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$255+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheap flight deals from Midway to Italy

Keep the following information in mind while searching for Midway to Italy flight deals. Data was last updated July 29, 2025.

Round-trip from

$539
(KLM)

One-way from

$255
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$941
From Chicago Midway to Italy
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One-way flight from Chicago Midway to Italy
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Highest demand for flights based on searches. 23% potential increase in price ($232 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find 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 July 29, 2025.

This KLM deal was found by Cheapflights users on 7/27. 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 12/11:05 pmMDW - FCO
1 stop14h 25mKLM
Sat 12/1312:40 pmFCO - MDW
1 stop16h 04mKLM
Deal found 7/27$539
This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 10/251:06 pmMDW - FCO
2 stops20h 14mDelta
Sat 11/86:00 amFCO - MDW
2 stops23h 14mDelta
Deal found 7/28$540
This KLM deal was found by Cheapflights users on 7/27. 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.
Fri 11/141:05 pmMDW - FCO
1 stop11h 50mMultiple Airlines
Thu 11/2010:05 amFCO - MDW
1 stop15h 31mMultiple Airlines
Deal found 7/27$552
This Delta deal was found by Cheapflights users on 7/27. 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 10/206:23 pmMDW - NAP
2 stops16h 52mDelta
Tue 11/186:15 amNAP - MDW
2 stops19h 21mDelta
Deal found 7/27$629
This Expedia deal was found by Cheapflights users on 7/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/410:31 amMDW - NAP
1 stop13h 29mMultiple Airlines
Wed 8/206:10 amNAP - MDW
2 stops18h 37mMultiple Airlines
Deal found 7/28$647
This Air France deal was found by Cheapflights users on 7/26. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1510:35 amMDW - NAP
1 stop13h 25mAir France
Sun 10/1912:05 pmNAP - MDW
2 stops37h 20mAir France
Deal found 7/26$688
This KLM deal was found by Cheapflights users on 7/28. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/256:00 amMDW - NAP
1 stop18h 00mKLM
Sun 8/319:00 amNAP - MDW
1 stop19h 12mKLM
Deal found 7/28$703
This Expedia deal was found by Cheapflights users on 7/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/181:08 pmMDW - PMO
2 stops15h 22mKLM
Wed 9/36:10 amPMO - MDW
2 stops19h 27mKLM
Deal found 7/28$761
This Delta deal was found by Cheapflights users on 7/29. 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 8/111:08 pmMDW - PMO
2 stops18h 52mDelta
Mon 8/253:45 pmPMO - MDW
2 stops32h 52mDelta
Deal found 7/29$771
This Delta deal was found by Cheapflights users on 7/28. 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.
Mon 11/241:05 pmMDW - VCE
2 stops18h 50mDelta
Tue 12/21:15 pmVCE - MDW
2 stops27h 36mDelta
Deal found 7/28$814
This Delta deal was found by Cheapflights users on 7/27. 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.
Tue 12/21:05 pmMDW - MXP
2 stops15h 35mDelta
Tue 12/1611:05 amMXP - MDW
1 stop17h 39mDelta
Deal found 7/27$849
This KLM deal was found by Cheapflights users on 7/29. 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 11/191:05 pmMDW - MXP
1 stop13h 00mKLM
Tue 11/2511:05 amMXP - MDW
1 stop17h 39mKLM
Deal found 7/29$865

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 July 29, 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

Mon 12/1

1:05 pm-10:30 am

1 stop14h 25m

Rome Fiumicino

Sat 12/13

12:40 pm-9:44 pm

1 stop16h 04m

$539

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 11/4

1:08 pm-11:45 am

2 stops15h 37m

Rome Fiumicino

Tue 11/11

6:00 am-6:36 pm

2 stops19h 36m

$543

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Fri 11/14

1:05 pm-7:55 am

1 stop11h 50m

Rome Fiumicino

Thu 11/20

10:05 am-6:36 pm

1 stop15h 31m

$552

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 10/20

6:23 pm-6:15 pm

2 stops16h 52m

Naples

Tue 11/18

6:15 am-6:36 pm

2 stops19h 21m

$629

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 10/15

10:35 am-7:00 am

1 stop13h 25m

Naples

Sun 10/19

12:05 pm-6:25 pm

2 stops37h 20m

$688

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 8/25

6:00 am-7:00 am

1 stop18h 00m

Naples

Sun 8/31

9:00 am-9:12 pm

1 stop19h 12m

$703

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Mon 8/18

1:08 pm-11:30 am

2 stops15h 22m

Palermo Punta Raisi

Wed 9/3

6:10 am-6:37 pm

2 stops19h 27m

$761

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Mon 8/11

1:08 pm-3:00 pm

2 stops18h 52m

Palermo Punta Raisi

Mon 8/25

3:45 pm-5:37 pm

2 stops32h 52m

$771

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 9/12

6:00 am-7:00 am

1 stop18h 00m

Naples

Thu 9/25

9:00 am-5:35 pm

1 stop15h 35m

$803

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 12/2

1:05 pm-11:40 am

2 stops15h 35m

Milan Malpensa

Tue 12/16

11:05 am-9:44 pm

1 stop17h 39m

$849

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 54 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

What is the cheapest time of day to fly from MDW to IT?

Find hourly flight availability from Midway to Italy. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Italy as you normally would.

Reviews of airlines servicing Italy

Get insights into the airlines that provide service to Italy. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Italy. Reviews last updated July 29, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Italy, such as Porter Airlines, Delta, and KLM. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
317 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
317 reviews
Porter Airlines
8.0
Very good
317 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,977 reviews
Porter Airlines
8.0
Very good
317 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
KLM
7.8
Good
1,383 reviews
Porter Airlines
8.0
Very good
317 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Transat
7.7
Good
424 reviews
Porter Airlines
8.0
Very good
317 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air France
7.5
Good
1,465 reviews
Porter Airlines
8.0
Very good
317 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Italy one-way?

    One-way options have recently been found by users for as low as $378 on KLM. Other airlines that offer cheap prices include Delta from $428 and Porter Airlines from $447 one-way.

  • 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.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Italy (average of $703). Flying from Chicago Midway Airport to Italy in June is currently the most expensive (average of $1,210). 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

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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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