time to fly to Italy from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Italy

What is the cheapest month to book a flight from Chicago to Italy?

Currently, January is the cheapest month in which you can book a flight from Chicago to Italy (average of $703). Flying from Chicago to Italy in June is currently the most expensive (average of $1,199). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to IT?

Find hourly flight availability from Chicago to Italy. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 26, 2025.

When flying from Chicago to Italy, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Italy

Explore weekly flight availability from Chicago to Italy. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 26, 2025.

The most flights from CHI to IT0 are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Italy

Get insights into the airlines that provide service to Italy. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Italy. Reviews last updated September 26, 2025.
Peruse reviews from past customers who have flown with United Airlines, Turkish Airlines, and American Airlines from Chicago to Italy to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,926 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
Turkish Airlines
7.3
Good
3,977 reviews
United Airlines
7.4
Good
8,926 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,926 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
Lufthansa
6.8
Okay
7,428 reviews
United Airlines
7.4
Good
8,926 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
ITA Airways
6.7
Okay
1,048 reviews
United Airlines
7.4
Good
8,926 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Italy. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Italy?

    Delta, Air France, and United Airlines can get you from Chicago to Italy in just under 9h. Your travel time can differ by up to 8h 56m. Chicago and Italy are separated by a distance of 4808 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Chicago to Italy?

    Most travelers choose Chicago O'Hare Intl - Rome Fiumicino, Chicago Midway - Rome Fiumicino or Chicago O'Hare Intl - Milan Malpensa when deciding on the best route from Chicago to Italy.

  • What are the cheapest flights from Chicago to Italy?

    Looking at all options, your cheapest flight can be booked for $474. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $335 on average, our data indicates $798 when flying from Chicago to Italy.

  • Can I find deals for flights from Chicago to Italy that include hotel bookings?

    Yes. In addition to deals on Chicago to Italy flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Italy?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Italy.

  • Can I find deals for business class flights from Chicago to Italy?

    Yes. Cheapflights offers flight deals from Chicago to Italy by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Italy?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Italy (average of $703). Flying from Chicago to Italy in June is currently the most expensive (average of $1,199). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Italy

See prices for flight routes from nearby airports that may be better suited for you.
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Top 10 airlines flying from Chicago to Italy

Discover the top 10 airlines that operate flights from Chicago to Italy. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$357Average$659FlexibilityNo cancel feeOn-timeN/A
IcelandairCheapest$380Average$650FlexibilityNo cancel feeOn-time76%
SWISSCheapest$413Average$1,068FlexibilityNo cancel feeOn-time79%
Scandinavian AirlinesCheapest$414Average$563FlexibilityNo cancel feeOn-time77%
DeltaCheapest$419Average$1,064FlexibilityNo cancel feeOn-timeN/A
IberiaCheapest$430Average$1,177FlexibilityNo cancel feeOn-time77%
Air FranceCheapest$458Average$907FlexibilityNo cancel feeOn-time77%
Turkish AirlinesCheapest$488Average$655FlexibilityNo cancel feeOn-time77%
KLMCheapest$491Average$829FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$496Average$1,002FlexibilityNo cancel feeOn-time69%

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