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$237+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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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 August 14, 2025.

Round-trip from

$453
(Delta)

One-way from

$237
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$762
From Chicago Midway to Italy
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One-way flight from Chicago Midway to Italy
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Highest demand for flights based on searches. 23% potential increase in price ($231 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/12. 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.
Fri 11/289:30 amMDW - FCO
2 stops17h 15mDelta
Tue 12/910:05 amFCO - MDW
1 stop15h 31mDelta
Deal found 8/12$453
This Delta deal was found by Cheapflights users on 8/12. 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 12/109:30 amMDW - FCO
2 stops15h 25mDelta
Tue 12/236:10 amFCO - MDW
2 stops18h 27mDelta
Deal found 8/12$472
This KLM deal was found by Cheapflights users on 8/11. 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.
Thu 11/271:05 pmMDW - FCO
1 stop14h 25mKLM
Sun 12/712:40 pmFCO - MDW
1 stop16h 04mKLM
Deal found 8/11$499
This Delta deal was found by Cheapflights users on 8/11. 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 11/151:00 pmMDW - FCO
2 stops13h 45mDelta
Sat 11/2210:05 amFCO - MDW
2 stops18h 39mDelta
Deal found 8/11$503
This Delta deal was found by Cheapflights users on 8/11. 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 11/126:00 amMDW - FCO
2 stops18h 05mDelta
Thu 11/2710:05 amFCO - MDW
2 stops18h 39mDelta
Deal found 8/11$511
This KLM deal was found by Cheapflights users on 8/13. 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.
Mon 11/241:05 pmMDW - FCO
1 stop11h 50mMultiple Airlines
Wed 12/312:40 pmFCO - MDW
1 stop16h 04mMultiple Airlines
Deal found 8/13$525
This Delta deal was found by Cheapflights users on 8/11. 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 11/49:35 amMDW - FCO
1 stop15h 20mDelta
Tue 11/116:00 amFCO - MDW
2 stops19h 36mDelta
Deal found 8/11$528
This Delta deal was found by Cheapflights users on 8/14. 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.
Wed 10/2210:35 amMDW - FCO
2 stops15h 45mDelta
Fri 11/712:40 pmFCO - MDW
1 stop16h 34mDelta
Deal found 8/14$529
This Delta deal was found by Cheapflights users on 8/12. 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 10/296:00 amMDW - FCO
2 stops18h 05mDelta
Fri 11/76:00 amFCO - MDW
2 stops19h 25mDelta
Deal found 8/12$533
This Delta deal was found by Cheapflights users on 8/12. 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 11/811:10 amMDW - FCO
1 stop13h 45mDelta
Wed 11/1910:05 amFCO - MDW
1 stop18h 39mDelta
Deal found 8/12$540
This Delta deal was found by Cheapflights users on 8/13. 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 10/131:08 pmMDW - FCO
1 stop13h 12mDelta
Wed 11/56:00 amFCO - MDW
2 stops23h 14mDelta
Deal found 8/13$546
This Delta deal was found by Cheapflights users on 8/14. 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.
Sat 12/276:25 pmMDW - LIN
2 stops36h 30mDelta
Mon 1/122:55 pmLIN - MDW
2 stops37h 51mDelta
Deal found 8/14$656

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 August 14, 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

Mon 10/27

1:08 pm-9:10 am

2 stops14h 02m

Rome Fiumicino

Wed 11/5

6:10 am-4:15 pm

2 stops17h 05m

$453

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 11/12

6:00 am-7:05 am

2 stops18h 05m

Rome Fiumicino

Thu 11/27

10:05 am-9:44 pm

2 stops18h 39m

$511

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 10/29

6:00 am-6:05 am

2 stops18h 05m

Rome Fiumicino

Fri 11/7

12:40 pm-10:14 pm

1 stop16h 34m

$511

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 11/10

1:05 pm-7:55 am

1 stop11h 50m

Rome Fiumicino

Fri 11/21

12:40 pm-9:44 pm

1 stop16h 04m

$525

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 11/11

1:05 pm-10:30 am

1 stop14h 25m

Rome Fiumicino

Fri 11/21

12:40 pm-9:44 pm

1 stop16h 04m

$525

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 11/10

1:05 pm-7:55 am

1 stop11h 50m

Rome Fiumicino

Thu 11/20

10:05 am-6:36 pm

1 stop15h 31m

$525

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 10/22

1:48 pm-12:45 pm

1 stop15h 57m

Rome Fiumicino

Fri 11/7

12:40 pm-10:14 pm

1 stop16h 34m

$525

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 11/12

1:05 pm-10:30 am

1 stop14h 25m

Rome Fiumicino

Wed 11/19

12:40 pm-9:44 pm

1 stop16h 04m

$525

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 10/13

1:08 pm-9:20 am

1 stop13h 12m

Rome Fiumicino

Thu 11/6

12:40 pm-10:14 pm

1 stop16h 34m

$525

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 11/12

1:05 pm-10:30 am

1 stop14h 25m

Rome Fiumicino

Fri 11/21

12:40 pm-9:44 pm

1 stop16h 04m

$525

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 results
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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 August 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Italy as you normally would.

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 August 14, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Italy, such as Delta. 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
7,980 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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 Midway 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 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 - Venice Marco Polo.

  • 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.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Italy (average of $703). Flying from Chicago Midway Airport to Italy in June is currently the most expensive (average of $1,206). 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 Midway to Italy

See prices for flight routes from nearby airports that may be better suited for you.
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O'Hare Intl to Prague flights
Midway to Frederic Chopin flights
O'Hare Intl to Sofia flights
O'Hare Intl to Oslo Gardermoen flights

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