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

KLM and Delta 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.

$309 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 - 2:30 pm

MDW

FCO

24h 00m

1 stop

7:05 pm - 11:09 am

FCO

MDW

23h 04m

2 stops

$634Multiple Airlines

Mon, Apr 20 - Tue, May 5

7:30 am - 2:30 pm

MDW

FCO

24h 00m

1 stop

7:05 pm - 11:09 am

FCO

MDW

23h 04m

2 stops

$649Multiple Airlines

Mon, Apr 20 - Tue, May 5

7:30 am - 2:30 pm

MDW

FCO

24h 00m

1 stop

7:05 pm - 11:09 am

FCO

MDW

23h 04m

2 stops

$652Multiple Airlines

Mon, Apr 20 - Tue, May 5

10:35 am - 7:35 am

MDW

FCO

14h 00m

1 stop

9:00 am - 6:31 pm

FCO

MDW

16h 31m

1 stop

$657KLM

Tue, Aug 18 - Thu, Aug 27

10:35 am - 10:50 am

MDW

FCO

17h 15m

1 stop

9:45 am - 9:46 pm

FCO

MDW

19h 01m

1 stop

$658Delta

Mon, Aug 10 - Wed, Aug 26

9:27 am - 10:10 am

MDW

FCO

17h 43m

2 stops

6:30 am - 5:58 pm

FCO

MDW

18h 28m

2 stops

$661Delta

Wed, Apr 15 - Thu, Apr 23

10:35 am - 7:35 am

MDW

FCO

14h 00m

1 stop

6:05 am - 4:27 pm

FCO

MDW

17h 22m

2 stops

$664Delta

Wed, Aug 12 - Wed, Aug 19

1:00 pm - 11:25 am

MDW

FCO

15h 25m

2 stops

6:05 am - 4:27 pm

FCO

MDW

17h 22m

2 stops

$668Delta

Wed, Aug 12 - Wed, Aug 19

1:05 pm - 8:55 am

MDW

VCE

12h 50m

1 stop

11:05 am - 9:46 pm

VCE

MDW

17h 41m

1 stop

$710KLM

Mon, Aug 17 - Thu, Aug 27

10:35 am - 8:55 am

MDW

VCE

15h 20m

1 stop

11:05 am - 9:46 pm

VCE

MDW

17h 41m

1 stop

$759Air France

Mon, Aug 17 - Thu, Aug 27

Air France flights from Chicago Midway Airport to Italy

Our best Air France deals on Chicago Midway Airport to Italy flight tickets

Air France

Aug 17

MDW10:35 amChicago Midway

15h 20m

1 stop

VCE8:55 amVenice Marco Polo

Aug 27

VCE11:05 amVenice Marco Polo

17h 41m

1 stop

MDW9:46 pmChicago Midway

$759

Air France

Apr 20

MDW10:41 amChicago Midway

13h 54m

1 stop

FCO7:35 amRome Fiumicino

May 5

FCO1:10 pmRome Fiumicino

16h 18m

1 stop

MDW10:28 pmChicago Midway

$890

Air France

Jun 8

MDW5:25 pmChicago Midway

17h 50m

2 stops

NAP6:15 pmNaples

Jun 23

NAP6:05 amNaples

19h 26m

2 stops

MDW6:31 pmChicago Midway

$1,333

Air Europa flights from Chicago Midway Airport to Italy

Our best Air Europa deals on Chicago Midway Airport to Italy flight tickets

Air Europa

Apr 17

MDW9:29 amChicago Midway

17h 41m

1 stop

FCO10:10 amRome Fiumicino

Apr 21

FCO9:45 amRome Fiumicino

19h 43m

1 stop

MDW10:28 pmChicago Midway

$759

Air Europa

Mar 29

MDW2:05 pmChicago Midway

13h 05m

1 stop

FCO10:10 amRome Fiumicino

Apr 5

FCO9:45 amRome Fiumicino

14h 37m

1 stop

MDW5:22 pmChicago Midway

$1,195

Air Europa

May 6

MDW1:24 pmChicago Midway

23h 21m

2 stops

PMO7:45 pmPalermo Punta Raisi

Jun 3

PMO6:10 amPalermo Punta Raisi

19h 23m

2 stops

MDW6:33 pmChicago Midway

$1,325

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

Cheapest round-trip

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 4/20

7:30 am-2:30 pm

1 stop24h 00m

Rome Fiumicino

Tue 5/5

7:05 pm-11:09 am

2 stops23h 04m

$634

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 4/20

7:30 am-2:30 pm

1 stop24h 00m

Rome Fiumicino

Tue 5/5

7:05 pm-11:09 am

2 stops23h 04m

$649

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 4/20

7:30 am-2:30 pm

1 stop24h 00m

Rome Fiumicino

Tue 5/5

7:05 pm-11:09 am

2 stops23h 04m

$652

Quickest round-trip

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 8/18

10:35 am-7:35 am

1 stop14h 00m

Rome Fiumicino

Thu 8/27

9:00 am-6:31 pm

1 stop16h 31m

$657

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 8/10

10:35 am-10:50 am

1 stop17h 15m

Rome Fiumicino

Wed 8/26

9:45 am-9:46 pm

1 stop19h 01m

$658

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 4/15

9:27 am-10:10 am

2 stops17h 43m

Rome Fiumicino

Thu 4/23

6:30 am-5:58 pm

2 stops18h 28m

$661

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 8/12

10:35 am-7:35 am

1 stop14h 00m

Rome Fiumicino

Wed 8/19

6:05 am-4:27 pm

2 stops17h 22m

$664

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 8/12

1:00 pm-11:25 am

2 stops15h 25m

Rome Fiumicino

Wed 8/19

6:05 am-4:27 pm

2 stops17h 22m

$668

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Mon 8/17

1:05 pm-8:55 am

1 stop12h 50m

Venice Marco Polo

Thu 8/27

11:05 am-9:46 pm

1 stop17h 41m

$710

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

$759

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.