Business Class Flight Deals from Chicago to Italy from $1914
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Top Deals on Business Class Flights from Chicago to Rome
Chicago, US (CHI) - Rome, IT (ROM)
Jan 12
Jan 13
Jan 28
Jan 28
as low as
$1914
Chicago, US (CHI) - Rome, IT (ROM)
Aug 11
Aug 12
Aug 25
Aug 26
as low as
$2498
Chicago, US (CHI) - Rome, IT (ROM)
Oct 21
Oct 22
Oct 28
Oct 28
as low as
$3103
Chicago, US (CHI) - Rome, IT (ROM)
Jul 29
Jul 30
Aug 12
Aug 12
as low as
$3536
Chicago, US (CHI) - Rome, IT (ROM)
Jul 29
Jul 30
Aug 12
Aug 12
as low as
$3550
Chicago, US (CHI) - Rome, IT (ROM)
Jul 29
Jul 30
Aug 12
Aug 12
as low as
$3550
Chicago, US (CHI) - Rome, IT (ROM)
Aug 18
Aug 19
Aug 26
Aug 26
as low as
$3551
Chicago, US (CHI) - Rome, IT (ROM)
Aug 5
Aug 6
Aug 11
Aug 11
as low as
$3558
Chicago, US (CHI) - Rome, IT (ROM)
Aug 5
Aug 6
Aug 11
Aug 11
as low as
$3558
Chicago, US (CHI) - Rome, IT (ROM)
Dec 15
Dec 16
Dec 30
Dec 30
as low as
$3592
Chicago, US (CHI) - Rome, IT (ROM)
Oct 20
Oct 21
Nov 18
Nov 18
as low as
$3682
Chicago, US (CHI) - Rome, IT (ROM)
Oct 20
Oct 21
Nov 18
Nov 18
as low as
$3693
Top Deals on Business Class Flights from Chicago to Milan
Chicago, US (CHI) - Milan, IT (MIL)
Dec 19
Dec 20
Jan 2
Jan 2
as low as
$2550
Chicago, US (CHI) - Milan, IT (MIL)
May 1
May 2
May 13
May 13
as low as
$2552
Chicago, US (CHI) - Milan, IT (MIL)
Feb 2
Feb 3
Feb 17
Feb 17
as low as
$2793
Chicago, US (CHI) - Milan, IT (MIL)
Feb 3
Feb 4
Feb 14
Feb 14
as low as
$3701
Chicago, US (CHI) - Milan, IT (MIL)
Jul 30
Jul 31
Aug 15
Aug 16
as low as
$3718
Chicago, US (CHI) - Milan, IT (MIL)
Aug 3
Aug 4
Aug 17
Aug 17
as low as
$4186
Chicago, US (CHI) - Milan, IT (MIL)
Oct 2
Oct 3
Oct 10
Oct 11
as low as
$4316
Chicago, US (CHI) - Milan, IT (MIL)
Aug 27
Aug 28
Sep 8
Sep 8
as low as
$4350
Chicago, US (CHI) - Milan, IT (MIL)
Nov 11
Nov 12
Nov 23
Nov 23
as low as
$4564
Chicago, US (CHI) - Milan, IT (MIL)
Aug 3
Aug 4
Aug 17
Aug 17
as low as
$4599
Chicago, US (CHI) - Milan, IT (MIL)
Aug 3
Aug 4
Aug 17
Aug 17
as low as
$4630
Chicago, US (CHI) - Milan, IT (MIL)
Aug 3
Aug 4
Aug 17
Aug 17
as low as
$4635
Top Deals on Business Class Flights from Chicago to Venice
Chicago, US (CHI) - Venice, IT (VCE)
Sep 23
Sep 25
Oct 4
Oct 5
as low as
$2533
Chicago, US (CHI) - Venice, IT (VCE)
Nov 2
Nov 3
Nov 17
Nov 18
as low as
$3061
Chicago, US (CHI) - Venice, IT (VCE)
Oct 20
Oct 21
Dec 1
Dec 1
as low as
$3389
Chicago, US (CHI) - Venice, IT (VCE)
Oct 30
Oct 31
Nov 14
Nov 15
as low as
$3919
Chicago, US (CHI) - Venice, IT (VCE)
Sep 2
Sep 3
Sep 16
Sep 16
as low as
$4923
Chicago, US (CHI) - Venice, IT (VCE)
Jun 2
Jun 3
Jun 11
Jun 11
as low as
$5689
Chicago, US (CHI) - Venice, IT (VCE)
Oct 22
Oct 23
Nov 4
Nov 5
as low as
$5846
Chicago, US (CHI) - Venice, IT (VCE)
Oct 22
Oct 23
Nov 4
Nov 5
as low as
$5874
Chicago, US (CHI) - Venice, IT (VCE)
Jul 4
Jul 5
Jul 9
Jul 9
as low as
$6309
Chicago, US (CHI) - Venice, IT (VCE)
Oct 31
Nov 1
Nov 15
Nov 15
as low as
$6939
Top Deals on Business Class Flights from Chicago to Naples
Chicago, US (CHI) - Naples, IT (NAP)
Jul 1
Jul 2
Jul 15
Jul 15
as low as
$2516
Chicago, US (CHI) - Naples, IT (NAP)
Oct 19
Oct 20
Nov 9
Nov 10
as low as
$2857
Chicago, US (CHI) - Naples, IT (NAP)
Aug 20
Aug 21
Aug 31
Sep 1
as low as
$4012
Chicago, US (CHI) - Naples, IT (NAP)
Aug 12
Aug 13
Aug 23
Aug 24
as low as
$4186
Chicago, US (CHI) - Naples, IT (NAP)
Aug 12
Aug 13
Aug 22
Aug 22
as low as
$4774
Chicago, US (CHI) - Naples, IT (NAP)
Aug 12
Aug 13
Aug 22
Aug 22
as low as
$4774
Chicago, US (CHI) - Naples, IT (NAP)
Aug 12
Aug 13
Aug 22
Aug 22
as low as
$4775
Chicago, US (CHI) - Naples, IT (NAP)
Aug 12
Aug 13
Aug 22
Aug 22
as low as
$4782
Chicago, US (CHI) - Naples, IT (NAP)
Aug 12
Aug 13
Aug 22
Aug 22
as low as
$4782
Chicago, US (CHI) - Naples, IT (NAP)
Aug 12
Aug 13
Aug 21
Aug 21
as low as
$5495
Chicago, US (CHI) - Naples, IT (NAP)
Aug 12
Aug 13
Aug 21
Aug 21
as low as
$5534
Chicago, US (CHI) - Naples, IT (NAP)
Aug 18
Aug 19
Aug 27
Aug 27
as low as
$5546
Top Deals on Business Class Flights from Chicago to Florence
Chicago, US (CHI) - Florence, IT (FLR)
Nov 6
Nov 7
Nov 13
Nov 13
as low as
$3030
Chicago, US (CHI) - Florence, IT (FLR)
Feb 26
Feb 27
Mar 8
Mar 9
as low as
$3884
Chicago, US (CHI) - Florence, IT (FLR)
Oct 17
Oct 18
Oct 24
Oct 25
as low as
$4051
Chicago, US (CHI) - Florence, IT (FLR)
Oct 11
Oct 12
Oct 17
Oct 18
as low as
$4061
Chicago, US (CHI) - Florence, IT (FLR)
Jul 3
Jul 4
Jul 15
Jul 16
as low as
$4801
Top Deals on Business Class Flights from Chicago to Bologna
Chicago, US (CHI) - Bologna, IT (BLQ)
May 27
May 29
Jun 4
Jun 5
as low as
$2840
Chicago, US (CHI) - Bologna, IT (BLQ)
Sep 1
Sep 2
Sep 24
Sep 25
as low as
$2974
Chicago, US (CHI) - Bologna, IT (BLQ)
Oct 17
Oct 18
Oct 24
Oct 25
as low as
$3712
Chicago, US (CHI) - Bologna, IT (BLQ)
Sep 1
Sep 2
Sep 24
Sep 24
as low as
$3886
Chicago, US (CHI) - Bologna, IT (BLQ)
Aug 13
Aug 14
Aug 23
Aug 23
as low as
$3904
Chicago, US (CHI) - Bologna, IT (BLQ)
May 27
May 28
Jun 4
Jun 4
as low as
$3974
Chicago, US (CHI) - Bologna, IT (BLQ)
May 27
May 28
Jun 4
Jun 4
as low as
$4000
Chicago, US (CHI) - Bologna, IT (BLQ)
Jun 17
Jun 18
Jul 8
Jul 8
as low as
$4101
Chicago, US (CHI) - Bologna, IT (BLQ)
Jun 17
Jun 19
Jul 8
Jul 8
as low as
$4312
Chicago, US (CHI) - Bologna, IT (BLQ)
May 27
May 28
Jun 4
Jun 4
as low as
$4364
Chicago, US (CHI) - Bologna, IT (BLQ)
Aug 13
Aug 14
Aug 23
Aug 24
as low as
$4565
Chicago, US (CHI) - Bologna, IT (BLQ)
May 28
May 29
Jun 5
Jun 5
as low as
$4645
Top Deals on Business Class Flights from Chicago to Catania
Chicago, US (CHI) - Catania, IT (CTA)
Aug 19
Aug 20
Aug 26
Aug 26
as low as
$2924
Chicago, US (CHI) - Catania, IT (CTA)
Aug 19
Aug 20
Aug 26
Aug 26
as low as
$3616
Chicago, US (CHI) - Catania, IT (CTA)
Oct 1
Oct 2
Oct 14
Oct 15
as low as
$3933
Chicago, US (CHI) - Catania, IT (CTA)
Sep 5
Sep 6
Sep 20
Sep 21
as low as
$5216
Chicago, US (CHI) - Catania, IT (CTA)
Sep 5
Sep 6
Sep 14
Sep 15
as low as
$5230
Chicago, US (CHI) - Catania, IT (CTA)
Oct 17
Oct 18
Nov 4
Nov 4
as low as
$5233
Chicago, US (CHI) - Catania, IT (CTA)
Oct 17
Oct 18
Nov 4
Nov 4
as low as
$5259
Chicago, US (CHI) - Catania, IT (CTA)
Oct 17
Oct 18
Nov 4
Nov 4
as low as
$5616
Chicago, US (CHI) - Catania, IT (CTA)
Oct 17
Oct 18
Nov 4
Nov 4
as low as
$5642
Chicago, US (CHI) - Catania, IT (CTA)
Oct 17
Oct 18
Nov 4
Nov 5
as low as
$5683
Chicago, US (CHI) - Catania, IT (CTA)
Oct 19
Oct 21
Nov 7
Nov 7
as low as
$5787
Chicago, US (CHI) - Catania, IT (CTA)
Aug 19
Aug 20
Aug 26
Aug 27
as low as
$6046
Top Deals on Business Class Flights from Chicago to Palermo
Chicago, US (CHI) - Palermo, IT (PMO)
Oct 14
Oct 16
Oct 28
Oct 29
as low as
$3026
Chicago, US (CHI) - Palermo, IT (PMO)
Oct 10
Oct 12
Oct 17
Oct 18
as low as
$4223
Chicago, US (CHI) - Palermo, IT (PMO)
Jun 23
Jun 24
Jun 28
Jun 28
as low as
$4456
Chicago, US (CHI) - Palermo, IT (PMO)
Jun 23
Jun 25
Jul 4
Jul 5
as low as
$4875
Chicago, US (CHI) - Palermo, IT (PMO)
Jul 22
Jul 23
Aug 6
Aug 6
as low as
$4997
Chicago, US (CHI) - Palermo, IT (PMO)
Jul 22
Jul 23
Aug 6
Aug 6
as low as
$5167
Chicago, US (CHI) - Palermo, IT (PMO)
Jul 22
Jul 23
Aug 6
Aug 6
as low as
$5171
Chicago, US (CHI) - Palermo, IT (PMO)
Jul 22
Jul 23
Aug 6
Aug 6
as low as
$5583
Chicago, US (CHI) - Palermo, IT (PMO)
Jul 22
Jul 23
Aug 6
Aug 7
as low as
$5825
Chicago, US (CHI) - Palermo, IT (PMO)
Jun 23
Jun 24
Jul 4
Jul 5
as low as
$6183
Chicago, US (CHI) - Palermo, IT (PMO)
Oct 21
Oct 22
Oct 28
Oct 29
as low as
$6192
Chicago, US (CHI) - Palermo, IT (PMO)
Sep 3
Sep 4
Sep 13
Sep 14
as low as
$6367
Top Deals on Business Class Flights from Chicago to Pisa
Chicago, US (CHI) - Pisa, IT (PSA)
Aug 7
Aug 8
Aug 13
Aug 13
as low as
$3954
Chicago, US (CHI) - Pisa, IT (PSA)
Aug 7
Aug 8
Aug 13
Aug 14
as low as
$4617
Chicago, US (CHI) - Pisa, IT (PSA)
Aug 7
Aug 9
Aug 13
Aug 14
as low as
$5235
Chicago, US (CHI) - Pisa, IT (PSA)
Aug 26
Aug 27
Sep 5
Sep 5
as low as
$5701
Chicago, US (CHI) - Pisa, IT (PSA)
Aug 26
Aug 27
Sep 5
Sep 5
as low as
$5715
Chicago, US (CHI) - Pisa, IT (PSA)
Aug 26
Aug 27
Sep 5
Sep 5
as low as
$6050
Chicago, US (CHI) - Pisa, IT (PSA)
Aug 26
Aug 27
Sep 5
Sep 5
as low as
$6417
Chicago, US (CHI) - Pisa, IT (PSA)
Aug 26
Aug 27
Sep 5
Sep 5
as low as
$6432
Chicago, US (CHI) - Pisa, IT (PSA)
Aug 26
Aug 27
Sep 5
Sep 5
as low as
$7199
Chicago, US (CHI) - Pisa, IT (PSA)
Jun 2
Jun 3
Jul 2
Jul 3
as low as
$9085
Chicago, US (CHI) - Pisa, IT (PSA)
Jun 2
Jun 3
Jul 2
Jul 2
as low as
$19175
Top Deals on Business Class Flights from Chicago to Bari
Chicago, US (CHI) - Bari, IT (BRI)
Oct 30
Oct 31
Nov 7
Nov 8
as low as
$3519
Chicago, US (CHI) - Bari, IT (BRI)
Dec 1
Dec 2
Mar 31
Apr 1
as low as
$3685
Chicago, US (CHI) - Bari, IT (BRI)
Dec 1
Dec 2
Mar 31
Mar 31
as low as
$5065
Chicago, US (CHI) - Bari, IT (BRI)
Dec 1
Dec 2
Mar 31
Mar 31
as low as
$5604
Chicago, US (CHI) - Bari, IT (BRI)
Sep 8
Sep 10
Sep 22
Sep 23
as low as
$6117
Chicago, US (CHI) - Bari, IT (BRI)
Sep 8
Sep 10
Sep 22
Sep 23
as low as
$7245
Chicago, US (CHI) - Bari, IT (BRI)
Sep 8
Sep 10
Sep 22
Sep 23
as low as
$7261
Chicago, US (CHI) - Bari, IT (BRI)
Sep 18
Sep 20
Sep 27
Sep 28
as low as
$8176
Good to Know
Essential information to help you plan your flight Business Class from Chicago to Italy
Cheapest Flight
$1914
The lowest price we found in the last two weeks, departing Jan 12 and returning Jan 28
1 stop ‧ 12h 30m ‧ businessFastest Flights
$3550
The fastest flight that we found in the last two weeks, departing Jul 29 and returning Aug 12
9h ‧ businessCheapest Flight Round-trip
$1914
Cheapest price found in the last 14 days, departing Jan 12 and returning Jan 28
1 stop ‧ 12h 30m ‧ businessCheapest Layover airport
$4312
The cheapest layover airport to Bologna is currently $4312
1 stop ‧ 29h 55m ‧ businessBest Arrival airport
$2516
The best arrival airport to Naples is currently $2516
2 stops ‧ 16h 25m ‧ businessBest Departure airport
$2516
The best departure airport to Naples is currently $2516
2 stops ‧ 16h 25m ‧ businessCheapest Airline
$2516
The cheapest airline to Naples is currently $2516
2 stops ‧ 16h 25m ‧ businessFlights to Italy
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