HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Italy

$204+ Cheap flights from Midway (MDW) 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Dec 16 — Dec 231
Tue 12/16
Tue 12/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway 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 Midway to Italy

Keep the following information in mind while searching for Midway to Italy flight deals. Data was last updated November 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$528
(Delta)

One-way from

$204
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$578
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 Midway to Italy
Search Deals
One-way flight from Chicago Midway to Italy
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($234 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 November 2025
Search Deals

Find flight deals from Midway to Italy

Cheapest flights from Midway to Italy
Explore the most affordable flight options available from Midway to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 16, 2025.

This KLM deal was found by Cheapflights users on 11/15. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/21:14 pmMDW - FCO
1 stop11h 41mKLM
Thu 12/1110:05 amFCO - MDW
1 stop14h 55mKLM
Deal found 11/15$527
This Delta deal was found by Cheapflights users on 11/15. 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.
Mon 11/2410:47 amMDW - FCO
1 stop14h 08mDelta
Tue 12/910:05 amFCO - MDW
1 stop14h 55mDelta
Deal found 11/15$528
This Delta deal was found by Cheapflights users on 11/15. 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.
Tue 12/29:59 amMDW - FCO
2 stops14h 56mDelta
Tue 12/1612:00 pmFCO - MDW
2 stops18h 47mDelta
Deal found 11/15$541
This Delta deal was found by Cheapflights users on 11/14. 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.
Mon 12/299:50 amMDW - FCO
1 stop15h 05mDelta
Thu 1/156:00 amFCO - MDW
2 stops18h 34mDelta
Deal found 11/14$542
This Delta deal was found by Cheapflights users on 11/15. 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 11/191:15 pmMDW - FCO
2 stops12h 55mDelta
Wed 11/2612:40 pmFCO - MDW
1 stop18h 00mDelta
Deal found 11/15$546
This Trip.com deal was found by Cheapflights users on 11/14. 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 11/246:00 amMDW - FCO
1 stop21h 30mKLM
Tue 12/912:40 pmFCO - MDW
1 stop18h 07mKLM
Deal found 11/14$555
This Trip.com deal was found by Cheapflights users on 11/15. 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 11/2410:47 amMDW - FCO
2 stops14h 53mAir France
Tue 12/912:00 pmFCO - MDW
2 stops18h 47mAir France
Deal found 11/15$567
This Delta deal was found by Cheapflights users on 11/14. 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.
Mon 12/11:15 pmMDW - NAP
2 stops19h 35mDelta
Mon 12/156:15 amNAP - MDW
2 stops19h 03mDelta
Deal found 11/14$681
This Delta deal was found by Cheapflights users on 11/14. 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.
Mon 12/810:49 amMDW - VCE
2 stops17h 26mDelta
Mon 12/153:55 pmVCE - MDW
2 stops33h 05mDelta
Deal found 11/14$818
This Delta deal was found by Cheapflights users on 11/15. 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.
Tue 12/210:49 amMDW - BLQ
2 stops16h 41mDelta
Tue 12/96:30 amBLQ - MDW
2 stops18h 30mDelta
Deal found 11/15$1,052
This Delta deal was found by Cheapflights users on 11/15. 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.
Sun 11/161:47 pmMDW - NAP
2 stops14h 48mDelta
Sun 11/2311:50 amNAP - MDW
2 stops18h 50mDelta
Deal found 11/15$1,115
This Trip.com deal was found by Cheapflights users on 11/15. 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 12/217:44 amMDW - LIN
2 stops24h 26mMultiple Airlines
Tue 1/137:30 amLIN - MDW
2 stops23h 29mMultiple Airlines
Deal found 11/15$1,178

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Italy that are best for you.

Fly from

Midway

Fly to

Italy

Route

Depart

Return

Price

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 12/3

12:50 pm-7:55 am

1 stop12h 05m

Rome Fiumicino

Tue 12/9

6:10 am-6:00 pm

2 stops18h 50m

$536

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 12/1

10:47 am-10:30 am

1 stop16h 43m

Rome Fiumicino

Tue 12/9

10:05 am-6:00 pm

1 stop14h 55m

$536

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 3/1

1:28 pm-11:45 am

2 stops15h 17m

Rome Fiumicino

Wed 3/11

11:40 am-9:46 pm

1 stop16h 06m

$540

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 2/18

6:40 pm-5:25 pm

2 stops15h 45m

Rome Fiumicino

Wed 3/4

6:10 am-5:37 pm

2 stops18h 27m

$541

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 12/2

9:59 am-7:55 am

2 stops14h 56m

Rome Fiumicino

Thu 12/11

10:05 am-6:00 pm

1 stop14h 55m

$541

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Fri 12/5

12:50 pm-10:30 am

1 stop14h 40m

Rome Fiumicino

Wed 12/10

6:10 am-4:34 pm

2 stops17h 24m

$586

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 3/3

6:17 pm-5:25 pm

2 stops16h 08m

Rome Fiumicino

Sat 3/14

8:20 am-9:46 pm

2 stops19h 26m

$595

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sat 11/29

9:34 am-7:55 am

1 stop15h 21m

Rome Fiumicino

Sat 12/6

6:10 am-6:18 pm

2 stops19h 08m

$637

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 12/1

1:15 pm-3:50 pm

2 stops19h 35m

Naples

Mon 12/15

6:15 am-6:00 pm

2 stops18h 45m

$681

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Thu 12/11

12:50 pm-10:30 am

1 stop14h 40m

Rome Fiumicino

Thu 12/18

12:00 pm-11:47 pm

2 stops18h 47m

$701

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

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

Best time to book a flight from Midway to Italy

Have a flexible travel schedule? Discover the best time to fly to Italy from Midway 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 Midway Airport to Italy

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

Find hourly flight availability from Midway 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 16, 2025.

It’s optimal to fly from Chicago Midway Airport to Italy in the evening. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight in the afternoon.

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Midway Airport to Italy?

    Departing from Chicago Midway Airport to Italy will take you 16h 43m. The distance from Chicago Midway Airport to Italy is about 4810 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The most popular route from Chicago Midway Airport to Italy is Chicago Midway - Rome Fiumicino. You may also consider Chicago Midway - Milan Malpensa or Chicago Midway - Milan Linate.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway 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.

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 Midway 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 Istanbul flights
O'Hare Intl to Orly flights
O'Hare Intl to Frankfurt flights
O'Hare Intl to Gatwick flights
O'Hare Intl to London City flights
O'Hare Intl to Barcelona-El Prat flights
O'Hare Intl to Athens flights
O'Hare Intl to Amsterdam flights
O'Hare Intl to Bruxelles-National flights
O'Hare Intl to Zurich flights
O'Hare Intl to Frederic Chopin flights
Midway to Heathrow flights
O'Hare Intl to Stansted flights
O'Hare Intl to Munich flights
O'Hare Intl to Lisbon flights
Midway to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Malpensa flights
Midway to Charles de Gaulle flights
O'Hare Intl to Krakow flights
O'Hare Intl to Copenhagen flights
O'Hare Intl to Luton flights
O'Hare Intl to Linate flights
O'Hare Intl to Keflavik Intl flights
Midway to Dublin flights
O'Hare Intl to Sabiha Gokcen flights
O'Hare Intl to Beauvais-Tille flights
Midway to Madrid flights
O'Hare Intl to Edinburgh flights
O'Hare Intl to Vienna flights
O'Hare Intl to Florence flights
Midway to Athens flights
O'Hare Intl to Oslo Gardermoen flights
Midway to Frankfurt flights
Midway to Keflavik Intl flights
O'Hare Intl to Vicenza flights
Midway to Barcelona-El Prat flights
O'Hare Intl to Prague flights
Midway to Frederic Chopin flights
O'Hare Intl to Bergamo flights
O'Hare Intl to Geneva flights
Midway to Malpensa flights
O'Hare Intl to Berlin flights
Midway to Lisbon flights
O'Hare Intl to Ciampino flights
O'Hare Intl to Katowice flights

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.