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$256+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — VCE
Jan 20 — Jan 271
Mon 1/20
Mon 1/27
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 January 15, 2025.

Round-trip from

$550
(KLM)

One-way from

$310
(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 January 15, 2025.

This KLM deal was found by Cheapflights users on 1/14. 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 2/96:00 amMDW - FCO
1 stop21h 30mKLM
Wed 2/1912:45 pmFCO - MDW
1 stop16h 35mKLM
Deal found 1/14$550
This Delta deal was found by Cheapflights users on 1/14. 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 1/2812:44 pmMDW - FCO
1 stop14h 46mDelta
Wed 2/1212:45 pmFCO - MDW
1 stop16h 35mDelta
Deal found 1/14$554
This Air France deal was found by Cheapflights users on 1/13. 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.
Sun 2/93:41 pmMDW - FCO
1 stop11h 49mMultiple Airlines
Thu 2/206:10 amFCO - MDW
2 stops17h 11mMultiple Airlines
Deal found 1/13$559
This AirNGo deal was found by Cheapflights users on 1/14. 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 AirNGo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/265:07 pmMDW - VCE
2 stops16h 33mKLM
Tue 2/116:30 amVCE - MDW
2 stops16h 51mKLM
Deal found 1/14$564
This Air France deal was found by Cheapflights users on 1/14. 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 2/182:08 pmMDW - VCE
2 stops14h 37mMultiple Airlines
Tue 2/256:30 amVCE - MDW
2 stops16h 51mMultiple Airlines
Deal found 1/14$570
This Air France deal was found by Cheapflights users on 1/15. 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 1/292:08 pmMDW - FCO
2 stops14h 37mAir France
Wed 2/512:45 pmFCO - MDW
1 stop16h 35mAir France
Deal found 1/15$576
This Delta deal was found by Cheapflights users on 1/15. 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 2/129:33 amMDW - VCE
2 stops18h 57mDelta
Wed 2/266:30 amVCE - MDW
2 stops18h 13mDelta
Deal found 1/15$586
This Delta deal was found by Cheapflights users on 1/15. 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 11/41:05 pmMDW - MXP
1 stop13h 00mDelta
Fri 11/1411:05 amMXP - MDW
1 stop17h 42mDelta
Deal found 1/15$648
This KLM deal was found by Cheapflights users on 1/14. 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 2/49:33 amMDW - NAP
2 stops17h 02mKLM
Tue 2/116:05 amNAP - MDW
2 stops18h 38mKLM
Deal found 1/14$652
This KLM deal was found by Cheapflights users on 1/15. 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 3/96:42 pmMDW - MXP
2 stops15h 28mKLM
Tue 3/2511:00 amMXP - MDW
2 stops28h 09mKLM
Deal found 1/15$664
This Billigflug deal was found by Cheapflights users on 1/14. 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 Billigflug is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/192:08 pmMDW - CTA
2 stops22h 42mMultiple Airlines
Wed 2/2610:15 amCTA - MDW
2 stops19h 05mMultiple Airlines
Deal found 1/14$671
This Delta deal was found by Cheapflights users on 1/15. 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.
Fri 2/72:08 pmMDW - NAP
2 stops18h 42mDelta
Wed 2/126:35 amNAP - MDW
2 stops22h 45mDelta
Deal found 1/15$694

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 January 15, 2025.

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Price

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 2/9

6:00 am-10:30 am

1 stop21h 30m

Rome Fiumicino

Wed 2/19

12:45 pm-10:20 pm

1 stop16h 35m

$550

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 1/28

12:44 pm-10:30 am

1 stop14h 46m

Rome Fiumicino

Wed 2/12

12:45 pm-10:20 pm

1 stop16h 35m

$554

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 2/9

3:41 pm-10:30 am

1 stop11h 49m

Rome Fiumicino

Thu 2/20

6:10 am-4:21 pm

2 stops17h 11m

$559

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Sun 1/26

5:07 pm-4:40 pm

2 stops16h 33m

Venice Marco Polo

Tue 2/11

6:30 am-4:21 pm

2 stops16h 51m

$564

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Tue 2/18

2:08 pm-11:45 am

2 stops14h 37m

Venice Marco Polo

Tue 2/25

6:30 am-4:21 pm

2 stops16h 51m

$570

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 1/29

2:08 pm-11:45 am

2 stops14h 37m

Rome Fiumicino

Wed 2/5

12:45 pm-10:20 pm

1 stop16h 35m

$576

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Tue 2/18

2:08 pm-3:00 pm

2 stops17h 52m

Venice Marco Polo

Tue 2/25

6:30 am-6:11 pm

2 stops18h 41m

$580

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 3/25

12:51 pm-8:05 am

1 stop13h 14m

Milan Malpensa

Wed 4/2

11:40 am-10:27 pm

1 stop17h 47m

$648

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 2/4

9:33 am-9:35 am

2 stops17h 02m

Naples

Tue 2/11

6:05 am-5:43 pm

2 stops18h 38m

$652

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 3/25

9:25 am-8:45 am

2 stops17h 20m

Milan Malpensa

Wed 4/2

11:40 am-10:27 pm

1 stop17h 47m

$653

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

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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 January 15, 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 January 15, 2025.
Peruse reviews from past customers who have flown with KLM, Air France and Delta 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.