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$366+ 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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
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 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$578
(KLM)

One-way from

$366
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$702
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 ($254 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($36 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 3, 2025.

This KLM deal was found by Cheapflights users on 4/2. 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.
Sun 4/139:52 amMDW - FCO
1 stop14h 43mKLM
Tue 4/299:45 amFCO - MDW
1 stop19h 37mKLM
Deal found 4/2$578
This Delta deal was found by Cheapflights users on 4/2. 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 4/139:23 amMDW - FCO
2 stops15h 12mDelta
Tue 4/2910:10 amFCO - MDW
2 stops19h 12mDelta
Deal found 4/2$591
This Aeromexico deal was found by Cheapflights users on 4/2. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/264:00 pmMDW - FCO
1 stop32h 35mAir France
Wed 5/79:45 amFCO - MDW
1 stop18h 43mAir France
Deal found 4/2$644
This Delta deal was found by Cheapflights users on 4/2. 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 4/225:59 pmMDW - BLQ
2 stops12h 51mDelta
Fri 5/26:30 amBLQ - MDW
2 stops18h 29mDelta
Deal found 4/2$716
This Delta deal was found by Cheapflights users on 4/2. 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 4/235:59 pmMDW - FLR
2 stops16h 21mDelta
Wed 4/306:30 amFLR - MDW
2 stops14h 52mDelta
Deal found 4/2$732
This Delta deal was found by Cheapflights users on 4/1. 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 8/43:40 pmMDW - VCE
1 stop13h 15mDelta
Tue 8/2611:20 amVCE - MDW
1 stop17h 27mDelta
Deal found 4/1$746
This Aeromexico deal was found by Cheapflights users on 4/3. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/181:00 pmMDW - BLQ
2 stops21h 05mAir France
Sun 8/2411:00 amBLQ - MDW
2 stops38h 03mAir France
Deal found 4/3$828
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Fri 6/69:40 amMDW - FCO
2 stops17h 45mPorter Airlines
Sat 6/1412:15 pmFCO - MDW
2 stops35h 39mPorter Airlines
Deal found 4/2$833
This Aeromexico deal was found by Cheapflights users on 4/1. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/61:16 pmMDW - VCE
2 stops15h 29mAir France
Wed 5/146:00 amVCE - MDW
2 stops16h 30mAir France
Deal found 4/1$841
This Delta deal was found by Cheapflights users on 4/2. 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 11/31:00 pmMDW - NAP
2 stops19h 50mDelta
Thu 11/136:05 amNAP - MDW
2 stops19h 02mDelta
Deal found 4/2$858
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Tue 6/179:40 amMDW - FCO
2 stops16h 35mMultiple Airlines
Tue 6/2411:30 amFCO - MDW
2 stops35h 54mMultiple Airlines
Deal found 4/2$873
This Aeromexico deal was found by Cheapflights users on 4/2. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/209:52 amMDW - PMO
2 stops21h 33mAir France
Tue 4/293:10 pmPMO - MDW
2 stops38h 12mAir France
Deal found 4/2$875

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 3, 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 4/13

9:52 am-7:35 am

1 stop14h 43m

Rome Fiumicino

Tue 4/29

9:45 am-10:22 pm

1 stop19h 37m

$578

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 9/29

1:00 pm-9:20 am

1 stop13h 20m

Rome Fiumicino

Wed 10/8

9:00 am-6:36 pm

1 stop16h 36m

$587

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sat 4/26

4:00 pm-7:35 am

1 stop32h 35m

Rome Fiumicino

Wed 5/7

9:45 am-9:28 pm

1 stop18h 43m

$644

ChicagoBologna

MDW - BLQ

MDWBLQ

Chicago Midway

Tue 4/22

5:59 pm-1:50 pm

2 stops12h 51m

Bologna Guglielmo Marconi

Fri 5/2

6:30 am-5:59 pm

2 stops18h 29m

$716

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Wed 4/23

5:59 pm-5:20 pm

2 stops16h 21m

Florence Peretola

Wed 4/30

6:30 am-2:22 pm

2 stops14h 52m

$732

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Mon 8/4

3:40 pm-11:55 am

1 stop13h 15m

Venice Marco Polo

Tue 8/26

11:20 am-9:47 pm

1 stop17h 27m

$746

ChicagoBologna

MDW - BLQ

MDWBLQ

Chicago Midway

Mon 8/18

1:00 pm-5:05 pm

2 stops21h 05m

Bologna Guglielmo Marconi

Sun 8/24

11:00 am-6:03 pm

2 stops38h 03m

$828

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Fri 6/6

9:40 am-10:25 am

2 stops17h 45m

Rome Fiumicino

Sat 6/14

12:15 pm-4:54 pm

2 stops35h 39m

$833

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Tue 5/6

1:16 pm-11:45 am

2 stops15h 29m

Venice Marco Polo

Wed 5/14

6:00 am-3:30 pm

2 stops16h 30m

$841

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 6/17

9:40 am-9:15 am

2 stops16h 35m

Rome Fiumicino

Tue 6/24

11:30 am-4:24 pm

2 stops35h 54m

$873

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 53 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 3, 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 3, 2025.
Peruse reviews from past customers who have flown with Delta, Porter Airlines 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.
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Porter Airlines
7.9
Good
279 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
KLM
7.8
Good
1,323 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Transat
7.8
Good
382 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air France
7.4
Good
1,427 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding 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 $413 on KLM. Other airlines that offer cheap prices include Delta from $499 and Air France from $519 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 - Milan Linate.

  • 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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O'Hare Intl to Malpensa flights
Midway to Heathrow flights
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Midway to Charles de Gaulle flights
Midway to Athens flights
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Midway to Barcelona-El Prat flights
O'Hare Intl to Linate flights
Midway to Madrid flights
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Midway to Lisbon flights
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Midway to Istanbul flights
Midway to Frederic Chopin flights
Midway to Amsterdam flights
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O'Hare Intl to Budapest flights
O'Hare Intl to Naples flights
Midway to Malpensa flights
O'Hare Intl to Prague flights
O'Hare Intl to Luton 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$575Average$1,091FlexibilityNo cancel feeOn-timeN/A

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