$200+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Dec 6 — Dec 131
1 adult, Economy
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Find cheap flights from Chicago to Italy with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 November 6, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $405 (Icelandair) |
One-way from | $200 (Mytrip) |
Popular in | June |
Cheapest in | November |
Average price | $577 |
Good round-trip deal | $761 or less |
Good one-way deal | $481 or less |
Find flight deals from Chicago to Italy
Cheapest flights from Chicago to ItalyExplore 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 November 6, 2025.
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 November 6, 2025.
This Icelandair deal was found by Cheapflights users on 11/5. 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.
Thu 11/276:30 pmORD - FCO
1 stop12h 30mIcelandair
Mon 12/1511:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 11/5![Icelandair logo]()
$405
This oojo deal was found by Cheapflights users on 11/6. 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 stop20h 40mTAP AIR PORTUGAL
Tue 11/257:35 pmFCO - ORD
1 stop26h 25mTAP AIR PORTUGAL
Deal found 11/6![TAP AIR PORTUGAL logo]()
$407
This oojo deal was found by Cheapflights users on 11/5. 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 11/127:10 pmORD - FCO
1 stop13h 40mTAP AIR PORTUGAL
Thu 11/207:35 pmFCO - ORD
1 stop26h 50mTAP AIR PORTUGAL
Deal found 11/5![TAP AIR PORTUGAL logo]()
$408
This Gotogate deal was found by Cheapflights users on 11/5. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:30 pmORD - FCO
1 stop12h 30mIcelandair
Thu 12/1111:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 11/5![Icelandair logo]()
$411
This oojo deal was found by Cheapflights users on 11/5. 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 11/5![TAP AIR PORTUGAL logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Wed 12/37:10 pmORD - FCO
1 stop13h 40mTAP AIR PORTUGAL
Fri 12/126:00 amFCO - ORD
1 stop16h 25mTAP AIR PORTUGAL
Deal found 11/6![TAP AIR PORTUGAL logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sun 11/308:25 pmORD - FCO
1 stop15h 20mTAP AIR PORTUGAL
Fri 12/126:00 amFCO - ORD
1 stop16h 25mTAP AIR PORTUGAL
Deal found 11/6![TAP AIR PORTUGAL logo]()
$418
This Icelandair deal was found by Cheapflights users on 11/5. 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.
Mon 11/176:30 pmORD - FCO
1 stop12h 30mIcelandair
Mon 11/2411:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 11/5![Icelandair logo]()
$425
This lol.travel deal was found by Cheapflights users on 11/5. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/167:10 amORD - MXP
2 stops29h 00mScandinavian Airlines
Tue 12/28:00 pmMXP - ORD
1 stop27h 45mScandinavian Airlines
Deal found 11/5![Scandinavian Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Fri 11/148:15 pmORD - FCO
1 stop32h 10mTAP AIR PORTUGAL
Sat 11/227:35 pmFCO - ORD
1 stop26h 10mTAP AIR PORTUGAL
Deal found 11/4![TAP AIR PORTUGAL logo]()
$426
This oojo deal was found by Cheapflights users on 11/4. 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 stop20h 40mTAP AIR PORTUGAL
Sun 11/235:45 amFCO - ORD
1 stop16h 00mTAP AIR PORTUGAL
Deal found 11/4![TAP AIR PORTUGAL logo]()
$428
This Trip.com deal was found by Cheapflights users on 11/5. 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.
Sun 11/98:25 pmORD - FCO
1 stop15h 20mTAP AIR PORTUGAL
Tue 11/2512:15 pmFCO - ORD
1 stop33h 45mTAP AIR PORTUGAL
Deal found 11/5![TAP AIR PORTUGAL logo]()
$432
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 November 6, 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
ChicagoMilan
ORD - MXP
ORDMXP
Chicago O'Hare Intl
Fri 12/5
7:20 pm-8:25 am
1 stop30h 05m
Milan Malpensa
Wed 12/10
8:00 pm-4:45 pm
1 stop27h 45m
$467
ChicagoMilan
ORD - MXP
ORDMXP
Chicago O'Hare Intl
Fri 1/9
7:20 pm-12:55 pm
2 stops34h 35m
Milan Malpensa
Thu 4/23
8:40 pm-4:10 pm
2 stops26h 30m
$475
ChicagoMilan
ORD - MXP
ORDMXP
Chicago O'Hare Intl
Thu 11/27
7:20 pm-7:10 pm
1 stop16h 50m
Milan Malpensa
Tue 12/2
8:00 pm-4:45 pm
1 stop27h 45m
$475
ChicagoMilan
ORD - MXP
ORDMXP
Chicago O'Hare Intl
Wed 1/7
7:20 pm-7:40 pm
2 stops17h 20m
Milan Malpensa
Wed 1/14
12:55 pm-4:45 pm
2 stops34h 50m
$480
ChicagoMilan
ORD - MXP
ORDMXP
Chicago O'Hare Intl
Wed 12/3
6:30 pm-8:25 am
2 stops54h 55m
Milan Malpensa
Tue 12/9
11:15 am-9:39 pm
2 stops41h 24m
$492
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Mon 12/8
1:00 pm-1:50 pm
2 stops17h 50m
Naples
Mon 12/15
3:00 pm-4:20 pm
1 stop32h 20m
$495
ChicagoBergamo
ORD - BGY
ORDBGY
Chicago O'Hare Intl
Wed 12/3
6:30 pm-10:10 pm
2 stops20h 40m
Bergamo Orio Al Serio
Sun 12/14
8:00 am-5:20 pm
2 stops16h 20m
$499
ChicagoRome
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Mon 2/2
5:10 pm-12:50 pm
1 stop12h 40m
Rome Fiumicino
Thu 2/19
7:40 am-1:50 pm
1 stop13h 10m
$512
ChicagoRome
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Tue 12/2
3:45 pm-7:45 am
Nonstop9h 00m
Rome Fiumicino
Tue 12/9
7:05 am-1:10 pm
1 stop13h 05m
$517
ChicagoRome
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Wed 12/3
3:45 pm-7:45 am
Nonstop9h 00m
Rome Fiumicino
Tue 12/9
9:45 am-3:20 pm
1 stop12h 35m
$517
Showing 1-10 of 60 results
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 $346). Flying from Chicago to Italy in June is currently the most expensive (average of $722). 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 November 6, 2025.
It’s optimal to fly from Chicago to Italy in the morning. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight at noon.
What is the cheapest day to fly from Chicago to Italy?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Italy. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Chicago to Italy flight should consider departing on Tuesday mornings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 November 6, 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.
Comfort
7.3
Overall
7.4
Crew
8.1
Boarding
7.7
Food
6.6
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreSebrena,Oct 2025
IAH - RSW
Comfort
7.3
Overall
7.4
Crew
8.1
Boarding
7.7
Food
6.6
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreSebrena,Oct 2025
IAH - RSW
Comfort
7.3
Overall
7.4
Crew
8.1
Boarding
7.7
Food
6.6
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreSebrena,Oct 2025
IAH - RSW
Comfort
7.3
Overall
7.4
Crew
8.1
Boarding
7.7
Food
6.6
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreSebrena,Oct 2025
IAH - RSW
Comfort
7.3
Overall
7.4
Crew
8.1
Boarding
7.7
Food
6.6
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreSebrena,Oct 2025
IAH - RSW
Comfort
7.3
Overall
7.4
Crew
8.1
Boarding
7.7
Food
6.6
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreSebrena,Oct 2025
IAH - RSW
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.
Browse thousands of different options on Cheapflights for your next trip
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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.
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 November 6, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$338 | Average$632 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$390 | Average$748 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$392 | Average$641 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$414 | Average$535 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$415 | Average$1,219 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$416 | Average$1,036 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$419 | Average$894 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$458 | Average$791 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$488 | Average$666 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$496 | Average$990 | FlexibilityNo cancel fee | On-time69% |