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$259+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Jan 29 — Feb 51
Thu 1/29
Thu 2/5
1 adult, Economy
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Cheap 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 December 30, 2025.

This Delta deal was found by Cheapflights users on 12/29. 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 12/319:29 amMDW - FCO
1 stop15h 26mDelta
Tue 1/136:10 amFCO - MDW
2 stops19h 22mDelta
Deal found 12/29$538
This Delta deal was found by Cheapflights users on 12/29. 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 12/296:08 pmMDW - FCO
1 stop30h 47mDelta
Tue 1/136:10 amFCO - MDW
2 stops19h 22mDelta
Deal found 12/29$544
This KLM deal was found by Cheapflights users on 12/29. 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.
Wed 12/319:29 amMDW - FCO
1 stop15h 26mKLM
Mon 1/1212:40 pmFCO - MDW
1 stop16h 27mKLM
Deal found 12/29$837
This Delta deal was found by Cheapflights users on 12/29. 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 12/316:08 pmMDW - FCO
2 stops16h 17mDelta
Mon 1/1212:40 pmFCO - MDW
1 stop16h 27mDelta
Deal found 12/29$841
This Delta deal was found by Cheapflights users on 12/30. 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.
Wed 12/316:00 amMDW - FCO
1 stop18h 55mDelta
Thu 1/86:10 amFCO - MDW
2 stops18h 24mDelta
Deal found 12/30$888
This Delta deal was found by Cheapflights users on 12/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:08 pmMDW - FCO
2 stops14h 07mDelta
Wed 1/76:10 amFCO - MDW
2 stops19h 22mDelta
Deal found 12/28$892
This KLM deal was found by Cheapflights users on 12/29. 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.
Wed 12/313:29 pmMDW - FCO
1 stop12h 01mMultiple Airlines
Thu 1/812:40 pmFCO - MDW
1 stop16h 27mMultiple Airlines
Deal found 12/29$998
This Delta deal was found by Cheapflights users on 12/30. 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.
Wed 12/316:08 pmMDW - FLR
2 stops18h 42mDelta
Wed 1/76:40 amFLR - MDW
2 stops18h 52mDelta
Deal found 12/30$1,839
This Delta deal was found by Cheapflights users on 12/29. 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 12/306:08 pmMDW - LIN
2 stops12h 47mDelta
Tue 1/66:30 amLIN - MDW
2 stops19h 02mDelta
Deal found 12/29$2,018
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/289:50 amMDW - MXP
1 stop16h 15mDelta
Tue 1/136:55 amMXP - MDW
2 stops18h 37mDelta
Deal found 12/27$2,141
This KLM deal was found by Cheapflights users on 12/27. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:45 pmMDW - MXP
1 stop13h 20mKLM
Mon 1/1211:05 amMXP - MDW
1 stop18h 02mKLM
Deal found 12/27$2,230
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:08 pmMDW - MXP
2 stops13h 47mDelta
Mon 1/1211:05 amMXP - MDW
1 stop18h 02mDelta
Deal found 12/27$2,234

Find flight deals from Midway to Italy

Keep the following information in mind while searching for Midway to Italy flight deals. Data was last updated December 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$502
(Ticket)

One-way from

$259
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$663
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 December 2025
Search Deals

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 December 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 1/27

10:48 am-10:30 am

1 stop16h 42m

Rome Fiumicino

Tue 2/3

12:40 pm-10:22 pm

1 stop16h 42m

$537

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 1/27

12:48 pm-10:30 am

1 stop14h 42m

Rome Fiumicino

Tue 2/3

12:40 pm-10:22 pm

1 stop16h 42m

$537

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 1/11

6:30 pm-3:15 pm

2 stops13h 45m

Rome Fiumicino

Wed 1/21

12:40 pm-10:22 pm

1 stop16h 42m

$541

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 3/3

6:20 pm-9:15 pm

2 stops19h 55m

Naples

Tue 3/10

12:20 pm-5:54 pm

2 stops35h 34m

$552

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 2/11

12:46 pm-11:30 am

2 stops15h 44m

Naples

Fri 3/6

6:15 am-5:37 pm

2 stops18h 22m

$557

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 2/8

10:48 am-11:30 am

2 stops17h 42m

Naples

Fri 3/6

6:15 am-6:40 pm

2 stops19h 25m

$557

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 2/9

6:14 pm-9:15 pm

2 stops20h 01m

Naples

Wed 3/4

6:15 am-5:45 pm

2 stops18h 30m

$558

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 2/8

9:33 am-11:30 am

2 stops18h 57m

Naples

Wed 3/4

6:15 am-5:45 pm

2 stops18h 30m

$558

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 2/10

6:14 pm-9:15 pm

2 stops20h 01m

Naples

Tue 3/3

6:15 am-6:40 pm

2 stops19h 25m

$558

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 2/11

12:46 pm-11:30 am

2 stops15h 44m

Naples

Wed 3/4

6:15 am-10:31 pm

2 stops23h 16m

$558

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

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
No data available for this route at this time. Please check back soon.

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 14h 42m. 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.

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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Midway to Heathrow flights
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Midway to Charles de Gaulle flights
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Midway to Dublin flights
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Midway to Madrid flights
Midway to Athens flights
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Midway to Frederic Chopin flights
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Midway to Lisbon flights
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Midway to Barcelona-El Prat flights
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O'Hare Intl to Vicenza flights
O'Hare Intl to Katowice flights
Midway to Keflavik Intl flights
O'Hare Intl to Arlanda flights
O'Hare Intl to Prague flights
Midway to Malpensa flights
O'Hare Intl to Bergamo flights
Midway to Frankfurt flights

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