Flights Europe Italy Chicago to Italy

Cheap flights from Chicago to Italy

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Easily compare round-trip flights from Chicago to Italy

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Italy by changing tabs
Quickest
Cheapest
SAS
SAS
23 Nov
ORD
11:00 pm
Chicago O'Hare Intl airport
19h 15m
1 Stop
1:15 am
+2
LIN
Milan Linate airport
SAS
01 Dec
LIN
6:00 am
Milan Linate airport
24h 30m
1 Stop
11:30 pm
ORD
Chicago O'Hare Intl airport
448 USD
TAP AIR PORTUGAL
TAP AIR PORTUGAL
26 Jan
ORD
11:00 pm
Chicago O'Hare Intl airport
16h 55m
1 Stop
10:55 pm
+1
MXP
Milan Malpensa airport
TAP AIR PORTUGAL
02 Feb
MXP
6:00 am
Milan Malpensa airport
28h 30m
1 Stop
3:30 am
+1
ORD
Chicago O'Hare Intl airport
475 USD
TAP AIR PORTUGAL
TAP AIR PORTUGAL
09 Feb
ORD
11:00 pm
Chicago O'Hare Intl airport
16h 55m
1 Stop
10:55 pm
+1
MXP
Milan Malpensa airport
TAP AIR PORTUGAL
15 Feb
MXP
6:00 am
Milan Malpensa airport
28h 30m
1 Stop
3:30 am
+1
ORD
Chicago O'Hare Intl airport
512 USD
TAP AIR PORTUGAL
TAP AIR PORTUGAL
27 Jan
ORD
11:00 pm
Chicago O'Hare Intl airport
12h 40m
1 Stop
6:40 pm
+1
FCO
Rome Fiumicino airport
TAP AIR PORTUGAL
03 Feb
FCO
6:00 am
Rome Fiumicino airport
17h 25m
1 Stop
4:25 pm
ORD
Chicago O'Hare Intl airport
550 USD
Turkish Airlines
Turkish Airlines
08 Dec
ORD
11:00 pm
Chicago O'Hare Intl airport
16h 55m
1 Stop
10:55 pm
+1
MXP
Milan Malpensa airport
Turkish Airlines
18 Dec
MXP
6:00 am
Milan Malpensa airport
17h 45m
1 Stop
4:45 pm
ORD
Chicago O'Hare Intl airport
556 USD
Air Canada
Air Canada
29 Sep
ORD
11:00 pm
Chicago O'Hare Intl airport
10h 55m
1 Stop
4:55 pm
+1
MXP
Milan Malpensa airport
Air Canada
08 Oct
MXP
6:00 am
Milan Malpensa airport
13h 05m
1 Stop
12:05 pm
ORD
Chicago O'Hare Intl airport
571 USD
Finnair
Finnair
13 Oct
ORD
11:00 pm
Chicago O'Hare Intl airport
8h 55m
2:55 pm
+1
FCO
Rome Fiumicino airport
Finnair
17 Oct
FCO
6:00 am
Rome Fiumicino airport
10h 40m
9:40 am
ORD
Chicago O'Hare Intl airport
626 USD
Finnair
Finnair
07 Oct
ORD
11:00 pm
Chicago O'Hare Intl airport
8h 55m
2:55 pm
+1
FCO
Rome Fiumicino airport
Finnair
16 Oct
FCO
6:00 am
Rome Fiumicino airport
10h 40m
9:40 am
ORD
Chicago O'Hare Intl airport
645 USD
Alitalia
Alitalia
10 Sep
ORD
11:00 pm
Chicago O'Hare Intl airport
9h 20m
3:20 pm
+1
FCO
Rome Fiumicino airport
Alitalia
17 Sep
FCO
6:00 am
Rome Fiumicino airport
10h 50m
9:50 am
ORD
Chicago O'Hare Intl airport
644 USD
Air Canada
Air Canada
29 Sep
ORD
11:00 pm
Chicago O'Hare Intl airport
10h 55m
1 Stop
4:55 pm
+1
MXP
Milan Malpensa airport
Air Canada
08 Oct
MXP
6:00 am
Milan Malpensa airport
13h 05m
1 Stop
12:05 pm
ORD
Chicago O'Hare Intl airport
571 USD
SWISS
SWISS
12 Nov
ORD
11:00 pm
Chicago O'Hare Intl airport
11h 45m
1 Stop
5:45 pm
+1
VCE
Venice Marco Polo airport
SWISS
20 Nov
VCE
6:00 am
Venice Marco Polo airport
12h 45m
1 Stop
11:45 am
ORD
Chicago O'Hare Intl airport
582 USD
Aer Lingus
Aer Lingus
08 Dec
ORD
11:00 pm
Chicago O'Hare Intl airport
12h 00m
1 Stop
6:00 pm
+1
LIN
Milan Linate airport
Aer Lingus
18 Dec
LIN
6:00 am
Milan Linate airport
14h 00m
1 Stop
1:00 pm
ORD
Chicago O'Hare Intl airport
624 USD

Alternative routes for Chicago to Italy

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Chicago to Rome
Fastest flight time
11h 30m
Cheapest price
384 USD
Chicago to Milan
Fastest flight time
11h 15m
Cheapest price
432 USD
Chicago to Venice
Fastest flight time
8h 40m
Cheapest price
498 USD
Chicago to Naples
Fastest flight time
15h 20m
Cheapest price
505 USD
Chicago to Florence
Fastest flight time
11h 45m
Cheapest price
563 USD
Chicago to Verona
Fastest flight time
11h 30m
Cheapest price
578 USD
Chicago to Palermo
Fastest flight time
16h 20m
Cheapest price
580 USD
Indianapolis to Rome
Fastest flight time
11h 40m
Cheapest price
589 USD
Indianapolis to Venice
Fastest flight time
14h 05m
Cheapest price
591 USD
Indianapolis to Naples
Fastest flight time
19h 10m
Cheapest price
679 USD
Indianapolis to Milan
Fastest flight time
23h 05m
Cheapest price
687 USD
View more

Flights from Chicago to:

Flights to Italy from:

  • Chicago
  • Illinois
  • United States
  • North America
Flights Europe Italy Chicago to Italy