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Cheap flights from Italy to Chicago from $384

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 2/27. 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
0 bags

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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
6:30 am - 10:07 pm
BLQ
-
MDW
22h 37m2 stops
Delta Logo
1:49 pm - 3:45 pm
MDW
-
BLQ
18h 56m2 stops
$624Delta
Thu, Jan 15 - Wed, Jan 21
Delta Logo
6:30 am - 5:29 pm
VCE
-
MDW
17h 59m2 stops
Delta Logo
10:48 am - 8:50 am
MDW
-
VCE
15h 02m2 stops
$631Delta
Tue, Jan 20 - Tue, Jan 27
Delta Logo
6:40 am - 5:54 pm
LIN
-
MDW
18h 14m2 stops
Delta Logo
6:34 pm - 1:55 pm
MDW
-
LIN
12h 21m2 stops
$631Delta
Fri, Apr 24 - Sun, Apr 26
Delta Logo
11:05 am - 10:07 pm
MXP
-
MDW
18h 02m1 stop
Delta Logo
1:26 pm - 11:40 am
MDW
-
MXP
15h 14m2 stops
$631Delta
Thu, Jan 15 - Wed, Jan 28
KLM Logo
11:05 am - 4:29 pm
MXP
-
MDW
36h 24m1 stop
KLM Logo
10:46 am - 9:05 am
MDW
-
MXP
15h 19m1 stop
$635KLM
Thu, Jan 15 - Wed, Jan 28
Air France Logo
6:15 am - 5:37 pm
NAP
-
MDW
18h 22m2 stops
Air France Logo
12:46 pm - 11:30 am
MDW
-
NAP
15h 44m2 stops
$640Air France
Thu, Feb 12 - Sun, Feb 22
Air France Logo
6:55 am - 5:29 pm
MXP
-
MDW
17h 34m2 stops
Air France Logo
12:48 pm - 9:05 am
MDW
-
MXP
13h 17m1 stop
$640Air France
Wed, Jan 21 - Wed, Jan 28
Multiple Airlines Logo
6:15 am - 5:29 pm
NAP
-
MDW
18h 14m2 stops
Multiple Airlines Logo
6:35 pm - 3:50 pm
MDW
-
NAP
14h 15m2 stops
$641Multiple Airlines
Tue, Feb 3 - Tue, Feb 10
KLM Logo
11:40 am - 10:29 pm
MXP
-
MDW
17h 49m1 stop
KLM Logo
10:49 am - 9:25 am
MDW
-
MXP
15h 36m1 stop
$647KLM
Wed, Apr 8 - Thu, Apr 16
Multiple Airlines Logo
7:15 am - 10:05 am
VRN
-
MDW
33h 50m3 stops
Multiple Airlines Logo
11:00 am - 3:45 pm
MDW
-
VRN
21h 45m3 stops
$850Multiple Airlines
Wed, Feb 11 - Sun, Feb 22

Delta flights from Italy to Chicago Midway Airport

Our best Delta deals on Italy to Chicago Midway Airport flight tickets
Delta
Jan 15
BLQ6:30 amBologna Guglielmo Marconi
22h 37m
2 stops
MDW10:07 pmChicago Midway
Jan 21
MDW1:49 pmChicago Midway
18h 56m
2 stops
BLQ3:45 pmBologna Guglielmo Marconi
$624
Find similar
Delta
Jan 20
VCE6:30 amVenice Marco Polo
17h 59m
2 stops
MDW5:29 pmChicago Midway
Jan 27
MDW10:48 amChicago Midway
15h 02m
2 stops
VCE8:50 amVenice Marco Polo
$631
Find similar
Delta
Jan 15
LIN6:30 amMilan Linate
19h 02m
2 stops
MDW6:32 pmChicago Midway
Jan 28
MDW1:26 pmChicago Midway
14h 49m
2 stops
LIN11:15 amMilan Linate
$632
Find similar

KLM flights from Italy to Chicago Midway Airport

Our best KLM deals on Italy to Chicago Midway Airport flight tickets
KLM
Jan 15
MXP11:05 amMilan Malpensa
36h 24m
1 stop
MDW4:29 pmChicago Midway
Jan 28
MDW10:46 amChicago Midway
15h 19m
1 stop
MXP9:05 amMilan Malpensa
$635
Find similar
KLM
Apr 8
MXP11:40 amMilan Malpensa
17h 49m
1 stop
MDW10:29 pmChicago Midway
Apr 16
MDW10:49 amChicago Midway
15h 36m
1 stop
MXP9:25 amMilan Malpensa
$647
Find similar
KLM
Feb 5
GOA7:00 amGenoa Cristoforo Colombo
22h 22m
2 stops
MDW10:22 pmChicago Midway
Feb 12
MDW1:28 pmChicago Midway
17h 07m
2 stops
GOA1:35 pmGenoa Cristoforo Colombo
$657
Find similar

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 December 23, 2025.
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

Thu 1/15

6:30 am-10:07 pm

2 stops22h 37m

Chicago Midway

Wed 1/21

1:49 pm-3:45 pm

2 stops18h 56m

$624

VeniceChicago

VCE - MDW

VCEMDW

Venice Marco Polo

Tue 1/20

6:30 am-5:29 pm

2 stops17h 59m

Chicago Midway

Tue 1/27

10:48 am-8:50 am

2 stops15h 02m

$631

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 4/24

6:40 am-5:54 pm

2 stops18h 14m

Chicago Midway

Sun 4/26

6:34 pm-1:55 pm

2 stops12h 21m

$631

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 1/15

11:05 am-10:07 pm

1 stop18h 02m

Chicago Midway

Wed 1/28

1:26 pm-11:40 am

2 stops15h 14m

$631

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 1/15

11:05 am-4:29 pm

1 stop36h 24m

Chicago Midway

Wed 1/28

10:46 am-9:05 am

1 stop15h 19m

$635

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 2/12

6:15 am-5:37 pm

2 stops18h 22m

Chicago Midway

Sun 2/22

12:46 pm-11:30 am

2 stops15h 44m

$640

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 1/21

6:55 am-5:29 pm

2 stops17h 34m

Chicago Midway

Wed 1/28

12:48 pm-9:05 am

1 stop13h 17m

$640

NaplesChicago

NAP - MDW

NAPMDW

Naples

Tue 2/3

6:15 am-5:29 pm

2 stops18h 14m

Chicago Midway

Tue 2/10

6:35 pm-3:50 pm

2 stops14h 15m

$641

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 4/8

11:40 am-10:29 pm

1 stop17h 49m

Chicago Midway

Thu 4/16

10:49 am-9:25 am

1 stop15h 36m

$647

VeronaChicago

VRN - MDW

VRNMDW

Verona

Wed 2/11

7:15 am-10:05 am

3 stops33h 50m

Chicago Midway

Sun 2/22

11:00 am-3:45 pm

3 stops21h 45m

$850

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?

Delta and KLM 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

14h 21m

Direct flights

None
The fastest flight from Italy to Chicago Midway Airport takes 14h 21m
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.

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
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.

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