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$231+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap 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 December 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/319:50 pmORD - FCO
1 stop13h 25mLufthansa
Tue 1/137:00 amFCO - ORD
1 stop14h 10mLufthansa
Deal found 12/22$489
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/316:50 pmORD - FCO
1 stop12h 10mSWISS
Mon 1/122:50 pmFCO - ORD
1 stop32h 30mSWISS
Deal found 12/22$511
This Mytrip deal was found by Cheapflights users on 12/22. 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 12/317:05 amORD - FCO
1 stop19h 15mMultiple Airlines
Tue 1/137:00 amFCO - ORD
2 stops17h 48mMultiple Airlines
Deal found 12/22$514
This Mytrip deal was found by Cheapflights users on 12/22. 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 12/3112:50 pmORD - FCO
1 stop13h 30mMultiple Airlines
Mon 1/122:50 pmFCO - ORD
1 stop32h 30mMultiple Airlines
Deal found 12/22$518
This oojo deal was found by Cheapflights users on 12/22. 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 12/318:25 amORD - FCO
1 stop19h 20mBritish Airways
Mon 1/125:50 pmFCO - ORD
2 stops30h 57mBritish Airways
Deal found 12/22$523
This Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:50 pmORD - FCO
1 stop12h 10mSWISS
Thu 1/88:15 pmFCO - ORD
2 stops24h 55mSWISS
Deal found 12/21$529
This Delta deal was found by Cheapflights users on 12/22. 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.
Wed 12/313:29 pmMDW - FCO
1 stop12h 01mDelta
Tue 1/136:10 amFCO - MDW
2 stops19h 22mDelta
Deal found 12/22$538
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:45 pmORD - FCO
2 stops14h 40mLufthansa
Mon 1/122:20 pmFCO - ORD
2 stops30h 50mLufthansa
Deal found 12/22$540
This United Airlines deal was found by Cheapflights users on 12/22. 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 12/3112:09 pmORD - FCO
2 stops15h 51mUnited Airlines
Tue 1/137:00 amFCO - ORD
2 stops18h 37mUnited Airlines
Deal found 12/22$544
This KAYAK deal was found by Cheapflights users on 12/22. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:50 pmORD - FCO
1 stop17h 35mSWISS
Thu 1/88:15 pmFCO - ORD
2 stops24h 55mSWISS
Deal found 12/22$552
This KAYAK deal was found by Cheapflights users on 12/22. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/285:50 pmORD - FCO
2 stops31h 50mSWISS
Thu 1/88:15 pmFCO - ORD
2 stops24h 55mSWISS
Deal found 12/22$559
This Ovago deal was found by Cheapflights users on 12/21. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:20 pmORD - MXP
1 stop16h 50mScandinavian Airlines
Fri 1/911:15 amMXP - ORD
1 stop12h 30mScandinavian Airlines
Deal found 12/21$829

Find flight deals from Chicago to Italy

Keep the following information in mind while searching for Chicago to Italy flight deals. Data was last updated December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$413
(Flightnetwork)

One-way from

$231
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$663

Good round-trip deal

$764 or less

Good one-way deal

$542 or less
Provider with most accurate pricing for Chicago (CHI)-Rome (ROM) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Rome (ROM) flights.
Search Deals
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 ($235 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 December 23, 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

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Fri 1/16

7:20 pm-10:15 am

1 stop31h 55m

Venice Marco Polo

Thu 1/29

11:20 am-4:55 pm

1 stop12h 35m

$445

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Sun 1/25

7:10 pm-7:20 pm

1 stop17h 10m

Bologna Guglielmo Marconi

Sun 2/8

8:00 pm-4:45 pm

1 stop27h 45m

$471

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Fri 4/10

6:00 pm-6:15 pm

1 stop17h 15m

Venice Marco Polo

Sat 4/18

7:10 pm-4:00 pm

1 stop27h 50m

$495

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Sun 1/18

8:25 pm-5:00 pm

1 stop13h 35m

Venice Marco Polo

Tue 2/3

5:50 pm-3:00 pm

1 stop28h 10m

$498

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 2/4

7:20 pm-8:25 am

1 stop30h 05m

Milan Malpensa

Sun 2/8

10:00 pm-4:45 pm

1 stop25h 45m

$498

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Wed 2/4

6:59 pm-10:30 am

2 stops32h 31m

Venice Marco Polo

Thu 2/12

11:20 am-4:45 pm

1 stop12h 25m

$508

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 3/9

4:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Tue 3/17

9:45 am-2:10 pm

Nonstop10h 25m

$522

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Thu 4/30

11:25 am-9:30 am

1 stop15h 05m

Bologna Guglielmo Marconi

Tue 5/5

7:20 pm-9:40 am

1 stop21h 20m

$529

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 2/18

7:00 am-8:55 am

2 stops18h 55m

Rome Fiumicino

Fri 3/6

6:10 am-2:20 pm

1 stop15h 10m

$532

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 1/7

4:25 pm-4:25 pm

1 stop17h 00m

Rome Fiumicino

Fri 1/23

6:10 am-2:20 pm

1 stop15h 10m

$533

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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 $332). Flying from Chicago to Italy in June is currently the most expensive (average of $609). 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 December 23, 2025.

It’s optimal to fly from Chicago to Italy in the morning. By choosing this option you can save up to 20% 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.

How often are flights from Chicago to Italy delayed?

About 29% of weekly flights between Chicago and Italy have experienced delays in the past year, with the average delay time being 162 minutes.

What is the most punctual flight time for Chicago to Italy flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Italy flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 25% of flights being delayed.

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 December 23, 2025.
Peruse reviews from past customers who have flown with Scandinavian Airlines, United 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.
Scandinavian Airlines
7.4
Good
1,620 reviews

Overall

7.4

Food

6.7

Entertainment

6.7

Comfort

7.3

Crew

8.0

Boarding

7.6

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
Scandinavian Airlines
7.4
Good
1,620 reviews
Scandinavian Airlines
7.4
Good
1,620 reviews

Overall

7.4

Food

6.7

Entertainment

6.7

Comfort

7.3

Crew

8.0

Boarding

7.6

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
United Airlines
7.4
Good
9,107 reviews
Scandinavian Airlines
7.4
Good
1,620 reviews

Overall

7.4

Food

6.7

Entertainment

6.7

Comfort

7.3

Crew

8.0

Boarding

7.6

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
American Airlines
7.2
Good
11,051 reviews
Scandinavian Airlines
7.4
Good
1,620 reviews

Overall

7.4

Food

6.7

Entertainment

6.7

Comfort

7.3

Crew

8.0

Boarding

7.6

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
Lufthansa
6.8
Okay
7,649 reviews
Scandinavian Airlines
7.4
Good
1,620 reviews

Overall

7.4

Food

6.7

Entertainment

6.7

Comfort

7.3

Crew

8.0

Boarding

7.6

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
ITA Airways
6.7
Okay
1,112 reviews
Scandinavian Airlines
7.4
Good
1,620 reviews

Overall

7.4

Food

6.7

Entertainment

6.7

Comfort

7.3

Crew

8.0

Boarding

7.6

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.

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?

    Scandinavian Airlines, TAP AIR PORTUGAL, and United Airlines can get you from Chicago to Italy in just under 9h. Your travel time can differ by up to 22h 55m. 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 cheapest airlines to fly from Chicago to Italy one-way?

    $113 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $124 and $133, respectively.

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

    Most travelers choose Chicago O'Hare Intl - Rome Fiumicino, Chicago O'Hare Intl - Milan Malpensa or Chicago Midway - Rome Fiumicino 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 $719. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $416 on average, our data indicates $1,049 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 $332). Flying from Chicago to Italy in June is currently the most expensive (average of $609). 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
IberiaCheapest$230Average$1,188FlexibilityNo cancel feeOn-time77%
TAP AIR PORTUGALCheapest$337Average$552FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$390Average$697FlexibilityNo cancel feeOn-time67%
IcelandairCheapest$392Average$629FlexibilityNo cancel feeOn-time76%
Scandinavian AirlinesCheapest$414Average$559FlexibilityNo cancel feeOn-time77%
SWISSCheapest$414Average$1,021FlexibilityNo cancel feeOn-time79%
DeltaCheapest$419Average$959FlexibilityNo cancel feeOn-timeN/A
Air FranceCheapest$458Average$881FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$459Average$869FlexibilityNo cancel feeOn-time70%
Turkish AirlinesCheapest$488Average$651FlexibilityNo cancel feeOn-time77%

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