Italy

$286+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
May 3 — May 101
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Cheap 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 April 3, 2026.

This Trip.com deal was found by Cheapflights users on 3/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:30 am
MDW
-
FCO
1 stop24h 00m
Multiple Airlines
Sun 4/197:05 pm
FCO
-
MDW
1 stop24h 55m
Multiple Airlines
Deal found 3/30$641
This Trip.com deal was found by Cheapflights users on 3/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:30 am
MDW
-
FCO
2 stops33h 05m
Multiple Airlines
Mon 4/207:05 am
FCO
-
MDW
2 stops36h 55m
Multiple Airlines
Deal found 3/31$712
This Delta deal was found by Cheapflights users on 3/31. 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 8/165:25 pm
MDW
-
FCO
1 stop12h 15m
Delta
Wed 8/266:30 am
FCO
-
MDW
2 stops18h 35m
Delta
Deal found 3/31$756
This KLM deal was found by Cheapflights users on 3/31. 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 4/152:12 pm
MDW
-
FCO
1 stop12h 58m
KLM
Thu 4/231:10 pm
FCO
-
MDW
1 stop16h 18m
KLM
Deal found 3/31$757
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:00 pm
MDW
-
FCO
2 stops15h 25m
Delta
Fri 8/216:30 am
FCO
-
MDW
2 stops18h 35m
Delta
Deal found 4/1$761
This Delta deal was found by Cheapflights users on 4/3. 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.
Tue 4/147:16 pm
MDW
-
FCO
1 stop31h 54m
Delta
Tue 4/216:30 am
FCO
-
MDW
2 stops19h 06m
Delta
Deal found 4/3$762
This Delta deal was found by Cheapflights users on 3/31. 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 8/1210:35 am
MDW
-
FCO
1 stop14h 00m
Delta
Wed 8/196:05 am
FCO
-
MDW
2 stops17h 22m
Delta
Deal found 3/31$764
This Delta deal was found by Cheapflights users on 4/3. 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 8/129:30 am
MDW
-
NAP
2 stops19h 00m
Delta
Fri 8/219:05 am
NAP
-
MDW
1 stop19h 41m
Delta
Deal found 4/3$768
This Delta deal was found by Cheapflights users on 4/2. 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 8/1810:35 am
MDW
-
NAP
1 stop13h 30m
Delta
Tue 8/256:05 am
NAP
-
MDW
2 stops19h 00m
Delta
Deal found 4/2$775
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:35 am
MDW
-
FCO
1 stop14h 00m
Delta
Mon 8/316:30 am
FCO
-
MDW
2 stops18h 35m
Delta
Deal found 4/1$806
This Delta deal was found by Cheapflights users on 3/30. 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 4/152:12 pm
MDW
-
FCO
1 stop12h 58m
Delta
Mon 4/206:30 am
FCO
-
MDW
2 stops18h 28m
Delta
Deal found 3/30$807
This Delta deal was found by Cheapflights users on 3/31. 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 10/265:59 pm
MDW
-
FCO
2 stops15h 16m
Delta
Mon 11/96:10 am
FCO
-
MDW
2 stops19h 27m
Delta
Deal found 3/31$810

Find flight deals from Midway to Italy

Keep the following information in mind while searching for Midway to Italy flight deals. Data was last updated April 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$630
(Kiwi.com)

One-way from

$286
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$762
Provider with most accurate pricing for Chicago (CHI)-Rome (ROM) flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Rome (ROM) flights.
From Chicago Midway to Italy
One-way flight from Chicago Midway to Italy
Highest demand for flights based on searches. 20% potential increase in price ($186 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($22 potential savings vs. average RT price).
Average for round-trip flights in April 2026

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 April 3, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Italy that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 4/15

12:52 pm-10:50 am

1 stop14h 58m

Rome Fiumicino

Thu 4/23

6:30 am-4:26 pm

2 stops16h 56m

$756

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 4/15

2:12 pm-10:10 am

1 stop12h 58m

Rome Fiumicino

Thu 4/23

9:00 am-5:58 pm

1 stop15h 58m

$757
Quickest round-trip

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 8/9

5:10 pm-12:40 pm

1 stop12h 30m

Rome Fiumicino

Tue 8/25

1:10 pm-9:46 pm

1 stop15h 36m

$757

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 8/18

10:35 am-11:30 am

2 stops17h 55m

Naples

Tue 8/25

6:05 am-6:05 pm

2 stops19h 00m

$779

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Thu 4/16

10:41 am-7:35 am

1 stop13h 54m

Rome Fiumicino

Wed 4/22

6:30 am-4:26 pm

2 stops16h 56m

$806

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Mon 8/17

10:35 am-8:55 am

1 stop15h 20m

Venice Marco Polo

Thu 8/27

11:05 am-9:46 pm

1 stop17h 41m

$810

ChicagoBologna

MDW - BLQ

MDWBLQ

Chicago Midway

Wed 8/12

5:59 pm-5:05 pm

2 stops16h 06m

Bologna Guglielmo Marconi

Fri 8/21

6:00 am-6:31 pm

2 stops19h 31m

$812

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 8/12

9:30 am-11:30 am

2 stops19h 00m

Naples

Fri 8/21

9:05 am-9:46 pm

1 stop19h 41m

$817

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 8/12

5:25 pm-7:05 am

1 stop30h 40m

Naples

Fri 8/21

9:05 am-9:46 pm

1 stop19h 41m

$821

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Wed 8/12

1:00 pm-12:10 pm

2 stops16h 10m

Florence Peretola

Wed 8/19

6:40 am-6:31 pm

2 stops18h 51m

$822

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 60 resultsSorted by cheapest first
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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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Italy
No data available for this route at this time. Please check back soon.

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.
  • How long is the flight from Chicago Midway Airport to Italy?

    Departing from Chicago Midway Airport to Italy will take you 14h 58m. The distance from Chicago Midway Airport to Italy is about 4810 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Chicago Midway Airport to Italy?

  • 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.

See more FAQs

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