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$221+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Mar 16 — Mar 231
Mon 3/16
Mon 3/23
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 February 14, 2026.

This Delta deal was found by Cheapflights users on 2/13. 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.
Sun 2/2210:49 am
MDW
-
FCO
1 stop16h 41m
Delta
Tue 3/109:05 am
FCO
-
MDW
1 stop14h 49m
Delta
Deal found 2/13$529
This KLM deal was found by Cheapflights users on 2/11. 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.
Sun 2/2210:49 am
MDW
-
FCO
1 stop16h 41m
KLM
Tue 3/109:05 am
FCO
-
MDW
1 stop14h 49m
KLM
Deal found 2/11$532
This Expedia deal was found by Cheapflights users on 2/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:17 pm
MDW
-
FCO
2 stops18h 28m
Air France
Tue 3/109:05 am
FCO
-
MDW
1 stop14h 49m
Air France
Deal found 2/11$536
This KLM deal was found by Cheapflights users on 2/13. 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.
Wed 2/1812:45 pm
MDW
-
FCO
1 stop14h 45m
KLM
Wed 2/2512:40 pm
FCO
-
MDW
1 stop16h 51m
KLM
Deal found 2/13$538
This Delta deal was found by Cheapflights users on 2/13. 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.
Sun 8/161:05 pm
MDW
-
FCO
1 stop14h 45m
Delta
Fri 8/286:30 am
FCO
-
MDW
2 stops18h 35m
Delta
Deal found 2/13$539
This Delta deal was found by Cheapflights users on 2/10. 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 3/231:10 pm
MDW
-
FCO
2 stops16h 35m
Delta
Wed 4/11:10 pm
FCO
-
MDW
1 stop16h 21m
Delta
Deal found 2/10$542
This Delta deal was found by Cheapflights users on 2/12. 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 2/189:50 am
MDW
-
FCO
2 stops16h 55m
Delta
Tue 3/312:40 pm
FCO
-
MDW
1 stop16h 53m
Delta
Deal found 2/12$543
This Delta deal was found by Cheapflights users on 2/13. 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.
Tue 3/36:20 pm
MDW
-
FCO
2 stops13h 55m
Delta
Tue 3/106:10 am
FCO
-
MDW
2 stops17h 12m
Delta
Deal found 2/13$544
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/277:30 am
MDW
-
FCO
2 stops33h 10m
Multiple Airlines
Fri 5/87:05 pm
FCO
-
MDW
1 stop24h 55m
Multiple Airlines
Deal found 2/13$545
This Delta deal was found by Cheapflights users on 2/13. 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.
Tue 8/186:00 am
MDW
-
NAP
1 stop18h 05m
Delta
Wed 8/269:15 am
NAP
-
MDW
1 stop19h 31m
Delta
Deal found 2/13$594
This Delta deal was found by Cheapflights users on 2/10. 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 3/21:49 pm
MDW
-
NAP
2 stops19h 01m
Delta
Mon 3/96:15 am
NAP
-
MDW
2 stops18h 25m
Delta
Deal found 2/10$609
This Delta deal was found by Cheapflights users on 2/13. 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 8/171:00 pm
MDW
-
PMO
2 stops19h 00m
Delta
Mon 8/243:45 pm
PMO
-
MDW
2 stops33h 46m
Delta
Deal found 2/13$616

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 February 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$538
(Delta)

One-way from

$221
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$593
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. 20% potential increase in price ($189 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 14, 2026.
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

Sun 2/22

10:49 am-10:30 am

1 stop16h 41m

Rome Fiumicino

Tue 3/10

9:05 am-5:54 pm

1 stop14h 49m

$529

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 2/18

12:45 pm-10:30 am

1 stop14h 45m

Rome Fiumicino

Tue 2/24

12:40 pm-10:33 pm

1 stop16h 53m

$538

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 2/24

12:45 pm-10:30 am

1 stop14h 45m

Rome Fiumicino

Wed 3/11

11:40 am-10:31 pm

1 stop16h 51m

$538

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 2/24

12:45 pm-10:30 am

1 stop14h 45m

Rome Fiumicino

Thu 3/12

11:40 am-10:31 pm

1 stop16h 51m

$538

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 2/25

1:49 pm-11:45 am

2 stops14h 56m

Rome Fiumicino

Thu 3/12

9:05 am-5:54 pm

1 stop14h 49m

$542

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 3/23

1:10 pm-11:45 am

2 stops16h 35m

Rome Fiumicino

Wed 4/1

1:10 pm-10:31 pm

1 stop16h 21m

$542

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 2/25

1:49 pm-11:45 am

2 stops14h 56m

Rome Fiumicino

Tue 3/3

12:40 pm-10:33 pm

1 stop16h 53m

$542

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 3/18

9:35 am-6:55 am

2 stops15h 20m

Rome Fiumicino

Tue 3/31

9:45 am-10:31 pm

1 stop19h 46m

$543

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 3/24

1:10 pm-9:10 am

2 stops14h 00m

Rome Fiumicino

Wed 4/1

9:45 am-5:22 pm

1 stop14h 37m

$548

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 4/15

9:31 am-10:15 am

1 stop17h 44m

Rome Fiumicino

Thu 4/23

6:30 am-5:58 pm

2 stops18h 28m

$574

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

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 12h 21m. The distance from Chicago Midway Airport to Italy is about 4539 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 - Naples.

  • 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 Leonardo da Vinci/Fiumicino flights
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Midway to Madrid flights
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O'Hare Intl to Naples flights
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Midway to Athens flights
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Midway to Barcelona-El Prat flights
O'Hare Intl to Vicenza flights
Midway to Lisbon flights
O'Hare Intl to Berlin flights
O'Hare Intl to Katowice flights
Midway to Frederic Chopin flights
O'Hare Intl to Skopje flights
O'Hare Intl to Geneva flights
O'Hare Intl to Florence flights
O'Hare Intl to Budapest flights
O'Hare Intl to Tirana flights
O'Hare Intl to Ciampino flights

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