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$309+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Mar 8 — Mar 151
Sat 3/8
Sat 3/15
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 March 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$554
(KLM)

One-way from

$309
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$710
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. 25% potential increase in price ($266 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 March 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 March 3, 2025.

This KLM deal was found by Cheapflights users on 3/2. 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.
Wed 4/29:54 amMDW - FCO
1 stop14h 41mKLM
Wed 4/911:35 amFCO - MDW
1 stop17h 46mKLM
Deal found 3/2$554
This Delta deal was found by Cheapflights users on 3/2. 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 3/1712:51 pmMDW - FCO
1 stop14h 34mDelta
Wed 4/29:45 amFCO - MDW
1 stop19h 38mDelta
Deal found 3/2$559
This Air France deal was found by Cheapflights users on 3/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/52:08 pmMDW - FCO
2 stops14h 37mAir France
Tue 3/1111:45 amFCO - MDW
1 stop16h 38mAir France
Deal found 3/2$587
This Delta deal was found by Cheapflights users on 3/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/29:25 amMDW - NAP
2 stops19h 10mDelta
Wed 4/96:35 amNAP - MDW
2 stops22h 46mDelta
Deal found 3/3$647
This Delta deal was found by Cheapflights users on 3/2. 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 4/12:55 pmMDW - BLQ
2 stops15h 55mDelta
Tue 4/86:00 amBLQ - MDW
2 stops19h 02mDelta
Deal found 3/2$654
This Delta deal was found by Cheapflights users on 3/2. 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.
Sat 11/85:59 pmMDW - FLR
2 stops13h 36mDelta
Sat 11/1510:00 amFLR - MDW
2 stops18h 47mDelta
Deal found 3/2$766
This Flighttix deal was found by Cheapflights users on 3/2. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/16:42 pmMDW - BRI
2 stops31h 03mKLM
Tue 4/810:25 pmBRI - MDW
2 stops26h 37mKLM
Deal found 3/2$771
This Air France deal was found by Cheapflights users on 3/3. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/89:33 amMDW - FCO
2 stops16h 37mMultiple Airlines
Sat 3/1510:05 amFCO - MDW
2 stops18h 22mMultiple Airlines
Deal found 3/3$790
This KLM deal was found by Cheapflights users on 3/3. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/19:54 amMDW - VCE
1 stop19h 01mKLM
Tue 4/811:20 amVCE - MDW
1 stop18h 01mKLM
Deal found 3/3$804
This Air France deal was found by Cheapflights users on 3/1. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/161:16 pmMDW - NAP
2 stops15h 19mAir France
Wed 4/236:10 amNAP - MDW
2 stops18h 09mAir France
Deal found 3/1$817
This Delta deal was found by Cheapflights users on 3/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/210:36 amMDW - VCE
2 stops15h 44mDelta
Tue 4/811:20 amVCE - MDW
1 stop18h 01mDelta
Deal found 3/3$829
This Flighttix deal was found by Cheapflights users on 3/2. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/112:51 pmMDW - BRI
2 stops20h 44mMultiple Airlines
Tue 4/810:25 pmBRI - MDW
2 stops26h 37mMultiple Airlines
Deal found 3/2$831

Find flights from Midway to Italy within your budget

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 March 3, 2025.

Fly from

Midway

Fly to

Italy

Route

Depart

Return

Price

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 4/2

9:54 am-7:35 am

1 stop14h 41m

Rome Fiumicino

Wed 4/9

11:35 am-10:21 pm

1 stop17h 46m

$554

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 4/2

10:36 am-10:05 am

2 stops16h 29m

Rome Fiumicino

Wed 4/9

10:10 am-10:21 pm

2 stops19h 11m

$576

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 4/2

9:25 am-11:35 am

2 stops19h 10m

Naples

Wed 4/9

6:35 am-10:21 pm

2 stops22h 46m

$647

ChicagoBologna

MDW - BLQ

MDWBLQ

Chicago Midway

Tue 4/1

2:55 pm-1:50 pm

2 stops15h 55m

Bologna Guglielmo Marconi

Tue 4/8

6:00 am-6:02 pm

2 stops19h 02m

$654

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sat 3/29

4:00 pm-6:35 am

1 stop32h 35m

Rome Fiumicino

Fri 4/11

9:45 am-10:21 pm

1 stop19h 36m

$710

ChicagoBari

MDW - BRI

MDWBRI

Chicago Midway

Tue 4/1

6:42 pm-8:45 am

2 stops31h 03m

Bari Palese

Tue 4/8

10:25 pm-6:02 pm

2 stops26h 37m

$771

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Tue 3/25

2:55 pm-11:40 am

2 stops14h 45m

Florence Peretola

Mon 3/31

6:30 am-6:18 pm

2 stops18h 48m

$790

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Tue 4/1

9:54 am-11:55 am

1 stop19h 01m

Venice Marco Polo

Tue 4/8

11:20 am-10:21 pm

1 stop18h 01m

$804

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 4/16

1:16 pm-11:35 am

2 stops15h 19m

Naples

Wed 4/23

6:10 am-5:19 pm

2 stops18h 09m

$817

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Wed 4/2

10:36 am-9:20 am

2 stops15h 44m

Venice Marco Polo

Tue 4/8

11:20 am-10:21 pm

1 stop18h 01m

$829

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

Showing 1-10 of 60 results
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6

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.

Travel insights for flights from Midway to Italy

Get recent, data-driven insights about flights from Midway to Italy including ideal travel times, pricing trends, and more.

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 March 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 March 3, 2025.
Peruse reviews from past customers who have flown with Delta, KLM and Air Transat 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
8,068 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Crew

8.5

Food

7.3

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
8,068 reviews
Delta
8.0
Very good
8,068 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Crew

8.5

Food

7.3

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
8,068 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Crew

8.5

Food

7.3

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
8,068 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Crew

8.5

Food

7.3

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
1,437 reviews
Delta
8.0
Very good
8,068 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Crew

8.5

Food

7.3

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.

WestJet
7.2
Good
2,788 reviews
Delta
8.0
Very good
8,068 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Crew

8.5

Food

7.3

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 $406 on KLM. Other airlines that offer cheap prices include Delta from $463 and Air France from $561 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 $1,286). 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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O'Hare Intl to Leonardo da Vinci/Fiumicino flights
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O'Hare Intl to Frankfurt flights
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Midway to Dublin flights
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Midway to Madrid flights
Midway to Lisbon flights
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O'Hare Intl to Budapest flights
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Midway to Amsterdam flights
O'Hare Intl to Prague flights
O'Hare Intl to Berlin flights
Midway to Istanbul flights
O'Hare Intl to Dubrovnik flights
Midway to Keflavik Intl flights
Midway to Oslo Gardermoen 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 March 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$575Average$1,178FlexibilityNo cancel feeOn-timeN/A
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