HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Italy

$207+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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 July 29, 2025.

Round-trip from

$506
(FlightHub)

One-way from

$207
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$941

Good round-trip deal

$728 or less

Good one-way deal

$399 or less
From Chicago (CHI) to Italy
Search Deals
One-way flight from Chicago (CHI) to Italy
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($232 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Italy.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Italy.
Search Deals

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 July 29, 2025.

This oojo deal was found by Cheapflights users on 7/29. 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 11/207:20 pmORD - MXP
1 stop32h 05mScandinavian Airlines
Sun 11/308:00 pmMXP - ORD
1 stop27h 45mScandinavian Airlines
Deal found 7/29$506
This FlightHub deal was found by Cheapflights users on 7/27. 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.
Wed 8/1311:25 amORD - MXP
1 stop23h 45mTurkish Airlines
Tue 8/268:10 pmMXP - ORD
1 stop32h 50mTurkish Airlines
Deal found 7/27$507
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/172:00 pmORD - MXP
2 stops18h 25mMultiple Airlines
Wed 9/2410:50 pmMXP - ORD
2 stops25h 43mMultiple Airlines
Deal found 7/28$508
This oojo deal was found by Cheapflights users on 7/29. 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 10/96:00 pmORD - MXP
1 stop15h 25mTAP AIR PORTUGAL
Sat 10/258:15 pmMXP - ORD
1 stop26h 45mTAP AIR PORTUGAL
Deal found 7/29$512
This oojo deal was found by Cheapflights users on 7/26. 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 10/127:15 pmORD - LIN
2 stops33h 55mScandinavian Airlines
Wed 10/221:00 pmLIN - ORD
2 stops34h 10mScandinavian Airlines
Deal found 7/26$518
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/109:50 pmORD - FCO
2 stops20h 05mMultiple Airlines
Sun 11/235:45 amFCO - ORD
2 stops20h 45mMultiple Airlines
Deal found 7/29$525
This Air Canada deal was found by Cheapflights users on 7/29. 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 Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/237:15 amORD - FCO
1 stop18h 40mAir Canada
Tue 12/29:45 amFCO - ORD
2 stops16h 45mAir Canada
Deal found 7/29$526
This oojo deal was found by Cheapflights users on 7/29. 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 8/107:25 pmORD - FCO
1 stop12h 10mIcelandair
Tue 8/193:45 pmFCO - ORD
1 stop33h 30mIcelandair
Deal found 7/29$527
This oojo deal was found by Cheapflights users on 7/29. 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 10/197:15 pmORD - FCO
1 stop32h 50mScandinavian Airlines
Tue 10/287:50 pmFCO - ORD
2 stops31h 15mScandinavian Airlines
Deal found 7/29$528
This Iberia deal was found by Cheapflights users on 7/28. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/112:44 pmORD - FCO
1 stop13h 36mIberia
Thu 8/286:25 amFCO - ORD
1 stop14h 05mIberia
Deal found 7/28$529
This Justfly.com deal was found by Cheapflights users on 7/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/147:50 pmORD - FCO
1 stop30h 30mTurkish Airlines
Thu 9/253:30 pmFCO - ORD
1 stop25h 10mTurkish Airlines
Deal found 7/29$531
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/63:50 pmORD - FCO
Nonstop9h 05mUnited Airlines
Fri 8/159:45 amFCO - ORD
Nonstop10h 25mUnited Airlines
Deal found 7/28$534

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 July 29, 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

Tue 9/23

11:25 am-8:45 am

1 stop14h 20m

Milan Malpensa

Tue 10/7

8:10 pm-9:40 am

1 stop20h 30m

$506

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 9/17

2:00 pm-3:25 pm

2 stops18h 25m

Milan Malpensa

Wed 9/24

10:50 pm-5:33 pm

2 stops25h 43m

$508

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 10/9

6:00 pm-4:25 pm

1 stop15h 25m

Milan Malpensa

Sat 10/25

8:15 pm-4:00 pm

1 stop26h 45m

$512

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 10/2

7:15 pm-7:55 pm

2 stops17h 40m

Milan Malpensa

Sat 10/18

7:35 pm-4:10 pm

2 stops27h 35m

$514

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 10/12

7:15 pm-12:10 pm

2 stops33h 55m

Milan Linate

Wed 10/22

1:00 pm-4:10 pm

2 stops34h 10m

$518

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 8/10

7:25 pm-2:35 pm

1 stop12h 10m

Rome Fiumicino

Tue 8/19

3:45 pm-6:15 pm

1 stop33h 30m

$527

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 10/19

7:15 pm-7:20 pm

2 stops17h 05m

Rome Fiumicino

Tue 10/28

7:50 pm-9:05 pm

2 stops31h 15m

$528

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 8/11

2:44 pm-11:20 am

1 stop13h 36m

Rome Fiumicino

Thu 8/28

6:25 am-1:30 pm

1 stop14h 05m

$529

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 9/14

7:50 pm-9:20 am

1 stop30h 30m

Rome Fiumicino

Thu 9/25

3:30 pm-9:40 am

1 stop25h 10m

$531

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 8/6

3:50 pm-7:55 am

Nonstop9h 05m

Rome Fiumicino

Fri 8/15

9:45 am-1:10 pm

Nonstop10h 25m

$534

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 60 results
1
2
3
...
6

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 $1,210). 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 July 29, 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 July 29, 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 July 29, 2025.
Peruse reviews from past customers who have flown with Delta, Porter Airlines, and KLM 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.
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Porter Airlines
8.0
Very good
317 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,383 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Transat
7.7
Good
424 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Austrian Airlines
7.6
Good
821 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines to fly from Chicago to Italy one-way?

    $242 is the cheapest one-way deal found within the past few days, from ITA Airways. You may also be able to find cheap deals on TAP AIR PORTUGAL and WestJet, with prices starting from $251 and $258, respectively.

  • 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 $438. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $334 on average our data indicates $726 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 $1,210). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Italy

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Heathrow flights
O'Hare Intl to Charles de Gaulle flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Madrid flights
O'Hare Intl to Dublin flights
O'Hare Intl to Athens flights
O'Hare Intl to Istanbul flights
O'Hare Intl to Orly flights
O'Hare Intl to Gatwick flights
O'Hare Intl to Frederic Chopin flights
O'Hare Intl to Frankfurt flights
O'Hare Intl to London City flights
O'Hare Intl to Barcelona-El Prat flights
O'Hare Intl to Munich flights
Midway to Heathrow flights
O'Hare Intl to Amsterdam flights
O'Hare Intl to Edinburgh flights
O'Hare Intl to Zurich flights
Midway to Charles de Gaulle flights
O'Hare Intl to Stansted flights
Midway to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Malpensa flights
O'Hare Intl to Bruxelles-National flights
O'Hare Intl to Keflavik Intl flights
O'Hare Intl to Luton flights
O'Hare Intl to Krakow flights
O'Hare Intl to Vienna flights
O'Hare Intl to Lisbon flights
Midway to Madrid flights
O'Hare Intl to Sabiha Gokcen flights
O'Hare Intl to Copenhagen flights
Midway to Dublin flights
Midway to Athens flights
O'Hare Intl to Beauvais-Tille flights
Midway to Frederic Chopin flights
O'Hare Intl to Linate flights
O'Hare Intl to Otopeni Intl flights
O'Hare Intl to Sofia flights
Midway to Barcelona-El Prat flights
Midway to Frankfurt flights
O'Hare Intl to Naples flights
Midway to Lisbon flights
St. Louis to Frankfurt flights
O'Hare Intl to Berlin flights
O'Hare Intl to Belgrade flights
O'Hare Intl to Vicenza flights
O'Hare Intl to Oslo Gardermoen flights
Midway to Keflavik Intl flights
St. Louis to Heathrow flights
O'Hare Intl to Glasgow Intl flights

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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
IcelandairCheapest$365Average$647FlexibilityNo cancel feeOn-time76%
TAP AIR PORTUGALCheapest$374Average$594FlexibilityNo cancel feeOn-timeN/A
SWISSCheapest$413Average$1,061FlexibilityNo cancel feeOn-time79%
Scandinavian AirlinesCheapest$414Average$585FlexibilityNo cancel feeOn-time77%
DeltaCheapest$419Average$1,026FlexibilityNo cancel feeOn-timeN/A
KLMCheapest$455Average$719FlexibilityNo cancel feeOn-time75%
Air FranceCheapest$458Average$876FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$497Average$857FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$500Average$688FlexibilityNo cancel feeOn-time67%
Aer LingusCheapest$506Average$851FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.