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$357+ Cheap flights from Italy to Midway (MDW)

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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — MDW
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheap flight deals from Italy to Midway

Keep the following information in mind while searching for Italy to Midway flight deals. Data was last updated November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$625
(Delta)

One-way from

$357
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$703
Provider with most accurate pricing for Rome (ROM)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Rome (ROM)-Chicago (CHI) flights.
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From Italy to Chicago Midway
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One-way flight from Italy to Chicago Midway
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Highest demand for flights based on searches. 4% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Italy to Midway

Cheapest flights from Italy to Midway
Explore the most affordable flight options available from Italy to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Delta deal was found by Cheapflights users on 11/11. 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.
Fri 12/56:15 amNAP - MDW
2 stops18h 45mDelta
Tue 12/91:50 pmMDW - NAP
2 stops19h 00mDelta
Deal found 11/11$625
This Delta deal was found by Cheapflights users on 11/10. 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.
Thu 12/46:10 amFCO - MDW
2 stops17h 08mDelta
Wed 2/41:28 pmMDW - FCO
2 stops18h 47mDelta
Deal found 11/10$634
This Delta deal was found by Cheapflights users on 11/11. 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.
Thu 12/41:00 pmBLQ - MDW
2 stops17h 47mDelta
Wed 12/105:29 pmMDW - BLQ
2 stops15h 56mDelta
Deal found 11/11$635
This Delta deal was found by Cheapflights users on 11/12. 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 12/611:50 amNAP - MDW
2 stops18h 57mDelta
Wed 12/101:14 pmMDW - NAP
2 stops14h 56mDelta
Deal found 11/12$638
This Delta deal was found by Cheapflights users on 11/11. 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.
Thu 12/46:10 amFCO - MDW
2 stops19h 08mDelta
Wed 12/1712:50 pmMDW - FCO
1 stop14h 40mDelta
Deal found 11/11$638
This Delta deal was found by Cheapflights users on 11/12. 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 12/106:10 amFCO - MDW
2 stops19h 08mDelta
Sun 12/146:00 amMDW - FCO
1 stop18h 55mDelta
Deal found 11/12$639
This Delta deal was found by Cheapflights users on 11/11. 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.
Fri 12/56:30 amLIN - MDW
2 stops16h 48mDelta
Mon 12/81:50 pmMDW - LIN
2 stops14h 25mDelta
Deal found 11/11$640
This Delta deal was found by Cheapflights users on 11/11. 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.
Fri 12/56:55 amMXP - MDW
2 stops18h 05mDelta
Mon 12/81:14 pmMDW - MXP
2 stops14h 21mDelta
Deal found 11/11$641
This Delta deal was found by Cheapflights users on 11/10. 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.
Tue 12/212:00 pmMXP - MDW
2 stops18h 47mDelta
Sun 12/79:34 amMDW - MXP
2 stops17h 11mDelta
Deal found 11/10$643
This Delta deal was found by Cheapflights users on 11/11. 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.
Thu 12/410:05 amFCO - MDW
1 stop14h 55mDelta
Sun 12/146:00 amMDW - FCO
1 stop18h 55mDelta
Deal found 11/11$645
This Expedia deal was found by Cheapflights users on 11/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:10 amFCO - MDW
2 stops17h 08mKLM
Wed 2/46:17 pmMDW - FCO
1 stop33h 13mKLM
Deal found 11/10$650
This Trip.com deal was found by Cheapflights users on 11/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:15 amNAP - MDW
2 stops24h 32mAir France
Tue 12/91:50 pmMDW - NAP
2 stops19h 00mAir France
Deal found 11/12$652

Cheapflights Fare Finder

 
Customize your flight search to find flights from Italy to Midway 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 13, 2025.
Use the filters below to find and compare flights from Italy to Chicago Midway Airport that are best for you.

Fly from

Italy

Fly to

Midway

Route

Depart

Return

Price

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 12/5

6:15 am-6:00 pm

2 stops18h 45m

Chicago Midway

Tue 12/9

1:50 pm-3:50 pm

2 stops19h 00m

$625

NaplesChicago

NAP - MDW

NAPMDW

Naples

Tue 2/10

6:15 am-10:26 pm

2 stops23h 11m

Chicago Midway

Sun 2/15

11:00 am-11:30 am

2 stops17h 30m

$626

BolognaChicago

BLQ - MDW

BLQMDW

Bologna Guglielmo Marconi

Thu 2/12

6:30 am-5:45 pm

2 stops18h 15m

Chicago Midway

Mon 2/16

1:28 pm-3:45 pm

2 stops19h 17m

$631

BolognaChicago

BLQ - MDW

BLQMDW

Bologna Guglielmo Marconi

Thu 12/4

1:00 pm-11:47 pm

2 stops17h 47m

Chicago Midway

Wed 12/10

5:29 pm-4:25 pm

2 stops15h 56m

$635

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Wed 2/11

6:10 am-5:55 pm

2 stops18h 45m

Chicago Midway

Wed 2/18

6:40 pm-5:25 pm

2 stops15h 45m

$635

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 1/16

6:15 am-10:09 pm

2 stops22h 54m

Chicago Midway

Thu 1/22

1:28 pm-3:50 pm

2 stops19h 22m

$638

NaplesChicago

NAP - MDW

NAPMDW

Naples

Sat 12/6

11:50 am-11:47 pm

2 stops18h 57m

Chicago Midway

Wed 12/10

10:49 am-11:10 am

2 stops17h 21m

$638

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Tue 12/9

6:10 am-6:00 pm

2 stops18h 50m

Chicago Midway

Tue 12/16

9:34 am-7:55 am

1 stop15h 21m

$638

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Wed 12/10

6:10 am-6:00 pm

2 stops18h 50m

Chicago Midway

Mon 12/15

12:50 pm-7:55 am

1 stop12h 05m

$638

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Thu 12/4

6:10 am-6:18 pm

2 stops19h 08m

Chicago Midway

Wed 12/17

12:50 pm-10:30 am

1 stop14h 40m

$638

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 60 results
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Best time to book a flight from Italy to Midway

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

    A quick flight from Italy to Chicago Midway Airport can take about 18h 45m. Delta provides one of the quickest options available for as low as $625. Italy and Chicago Midway Airport are separated by a distance of 4931 mi. This flight may include one or multiple stops.

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

    Most travelers choose Rome Fiumicino - Chicago Midway, Milan Malpensa - Chicago Midway or Milan Linate - Chicago Midway when deciding on the best route from Italy to Chicago Midway Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Italy to Midway 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Alternative routes for Italy to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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