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$231+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Oct 30 — Nov 61
Thu 10/30
Thu 11/6
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 September 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$477
(Flysmarter)

One-way from

$231
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$849
Provider with most accurate pricing for Chicago (CHI)-Rome (ROM) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Rome (ROM) flights.
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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. 22% potential increase in price ($225 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 30, 2025.

This Flysmarter deal was found by Cheapflights users on 9/28. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/111:15 pmMDW - FCO
1 stop11h 40mMultiple Airlines
Tue 11/1810:05 amFCO - MDW
1 stop15h 03mMultiple Airlines
Deal found 9/28$477
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/21:14 pmMDW - FCO
1 stop11h 41mDelta
Thu 12/1110:05 amFCO - MDW
1 stop14h 55mDelta
Deal found 9/29$490
This Delta deal was found by Cheapflights users on 9/30. 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 11/99:34 amMDW - FCO
2 stops17h 11mDelta
Tue 11/2510:05 amFCO - MDW
1 stop15h 03mDelta
Deal found 9/30$495
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/251:15 pmMDW - FCO
1 stop11h 40mDelta
Fri 12/56:00 amFCO - MDW
2 stops19h 18mDelta
Deal found 9/29$511
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1712:47 pmMDW - FCO
1 stop14h 43mDelta
Wed 12/312:45 pmFCO - MDW
2 stops18h 04mDelta
Deal found 9/29$513
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:23 pmMDW - FCO
2 stops16h 02mDelta
Tue 11/1811:05 amFCO - MDW
2 stops29h 47mDelta
Deal found 9/29$514
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/510:40 amMDW - FCO
2 stops15h 30mDelta
Wed 11/2610:05 amFCO - MDW
1 stop20h 35mDelta
Deal found 9/29$522
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/159:35 amMDW - FCO
2 stops17h 30mDelta
Mon 11/1712:45 pmFCO - MDW
2 stops36h 23mDelta
Deal found 9/29$529
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:23 pmMDW - FCO
2 stops16h 02mDelta
Mon 11/1712:45 pmFCO - MDW
2 stops36h 23mDelta
Deal found 9/29$532
This KLM deal was found by Cheapflights users on 9/29. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:05 pmMDW - FCO
1 stop14h 25mKLM
Thu 11/2010:05 amFCO - MDW
1 stop15h 03mKLM
Deal found 9/29$533
This Delta deal was found by Cheapflights users on 9/30. 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 11/171:15 pmMDW - BLQ
2 stops19h 30mDelta
Wed 12/36:30 amBLQ - MDW
2 stops18h 48mDelta
Deal found 9/30$592
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/55:09 pmMDW - FLR
2 stops16h 11mDelta
Wed 11/126:40 amFLR - MDW
2 stops18h 38mDelta
Deal found 9/29$604

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 September 30, 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

Tue 12/2

1:14 pm-7:55 am

1 stop11h 41m

Rome Fiumicino

Tue 12/9

10:05 am-6:00 pm

1 stop14h 55m

$490

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

$490

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 12/2

9:34 am-10:30 am

2 stops17h 56m

Rome Fiumicino

Thu 12/11

10:05 am-6:00 pm

1 stop14h 55m

$495

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 2/8

5:59 pm-5:25 pm

2 stops16h 26m

Rome Fiumicino

Wed 2/18

12:40 pm-9:46 pm

1 stop16h 06m

$509

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 11/17

9:34 am-10:30 am

2 stops17h 56m

Rome Fiumicino

Wed 12/3

12:45 pm-11:49 pm

2 stops18h 04m

$517

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 2/8

1:00 pm-11:45 am

2 stops15h 45m

Rome Fiumicino

Tue 2/17

6:00 am-6:08 pm

2 stops19h 08m

$530

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 11/5

10:40 am-9:10 am

2 stops15h 30m

Rome Fiumicino

Wed 11/26

9:55 am-11:40 pm

2 stops20h 45m

$543

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 1/13

5:59 pm-3:15 pm

2 stops14h 16m

Rome Fiumicino

Mon 1/19

12:40 pm-9:46 pm

1 stop16h 06m

$559

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Fri 11/14

12:47 pm-10:30 am

1 stop14h 43m

Rome Fiumicino

Fri 11/21

6:00 am-6:14 pm

2 stops19h 14m

$561

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sat 11/8

10:35 am-10:30 am

1 stop16h 55m

Rome Fiumicino

Wed 11/19

6:00 am-6:08 pm

2 stops19h 08m

$561

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/30

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 September 30, 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 September 30, 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
7,964 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

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
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

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.

  • How long is the flight from Chicago Midway Airport to Italy?

    Departing from Chicago Midway Airport to Italy will take you 11h 41m. 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 - Florence Peretola.

  • 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 $1,197). 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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