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$300+ 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — FCO
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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Cheap flight deals from Midway to Italy

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Italy (IT0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$531
(Delta)

One-way from

$300
(Kiwi.com)
From Chicago Midway to Italy
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One-way flight from Chicago Midway to Italy
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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 December 18, 2024.

This Delta deal was found by Cheapflights users on 12/17. 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 12/2812:10 pmMDW - FCO
1 stop15h 20mDelta
Fri 1/1712:45 pmFCO - MDW
1 stop28h 27mDelta
Deal found 12/17$615
This Air France deal was found by Cheapflights users on 12/17. 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 12/2812:10 pmMDW - FCO
1 stop15h 20mMultiple Airlines
Fri 1/176:10 amFCO - MDW
2 stops19h 04mMultiple Airlines
Deal found 12/17$624
This Aeromexico deal was found by Cheapflights users on 12/17. 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.
Thu 12/265:03 pmMDW - FCO
1 stop34h 27mAir France
Sun 1/128:45 pmFCO - MDW
2 stops32h 35mAir France
Deal found 12/17$969
This KLM deal was found by Cheapflights users on 12/17. 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 12/2710:08 amMDW - FCO
1 stop17h 22mKLM
Tue 12/3110:15 amFCO - MDW
1 stop18h 51mKLM
Deal found 12/17$1,298
This Delta deal was found by Cheapflights users on 12/17. 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 12/189:38 amMDW - MXP
2 stops17h 07mDelta
Fri 12/2711:05 amMXP - MDW
1 stop18h 01mDelta
Deal found 12/17$1,364
This Aeromexico deal was found by Cheapflights users on 12/17. 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 12/295:03 pmMDW - BRI
2 stops42h 27mAir France
Sat 3/156:20 amBRI - MDW
2 stops22h 07mAir France
Deal found 12/17$1,423
This Delta deal was found by Cheapflights users on 12/18. 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 12/2910:08 amMDW - BRI
2 stops21h 27mDelta
Sat 3/156:20 amBRI - MDW
2 stops22h 07mDelta
Deal found 12/18$1,556
This Delta deal was found by Cheapflights users on 12/17. 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 12/269:30 amMDW - FLR
2 stops18h 50mDelta
Mon 12/306:40 amFLR - MDW
2 stops16h 37mDelta
Deal found 12/17$2,189
This Air France deal was found by Cheapflights users on 12/17. 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.
Thu 12/2612:10 pmMDW - MXP
1 stop13h 55mAir France
Fri 1/1011:35 amMXP - MDW
2 stops17h 45mAir France
Deal found 12/17$2,213
This Delta deal was found by Cheapflights users on 12/18. 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 12/2612:10 pmMDW - BLQ
2 stops15h 25mDelta
Wed 1/16:30 amBLQ - MDW
2 stops16h 40mDelta
Deal found 12/18$2,458
This Delta deal was found by Cheapflights users on 12/17. 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 12/2611:48 amMDW - LIN
2 stops15h 42mDelta
Sat 1/46:30 amLIN - MDW
2 stops16h 54mDelta
Deal found 12/17$2,525
This Delta deal was found by Cheapflights users on 12/17. 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 12/2312:10 pmMDW - VCE
2 stops16h 35mDelta
Thu 12/266:30 amVCE - MDW
2 stops18h 14mDelta
Deal found 12/17$2,819

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 3/5

10:57 am-9:45 am

2 stops15h 48m

Milan Malpensa

Wed 3/19

10:05 am-10:27 pm

1 stop18h 22m

$531

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 1/20

12:44 pm-10:35 am

2 stops14h 51m

Milan Malpensa

Mon 1/27

6:40 pm-4:21 pm

2 stops28h 41m

$550

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 1/22

2:08 pm-11:45 am

2 stops14h 37m

Rome Fiumicino

Wed 1/29

12:45 pm-10:20 pm

1 stop16h 35m

$554

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Sun 2/9

5:05 pm-2:00 pm

2 stops13h 55m

Milan Linate

Wed 2/19

9:05 am-6:11 pm

2 stops16h 06m

$563

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 1/15

2:08 pm-11:55 am

2 stops14h 47m

Rome Fiumicino

Tue 1/21

6:10 am-4:21 pm

2 stops17h 11m

$569

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 1/22

2:08 pm-11:45 am

2 stops14h 37m

Rome Fiumicino

Wed 1/29

12:45 pm-10:20 pm

1 stop16h 35m

$586

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 4/9

10:10 am-9:25 am

1 stop16h 15m

Milan Malpensa

Wed 4/30

11:40 am-9:46 pm

1 stop17h 06m

$597

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Mon 1/20

2:08 pm-11:30 am

2 stops14h 22m

Venice Marco Polo

Wed 2/5

6:30 am-4:21 pm

2 stops16h 51m

$602

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Sun 1/19

5:05 pm-3:00 pm

2 stops14h 55m

Venice Marco Polo

Thu 1/30

6:30 am-4:21 pm

2 stops16h 51m

$610

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Sun 1/12

2:08 pm-3:00 pm

2 stops17h 52m

Venice Marco Polo

Tue 1/21

6:30 am-10:20 pm

2 stops22h 50m

$619

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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.

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 December 18, 2024.

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 December 18, 2024.
Peruse reviews from past customers who have flown with KLM, Delta and Air France 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
8,604 reviews

Crew

8.6

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,604 reviews
Delta
8.0
Very good
8,604 reviews

Crew

8.6

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

KLM
7.8
Good
1,349 reviews
Delta
8.0
Very good
8,604 reviews

Crew

8.6

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air France
7.4
Good
1,504 reviews
Delta
8.0
Very good
8,604 reviews

Crew

8.6

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 10

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 $352 on Delta. Other airlines that offer cheap prices include KLM from $374 and Air France from $1,209 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, December is the cheapest month in which you can book a flight from Chicago Midway Airport to Italy (average of $635). Flying from Chicago Midway Airport to Italy in June is currently the most expensive (average of $1,263). 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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Midway to Istanbul flights
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Midway to Krakow 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$578Average$1,178FlexibilityNo cancel feeOn-timeN/A
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