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

Delta, KLM, and Air France 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.

$299 Cheap Flights from Chicago Midway Airport to Italy in 2026

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.

12:46 pm - 8:55 am

MDW

VCE

13h 09m

1 stop

11:05 am - 10:36 pm

VCE

MDW

18h 31m

1 stop

$726Delta

Mon, Aug 17 - Thu, Aug 27

1:25 pm - 2:35 pm

MDW

VCE

18h 10m

2 stops

11:05 am - 10:36 pm

VCE

MDW

18h 31m

1 stop

$730Delta

Mon, Aug 17 - Thu, Aug 27

1:05 pm - 3:50 pm

MDW

NAP

19h 45m

2 stops

6:35 am - 10:10 pm

NAP

MDW

22h 35m

2 stops

$739Air France

Wed, Dec 2 - Wed, Dec 9

8:15 am - 9:20 pm

MDW

MXP

30h 05m

2 stops

6:55 am - 8:20 pm

MXP

MDW

20h 25m

2 stops

$760Multiple Airlines

Mon, Aug 24 - Mon, Aug 31

9:24 am - 11:00 am

MDW

FCO

18h 36m

1 stop

9:45 am - 10:36 pm

FCO

MDW

19h 51m

1 stop

$765KLM

Wed, Aug 19 - Tue, Aug 25

10:54 am - 7:35 am

MDW

FCO

13h 41m

1 stop

9:00 am - 6:33 pm

FCO

MDW

16h 33m

1 stop

$766Air France

Sun, Aug 16 - Sun, Aug 23

10:54 am - 7:35 am

MDW

FCO

13h 41m

1 stop

9:00 am - 6:33 pm

FCO

MDW

16h 33m

1 stop

$767Air France

Sun, Aug 16 - Sun, Aug 23

1:25 pm - 11:00 am

MDW

FCO

14h 35m

1 stop

9:00 am - 6:33 pm

FCO

MDW

16h 33m

1 stop

$768KLM

Fri, Aug 14 - Fri, Aug 21

1:25 pm - 11:00 am

MDW

FCO

14h 35m

1 stop

9:00 am - 6:33 pm

FCO

MDW

16h 33m

1 stop

$769KLM

Fri, Aug 14 - Fri, Aug 21

6:00 am - 11:00 am

MDW

MXP

22h 00m

2 stops

6:55 am - 10:00 pm

MXP

MDW

22h 05m

2 stops

$797Multiple Airlines

Sun, Aug 23 - Fri, Aug 28

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Delta flights from Chicago Midway Airport to Italy

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

Delta

Aug 17

MDW12:46 pmChicago Midway

13h 09m

1 stop

VCE8:55 amVenice Marco Polo

Aug 27

VCE11:05 amVenice Marco Polo

18h 31m

1 stop

MDW10:36 pmChicago Midway

$726

Delta

Aug 17

MDW1:25 pmChicago Midway

18h 10m

2 stops

VCE2:35 pmVenice Marco Polo

Aug 27

VCE11:05 amVenice Marco Polo

18h 31m

1 stop

MDW10:36 pmChicago Midway

$730

Delta

Aug 16

MDW10:54 amChicago Midway

16h 56m

1 stop

FCO10:50 amRome Fiumicino

Aug 30

FCO6:30 amRome Fiumicino

19h 03m

2 stops

MDW6:33 pmChicago Midway

$776

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 2

MDW1:05 pmChicago Midway

19h 45m

2 stops

NAP3:50 pmNaples

Dec 9

NAP6:35 amNaples

22h 35m

2 stops

MDW10:10 pmChicago Midway

$739

Air France

Aug 16

MDW10:54 amChicago Midway

13h 41m

1 stop

FCO7:35 amRome Fiumicino

Aug 23

FCO9:00 amRome Fiumicino

16h 33m

1 stop

MDW6:33 pmChicago Midway

$766

Air France

Aug 16

MDW10:54 amChicago Midway

13h 41m

1 stop

FCO7:35 amRome Fiumicino

Aug 23

FCO9:00 amRome Fiumicino

16h 33m

1 stop

MDW6:33 pmChicago Midway

$767

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

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Mon 8/17

12:46 pm-8:55 am

1 stop13h 09m

Venice Marco Polo

Thu 8/27

11:05 am-10:36 pm

1 stop18h 31m

$726

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Mon 8/17

1:25 pm-2:35 pm

2 stops18h 10m

Venice Marco Polo

Thu 8/27

11:05 am-10:36 pm

1 stop18h 31m

$730

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 12/2

1:05 pm-3:50 pm

2 stops19h 45m

Naples

Wed 12/9

6:35 am-10:10 pm

2 stops22h 35m

$739

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/24

8:15 am-9:20 pm

2 stops30h 05m

Milan Malpensa

Mon 8/31

6:55 am-8:20 pm

2 stops20h 25m

$760

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 8/19

9:24 am-11:00 am

1 stop18h 36m

Rome Fiumicino

Tue 8/25

9:45 am-10:36 pm

1 stop19h 51m

$765

Quickest round-trip

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 8/16

10:54 am-7:35 am

1 stop13h 41m

Rome Fiumicino

Sun 8/23

9:00 am-6:33 pm

1 stop16h 33m

$766

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 8/16

10:54 am-7:35 am

1 stop13h 41m

Rome Fiumicino

Sun 8/23

9:00 am-6:33 pm

1 stop16h 33m

$767

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Fri 8/14

1:25 pm-11:00 am

1 stop14h 35m

Rome Fiumicino

Fri 8/21

9:00 am-6:33 pm

1 stop16h 33m

$768

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Fri 8/14

1:25 pm-11:00 am

1 stop14h 35m

Rome Fiumicino

Fri 8/21

9:00 am-6:33 pm

1 stop16h 33m

$769

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 8/23

6:00 am-11:00 am

2 stops22h 00m

Milan Malpensa

Fri 8/28

6:55 am-10:00 pm

2 stops22h 05m

$797

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 31% 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	12h 10m
Direct flights	None

The fastest flight from Chicago Midway Airport to Italy takes 12h 10m

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

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Frequently asked questions about flying 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.