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Cheap flights from Italy to Chicago from $340

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Italy to Chicago departing on 8/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Italy to Chicago

Recent round-trip flight deals from Italy to Chicago

Enter your travel dates to find the best prices.
Delta Logo
6:10 am - 6:37 pm
NAP
-
MDW
19h 27m
2 stops
Delta Logo
1:05 pm - 3:50 pm
MDW
-
NAP
20h 45m
2 stops
$630Delta
Tue, Dec 15 - Mon, Mar 15
Delta Logo
6:10 am - 6:37 pm
NAP
-
MDW
19h 27m
2 stops
Delta Logo
1:05 pm - 3:50 pm
MDW
-
NAP
20h 45m
2 stops
$631Delta
Tue, Dec 15 - Mon, Mar 15
Delta Logo
9:05 am - 10:45 pm
NAP
-
MDW
20h 40m
1 stop
Delta Logo
11:25 am - 11:30 am
MDW
-
NAP
17h 05m
2 stops
$634Delta
Fri, Sep 11 - Sat, Sep 19
Delta Logo
6:05 am - 6:19 pm
NAP
-
MDW
19h 14m
2 stops
Delta Logo
9:49 am - 11:30 am
MDW
-
NAP
18h 41m
2 stops
$638Delta
Fri, Sep 11 - Sat, Sep 19
KLM Logo
11:20 am - 10:10 pm
NAP
-
MDW
17h 50m
2 stops
KLM Logo
1:00 pm - 9:35 am
MDW
-
NAP
14h 35m
2 stops
$649KLM
Thu, Dec 17 - Tue, Mar 16
Multiple Airlines Logo
10:00 am - 6:37 pm
FCO
-
MDW
15h 37m
1 stop
Multiple Airlines Logo
1:00 pm - 9:35 am
MDW
-
FCO
14h 35m
1 stop
$657Multiple Airlines
Wed, Dec 16 - Tue, Mar 16
KLM Logo
1:30 pm - 10:10 pm
FCO
-
MDW
15h 40m
1 stop
KLM Logo
1:05 pm - 8:15 am
MDW
-
FCO
13h 10m
1 stop
$658KLM
Wed, Dec 16 - Mon, Mar 15
Air France Logo
9:05 am - 3:25 pm
NAP
-
MDW
37h 20m
1 stop
Air France Logo
4:30 pm - 7:05 am
MDW
-
NAP
31h 35m
1 stop
$661Air France
Fri, Sep 11 - Sat, Sep 19
Air France Logo
9:45 am - 10:36 pm
FCO
-
MDW
19h 51m
1 stop
Air France Logo
4:39 pm - 7:35 am
MDW
-
FCO
31h 56m
1 stop
$691Air France
Sun, Aug 23 - Sun, Sep 6
Multiple Airlines Logo
6:30 am - 6:35 pm
VRN
-
MDW
19h 05m
2 stops
Multiple Airlines Logo
11:35 am - 10:25 pm
MDW
-
VRN
27h 50m
2 stops
$1,172Multiple Airlines
Mon, Aug 3 - Mon, Aug 10

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Delta flights from Italy to Chicago Midway Airport

Our best Delta deals on Italy to Chicago Midway Airport flight tickets
Delta
Dec 15
NAP6:10 amNaples
19h 27m
2 stops
MDW6:37 pmChicago Midway
Mar 15
MDW1:05 pmChicago Midway
20h 45m
2 stops
NAP3:50 pmNaples
$630
Delta
Dec 15
NAP6:10 amNaples
19h 27m
2 stops
MDW6:37 pmChicago Midway
Mar 15
MDW1:05 pmChicago Midway
20h 45m
2 stops
NAP3:50 pmNaples
$631
Delta
Sep 11
NAP9:05 amNaples
20h 40m
1 stop
MDW10:45 pmChicago Midway
Sep 19
MDW11:25 amChicago Midway
17h 05m
2 stops
NAP11:30 amNaples
$634

KLM flights from Italy to Chicago Midway Airport

Our best KLM deals on Italy to Chicago Midway Airport flight tickets
KLM
Dec 17
NAP11:20 amNaples
17h 50m
2 stops
MDW10:10 pmChicago Midway
Mar 16
MDW1:00 pmChicago Midway
14h 35m
2 stops
NAP9:35 amNaples
$649
KLM
Dec 16
FCO1:30 pmRome Fiumicino
15h 40m
1 stop
MDW10:10 pmChicago Midway
Mar 15
MDW1:05 pmChicago Midway
13h 10m
1 stop
FCO8:15 amRome Fiumicino
$658
KLM
Aug 31
FCO9:00 amRome Fiumicino
14h 59m
1 stop
MDW4:59 pmChicago Midway
Oct 21
MDW10:35 amChicago Midway
14h 00m
1 stop
FCO7:35 amRome Fiumicino
$660

momondo Fare Finder

 
Customize your flight search to find flights from Italy to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated June 21, 2026.
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

Cheapest round-trip

NaplesChicago

NAP - MDW

NAPMDW

Naples

Tue 12/15

6:10 am-6:37 pm

2 stops19h 27m

Chicago Midway

Mon 3/15

1:05 pm-3:50 pm

2 stops20h 45m

$630

NaplesChicago

NAP - MDW

NAPMDW

Naples

Tue 12/15

6:10 am-6:37 pm

2 stops19h 27m

Chicago Midway

Mon 3/15

1:05 pm-3:50 pm

2 stops20h 45m

$631

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 9/11

9:05 am-10:45 pm

1 stop20h 40m

Chicago Midway

Sat 9/19

11:25 am-11:30 am

2 stops17h 05m

$634

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 9/11

6:05 am-6:19 pm

2 stops19h 14m

Chicago Midway

Sat 9/19

9:49 am-11:30 am

2 stops18h 41m

$638

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 12/17

11:20 am-10:10 pm

2 stops17h 50m

Chicago Midway

Tue 3/16

1:00 pm-9:35 am

2 stops14h 35m

$649

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Wed 12/16

10:00 am-6:37 pm

1 stop15h 37m

Chicago Midway

Tue 3/16

1:00 pm-9:35 am

1 stop14h 35m

$657
Quickest round-trip

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Wed 12/16

1:30 pm-10:10 pm

1 stop15h 40m

Chicago Midway

Mon 3/15

1:05 pm-8:15 am

1 stop13h 10m

$658

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 9/11

9:05 am-3:25 pm

1 stop37h 20m

Chicago Midway

Sat 9/19

4:30 pm-7:05 am

1 stop31h 35m

$661

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Sun 8/23

9:45 am-10:36 pm

1 stop19h 51m

Chicago Midway

Sun 9/6

4:39 pm-7:35 am

1 stop31h 56m

$691

VeronaChicago

VRN - MDW

VRNMDW

Verona

Mon 8/3

6:30 am-6:35 pm

2 stops19h 05m

Chicago Midway

Mon 8/10

11:35 am-10:25 pm

2 stops27h 50m

$1,172

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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

KLM and Delta are the most popular carriers 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

15h 41m

Direct flights

None
The fastest flight from Italy to Chicago Midway Airport takes 15h 41m
There are no direct flights from Italy to Chicago Midway Airport. There are no popular flight routes from Italy to Chicago Midway Airport.
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Frequently asked questions about flying from Italy to Chicago Midway Airport

  • 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Saint Joseph
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.

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