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.

$340 Cheap Flights from Chicago Midway Airport to Italy in 2026

1 adult

0 bags

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.

10:54 am - 9:25 am

MDW

MXP

15h 31m

1 stop

11:40 am - 10:36 pm

MXP

MDW

17h 56m

1 stop

$792KLM

Mon, Aug 17 - Fri, Aug 28

9:24 am - 10:25 am

MDW

MXP

18h 01m

2 stops

11:40 am - 10:36 pm

MXP

MDW

17h 56m

1 stop

$796Delta

Mon, Aug 17 - Fri, Aug 28

9:24 am - 9:25 am

MDW

MXP

17h 01m

2 stops

9:00 am - 10:36 pm

MXP

MDW

20h 36m

2 stops

$797Delta

Mon, Aug 17 - Fri, Aug 28

10:35 am - 7:35 am

MDW

FCO

14h 00m

1 stop

1:10 pm - 9:46 pm

FCO

MDW

15h 36m

1 stop

$808KLM

Sat, Aug 15 - Wed, Aug 26

1:00 pm - 11:00 am

MDW

FCO

16h 00m

2 stops

1:30 pm - 9:45 pm

FCO

MDW

15h 15m

1 stop

$812Delta

Wed, Oct 28 - Sun, Nov 8

1:05 pm - 9:35 am

MDW

FCO

14h 30m

2 stops

10:00 am - 6:37 pm

FCO

MDW

15h 37m

1 stop

$813Delta

Wed, Oct 28 - Sun, Nov 8

5:10 pm - 4:35 pm

MDW

BRI

16h 25m

2 stops

6:30 am - 6:31 pm

BRI

MDW

19h 01m

2 stops

$819Multiple Airlines

Mon, Aug 17 - Mon, Aug 31

12:46 pm - 9:25 am

MDW

MXP

13h 39m

1 stop

11:40 am - 10:36 pm

MXP

MDW

17h 56m

1 stop

$839Air France

Wed, Aug 12 - Thu, Aug 27

1:27 pm - 10:25 am

MDW

MXP

13h 58m

2 stops

11:40 am - 10:36 pm

MXP

MDW

17h 56m

1 stop

$843Multiple Airlines

Wed, Aug 12 - Thu, Aug 27

1:27 pm - 10:25 am

MDW

MXP

13h 58m

2 stops

6:45 am - 6:01 pm

MXP

MDW

18h 16m

2 stops

$855Air France

Wed, Aug 12 - Thu, Aug 27

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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

MDW9:24 amChicago Midway

18h 01m

2 stops

MXP10:25 amMilan Malpensa

Aug 28

MXP11:40 amMilan Malpensa

17h 56m

1 stop

MDW10:36 pmChicago Midway

$796

Delta

Aug 17

MDW9:24 amChicago Midway

17h 01m

2 stops

MXP9:25 amMilan Malpensa

Aug 28

MXP9:00 amMilan Malpensa

20h 36m

2 stops

MDW10:36 pmChicago Midway

$797

Delta

Oct 28

MDW1:00 pmChicago Midway

16h 00m

2 stops

FCO11:00 amRome Fiumicino

Nov 8

FCO1:30 pmRome Fiumicino

15h 15m

1 stop

MDW9:45 pmChicago Midway

$812

KLM flights from Chicago Midway Airport to Italy

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

KLM

Aug 17

MDW10:54 amChicago Midway

15h 31m

1 stop

MXP9:25 amMilan Malpensa

Aug 28

MXP11:40 amMilan Malpensa

17h 56m

1 stop

MDW10:36 pmChicago Midway

$792

KLM

Aug 15

MDW10:35 amChicago Midway

14h 00m

1 stop

FCO7:35 amRome Fiumicino

Aug 26

FCO1:10 pmRome Fiumicino

15h 36m

1 stop

MDW9:46 pmChicago Midway

$808

KLM

Aug 14

MDW1:00 pmChicago Midway

15h 00m

1 stop

FCO11:00 amRome Fiumicino

Aug 31

FCO9:00 amRome Fiumicino

16h 31m

1 stop

MDW6:31 pmChicago Midway

$858

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

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/17

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Fri 8/28

11:40 am-10:36 pm

1 stop17h 56m

$792

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/17

9:24 am-10:25 am

2 stops18h 01m

Milan Malpensa

Fri 8/28

11:40 am-10:36 pm

1 stop17h 56m

$796

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/17

9:24 am-9:25 am

2 stops17h 01m

Milan Malpensa

Fri 8/28

9:00 am-10:36 pm

2 stops20h 36m

$797

Quickest round-trip

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sat 8/15

10:35 am-7:35 am

1 stop14h 00m

Rome Fiumicino

Wed 8/26

1:10 pm-9:46 pm

1 stop15h 36m

$808

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 10/28

1:00 pm-11:00 am

2 stops16h 00m

Rome Fiumicino

Sun 11/8

1:30 pm-9:45 pm

1 stop15h 15m

$812

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 10/28

1:05 pm-9:35 am

2 stops14h 30m

Rome Fiumicino

Sun 11/8

10:00 am-6:37 pm

1 stop15h 37m

$813

ChicagoBari

MDW - BRI

MDWBRI

Chicago Midway

Mon 8/17

5:10 pm-4:35 pm

2 stops16h 25m

Bari Palese

Mon 8/31

6:30 am-6:31 pm

2 stops19h 01m

$819

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 8/12

12:46 pm-9:25 am

1 stop13h 39m

Milan Malpensa

Thu 8/27

11:40 am-10:36 pm

1 stop17h 56m

$839

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 8/12

1:27 pm-10:25 am

2 stops13h 58m

Milan Malpensa

Thu 8/27

11:40 am-10:36 pm

1 stop17h 56m

$843

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 8/12

1:27 pm-10:25 am

2 stops13h 58m

Milan Malpensa

Thu 8/27

6:45 am-6:01 pm

2 stops18h 16m

$855

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	12h 30m
Direct flights	None

The fastest flight from Chicago Midway Airport to Italy takes 12h 30m

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

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.