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

Delta, KLM, and Air Transat 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.

$238 Cheap Flights from Chicago Midway Airport to Italy in 2026

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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.

7:30 am - 11:40 pm

MDW

FCO

33h 10m

2 stops

7:05 pm - 1:00 pm

FCO

MDW

24h 55m

1 stop

$507Multiple Airlines

Wed, May 6 - Wed, May 13

12:45 pm - 10:30 am

MDW

FCO

14h 45m

1 stop

11:40 am - 10:31 pm

FCO

MDW

16h 51m

1 stop

$532Delta

Sun, Feb 22 - Tue, Mar 10

12:45 pm - 10:30 am

MDW

FCO

14h 45m

1 stop

9:05 am - 5:54 pm

FCO

MDW

14h 49m

1 stop

$533Delta

Sun, Feb 22 - Tue, Mar 10

10:49 am - 10:30 am

MDW

FCO

16h 41m

1 stop

9:05 am - 5:54 pm

FCO

MDW

14h 49m

1 stop

$535KLM

Sun, Feb 22 - Tue, Mar 10

6:00 am - 10:30 am

MDW

FCO

21h 30m

1 stop

12:40 pm - 10:33 pm

FCO

MDW

16h 53m

1 stop

$538KLM

Tue, Feb 24 - Tue, Mar 3

10:45 am - 9:30 am

MDW

FCO

16h 45m

1 stop

9:05 am - 10:31 pm

FCO

MDW

19h 26m

1 stop

$539Delta

Mon, Mar 9 - Wed, Mar 18

10:45 am - 9:30 am

MDW

FCO

16h 45m

1 stop

6:10 am - 5:54 pm

FCO

MDW

17h 44m

2 stops

$540Delta

Mon, Mar 9 - Wed, Mar 18

1:10 pm - 8:45 am

MDW

FCO

13h 35m

2 stops

11:00 am - 10:31 pm

FCO

MDW

17h 31m

2 stops

$543Delta

Mon, Mar 9 - Tue, Mar 17

6:00 am - 2:30 pm

MDW

BRI

25h 30m

2 stops

6:20 am - 10:31 pm

BRI

MDW

22h 11m

2 stops

$772Air Europa

Sun, Mar 1 - Mon, Mar 9

12:46 pm - 2:40 pm

MDW

CTA

18h 54m

2 stops

10:15 am - 10:31 pm

CTA

MDW

19h 16m

2 stops

$1,913Air Europa

Tue, Feb 10 - Fri, Feb 13

Scandinavian Airlines flights from Chicago Midway Airport to Italy

Our best Scandinavian Airlines deals on Chicago Midway Airport to Italy flight tickets

Scandinavian Airlines

Feb 2

MDW10:46 amChicago Midway

16h 44m

1 stop

FCO10:30 amRome Fiumicino

Feb 16

FCO12:40 pmRome Fiumicino

16h 51m

1 stop

MDW10:31 pmChicago Midway

$717

Scandinavian Airlines

Feb 20

MDW1:26 pmChicago Midway

14h 44m

2 stops

NAP11:10 amNaples

Feb 22

NAP11:50 amNaples

36h 55m

2 stops

MDW5:45 pmChicago Midway

$943

Scandinavian Airlines

Jun 27

MDW4:30 pmChicago Midway

31h 35m

1 stop

NAP7:05 amNaples

Jul 8

NAP9:15 amNaples

19h 31m

1 stop

MDW9:46 pmChicago Midway

$1,255

KLM flights from Chicago Midway Airport to Italy

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

KLM

Feb 9

MDW10:46 amChicago Midway

16h 44m

1 stop

FCO10:30 amRome Fiumicino

Feb 25

FCO12:40 pmRome Fiumicino

36h 05m

1 stop

MDW5:45 pmChicago Midway

$532

KLM

Feb 22

MDW10:49 amChicago Midway

16h 41m

1 stop

FCO10:30 amRome Fiumicino

Mar 10

FCO9:05 amRome Fiumicino

14h 49m

1 stop

MDW5:54 pmChicago Midway

$535

KLM

Feb 24

MDW6:00 amChicago Midway

21h 30m

1 stop

FCO10:30 amRome Fiumicino

Mar 3

FCO12:40 pmRome Fiumicino

16h 53m

1 stop

MDW10:33 pmChicago Midway

$538

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 5/6

7:30 am-11:40 pm

2 stops33h 10m

Rome Fiumicino

Wed 5/13

7:05 pm-1:00 pm

1 stop24h 55m

$507

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 2/22

12:45 pm-10:30 am

1 stop14h 45m

Rome Fiumicino

Tue 3/10

11:40 am-10:31 pm

1 stop16h 51m

$532

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 2/22

12:45 pm-10:30 am

1 stop14h 45m

Rome Fiumicino

Tue 3/10

9:05 am-5:54 pm

1 stop14h 49m

$533

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 2/22

10:49 am-10:30 am

1 stop16h 41m

Rome Fiumicino

Tue 3/10

9:05 am-5:54 pm

1 stop14h 49m

$535

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 2/24

6:00 am-10:30 am

1 stop21h 30m

Rome Fiumicino

Tue 3/3

12:40 pm-10:33 pm

1 stop16h 53m

$538

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 3/9

10:45 am-9:30 am

1 stop16h 45m

Rome Fiumicino

Wed 3/18

9:05 am-10:31 pm

1 stop19h 26m

$539

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 3/9

10:45 am-9:30 am

1 stop16h 45m

Rome Fiumicino

Wed 3/18

6:10 am-5:54 pm

2 stops17h 44m

$540

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 3/9

1:10 pm-8:45 am

2 stops13h 35m

Rome Fiumicino

Tue 3/17

11:00 am-10:31 pm

2 stops17h 31m

$543

ChicagoBari

MDW - BRI

MDWBRI

Chicago Midway

Sun 3/1

6:00 am-2:30 pm

2 stops25h 30m

Bari Palese

Mon 3/9

6:20 am-10:31 pm

2 stops22h 11m

$772

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Tue 2/10

12:46 pm-2:40 pm

2 stops18h 54m

Catania Fontanarossa

Fri 2/13

10:15 am-10:31 pm

2 stops19h 16m

$1,913

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

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

Fastest flight time	11h 45m
Direct flights	None

The fastest flight from Chicago Midway Airport to Italy takes 11h 45m

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.