Find Cheap Flights to Italy

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to Italy

(Round-trip)
Depart: Mon Oct 2 2017 Return: Mon Oct 9 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
MDW
LIN
28h 53m
3 stops
LIN
MDW
38h 40m
3 stops
Depart: Sun Jan 14 2018 Return: Mon Jan 22 2018 Trip spans 9 days
Air France
Air France
MDW
FCO
13h 00m
1 stop
FCO
MDW
16h 43m
1 stop
Depart: Sun Feb 4 2018 Return: Mon Feb 12 2018 Trip spans 9 days
KLM
KLM
MDW
FCO
14h 40m
1 stop
FCO
MDW
16h 43m
1 stop
Depart: Mon Oct 30 2017 Return: Tue Nov 7 2017 Trip spans 9 days
Delta
Delta
MDW
FCO
16h 40m
2 stops
FCO
MDW
16h 49m
2 stops
Depart: Fri Aug 25 2017 Return: Mon Sep 4 2017 Trip spans 11 days
Iberia
Iberia
ORD
FCO
8h 55m
nonstop
FCO
ORD
26h 00m
1 stop
Depart: Thu Aug 24 2017 Return: Mon Aug 28 2017 Trip spans 5 days
airberlin
airberlin
ORD
FLR
18h 30m
2 stops
FLR
ORD
25h 10m
2 stops
Depart: Sat Aug 26 2017 Return: Wed Sep 6 2017 Trip spans 12 days
$1156
Select
SAS
SAS
ORD
BLQ
14h 25m
1 stop
BLQ
ORD
14h 05m
1 stop
Depart: Mon Sep 25 2017 Return: Tue Oct 3 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
MDW
LIN
28h 58m
3 stops
LIN
MDW
39h 17m
3 stops
Depart: Mon Jan 29 2018 Return: Mon Feb 12 2018 Trip spans 15 days
Air France
Air France
MDW
FCO
13h 00m
1 stop
FCO
MDW
16h 43m
1 stop
Depart: Thu Oct 19 2017 Return: Sat Oct 28 2017 Trip spans 10 days
Multiple Airlines
Multiple Airlines
MDW
LIN
21h 03m
3 stops
LIN
MDW
42h 18m
3 stops
Depart: Tue Oct 31 2017 Return: Tue Nov 7 2017 Trip spans 8 days
KLM
KLM
MDW
FCO
14h 37m
2 stops
FCO
MDW
19h 15m
2 stops
Depart: Fri Oct 13 2017 Return: Mon Oct 23 2017 Trip spans 11 days
Delta
Delta
MDW
MXP
16h 17m
2 stops
MXP
MDW
17h 31m
2 stops
Depart: Mon Nov 20 2017 Return: Wed Nov 29 2017 Trip spans 10 days
KLM
KLM
MDW
FCO
14h 00m
2 stops
FCO
MDW
17h 12m
2 stops
Depart: Mon Dec 4 2017 Return: Wed Dec 13 2017 Trip spans 10 days
Multiple Airlines
Multiple Airlines
MDW
FCO
12h 40m
1 stop
FCO
MDW
27h 11m
2 stops
Depart: Sun Nov 5 2017 Return: Tue Nov 14 2017 Trip spans 10 days
Delta
Delta
MDW
MXP
17h 30m
2 stops
MXP
MDW
18h 13m
2 stops
Depart: Fri Aug 25 2017 Return: Fri Sep 1 2017 Trip spans 8 days
Iberia
Iberia
ORD
FCO
8h 55m
nonstop
FCO
ORD
10h 35m
nonstop
Depart: Wed Oct 18 2017 Return: Tue Oct 31 2017 Trip spans 14 days
KLM
KLM
MDW
FCO
13h 42m
1 stop
FCO
MDW
22h 02m
2 stops
Depart: Fri Aug 25 2017 Return: Fri Sep 1 2017 Trip spans 8 days
airberlin
airberlin
ORD
VCE
24h 35m
2 stops
VCE
ORD
30h 40m
2 stops
Depart: Fri Oct 13 2017 Return: Mon Oct 16 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
MDW
NAP
22h 57m
4 stops
NAP
MDW
34h 10m
4 stops
Depart: Sun Sep 24 2017 Return: Thu Nov 2 2017 Trip spans 40 days
Delta
Delta
MDW
FCO
17h 07m
1 stop
FCO
MDW
20h 25m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
only $772
only $613
Destination

Bologna
$1156
Rome
$660
Milan
only $736
only $613
Florence
$898
Naples
$684
Venice
$905