Cheap flights from Chicago Midway Airport to Italy from $205

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Italy departing on 11/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Delta Logo
12:47 pm - 7:55 amMDW-FCO
12h 08m1 stop
Delta Logo
12:40 pm - 9:44 pmFCO-MDW
16h 04m1 stop
$490Delta
Find Deal
lun., nov. 17 - jue., dic. 18
Delta Logo
10:47 am - 9:45 amMDW-FCO
15h 58m2 stops
Delta Logo
12:40 pm - 9:44 pmFCO-MDW
16h 04m1 stop
$494Delta
Find Deal
lun., dic. 1 - mié., dic. 17
Delta Logo
1:14 pm - 9:45 amMDW-FCO
13h 31m2 stops
Delta Logo
12:40 pm - 9:44 pmFCO-MDW
16h 04m1 stop
$495Delta
Find Deal
mar., nov. 18 - mar., dic. 16
Delta Logo
5:59 pm - 5:25 pmMDW-FCO
16h 26m2 stops
Delta Logo
12:40 pm - 9:46 pmFCO-MDW
16h 06m1 stop
$509Delta
Find Deal
mié., ene. 7 - jue., ene. 15
KLM Logo
10:47 am - 7:55 amMDW-FCO
14h 08m1 stop
KLM Logo
12:40 pm - 9:44 pmFCO-MDW
16h 04m1 stop
$540KLM
Find Deal
lun., nov. 17 - lun., dic. 15
 Logo
5:56 pm - 2:30 pmMDW-FCO
13h 34m1 stop
 Logo
7:10 pm - 11:25 pmFCO-MDW
35h 15m1 stop
mar., nov. 18 - mié., dic. 3
 Logo
5:56 pm - 2:30 pmMDW-FCO
13h 34m1 stop
 Logo
7:10 pm - 11:25 pmFCO-MDW
35h 15m1 stop
mar., nov. 18 - mié., dic. 3
Air France Logo
10:35 am - 7:55 amMDW-FCO
14h 20m1 stop
Air France Logo
12:40 pm - 9:44 pmFCO-MDW
16h 04m1 stop
$605Air France
Find Deal
dom., dic. 7 - vie., dic. 12
Air France Logo
1:08 pm - 9:20 amMDW-FCO
13h 12m1 stop
Air France Logo
12:40 pm - 10:14 pmFCO-MDW
16h 34m1 stop
$614Air France
Find Deal
mar., oct. 21 - mié., nov. 5
KLM Logo
6:30 pm - 7:00 amMDW-NAP
29h 30m1 stop
KLM Logo
9:00 am - 10:14 pmNAP-MDW
20h 14m1 stop
$828KLM
Find Deal
dom., sep. 28 - mar., oct. 14

KLM flights from Chicago Midway Airport to Italy

Our best KLM deals on Chicago Midway Airport to Italy flight tickets
KLM
Nov 17
MDW10:47 amChicago Midway
14h 08m
1 stop
FCO7:55 amRome Fiumicino
Dec 15
FCO12:40 pmRome Fiumicino
16h 04m
1 stop
MDW9:44 pmChicago Midway
KLM
Sep 9
MDW1:08 pmChicago Midway
13h 12m
1 stop
FCO9:20 amRome Fiumicino
Sep 19
FCO9:45 amRome Fiumicino
14h 50m
1 stop
MDW5:35 pmChicago Midway
KLM
Sep 8
MDW1:08 pmChicago Midway
13h 12m
1 stop
FCO9:20 amRome Fiumicino
Sep 24
FCO9:45 amRome Fiumicino
14h 50m
1 stop
MDW5:35 pmChicago Midway

Air France flights from Chicago Midway Airport to Italy

Our best Air France deals on Chicago Midway Airport to Italy flight tickets
Air France
Dec 7
MDW10:35 amChicago Midway
14h 20m
1 stop
FCO7:55 amRome Fiumicino
Dec 12
FCO12:40 pmRome Fiumicino
16h 04m
1 stop
MDW9:44 pmChicago Midway
Air France
Oct 21
MDW1:08 pmChicago Midway
13h 12m
1 stop
FCO9:20 amRome Fiumicino
Nov 5
FCO12:40 pmRome Fiumicino
16h 34m
1 stop
MDW10:14 pmChicago Midway
Air France
Oct 19
MDW10:35 amChicago Midway
15h 50m
1 stop
MXP9:25 amMilan Malpensa
Nov 4
MXP11:05 amMilan Malpensa
18h 09m
1 stop
MDW10:14 pmChicago Midway

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated agosto 28, 2025.
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

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

lun. 11/17

12:47 pm-7:55 am

1 stop12h 08m

Rome Fiumicino

jue. 12/18

12:40 pm-9:44 pm

1 stop16h 04m

$490

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

lun. 12/1

10:47 am-9:45 am

2 stops15h 58m

Rome Fiumicino

mié. 12/17

12:40 pm-9:44 pm

1 stop16h 04m

$494

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

mar. 11/18

1:14 pm-9:45 am

2 stops13h 31m

Rome Fiumicino

mar. 12/16

12:40 pm-9:44 pm

1 stop16h 04m

$495

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

mié. 1/7

5:59 pm-5:25 pm

2 stops16h 26m

Rome Fiumicino

jue. 1/15

12:40 pm-9:46 pm

1 stop16h 06m

$509

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

lun. 11/17

10:47 am-7:55 am

1 stop14h 08m

Rome Fiumicino

lun. 12/15

12:40 pm-9:44 pm

1 stop16h 04m

$540

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

mar. 11/18

5:56 pm-2:30 pm

1 stop13h 34m

Rome Fiumicino

mié. 12/3

7:10 pm-11:25 pm

1 stop35h 15m

$553

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

mar. 11/18

5:56 pm-2:30 pm

1 stop13h 34m

Rome Fiumicino

mié. 12/3

7:10 pm-11:25 pm

1 stop35h 15m

$576

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

dom. 12/7

10:35 am-7:55 am

1 stop14h 20m

Rome Fiumicino

vie. 12/12

12:40 pm-9:44 pm

1 stop16h 04m

$605

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

mar. 10/21

1:08 pm-9:20 am

1 stop13h 12m

Rome Fiumicino

mié. 11/5

12:40 pm-10:14 pm

1 stop16h 34m

$614

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

dom. 9/28

6:30 pm-7:00 am

1 stop29h 30m

Naples

mar. 10/14

9:00 am-10:14 pm

1 stop20h 14m

$828

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Italy from

How to get the cheapest flight ticket from Chicago Midway Airport to Italy

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Italy?

The cheapest month to fly to Italy from Chicago Midway Airport is in February. Flight prices, which tend to average around $586, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Italy from Chicago Midway Airport during June instead. Flights to Italy in June, while not as cheap as those in February, still average around $600.

What is the cheapest day to depart on your flight to Italy?

According to our data, Sunday is the cheapest day to fly to Italy from Chicago Midway Airport. The lowest ticket price found for a Sunday departure recently was $946. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Italy for around $1,227.

What is the cheapest time of day to depart on your flight to Italy?

Our data shows that the cheapest Chicago Midway Airport to Italy flights are usually those with departure times in the evening. Our users have found flights to Italy in the evening for as low as $835. In contrast, the most expensive time of day to depart to Italy is in the morning when prices are around $1,512.

Can stopping save me money on Chicago Midway Airport to Italy flights?

You could potentially save up to 15% on your flight if you consider stops on a Chicago Midway Airport to Italy flight.

Cheap Chicago Midway Airport to Italy flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Italy

Direct flights

None
There are no direct flights from Chicago Midway Airport to Italy. There are no popular flight routes from Chicago Midway Airport to Italy.
  • When did momondo last update prices for flights from Chicago Midway Airport to Italy?

    Prices for flights from Chicago Midway Airport to Italy are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Italy?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Italy.

  • What documentation or ID do you need to fly to Italy?

    The necessary travel and health documents for your Italy trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Italy?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Italy. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Italy with flexible booking policies on momondo?

Yes. All flights to Italy from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Italy?

Once you have performed a search for Chicago to Italy flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Italy right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Italy flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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1 adult
mar. 9/2
mar. 9/9

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