What day of the week experiences the fewest flight delays on this route?

Monday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

How long does it take to fly to Chicago Midway Airport?

On average, it takes 9h 40m to fly from Italy to Chicago Midway Airport if you fly out of Milan (the most popular airport in Italy) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of Rome and into Chicago O'Hare Intl Airport, then the flight time is around 10h 20m.

How often are flights from Italy to Chicago delayed?

Historically, on average around 0% of flights between Italy and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 0 minutes.

What is the most punctual flight time for Italy to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

When did momondo last update prices for flights from Italy to Chicago Midway Airport?

Prices for flights from Italy to Chicago Midway Airport are updated daily.

How old do you have to be to fly from Italy to Chicago Midway Airport?

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 Italy to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$267 Cheap Flights from Italy to Chicago Midway Airport in 2026

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Find the cheapest flights from Italy to Chicago

Round-trip

One-way

Last minute

Recent round-trip flight deals from Italy to Chicago

Enter your travel dates to find the best prices.

6:00 am - 6:36 pm

BLQ

MDW

19h 36m

2 stops

9:29 am - 8:40 am

MDW

BLQ

16h 11m

2 stops

$621Delta

Wed, Apr 15 - Wed, Apr 22

6:40 am - 5:58 pm

LIN

MDW

18h 18m

2 stops

10:41 am - 8:50 am

MDW

LIN

15h 09m

2 stops

$622Delta

Wed, Apr 22 - Tue, May 5

9:00 am - 10:28 pm

MXP

MDW

20h 28m

2 stops

1:24 pm - 2:45 pm

MDW

MXP

18h 21m

2 stops

$622Delta

Fri, Apr 17 - Mon, Apr 20

6:40 am - 5:54 pm

LIN

MDW

18h 14m

2 stops

1:24 pm - 11:20 am

MDW

LIN

14h 56m

2 stops

$623Delta

Thu, Apr 9 - Tue, Apr 21

6:45 am - 5:54 pm

MXP

MDW

18h 09m

2 stops

1:24 pm - 2:45 pm

MDW

MXP

18h 21m

2 stops

$626Delta

Thu, Apr 9 - Wed, Apr 22

11:25 am - 10:28 pm

MXP

MDW

18h 03m

2 stops

5:21 pm - 9:25 am

MDW

MXP

33h 04m

1 stop

$629Multiple Airlines

Fri, Apr 17 - Sat, May 2

12:15 pm - 10:31 pm

NAP

MDW

40h 16m

2 stops

12:47 pm - 6:15 pm

MDW

NAP

22h 28m

2 stops

$636Air France

Mon, Mar 23 - Tue, Mar 31

1:10 pm - 10:28 pm

FCO

MDW

16h 18m

1 stop

10:41 am - 7:35 am

MDW

FCO

13h 54m

1 stop

$642KLM

Thu, Apr 23 - Tue, Apr 28

11:05 am - 10:31 pm

VCE

MDW

18h 26m

1 stop

10:45 am - 8:55 am

MDW

VCE

15h 10m

1 stop

$650KLM

Wed, Apr 1 - Wed, Apr 8

6:15 am - 5:54 pm

NAP

MDW

17h 39m

2 stops

1:10 pm - 9:55 am

MDW

NAP

13h 45m

2 stops

$1,002Multiple Airlines

Mon, Mar 23 - Tue, Mar 31

KLM flights from Italy to Chicago Midway Airport

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

KLM

Apr 23

FCO1:10 pmRome Fiumicino

16h 18m

1 stop

MDW10:28 pmChicago Midway

Apr 28

MDW10:41 amChicago Midway

13h 54m

1 stop

FCO7:35 amRome Fiumicino

$642

KLM

Apr 1

VCE11:05 amVenice Marco Polo

18h 26m

1 stop

MDW10:31 pmChicago Midway

Apr 8

MDW10:45 amChicago Midway

15h 10m

1 stop

VCE8:55 amVenice Marco Polo

$650

KLM

Apr 1

VCE11:05 amVenice Marco Polo

18h 26m

1 stop

MDW10:31 pmChicago Midway

Apr 8

MDW12:47 pmChicago Midway

13h 08m

1 stop

VCE8:55 amVenice Marco Polo

$651

Delta flights from Italy to Chicago Midway Airport

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

Delta

Apr 15

BLQ6:00 amBologna Guglielmo Marconi

19h 36m

2 stops

MDW6:36 pmChicago Midway

Apr 22

MDW9:29 amChicago Midway

16h 11m

2 stops

BLQ8:40 amBologna Guglielmo Marconi

$621

Delta

Apr 22

LIN6:40 amMilan Linate

18h 18m

2 stops

MDW5:58 pmChicago Midway

May 5

MDW10:41 amChicago Midway

15h 09m

2 stops

LIN8:50 amMilan Linate

$622

Delta

Apr 9

LIN6:40 amMilan Linate

18h 14m

2 stops

MDW5:54 pmChicago Midway

Apr 21

MDW1:24 pmChicago Midway

14h 56m

2 stops

LIN11:20 amMilan Linate

$623

momondo Fare Finder

Use the filters below to find and compare flights from Italy to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BolognaChicago

BLQ - MDW

BLQMDW

Bologna Guglielmo Marconi

Wed 4/15

6:00 am-6:36 pm

2 stops19h 36m

Chicago Midway

Wed 4/22

9:29 am-8:40 am

2 stops16h 11m

$621

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Wed 4/22

6:40 am-5:58 pm

2 stops18h 18m

Chicago Midway

Tue 5/5

10:41 am-8:50 am

2 stops15h 09m

$622

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 4/17

9:00 am-10:28 pm

2 stops20h 28m

Chicago Midway

Mon 4/20

1:24 pm-2:45 pm

2 stops18h 21m

$622

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 4/9

6:40 am-5:54 pm

2 stops18h 14m

Chicago Midway

Tue 4/21

1:24 pm-11:20 am

2 stops14h 56m

$623

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 4/9

6:45 am-5:54 pm

2 stops18h 09m

Chicago Midway

Wed 4/22

1:24 pm-2:45 pm

2 stops18h 21m

$626

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 4/17

11:25 am-10:28 pm

2 stops18h 03m

Chicago Midway

Sat 5/2

5:21 pm-9:25 am

1 stop33h 04m

$629

NaplesChicago

NAP - MDW

NAPMDW

Naples

Mon 3/23

12:15 pm-10:31 pm

2 stops40h 16m

Chicago Midway

Tue 3/31

12:47 pm-6:15 pm

2 stops22h 28m

$636

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Thu 4/23

1:10 pm-10:28 pm

1 stop16h 18m

Chicago Midway

Tue 4/28

10:41 am-7:35 am

1 stop13h 54m

$642

VeniceChicago

VCE - MDW

VCEMDW

Venice Marco Polo

Wed 4/1

11:05 am-10:31 pm

1 stop18h 26m

Chicago Midway

Wed 4/8

10:45 am-8:55 am

1 stop15h 10m

$650

NaplesChicago

NAP - MDW

NAPMDW

Naples

Mon 3/23

6:15 am-5:54 pm

2 stops17h 39m

Chicago Midway

Tue 3/31

1:10 pm-9:55 am

2 stops13h 45m

$1,002

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 Italy to Chicago Midway Airport

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

Airlines

Delays

Other information

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

Delta is the most popular carrier operating from Italy to Chicago Midway

Cheap Italy to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Italy to Chicago Midway Airport

Fastest flight time	14h 33m
Direct flights	None

The fastest flight from Italy to Chicago Midway Airport takes 14h 33m

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

Search flight deals

When did momondo last update prices for flights from Italy to Chicago Midway Airport?
Prices for flights from Italy to Chicago Midway Airport are updated daily.
How old do you have to be to fly from Italy to Chicago Midway Airport?
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 Italy to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Italy to Chicago?

It is quick and easy to find Italy to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Italy to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Italy on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Italy to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Italy. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Italy to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Italy are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.