$293+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Jun 17 — Jun 241
1 adult, Economy
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Find cheap flights from Midway to Italy with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 June 12, 2025.
Round-trip from | $677 (Delta) |
|---|---|
One-way from | $293 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $1,118 |
Find flight deals from Midway to Italy
Cheapest flights from Midway to ItalyExplore 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 June 12, 2025.
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 June 12, 2025.
This Delta deal was found by Cheapflights users on 6/11. 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 9/61:08 pmMDW - LIN
2 stops15h 52mDelta
Sat 9/136:40 amLIN - MDW
2 stops18h 56mDelta
Deal found 6/11![Delta logo]()
$677
This Delta deal was found by Cheapflights users on 6/12. 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 10/141:00 pmMDW - FCO
1 stop13h 20mDelta
Tue 10/216:30 amFCO - MDW
2 stops18h 37mDelta
Deal found 6/12![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 6/9. 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 11/122:00 pmMDW - FLR
2 stops14h 20mDelta
Sun 11/166:50 amFLR - MDW
2 stops18h 46mDelta
Deal found 6/9![Delta logo]()
$682
This KLM deal was found by Cheapflights users on 6/12. 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.
Mon 8/41:09 pmMDW - FCO
1 stop13h 11mKLM
Mon 8/182:30 pmFCO - MDW
1 stop14h 19mKLM
Deal found 6/12![KLM logo]()
$685
This Expedia deal was found by Cheapflights users on 6/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2310:26 amMDW - FCO
1 stop14h 09mAir France
Tue 7/86:05 amFCO - MDW
2 stops18h 34mAir France
Deal found 6/12![Air France logo]()
$709
This KLM deal was found by Cheapflights users on 6/11. 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 10/151:05 pmMDW - MXP
1 stop13h 20mKLM
Tue 10/2111:40 amMXP - MDW
1 stop17h 04mKLM
Deal found 6/11![KLM logo]()
$719
This Delta deal was found by Cheapflights users on 6/11. 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 10/159:30 amMDW - MXP
2 stops16h 55mDelta
Tue 10/2111:40 amMXP - MDW
1 stop17h 04mDelta
Deal found 6/11![Delta logo]()
$723
This Air France deal was found by Cheapflights users on 6/11. 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.
Mon 8/46:00 amMDW - MXP
1 stop20h 25mMultiple Airlines
Wed 8/2011:40 amMXP - MDW
1 stop17h 09mMultiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$741
This Air France deal was found by Cheapflights users on 6/12. 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 11/61:00 pmMDW - FCO
1 stop11h 55mMultiple Airlines
Sat 11/1510:05 amFCO - MDW
1 stop15h 31mMultiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$768
This KLM deal was found by Cheapflights users on 6/10. 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.
Mon 9/226:00 amMDW - NAP
1 stop18h 00mKLM
Mon 9/296:10 amNAP - MDW
2 stops17h 13mKLM
Deal found 6/10![KLM logo]()
$781
This Delta deal was found by Cheapflights users on 6/11. 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 8/166:04 amMDW - NAP
1 stop17h 56mDelta
Sat 8/236:10 amNAP - MDW
2 stops18h 27mDelta
Deal found 6/11![Delta logo]()
$788
This Delta deal was found by Cheapflights users on 6/11. 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 11/231:00 pmMDW - VCE
2 stops15h 15mDelta
Tue 12/26:30 amVCE - MDW
2 stops19h 06mDelta
Deal found 6/11![Delta logo]()
$834
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 June 12, 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
ChicagoMilan
MDW - LIN
MDWLIN
Chicago Midway
Sat 9/6
1:08 pm-12:00 pm
2 stops15h 52m
Milan Linate
Sat 9/13
6:40 am-6:36 pm
2 stops18h 56m
$677
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Mon 8/4
1:09 pm-9:20 am
1 stop13h 11m
Rome Fiumicino
Mon 8/18
2:30 pm-9:49 pm
1 stop14h 19m
$685
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Sun 6/15
6:20 pm-4:35 pm
2 stops15h 15m
Rome Fiumicino
Sun 6/22
6:00 am-6:41 pm
2 stops19h 41m
$694
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Mon 6/23
10:26 am-7:35 am
1 stop14h 09m
Rome Fiumicino
Tue 7/8
6:05 am-5:39 pm
2 stops18h 34m
$709
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Wed 10/15
1:05 pm-9:25 am
1 stop13h 20m
Milan Malpensa
Tue 10/21
11:40 am-9:44 pm
1 stop17h 04m
$719
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Wed 10/15
9:30 am-9:25 am
2 stops16h 55m
Milan Malpensa
Tue 10/21
11:40 am-9:44 pm
1 stop17h 04m
$723
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Mon 8/4
6:00 am-9:25 am
1 stop20h 25m
Milan Malpensa
Wed 8/20
11:40 am-9:49 pm
1 stop17h 09m
$741
ChicagoNaples
MDW - NAP
MDWNAP
Chicago Midway
Sat 8/16
6:04 am-7:00 am
1 stop17h 56m
Naples
Sat 8/23
6:10 am-5:37 pm
2 stops18h 27m
$788
ChicagoFlorence
MDW - FLR
MDWFLR
Chicago Midway
Tue 9/9
1:08 pm-11:50 am
2 stops15h 42m
Florence Peretola
Wed 9/17
7:00 am-6:36 pm
2 stops18h 36m
$791
ChicagoNaples
MDW - NAP
MDWNAP
Chicago Midway
Sat 8/16
10:11 am-7:00 am
1 stop13h 49m
Naples
Sat 8/23
9:00 am-9:12 pm
1 stop19h 12m
$815
Showing 1-10 of 56 results
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 June 12, 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 June 12, 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.
Crew
8.7
Overall
8.0
Boarding
8.2
Comfort
8.1
Food
7.6
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Crew
8.7
Overall
8.0
Boarding
8.2
Comfort
8.1
Food
7.6
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Crew
8.7
Overall
8.0
Boarding
8.2
Comfort
8.1
Food
7.6
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Crew
8.7
Overall
8.0
Boarding
8.2
Comfort
8.1
Food
7.6
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Crew
8.7
Overall
8.0
Boarding
8.2
Comfort
8.1
Food
7.6
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Crew
8.7
Overall
8.0
Boarding
8.2
Comfort
8.1
Food
7.6
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ