$349+ Cheap flights from Italy to Midway (MDW)
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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — MDW
Jan 25 — Feb 11
1 adult, Economy
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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 Italy to Midway
Cheapest flights from Italy to MidwayExplore the most affordable flight options available from Italy to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 26, 2025.
Explore the most affordable flight options available from Italy to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 26, 2025.
This Delta deal was found by Cheapflights users on 12/25. 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 12/3110:55 amLIN - MDW
2 stops28h 54mDelta
Mon 3/166:34 pmMDW - LIN
2 stops13h 21mDelta
Deal found 12/25![Delta logo]()
$1,038
This Delta deal was found by Cheapflights users on 12/25. 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 12/3010:05 amFCO - MDW
1 stop29h 44mDelta
Mon 3/166:34 pmMDW - FCO
2 stops16h 51mDelta
Deal found 12/25![Delta logo]()
$1,040
This Delta deal was found by Cheapflights users on 12/25. 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 12/3112:40 pmFCO - MDW
1 stop27h 25mDelta
Tue 3/179:35 amMDW - FCO
1 stop15h 20mDelta
Deal found 12/25![Delta logo]()
$1,044
This Delta deal was found by Cheapflights users on 12/24. 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 12/2812:40 pmFCO - MDW
1 stop27h 25mDelta
Tue 3/1712:47 pmMDW - FCO
1 stop14h 43mDelta
Deal found 12/24![Delta logo]()
$1,056
This Delta deal was found by Cheapflights users on 12/25. 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 12/2912:40 pmFCO - MDW
1 stop16h 42mDelta
Wed 3/2510:45 amMDW - FCO
1 stop14h 10mDelta
Deal found 12/25![Delta logo]()
$1,064
This Delta deal was found by Cheapflights users on 12/25. 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 12/2910:05 amFCO - MDW
1 stop14h 21mDelta
Fri 3/136:34 pmMDW - FCO
1 stop30h 21mDelta
Deal found 12/25![Delta logo]()
$1,068
This Delta deal was found by Cheapflights users on 12/24. 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 12/2910:05 amFCO - MDW
1 stop14h 21mDelta
Tue 10/131:00 pmMDW - FCO
1 stop15h 00mDelta
Deal found 12/24![Delta logo]()
$1,073
This Delta deal was found by Cheapflights users on 12/25. 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 12/2912:40 pmFCO - MDW
1 stop16h 42mDelta
Sat 3/141:10 pmMDW - FCO
1 stop11h 45mDelta
Deal found 12/25![Delta logo]()
$1,076
This Delta deal was found by Cheapflights users on 12/26. 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 12/296:30 amLIN - MDW
2 stops16h 50mDelta
Wed 1/71:28 pmMDW - LIN
2 stops14h 47mDelta
Deal found 12/26![Delta logo]()
$1,114
This Delta deal was found by Cheapflights users on 12/25. 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 12/3112:40 pmFCO - MDW
1 stop27h 25mDelta
Thu 3/266:25 amMDW - FCO
1 stop21h 05mDelta
Deal found 12/25![Delta logo]()
$1,114
This Delta deal was found by Cheapflights users on 12/24. 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 12/2911:35 amMXP - MDW
2 stops17h 47mDelta
Wed 1/71:28 pmMDW - MXP
2 stops14h 07mDelta
Deal found 12/24![Delta logo]()
$1,116
This Delta deal was found by Cheapflights users on 12/24. 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 12/2810:05 amFCO - MDW
2 stops19h 17mDelta
Mon 1/56:45 amMDW - FCO
1 stop18h 10mDelta
Deal found 12/24![Delta logo]()
$1,120
Find flight deals from Italy to Midway
Keep the following information in mind while searching for Italy to Midway flight deals. Data was last updated December 26, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $628 (Delta) |
One-way from | $349 (Kiwi.com) |
Popular in | August |
Cheapest in | April |
Average price | $691 |
Cheapflights Fare Finder
Customize your flight search to find flights from Italy to Midway 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 26, 2025.
Use the filters below to find and compare flights from Italy to Chicago Midway Airport that are best for you.
Fly from
Italy
Fly to
Midway
Route
Depart
Return
Price
BolognaChicago
BLQ - MDW
BLQMDW
Bologna Guglielmo Marconi
Fri 1/16
6:30 am-10:07 pm
2 stops22h 37m
Chicago Midway
Tue 1/20
10:48 am-10:30 am
2 stops16h 42m
$628
BolognaChicago
BLQ - MDW
BLQMDW
Bologna Guglielmo Marconi
Thu 2/12
6:30 am-5:45 pm
2 stops18h 15m
Chicago Midway
Mon 2/16
1:26 pm-3:45 pm
2 stops19h 19m
$629
VeniceChicago
VCE - MDW
VCEMDW
Venice Marco Polo
Thu 4/23
6:00 am-5:54 pm
2 stops18h 54m
Chicago Midway
Mon 4/27
1:10 pm-11:50 am
2 stops15h 40m
$633
MilanChicago
LIN - MDW
LINMDW
Milan Linate
Fri 4/24
6:40 am-4:36 pm
2 stops16h 56m
Chicago Midway
Sun 4/26
6:34 pm-1:55 pm
2 stops12h 21m
$635
MilanChicago
MXP - MDW
MXPMDW
Milan Malpensa
Thu 1/15
11:05 am-10:07 pm
1 stop18h 02m
Chicago Midway
Wed 1/28
1:49 pm-11:40 am
2 stops14h 51m
$635
MilanChicago
MXP - MDW
MXPMDW
Milan Malpensa
Thu 2/19
1:20 pm-10:31 pm
1 stop16h 11m
Chicago Midway
Sun 2/22
6:17 pm-2:55 pm
2 stops13h 38m
$635
BolognaChicago
BLQ - MDW
BLQMDW
Bologna Guglielmo Marconi
Thu 2/5
6:30 am-5:29 pm
2 stops17h 59m
Chicago Midway
Wed 2/11
6:14 pm-4:25 pm
2 stops15h 11m
$635
MilanChicago
LIN - MDW
LINMDW
Milan Linate
Wed 1/28
6:30 am-5:29 pm
2 stops17h 59m
Chicago Midway
Mon 2/2
1:26 pm-11:15 am
2 stops14h 49m
$636
MilanChicago
LIN - MDW
LINMDW
Milan Linate
Thu 1/15
6:30 am-6:32 pm
2 stops19h 02m
Chicago Midway
Wed 1/28
10:46 am-8:45 am
2 stops14h 59m
$636
MilanChicago
LIN - MDW
LINMDW
Milan Linate
Fri 1/23
6:30 am-5:29 pm
2 stops17h 59m
Chicago Midway
Sun 1/25
6:35 pm-1:55 pm
2 stops12h 20m
$636
Showing 1-10 of 60 results
Best time to book a flight from Italy to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Italy 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 Italy to Chicago Midway Airport
How often are flights from Italy to Chicago delayed?
About 0% of weekly flights between Italy and Chicago have experienced delays in the past year, with the average delay time being 0 minutes.
What is the most punctual flight time for Italy to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Monday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Related info for your journey
Find useful and relevant information for your journey from Italy to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor