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$398+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — MDW
oct. 30 — nov. 61
jue. 10/30
jue. 11/6
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 septiembre 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$572
(Delta)

One-way from

$398
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$647
Provider with most accurate pricing for Rome (ROM)-Chicago (CHI) flight deals.
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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. 6% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 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 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 septiembre 30, 2025.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/76:10 amFCO - MDW
2 stops18h 33mDelta
mar. 11/111:47 pmMDW - FCO
2 stops14h 58mDelta
Deal found 9/28$572
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.
mar. 11/116:10 amFCO - MDW
2 stops18h 58mDelta
lun. 11/171:47 pmMDW - FCO
2 stops14h 58mDelta
Deal found 9/30$573
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.
vie. 11/76:10 amFCO - MDW
2 stops18h 33mDelta
dom. 11/166:00 amMDW - FCO
1 stop18h 55mDelta
Deal found 9/29$575
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.
jue. 11/66:05 amBLQ - MDW
2 stops19h 20mDelta
mié. 11/121:47 pmMDW - BLQ
2 stops18h 58mDelta
Deal found 9/29$577
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.
jue. 11/66:10 amFCO - MDW
2 stops19h 15mDelta
mié. 11/199:34 amMDW - FCO
2 stops16h 36mDelta
Deal found 9/29$577
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.
mié. 10/1510:15 amNAP - MDW
2 stops18h 59mDelta
dom. 10/199:35 amMDW - NAP
2 stops19h 00mDelta
Deal found 9/29$582
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.
jue. 10/169:00 amNAP - MDW
1 stop20h 14mDelta
lun. 10/209:35 amMDW - NAP
2 stops19h 00mDelta
Deal found 9/30$583
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.
mar. 11/46:30 amLIN - MDW
2 stops18h 13mDelta
mar. 11/1110:47 amMDW - LIN
2 stops14h 58mDelta
Deal found 9/29$583
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.
jue. 11/206:10 amFCO - MDW
2 stops19h 08mDelta
jue. 11/275:34 pmMDW - FCO
2 stops16h 51mDelta
Deal found 9/29$583
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/1212:00 pmMXP - MDW
2 stops18h 40mDelta
mié. 11/1910:47 amMDW - MXP
1 stop15h 18mDelta
Deal found 9/28$584
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/99:00 amNAP - MDW
2 stops16h 25mKLM
lun. 10/1310:35 amMDW - NAP
1 stop13h 25mKLM
Deal found 9/30$585
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/2212:45 pmFCO - MDW
2 stops17h 55mDelta
lun. 12/110:47 amMDW - FCO
1 stop16h 43mDelta
Deal found 9/28$587

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 septiembre 30, 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

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

vie. 11/7

6:10 am-5:43 pm

2 stops18h 33m

Chicago Midway

mar. 11/11

1:47 pm-11:45 am

2 stops14h 58m

$572

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

vie. 11/21

6:10 am-6:14 pm

2 stops19h 04m

Chicago Midway

lun. 12/1

1:15 pm-11:45 am

2 stops15h 30m

$572

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

mar. 11/11

6:10 am-6:08 pm

2 stops18h 58m

Chicago Midway

lun. 11/17

1:47 pm-11:45 am

2 stops14h 58m

$573

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

vie. 11/7

6:10 am-5:43 pm

2 stops18h 33m

Chicago Midway

dom. 11/16

6:00 am-7:55 am

1 stop18h 55m

$575

BolognaChicago

BLQ - MDW

BLQMDW

Bologna Guglielmo Marconi

jue. 11/6

6:05 am-6:25 pm

2 stops19h 20m

Chicago Midway

mié. 11/12

1:15 pm-3:45 pm

2 stops19h 30m

$577

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

mié. 11/12

12:45 pm-11:40 pm

2 stops17h 55m

Chicago Midway

lun. 11/17

12:47 pm-7:55 am

1 stop12h 08m

$577

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

jue. 11/6

6:10 am-6:25 pm

2 stops19h 15m

Chicago Midway

mié. 11/19

9:34 am-9:10 am

2 stops16h 36m

$577

NaplesChicago

NAP - MDW

NAPMDW

Naples

mié. 10/15

10:15 am-10:14 pm

2 stops18h 59m

Chicago Midway

dom. 10/19

9:35 am-11:35 am

2 stops19h 00m

$582

MilanChicago

LIN - MDW

LINMDW

Milan Linate

mar. 2/3

6:30 am-6:34 pm

2 stops19h 04m

Chicago Midway

mié. 2/25

5:59 pm-1:55 pm

2 stops12h 56m

$582

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

vie. 1/30

11:05 am-9:46 pm

1 stop17h 41m

Chicago Midway

dom. 2/1

5:59 pm-2:55 pm

2 stops13h 56m

$582

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 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 33m. Delta provides one of the quickest options available for as low as $572. Italy and Chicago Midway Airport are separated by a distance of 4810 mi. This flight may include one or multiple stops.

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

    Most travelers choose Milan Malpensa - Chicago Midway, Rome Fiumicino - 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.

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

    Currently, April is the cheapest month in which you can book a flight from Italy to Chicago Midway Airport (average of $160). Flying from Italy to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

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

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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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Leonardo da Vinci/Fiumicino to O'Hare Intl flights
Luton to O'Hare Intl flights
Frankfurt-Hahn to O'Hare Intl flights
Barcelona-El Prat to Midway flights
Linate to O'Hare Intl flights
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Istanbul to O'Hare Intl flights
Madrid to Midway flights
Bruxelles-National to Midway flights
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Basel to O'Hare Intl flights
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