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$319+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$800
(Delta)

One-way from

$319
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$748
Provider with most accurate pricing for Chicago (CHI)-Rome (ROM) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Rome (ROM) flights.
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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. 24% potential increase in price ($244 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Delta deal was found by Cheapflights users on 4/23. 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 - FCO
1 stop14h 25mDelta
Sun 12/712:45 pmFCO - MDW
1 stop15h 59mDelta
Deal found 4/23$626
This KLM deal was found by Cheapflights users on 4/24. 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 - FCO
1 stop14h 25mKLM
Tue 11/2510:05 amFCO - MDW
1 stop15h 31mKLM
Deal found 4/24$735
This Trip.com deal was found by Cheapflights users on 4/22. 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.
Sat 4/2612:19 pmMDW - FCO
2 stops23h 51mMultiple Airlines
Mon 4/288:50 amFCO - MDW
2 stops31h 26mMultiple Airlines
Deal found 4/22$803
This Delta deal was found by Cheapflights users on 4/23. 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 10/233:40 pmMDW - FLR
2 stops16h 05mDelta
Sat 11/16:35 amFLR - MDW
2 stops17h 32mDelta
Deal found 4/23$857
This Delta deal was found by Cheapflights users on 4/23. 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 10/269:30 amMDW - MXP
2 stops17h 15mDelta
Thu 11/611:05 amMXP - MDW
1 stop17h 39mDelta
Deal found 4/23$876
This Delta deal was found by Cheapflights users on 4/24. 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 8/185:59 pmMDW - BLQ
2 stops16h 06mDelta
Sun 8/246:00 amBLQ - MDW
2 stops19h 03mDelta
Deal found 4/24$890
This Delta deal was found by Cheapflights users on 4/23. 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 9/305:59 pmMDW - NAP
2 stops17h 16mDelta
Tue 10/76:35 amNAP - MDW
2 stops18h 23mDelta
Deal found 4/23$918
This Delta deal was found by Cheapflights users on 4/23. 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 10/153:40 pmMDW - VCE
1 stop13h 15mDelta
Fri 10/246:00 amVCE - MDW
2 stops19h 36mDelta
Deal found 4/23$934
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/25:20 pmMDW - FCO
2 stops34h 05mPorter Airlines
Mon 7/712:15 pmFCO - MDW
2 stops27h 30mPorter Airlines
Deal found 4/23$947
This Mytrip deal was found by Cheapflights users on 4/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/79:40 amMDW - NAP
2 stops17h 00mMultiple Airlines
Fri 6/136:40 amNAP - MDW
3 stops33h 05mMultiple Airlines
Deal found 4/22$975
This Air France deal was found by Cheapflights users on 4/24. 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.
Tue 11/181:00 pmMDW - FCO
1 stop11h 55mAir France
Wed 11/2612:45 pmFCO - MDW
1 stop15h 59mAir France
Deal found 4/24$980
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Sun 5/1110:55 amMDW - VCE
2 stops28h 10mMultiple Airlines
Sat 5/241:25 pmVCE - MDW
1 stop26h 20mMultiple Airlines
Deal found 4/23$1,034

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 April 24, 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

Sun 10/19

3:40 pm-11:05 am

1 stop12h 25m

Rome Fiumicino

Sat 11/1

6:10 am-6:07 pm

2 stops17h 57m

$800

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Thu 10/16

1:00 pm-9:20 am

1 stop13h 20m

Rome Fiumicino

Tue 10/21

9:00 am-6:36 pm

1 stop16h 36m

$845

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Fri 6/6

9:40 am-9:15 am

2 stops16h 35m

Rome Fiumicino

Tue 6/10

11:30 am-8:45 am

2 stops28h 15m

$868

ChicagoBologna

MDW - BLQ

MDWBLQ

Chicago Midway

Mon 8/18

5:59 pm-5:05 pm

2 stops16h 06m

Bologna Guglielmo Marconi

Sun 8/24

6:00 am-6:03 pm

2 stops19h 03m

$890

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Sat 5/10

1:08 pm-12:00 pm

2 stops15h 52m

Florence Peretola

Tue 5/20

6:30 am-6:45 pm

2 stops19h 15m

$897

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 9/30

5:59 pm-6:15 pm

2 stops17h 16m

Naples

Tue 10/7

6:35 am-5:58 pm

2 stops18h 23m

$918

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 10/15

10:35 am-9:25 am

1 stop15h 50m

Milan Malpensa

Mon 11/3

11:05 am-9:44 pm

1 stop17h 39m

$921

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 10/15

1:00 pm-12:05 pm

2 stops16h 05m

Milan Malpensa

Mon 11/3

11:05 am-9:44 pm

1 stop17h 39m

$926

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Wed 10/15

3:40 pm-11:55 am

1 stop13h 15m

Venice Marco Polo

Fri 10/24

6:00 am-6:36 pm

2 stops19h 36m

$934

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 7/2

5:20 pm-10:25 am

2 stops34h 05m

Rome Fiumicino

Mon 7/7

12:15 pm-8:45 am

2 stops27h 30m

$947

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 50 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 April 24, 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.

Rainfall in Italy by month

Plan your trip to Italy by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Italy ranges from 0.6 - 4.4 inches per month. November is typically the wettest month, when rainfall can reach 4.4 in. June is typically the driest time to visit Italy when rainfall is around 0.6 in.

Temperature in Italy by month

Plan your trip to Italy by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Italy, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 75.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 46.4 F).

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 April 24, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta and KLM from Chicago to Italy to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
284 reviews

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.8

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
284 reviews
Porter Airlines
8.0
Very good
284 reviews

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.8

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,920 reviews
Porter Airlines
8.0
Very good
284 reviews

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.8

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
KLM
7.8
Good
1,333 reviews
Porter Airlines
8.0
Very good
284 reviews

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.8

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air France
7.4
Good
1,442 reviews
Porter Airlines
8.0
Very good
284 reviews

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.8

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,816 reviews
Porter Airlines
8.0
Very good
284 reviews

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.8

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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 $506 on Delta. Other airlines that offer cheap prices include Porter Airlines from $616 and KLM from $663 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 - Venice Marco Polo.

  • 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 $1,273). 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.
O'Hare Intl to Heathrow flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
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Midway to Heathrow flights
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Midway to Barcelona-El Prat flights
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Midway to Madrid flights
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Midway to Frederic Chopin flights
Midway to Keflavik Intl flights
Midway to Istanbul flights
O'Hare Intl to Skopje flights
Midway to Frankfurt flights
O'Hare Intl to Budapest flights
O'Hare Intl to Berlin flights

Top airline flying from Midway to Italy

Discover the top airline that operate flights from Midway to Italy. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$575Average$1,091FlexibilityNo cancel feeOn-timeN/A

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