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Cheap flights from Italy to Chicago from $361

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 9/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Italy to Chicago

Recent round-trip flight deals from Italy to Chicago

Delta Logo
6:00 am - 6:35 pmBLQ-MDW
19h 35m2 stops
Delta Logo
6:15 pm - 5:05 pmMDW-BLQ
15h 50m2 stops
$600Delta
Find Deal
Mon, Sep 15 - Mon, Sep 22
Delta Logo
9:00 am - 9:26 pmNAP-MDW
19h 26m1 stop
Delta Logo
9:30 am - 11:35 amMDW-NAP
19h 05m2 stops
$601Delta
Find Deal
Tue, Sep 2 - Mon, Sep 8
Delta Logo
9:00 am - 9:36 pmNAP-MDW
19h 36m1 stop
Delta Logo
10:35 am - 7:00 amMDW-NAP
13h 25m1 stop
$602Delta
Find Deal
Thu, Oct 2 - Wed, Oct 8
Delta Logo
9:15 am - 6:37 pmBLQ-MDW
16h 22m2 stops
Delta Logo
1:08 pm - 1:50 pmMDW-BLQ
17h 42m2 stops
$603Delta
Find Deal
Thu, Aug 28 - Sat, Sep 6
Air France Logo
9:00 am - 9:26 pmNAP-MDW
19h 26m1 stop
Air France Logo
11:00 am - 7:00 amMDW-NAP
13h 00m1 stop
$606Air France
Find Deal
Thu, Sep 4 - Sat, Sep 13
Logo
6:50 am - 5:35 pmMXP-MDW
17h 45m2 stops
Logo
12:48 pm - 9:25 amMDW-MXP
13h 37m1 stop
$618
Find Deal
Wed, Oct 1 - Wed, Oct 15
Logo
6:40 am - 4:23 pmFLR-MDW
16h 43m2 stops
Logo
2:00 pm - 11:20 amMDW-FLR
14h 20m2 stops
$628
Find Deal
Wed, Nov 19 - Tue, Nov 25
KLM Logo
9:00 am - 9:26 pmNAP-MDW
19h 26m1 stop
KLM Logo
6:00 am - 7:00 amMDW-NAP
18h 00m1 stop
$667KLM
Find Deal
Thu, Sep 4 - Mon, Sep 8
KLM Logo
9:00 am - 5:47 pmNAP-MDW
15h 47m1 stop
KLM Logo
6:00 am - 7:00 amMDW-NAP
18h 00m1 stop
$685KLM
Find Deal
Thu, Aug 21 - Mon, Sep 1
Air France Logo
9:00 am - 5:47 pmVCE-MDW
15h 47m1 stop
Air France Logo
10:31 am - 7:00 amMDW-VCE
13h 29m1 stop
$853Air France
Find Deal
Fri, Aug 15 - Thu, Aug 21

KLM flights from Italy to Chicago Midway Airport

Our best KLM deals on Italy to Chicago Midway Airport flight tickets
KLM
Sep 4
NAP9:00 amNaples
19h 26m
1 stop
MDW9:26 pmChicago Midway
Sep 8
MDW6:00 amChicago Midway
18h 00m
1 stop
NAP7:00 amNaples
$667
Find similar
KLM
Aug 21
NAP9:00 amNaples
15h 47m
1 stop
MDW5:47 pmChicago Midway
Sep 1
MDW6:00 amChicago Midway
18h 00m
1 stop
NAP7:00 amNaples
$685
Find similar
KLM
Aug 21
NAP9:00 amNaples
15h 47m
1 stop
MDW5:47 pmChicago Midway
Aug 31
MDW4:25 pmChicago Midway
31h 35m
1 stop
NAP7:00 amNaples
$791
Find similar

Delta flights from Italy to Chicago Midway Airport

Our best Delta deals on Italy to Chicago Midway Airport flight tickets
Delta
Sep 15
BLQ6:00 amBologna Guglielmo Marconi
19h 35m
2 stops
MDW6:35 pmChicago Midway
Sep 22
MDW6:15 pmChicago Midway
15h 50m
2 stops
BLQ5:05 pmBologna Guglielmo Marconi
$600
Find similar
Delta
Sep 2
NAP9:00 amNaples
19h 26m
1 stop
MDW9:26 pmChicago Midway
Sep 8
MDW9:30 amChicago Midway
19h 05m
2 stops
NAP11:35 amNaples
$601
Find similar
Delta
Oct 2
NAP9:00 amNaples
19h 36m
1 stop
MDW9:36 pmChicago Midway
Oct 8
MDW10:35 amChicago Midway
13h 25m
1 stop
NAP7:00 amNaples
$602
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 August 2, 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

Mon 9/15

6:00 am-6:35 pm

2 stops19h 35m

Chicago Midway

Mon 9/22

6:15 pm-5:05 pm

2 stops15h 50m

$600

NaplesChicago

NAP - MDW

NAPMDW

Naples

Tue 9/2

9:00 am-9:26 pm

1 stop19h 26m

Chicago Midway

Mon 9/8

9:30 am-11:35 am

2 stops19h 05m

$601

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 10/2

9:00 am-9:36 pm

1 stop19h 36m

Chicago Midway

Wed 10/8

10:35 am-7:00 am

1 stop13h 25m

$602

BolognaChicago

BLQ - MDW

BLQMDW

Bologna Guglielmo Marconi

Thu 8/28

9:15 am-6:37 pm

2 stops16h 22m

Chicago Midway

Sat 9/6

1:08 pm-1:50 pm

2 stops17h 42m

$603

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 9/4

9:00 am-9:26 pm

1 stop19h 26m

Chicago Midway

Sat 9/13

11:00 am-7:00 am

1 stop13h 00m

$606

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 10/1

6:50 am-5:35 pm

2 stops17h 45m

Chicago Midway

Wed 10/15

12:48 pm-9:25 am

1 stop13h 37m

$618

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Wed 11/19

6:40 am-4:23 pm

2 stops16h 43m

Chicago Midway

Tue 11/25

2:00 pm-11:20 am

2 stops14h 20m

$628

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 9/4

9:00 am-9:26 pm

1 stop19h 26m

Chicago Midway

Mon 9/8

6:00 am-7:00 am

1 stop18h 00m

$667

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 8/21

9:00 am-5:47 pm

1 stop15h 47m

Chicago Midway

Mon 9/1

6:00 am-7:00 am

1 stop18h 00m

$685

VeniceChicago

VCE - MDW

VCEMDW

Venice Marco Polo

Fri 8/15

9:00 am-5:47 pm

1 stop15h 47m

Chicago Midway

Thu 8/21

10:31 am-7:00 am

1 stop13h 29m

$853

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

Best Price Found

$361

Fastest flight time

14h 50m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Italy in the past 72 hours is $361. The best round-trip flight deal from Italy to Chicago Midway Airport found on momondo in the last 72 hours is $600.
The fastest flight from Italy to Chicago Midway Airport takes 14h 50m
There are no direct flights from Italy to Chicago Midway Airport. Popular non-direct routes for this connection are Naples Airport - Chicago Midway Airport, Rome Fiumicino Airport - Chicago Midway Airport and Florence Peretola Airport - Chicago Midway Airport.
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  • 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
Schererville
Valparaiso
Crown Point
Munster
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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