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$372+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$574
(Delta)

One-way from

$372
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$802
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. 5% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. 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 10/26:10 amNAP - MDW
2 stops19h 25mDelta
Mon 10/61:08 pmMDW - NAP
2 stops15h 27mDelta
Deal found 8/14$574
This Delta deal was found by Cheapflights users on 8/14. 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 9/229:00 amFCO - MDW
2 stops19h 36mDelta
Sun 10/56:15 pmMDW - FCO
2 stops14h 45mDelta
Deal found 8/14$591
This Delta deal was found by Cheapflights users on 8/14. 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 8/289:00 amFCO - MDW
1 stop16h 37mDelta
Tue 9/91:08 pmMDW - FCO
1 stop13h 12mDelta
Deal found 8/14$594
This Delta deal was found by Cheapflights users on 8/14. 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 8/259:00 amFCO - MDW
2 stops19h 44mDelta
Sun 9/71:43 pmMDW - FCO
1 stop16h 02mDelta
Deal found 8/14$595
This Trip.com deal was found by Cheapflights users on 8/14. 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.
Thu 10/26:10 amNAP - MDW
2 stops19h 25mAir France
Mon 10/612:48 pmMDW - NAP
2 stops15h 47mAir France
Deal found 8/14$598
This Delta deal was found by Cheapflights users on 8/14. 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 11/216:30 amVCE - MDW
2 stops16h 53mDelta
Sun 11/231:05 pmMDW - VCE
2 stops15h 15mDelta
Deal found 8/14$613
This Delta deal was found by Cheapflights users on 8/14. 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 8/286:50 amMXP - MDW
2 stops17h 47mDelta
Wed 9/106:00 amMDW - MXP
2 stops17h 45mDelta
Deal found 8/14$617
This Trip.com deal was found by Cheapflights users on 8/14. 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.
Mon 8/256:05 amFCO - MDW
2 stops22h 39mAir France
Sun 9/76:17 pmMDW - FCO
1 stop32h 03mAir France
Deal found 8/14$625
This Trip.com deal was found by Cheapflights users on 8/14. 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.
Mon 8/252:55 pmFCO - MDW
1 stop33h 42mKLM
Sun 9/71:43 pmMDW - FCO
1 stop16h 02mKLM
Deal found 8/14$627
This Trip.com deal was found by Cheapflights users on 8/14. 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 10/1011:40 amMXP - MDW
1 stop17h 34mMultiple Airlines
Sun 10/196:00 amMDW - MXP
1 stop20h 25mMultiple Airlines
Deal found 8/14$639
This Delta deal was found by Cheapflights users on 8/14. 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 9/219:00 amFCO - MDW
1 stop16h 35mDelta
Sun 9/286:15 pmMDW - FCO
2 stops13h 35mDelta
Deal found 8/14$655
This Delta deal was found by Cheapflights users on 8/14. 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 9/136:30 amLIN - MDW
2 stops18h 05mDelta
Sat 9/206:15 pmMDW - LIN
2 stops14h 40mDelta
Deal found 8/14$676

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 August 14, 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

Thu 10/2

6:10 am-6:35 pm

2 stops19h 25m

Chicago Midway

Mon 10/6

1:08 pm-11:35 am

2 stops15h 27m

$574

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Thu 9/18

9:45 am-5:35 pm

1 stop14h 50m

Chicago Midway

Mon 9/22

6:15 pm-2:50 pm

2 stops13h 35m

$591

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Mon 9/22

9:00 am-6:35 pm

1 stop16h 35m

Chicago Midway

Sun 10/5

6:15 pm-4:00 pm

2 stops14h 45m

$591

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Wed 9/17

11:35 am-9:36 pm

1 stop17h 01m

Chicago Midway

Sun 9/28

6:15 pm-2:50 pm

2 stops13h 35m

$591

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Thu 8/28

9:00 am-6:37 pm

1 stop16h 37m

Chicago Midway

Tue 9/9

1:08 pm-9:20 am

1 stop13h 12m

$594

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Mon 8/25

9:00 am-9:44 pm

2 stops19h 44m

Chicago Midway

Sun 9/7

1:43 pm-12:45 pm

1 stop16h 02m

$595

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 10/2

6:10 am-6:35 pm

2 stops19h 25m

Chicago Midway

Mon 10/6

12:48 pm-11:35 am

2 stops15h 47m

$598

VeniceChicago

VCE - MDW

VCEMDW

Venice Marco Polo

Fri 11/21

6:30 am-4:23 pm

2 stops16h 53m

Chicago Midway

Sun 11/23

1:05 pm-11:20 am

2 stops15h 15m

$613

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 8/28

6:50 am-5:37 pm

2 stops17h 47m

Chicago Midway

Wed 9/10

6:00 am-6:45 am

2 stops17h 45m

$617

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 11/7

6:55 am-5:43 pm

2 stops17h 48m

Chicago Midway

Fri 11/14

1:05 pm-9:05 am

1 stop13h 00m

$617

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

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.

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

    Most travelers choose Milan Linate - Chicago Midway, Milan Malpensa - Chicago Midway or Naples - 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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Dublin to O'Hare Intl flights
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Zurich to O'Hare Intl flights
Vienna to O'Hare Intl flights
Beauvais-Tille to O'Hare Intl flights
Amsterdam to O'Hare Intl flights
Madrid to Midway flights
Barcelona-El Prat to Midway flights
Frankfurt-Hahn to O'Hare Intl flights
Stansted to O'Hare Intl flights
Krakow to O'Hare Intl flights
Modlin to O'Hare Intl flights
Luton to O'Hare Intl flights
Athens to O'Hare Intl flights
Bergamo to O'Hare Intl flights
Vicenza to O'Hare Intl flights
Istanbul to Midway flights
Munich to Midway flights
Naples to O'Hare Intl flights
Bruxelles-National to Midway flights
Duesseldorf Intl to O'Hare Intl flights
Vilnius to O'Hare Intl flights
Amsterdam to Midway flights
Sabiha Gokcen to O'Hare Intl flights
Ciampino to O'Hare Intl flights
Berlin to O'Hare Intl flights

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