What is the cheapest airline that flies from Chicago Midway to Italy?

Delta and KLM are the most popular carriers operating from Chicago Midway 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.

$271 Cheap Flights from Chicago Midway Airport to Italy in 2025/26

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago Midway Airport to Italy

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:48 pm - 10:30 am

MDW

FCO

14h 42m1 stop

12:40 pm - 10:22 pm

FCO

MDW

16h 42m1 stop

$529Air France

Wed, Jan 21 - Wed, Jan 28

10:46 am - 10:30 am

MDW

FCO

16h 44m1 stop

12:40 pm - 10:22 pm

FCO

MDW

16h 42m1 stop

$530Air France

Wed, Jan 21 - Wed, Jan 28

12:48 pm - 10:30 am

MDW

FCO

14h 42m1 stop

12:40 pm - 10:22 pm

FCO

MDW

16h 42m1 stop

$536Air France

Wed, Jan 21 - Wed, Jan 28

10:46 am - 10:30 am

MDW

FCO

16h 44m1 stop

6:10 am - 5:29 pm

FCO

MDW

18h 19m2 stops

$537Delta

Wed, Jan 21 - Wed, Jan 28

1:28 pm - 11:45 am

MDW

FCO

15h 17m2 stops

9:05 am - 10:29 pm

FCO

MDW

19h 24m1 stop

$540Delta

Sun, Mar 1 - Wed, Mar 11

6:17 pm - 3:15 pm

MDW

FCO

13h 58m2 stops

11:40 am - 10:29 pm

FCO

MDW

16h 49m1 stop

$541Delta

Sun, Mar 1 - Tue, Mar 10

10:48 am - 10:30 am

MDW

FCO

16h 42m1 stop

12:40 pm - 10:22 pm

FCO

MDW

16h 42m1 stop

$567KLM

Thu, Jan 22 - Thu, Jan 29

10:46 am - 9:45 am

MDW

FCO

15h 59m2 stops

6:10 am - 5:29 pm

FCO

MDW

18h 19m2 stops

$571KLM

Wed, Jan 21 - Wed, Jan 28

6:35 pm - 3:50 pm

MDW

NAP

14h 15m2 stops

6:15 am - 5:29 pm

NAP

MDW

18h 14m2 stops

$606Multiple Airlines

Thu, Jan 22 - Thu, Jan 29

6:30 pm - 9:15 pm

MDW

NAP

19h 45m2 stops

1:15 pm - 5:29 pm

NAP

MDW

35h 14m2 stops

$729Multiple Airlines

Sun, Jan 11 - Mon, Jan 26

KLM flights from Chicago Midway Airport to Italy

Our best KLM deals on Chicago Midway Airport to Italy flight tickets

KLM

Dec 10

MDW1:05 pmChicago Midway

14h 25m

1 stop

FCO10:30 amRome Fiumicino

Dec 17

FCO12:40 pmRome Fiumicino

18h 07m

1 stop

MDW11:47 pmChicago Midway

$536

Find similar

KLM

Jan 22

MDW10:48 amChicago Midway

16h 42m

1 stop

FCO10:30 amRome Fiumicino

Jan 29

FCO12:40 pmRome Fiumicino

16h 42m

1 stop

MDW10:22 pmChicago Midway

$567

Find similar

KLM

Jan 21

MDW10:46 amChicago Midway

15h 59m

2 stops

FCO9:45 amRome Fiumicino

Jan 28

FCO6:10 amRome Fiumicino

18h 19m

2 stops

MDW5:29 pmChicago Midway

$571

Find similar

Delta flights from Chicago Midway Airport to Italy

Our best Delta deals on Chicago Midway Airport to Italy flight tickets

Delta

Jan 21

MDW10:46 amChicago Midway

16h 44m

1 stop

FCO10:30 amRome Fiumicino

Jan 28

FCO6:10 amRome Fiumicino

18h 19m

2 stops

MDW5:29 pmChicago Midway

$537

Find similar

Delta

Mar 1

MDW1:28 pmChicago Midway

15h 17m

2 stops

FCO11:45 amRome Fiumicino

Mar 11

FCO9:05 amRome Fiumicino

19h 24m

1 stop

MDW10:29 pmChicago Midway

$540

Find similar

Delta

Dec 10

MDW9:34 amChicago Midway

17h 56m

2 stops

FCO10:30 amRome Fiumicino

Dec 17

FCO12:40 pmRome Fiumicino

18h 07m

1 stop

MDW11:47 pmChicago Midway

$541

Find similar

momondo Fare Finder

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

Wed 1/21

12:48 pm-10:30 am

1 stop14h 42m

Rome Fiumicino

Wed 1/28

12:40 pm-10:22 pm

1 stop16h 42m

$529

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 1/21

10:46 am-10:30 am

1 stop16h 44m

Rome Fiumicino

Wed 1/28

12:40 pm-10:22 pm

1 stop16h 42m

$530

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 1/21

12:48 pm-10:30 am

1 stop14h 42m

Rome Fiumicino

Wed 1/28

12:40 pm-10:22 pm

1 stop16h 42m

$536

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 1/21

10:46 am-10:30 am

1 stop16h 44m

Rome Fiumicino

Wed 1/28

6:10 am-5:29 pm

2 stops18h 19m

$537

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 3/1

1:28 pm-11:45 am

2 stops15h 17m

Rome Fiumicino

Wed 3/11

9:05 am-10:29 pm

1 stop19h 24m

$540

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 3/1

6:17 pm-3:15 pm

2 stops13h 58m

Rome Fiumicino

Tue 3/10

11:40 am-10:29 pm

1 stop16h 49m

$541

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Thu 1/22

10:48 am-10:30 am

1 stop16h 42m

Rome Fiumicino

Thu 1/29

12:40 pm-10:22 pm

1 stop16h 42m

$567

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 1/21

10:46 am-9:45 am

2 stops15h 59m

Rome Fiumicino

Wed 1/28

6:10 am-5:29 pm

2 stops18h 19m

$571

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 1/22

6:35 pm-3:50 pm

2 stops14h 15m

Naples

Thu 1/29

6:15 am-5:29 pm

2 stops18h 14m

$606

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 1/11

6:30 pm-9:15 pm

2 stops19h 45m

Naples

Mon 1/26

1:15 pm-5:29 pm

2 stops35h 14m

$729

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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 5% 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

Fastest flight time	11h 41m
Direct flights	None

The fastest flight from Chicago Midway Airport to Italy takes 11h 41m

There are no direct flights from Chicago Midway Airport to Italy. There are no popular flight routes from Chicago Midway Airport to Italy.

Search flight deals

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.