24/7 Support
(855-706-2925)

Flight Deals from Chicago to Italy from $358
Top flight deals from leading airlines:







... and +100s more
Cancel within 24 hours for a full refund—no questions asked.
We’ll refund the difference if the price drops before you fly.
The prices shown are exactly what you pay, with no hidden taxes or fees.
Expert travel agents, ready to help anytime by phone, chat, or email.
Top Deals on flights from Chicago to Rome
Chicago, US (CHI) - Rome, IT (ROM)

Feb 8
Feb 10

Feb 17
Feb 18
as low as
$358
Chicago, US (CHI) - Rome, IT (ROM)

Feb 12
Feb 13

Feb 26
Feb 26
as low as
$417
Chicago, US (CHI) - Rome, IT (ROM)

Feb 3
Feb 4

Feb 19
Feb 20
as low as
$439
Chicago, US (CHI) - Rome, IT (ROM)

Feb 16
Feb 17

Feb 24
Feb 24
as low as
$489
Chicago, US (CHI) - Rome, IT (ROM)

Feb 23
Feb 24

Mar 11
Mar 11
as low as
$489
Chicago, US (CHI) - Rome, IT (ROM)

Feb 10
Feb 11

Feb 19
Feb 19
as low as
$504
Chicago, US (CHI) - Rome, IT (ROM)

Feb 3
Feb 4

Feb 19
Feb 19
as low as
$511
Chicago, US (CHI) - Rome, IT (ROM)

Mar 1
Mar 2

Mar 11
Mar 11
as low as
$513
Chicago, US (CHI) - Rome, IT (ROM)

Feb 9
Feb 10

Feb 18
Feb 18
as low as
$515
Chicago, US (CHI) - Rome, IT (ROM)

Feb 10
Feb 11

Mar 3
Mar 3
as low as
$515
Chicago, US (CHI) - Rome, IT (ROM)

Feb 22
Feb 23

Mar 3
Mar 4
as low as
$517
Chicago, US (CHI) - Rome, IT (ROM)

Mar 1
Mar 3

Mar 12
Mar 12
as low as
$519
Top Deals on flights from Chicago to Milan
Chicago, US (CHI) - Milan, IT (MIL)

Feb 24
Feb 25

Mar 8
Mar 8
as low as
$418
Chicago, US (CHI) - Milan, IT (MIL)

Feb 1
Feb 2

Mar 2
Mar 2
as low as
$457
Chicago, US (CHI) - Milan, IT (MIL)

Feb 1
Feb 3

Mar 2
Mar 2
as low as
$461
Chicago, US (CHI) - Milan, IT (MIL)

Feb 8
Feb 9

Feb 18
Feb 18
as low as
$470
Chicago, US (CHI) - Milan, IT (MIL)

Mar 12
Mar 13

Mar 16
Mar 16
as low as
$474
Chicago, US (CHI) - Milan, IT (MIL)

Nov 9
Nov 11

Feb 24
Feb 25
as low as
$484
Chicago, US (CHI) - Milan, IT (MIL)

Nov 10
Nov 11

Feb 24
Feb 25
as low as
$488
Chicago, US (CHI) - Milan, IT (MIL)

Feb 12
Feb 13

Feb 24
Feb 25
as low as
$642
Chicago, US (CHI) - Milan, IT (MIL)

Nov 8
Nov 10

Feb 26
Feb 27
as low as
$696
Chicago, US (CHI) - Milan, IT (MIL)

Feb 23
Feb 25

Feb 26
Feb 26
as low as
$766
Chicago, US (CHI) - Milan, IT (MIL)

Nov 10
Nov 12

Feb 19
Feb 19
as low as
$796
Chicago, US (CHI) - Milan, IT (MIL)

Feb 1
Feb 2

Feb 21
Feb 21
as low as
$812
Top Deals on flights from Chicago to Venice
Chicago, US (CHI) - Venice, IT (VCE)

Feb 8
Feb 10

Feb 19
Feb 19
as low as
$469
Chicago, US (CHI) - Venice, IT (VCE)

Feb 20
Feb 21

Mar 14
Mar 15
as low as
$520
Chicago, US (CHI) - Venice, IT (VCE)

Mar 4
Mar 6

Mar 9
Mar 11
as low as
$575
Chicago, US (CHI) - Venice, IT (VCE)

Feb 18
Feb 19

Feb 26
Feb 26
as low as
$643
Chicago, US (CHI) - Venice, IT (VCE)

Feb 8
Feb 10

Feb 19
Feb 21
as low as
$717
Chicago, US (CHI) - Venice, IT (VCE)

Mar 8
Mar 9

Mar 16
Mar 18
as low as
$784
Chicago, US (CHI) - Venice, IT (VCE)

Feb 24
Feb 25

Mar 1
Mar 1
as low as
$796
Chicago, US (CHI) - Venice, IT (VCE)

Mar 3
Mar 5

Mar 12
Mar 12
as low as
$798
Chicago, US (CHI) - Venice, IT (VCE)

Feb 14
Feb 16

Feb 19
Feb 20
as low as
$812
Chicago, US (CHI) - Venice, IT (VCE)

Mar 3
Mar 4

Mar 12
Mar 12
as low as
$814
Chicago, US (CHI) - Venice, IT (VCE)

Mar 3
Mar 4

Mar 12
Mar 12
as low as
$817
Chicago, US (CHI) - Venice, IT (VCE)

Mar 3
Mar 4

Mar 12
Mar 12
as low as
$818
Top Deals on flights from Chicago to Naples
Chicago, US (CHI) - Naples, IT (NAP)

Mar 3
Mar 5

Mar 10
Mar 11
as low as
$571
Chicago, US (CHI) - Naples, IT (NAP)

Mar 9
Mar 10

Mar 16
Mar 17
as low as
$574
Chicago, US (CHI) - Naples, IT (NAP)

Mar 7
Mar 8

Mar 14
Mar 15
as low as
$574
Chicago, US (CHI) - Naples, IT (NAP)

Feb 18
Feb 19

Feb 25
Feb 25
as low as
$579
Chicago, US (CHI) - Naples, IT (NAP)

Feb 18
Feb 19

Feb 25
Feb 25
as low as
$580
Chicago, US (CHI) - Naples, IT (NAP)

Feb 24
Feb 25

Mar 3
Mar 4
as low as
$582
Chicago, US (CHI) - Naples, IT (NAP)

Feb 24
Feb 25

Mar 3
Mar 4
as low as
$587
Chicago, US (CHI) - Naples, IT (NAP)

Feb 24
Feb 25

Mar 3
Mar 3
as low as
$590
Chicago, US (CHI) - Naples, IT (NAP)

Feb 18
Feb 19

Feb 25
Feb 26
as low as
$616
Chicago, US (CHI) - Naples, IT (NAP)

Mar 1
Mar 2

Mar 8
Mar 8
as low as
$619
Chicago, US (CHI) - Naples, IT (NAP)

Feb 23
Feb 24

Mar 4
Mar 5
as low as
$626
Chicago, US (CHI) - Naples, IT (NAP)

Mar 1
Mar 2

Mar 8
Mar 9
as low as
$635
Top Deals on flights from Chicago to Florence
Chicago, US (CHI) - Florence, IT (FLR)

Mar 1
Mar 2

Mar 7
Mar 8
as low as
$527
Chicago, US (CHI) - Florence, IT (FLR)

Feb 1
Feb 2

Feb 16
Feb 17
as low as
$626
Chicago, US (CHI) - Florence, IT (FLR)

Feb 1
Feb 2

Feb 16
Feb 17
as low as
$630
Chicago, US (CHI) - Florence, IT (FLR)

Feb 15
Feb 16

Feb 24
Feb 24
as low as
$640
Chicago, US (CHI) - Florence, IT (FLR)

Feb 15
Feb 16

Feb 24
Feb 24
as low as
$640
Chicago, US (CHI) - Florence, IT (FLR)

Jan 4
Jan 5

Mar 13
Mar 13
as low as
$641
Chicago, US (CHI) - Florence, IT (FLR)

Jan 26
Jan 27

Feb 21
Feb 21
as low as
$644
Chicago, US (CHI) - Florence, IT (FLR)

Jan 26
Jan 28

Feb 21
Feb 21
as low as
$648
Chicago, US (CHI) - Florence, IT (FLR)

Feb 1
Feb 2

Feb 21
Feb 21
as low as
$648
Chicago, US (CHI) - Florence, IT (FLR)

Mar 1
Mar 2

Mar 7
Mar 8
as low as
$664
Chicago, US (CHI) - Florence, IT (FLR)

Jan 4
Jan 5

Mar 13
Mar 14
as low as
$664
Chicago, US (CHI) - Florence, IT (FLR)

Mar 1
Mar 2

Mar 7
Mar 8
as low as
$667
Top Deals on flights from Chicago to Bologna
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 22
Feb 23

Feb 26
Feb 27
as low as
$531
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 1
Feb 2

Feb 21
Feb 21
as low as
$617
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 1
Feb 2

Feb 21
Feb 21
as low as
$621
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 1
Feb 2

Feb 21
Feb 21
as low as
$642
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 1
Feb 2

Feb 21
Feb 21
as low as
$643
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 1
Feb 2

Feb 21
Feb 21
as low as
$656
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 13
Feb 14

Feb 20
Feb 20
as low as
$656
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 13
Feb 14

Feb 20
Feb 20
as low as
$665
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 1
Feb 2

Feb 21
Feb 21
as low as
$671
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 1
Feb 2

Feb 21
Feb 21
as low as
$708
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 13
Feb 15

Feb 20
Feb 21
as low as
$726
Chicago, US (CHI) - Bologna, IT (BLQ)

Feb 22
Feb 23

Feb 26
Feb 26
as low as
$754
Top Deals on flights from Chicago to Catania
Chicago, US (CHI) - Catania, IT (CTA)

Feb 26
Feb 27

Mar 3
Mar 4
as low as
$637
Chicago, US (CHI) - Catania, IT (CTA)

Feb 25
Feb 26

Mar 2
Mar 3
as low as
$669
Chicago, US (CHI) - Catania, IT (CTA)

Feb 4
Feb 6

Feb 14
Feb 15
as low as
$699
Chicago, US (CHI) - Catania, IT (CTA)

Feb 3
Feb 4

Feb 16
Feb 17
as low as
$720
Chicago, US (CHI) - Catania, IT (CTA)

Feb 3
Feb 4

Feb 15
Feb 15
as low as
$775
Chicago, US (CHI) - Catania, IT (CTA)

Feb 25
Feb 27

Mar 2
Mar 3
as low as
$777
Chicago, US (CHI) - Catania, IT (CTA)

Feb 4
Feb 6

Feb 15
Feb 16
as low as
$784
Chicago, US (CHI) - Catania, IT (CTA)

Feb 27
Feb 28

Mar 7
Mar 8
as low as
$858
Chicago, US (CHI) - Catania, IT (CTA)

Feb 9
Feb 11

Feb 16
Feb 17
as low as
$883
Chicago, US (CHI) - Catania, IT (CTA)

Feb 4
Feb 6

Feb 15
Feb 15
as low as
$912
Chicago, US (CHI) - Catania, IT (CTA)

Jan 28
Jan 29

Feb 27
Feb 27
as low as
$956
Chicago, US (CHI) - Catania, IT (CTA)

Feb 26
Feb 27

Mar 3
Mar 4
as low as
$969
Top Deals on flights from Chicago to Palermo
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 24
Feb 25

Mar 4
Mar 5
as low as
$637
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 15
Feb 17

Mar 7
Mar 8
as low as
$670
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 24
Feb 25

Mar 4
Mar 5
as low as
$675
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 8
Feb 9

Feb 28
Mar 1
as low as
$719
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 3
Feb 4

Feb 15
Feb 15
as low as
$764
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 4
Feb 5

Feb 16
Feb 17
as low as
$858
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 15
Feb 16

Mar 7
Mar 8
as low as
$911
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 11
Feb 12

Mar 7
Mar 7
as low as
$912
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 4
Feb 5

Feb 15
Feb 16
as low as
$953
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 24
Feb 25

Mar 4
Mar 5
as low as
$960
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 24
Feb 25

Mar 4
Mar 4
as low as
$983
Chicago, US (CHI) - Palermo, IT (PMO)

Feb 8
Feb 9

Feb 28
Mar 1
as low as
$1002
Top Deals on flights from Chicago to Pisa
Chicago, US (CHI) - Pisa, IT (PSA)

Feb 1
Feb 3

Feb 21
Feb 21
as low as
$615
Chicago, US (CHI) - Pisa, IT (PSA)

Jan 27
Jan 29

Feb 21
Feb 21
as low as
$620
Chicago, US (CHI) - Pisa, IT (PSA)

Feb 1
Feb 3

Feb 21
Feb 22
as low as
$626
Chicago, US (CHI) - Pisa, IT (PSA)

Jan 27
Jan 29

Feb 21
Feb 22
as low as
$626
Chicago, US (CHI) - Pisa, IT (PSA)

Jan 27
Jan 29

Feb 21
Feb 22
as low as
$755
Chicago, US (CHI) - Pisa, IT (PSA)

Feb 1
Feb 3

Feb 21
Feb 21
as low as
$770
Chicago, US (CHI) - Pisa, IT (PSA)

Feb 9
Feb 12

Mar 7
Mar 7
as low as
$771
Chicago, US (CHI) - Pisa, IT (PSA)

Feb 1
Feb 3

Feb 21
Feb 21
as low as
$780
Chicago, US (CHI) - Pisa, IT (PSA)

Feb 1
Feb 3

Feb 21
Feb 21
as low as
$1000
Chicago, US (CHI) - Pisa, IT (PSA)

Feb 1
Feb 3

Feb 21
Feb 22
as low as
$1512
Chicago, US (CHI) - Pisa, IT (PSA)

Feb 1
Feb 3

Feb 21
Feb 22
as low as
$5630
Chicago, US (CHI) - Pisa, IT (PSA)

Feb 1
Feb 3

Feb 21
Feb 22
as low as
$5630
Top Deals on flights from Chicago to Bari
Chicago, US (CHI) - Bari, IT (BRI)

Feb 26
Feb 27

Mar 6
Mar 7
as low as
$615
Chicago, US (CHI) - Bari, IT (BRI)

Feb 26
Feb 27

Mar 6
Mar 7
as low as
$786
Chicago, US (CHI) - Bari, IT (BRI)

Feb 26
Feb 28

Mar 6
Mar 7
as low as
$806
Chicago, US (CHI) - Bari, IT (BRI)

Feb 11
Feb 13

Feb 17
Feb 18
as low as
$896
Chicago, US (CHI) - Bari, IT (BRI)

Feb 11
Feb 13

Feb 17
Feb 18
as low as
$906
Chicago, US (CHI) - Bari, IT (BRI)

Dec 28
Dec 29

Mar 14
Mar 15
as low as
$912
Chicago, US (CHI) - Bari, IT (BRI)

Feb 26
Feb 28

Mar 6
Mar 7
as low as
$929
Chicago, US (CHI) - Bari, IT (BRI)

Dec 28
Dec 30

Mar 14
Mar 15
as low as
$973
Chicago, US (CHI) - Bari, IT (BRI)

Dec 28
Dec 29

Mar 14
Mar 15
as low as
$980
Chicago, US (CHI) - Bari, IT (BRI)

Dec 28
Dec 29

Mar 14
Mar 15
as low as
$1258
Chicago, US (CHI) - Bari, IT (BRI)

Dec 28
Dec 29

Mar 14
Mar 15
as low as
$1397
Chicago, US (CHI) - Bari, IT (BRI)

Dec 28
Dec 30

Mar 14
Mar 15
as low as
$1592
Flights to Italy
- Flights
- Europe
- Italy
- Flights
- North America
- United States
- Illinois
- Chicago