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Cheap flights from Chicago to Italy from $210

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Italy departing on 2/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Italy

Cheap round-trip flights

Enter your travel dates to find the best prices.
Scandinavian Airlines Logo
7:20 pm - 7:20 pm
ORD
-
BLQ
17h 00m1 stop
Scandinavian Airlines Logo
8:00 pm - 4:45 pm
BLQ
-
ORD
27h 45m1 stop
$399Scandinavian Airlines
Sat, Feb 7 - Fri, Feb 20
Scandinavian Airlines Logo
7:20 pm - 7:20 pm
ORD
-
BLQ
17h 00m1 stop
Scandinavian Airlines Logo
8:00 pm - 4:45 pm
BLQ
-
ORD
27h 45m1 stop
$401Scandinavian Airlines
Sat, Feb 7 - Fri, Feb 20
TAP AIR PORTUGAL Logo
6:00 pm - 6:25 pm
ORD
-
NAP
17h 25m1 stop
TAP AIR PORTUGAL Logo
7:15 pm - 4:00 pm
NAP
-
ORD
27h 45m1 stop
$412TAP AIR PORTUGAL
Wed, Apr 29 - Thu, May 14
TAP AIR PORTUGAL Logo
6:00 pm - 6:15 pm
ORD
-
VCE
17h 15m1 stop
TAP AIR PORTUGAL Logo
7:10 pm - 4:00 pm
VCE
-
ORD
27h 50m1 stop
$412TAP AIR PORTUGAL
Sun, Apr 26 - Tue, May 12
Lufthansa Logo
9:50 pm - 5:25 pm
ORD
-
NAP
12h 35m1 stop
Lufthansa Logo
3:05 pm - 1:25 pm
NAP
-
ORD
29h 20m2 stops
$490Lufthansa
Wed, Jan 21 - Mon, Feb 2
Lufthansa Logo
6:00 pm - 10:40 pm
ORD
-
NAP
21h 40m2 stops
Lufthansa Logo
6:15 pm - 2:10 pm
NAP
-
ORD
26h 55m1 stop
$504Lufthansa
Wed, Feb 4 - Wed, Feb 11
Turkish Airlines Logo
11:25 am - 9:30 am
ORD
-
BLQ
15h 05m1 stop
Turkish Airlines Logo
3:25 pm - 9:40 am
BLQ
-
ORD
25h 15m1 stop
$516Turkish Airlines
Tue, Apr 7 - Tue, Apr 14
Turkish Airlines Logo
7:50 pm - 6:20 pm
ORD
-
BLQ
15h 30m1 stop
Turkish Airlines Logo
10:30 am - 9:40 am
BLQ
-
ORD
30h 10m1 stop
$518Turkish Airlines
Wed, May 6 - Wed, May 27
British Airways Logo
4:14 pm - 9:20 pm
ORD
-
BLQ
22h 06m2 stops
British Airways Logo
8:15 pm - 1:50 pm
BLQ
-
ORD
24h 35m1 stop
$537British Airways
Mon, Feb 2 - Mon, Feb 9
British Airways Logo
11:44 am - 11:40 am
ORD
-
BLQ
16h 56m2 stops
British Airways Logo
8:15 pm - 8:04 pm
BLQ
-
ORD
30h 49m2 stops
$538British Airways
Mon, Feb 2 - Mon, Feb 9

Lufthansa flights from Chicago to Italy

Our best Lufthansa deals on Chicago to Italy flight tickets
Lufthansa
Jan 21
ORD9:50 pmChicago O'Hare Intl
12h 35m
1 stop
NAP5:25 pmNaples
Feb 2
NAP3:05 pmNaples
29h 20m
2 stops
ORD1:25 pmChicago O'Hare Intl
$490
Find similar
Lufthansa
Feb 4
ORD6:00 pmChicago O'Hare Intl
21h 40m
2 stops
NAP10:40 pmNaples
Feb 11
NAP6:15 pmNaples
26h 55m
1 stop
ORD2:10 pmChicago O'Hare Intl
$504
Find similar
Lufthansa
Jan 25
ORD6:00 pmChicago O'Hare Intl
11h 30m
1 stop
NAP12:30 pmNaples
Feb 9
NAP1:15 pmNaples
31h 55m
1 stop
ORD2:10 pmChicago O'Hare Intl
$513
Find similar

KLM flights from Chicago to Italy

Our best KLM deals on Chicago to Italy flight tickets
KLM
Jan 13
ORD5:20 pmChicago O'Hare Intl
15h 30m
1 stop
NAP3:50 pmNaples
Jan 27
NAP6:15 amNaples
15h 55m
1 stop
ORD3:10 pmChicago O'Hare Intl
$514
Find similar
KLM
Jan 21
ORD2:50 pmChicago O'Hare Intl
16h 30m
2 stops
NAP2:20 pmNaples
Feb 2
NAP1:15 pmNaples
34h 40m
2 stops
ORD4:55 pmChicago O'Hare Intl
$525
Find similar
KLM
Feb 22
MDW10:49 amChicago Midway
16h 41m
1 stop
FCO10:30 amRome Fiumicino
Mar 10
FCO6:10 amRome Fiumicino
17h 44m
2 stops
MDW5:54 pmChicago Midway
$530
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Italy 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 January 7, 2026.
Use the filters below to find and compare flights from Chicago to Italy that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Sat 2/7

7:20 pm-7:20 pm

1 stop17h 00m

Bologna Guglielmo Marconi

Fri 2/20

8:00 pm-4:45 pm

1 stop27h 45m

$399

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Sat 2/7

7:20 pm-7:20 pm

1 stop17h 00m

Bologna Guglielmo Marconi

Fri 2/20

8:00 pm-4:45 pm

1 stop27h 45m

$401

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 4/29

6:00 pm-6:25 pm

1 stop17h 25m

Naples

Thu 5/14

7:15 pm-4:00 pm

1 stop27h 45m

$412

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Sun 4/26

6:00 pm-6:15 pm

1 stop17h 15m

Venice Marco Polo

Tue 5/12

7:10 pm-4:00 pm

1 stop27h 50m

$412

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 1/21

9:50 pm-5:25 pm

1 stop12h 35m

Naples

Mon 2/2

3:05 pm-1:25 pm

2 stops29h 20m

$490

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 2/4

6:00 pm-10:40 pm

2 stops21h 40m

Naples

Wed 2/11

6:15 pm-2:10 pm

1 stop26h 55m

$504

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Tue 4/7

11:25 am-9:30 am

1 stop15h 05m

Bologna Guglielmo Marconi

Tue 4/14

3:25 pm-9:40 am

1 stop25h 15m

$516

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Wed 5/6

7:50 pm-6:20 pm

1 stop15h 30m

Bologna Guglielmo Marconi

Wed 5/27

10:30 am-9:40 am

1 stop30h 10m

$518

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Mon 2/2

4:14 pm-9:20 pm

2 stops22h 06m

Bologna Guglielmo Marconi

Mon 2/9

8:15 pm-1:50 pm

1 stop24h 35m

$537

ChicagoBologna

ORD - BLQ

ORDBLQ

Chicago O'Hare Intl

Mon 2/2

11:44 am-11:40 am

2 stops16h 56m

Bologna Guglielmo Marconi

Mon 2/9

8:15 pm-8:04 pm

2 stops30h 49m

$538

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 Italy from

How to get the cheapest flight ticket from Chicago 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

What is the cheapest month to fly to Italy?

The cheapest month to fly to Italy from Chicago is in November. Flight prices, which tend to average around $570, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of November, then book flights to Italy from Chicago during January instead. Flights to Italy in January, while not as cheap as those in November, still average around $591.

What is the cheapest day to depart on your flight to Italy?

According to our data, Monday is the cheapest day to fly to Italy from Chicago. The lowest ticket price found for a Monday departure recently was $908. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Italy for around $1,022.

What is the cheapest Chicago to Italy flight route?

Fly from Chicago O'Hare Intl to Rome Fiumicino for the best Chicago - Italy flight prices

How far in advance should I book a flight to Italy?

You are more likely to see cheaper flights to Italy from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Italy for around $793 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Italy from Chicago for as low as $683 on momondo.

What cabin class options are available on Chicago to Italy flights?

There are 3 cabin classes available to choose from on Chicago to Italy flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Italy flights?

No. A direct flight is the cheapest option for a flight between Chicago to Italy.

Cheap Chicago to Italy flight deals and tips

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

Best Price Found

$568

Fastest flight time

8h 40m

Direct flights

Every day

Airports in Italy

416 airports
The best one-way flight to Italy from Chicago in the past 72 hours is $568. The best round-trip flight deal from Chicago to Italy found on momondo in the last 72 hours is $817.
The fastest flight from Chicago to Italy takes 8h 40m
Direct flights go from Chicago to Italy every day.
There are 416 airports in Italy. From Chicago there are direct flights to Rome Fiumicino (FCO), Milan Malpensa (MXP).
Search flight deals

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

    Prices for flights from Chicago to Italy refresh daily.

  • How many operators does momondo search for flights from Chicago to Italy?

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Italy.

  • What documentation or ID do you need to fly to Italy?

    The travel and health documents you'll need for your trip to Italy may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Italy. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Italy?

Best airlines flying from Chicago to Italy

Compare and see reviews for airlines that fly from Chicago to Italy with momondo
Airline
Rating
Free Cancellation
Price
IberiaPriceFrom $230Free CancellationRating
7.0
3,076 reviews
Search Iberia flights
TAP AIR PORTUGALPriceFrom $337Free CancellationRating
7.1
2,111 reviews
Search TAP AIR PORTUGAL flights
Air CanadaPriceFrom $390Free CancellationRating
7.1
10,603 reviews
Search Air Canada flights
IcelandairPriceFrom $392Free CancellationRating
7.1
593 reviews
Search Icelandair flights
Scandinavian AirlinesPriceFrom $414Free CancellationRating
7.3
1,635 reviews
Search Scandinavian Airlines flights
SWISSPriceFrom $414Free CancellationRating
7.5
1,840 reviews
Search SWISS flights
KLMPriceFrom $455Free CancellationRating
7.7
1,434 reviews
Search KLM flights
British AirwaysPriceFrom $457Free CancellationRating
6.7
7,657 reviews
Search British Airways flights
Air FrancePriceFrom $458Free CancellationRating
7.4
1,519 reviews
Search Air France flights
DeltaPriceFrom $481Free CancellationRating
7.9
8,025 reviews
Search Delta flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Italy from Chicago.

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

All flight searches from Chicago to Italy on momondo can be filtered to show those which offer flexible booking policies.

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

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

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

If you are not ready to book a flight from Chicago to Italy now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Italy and let you know when they change.

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Find better results for your trip to Italy

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Popular flights according to clicks in the last 7 days on momondo
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