Business Class Flight Deals from Italy to Chicago from $2563
Top flight deals from leading airlines:
... and +100s more
Free cancellation for many rates
If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference
VIP member priority support for seamless bookings and exclusive travel benefits
We’re always here for you - reach us 24 hours a day, 7 days a week
Top Deals on Business Class Flights from Rome to Chicago
Rome, IT (ROM) - Chicago, US (CHI)
Aug 27
Aug 27
Sep 8
Sep 9
as low as
$2563
Rome, IT (ROM) - Chicago, US (CHI)
Sep 2
Sep 3
Oct 4
Oct 5
as low as
$2673
Rome, IT (ROM) - Chicago, US (CHI)
Aug 21
Aug 21
Aug 31
Sep 1
as low as
$2883
Rome, IT (ROM) - Chicago, US (CHI)
Sep 10
Sep 10
Sep 14
Sep 15
as low as
$3778
Rome, IT (ROM) - Chicago, US (CHI)
Jul 31
Jul 31
Aug 8
Aug 9
as low as
$3798
Rome, IT (ROM) - Chicago, US (CHI)
Jul 31
Jul 31
Aug 8
Aug 9
as low as
$3798
Rome, IT (ROM) - Chicago, US (CHI)
Jul 31
Jul 31
Aug 8
Aug 9
as low as
$3815
Rome, IT (ROM) - Chicago, US (CHI)
Aug 21
Aug 21
Aug 31
Sep 1
as low as
$3825
Rome, IT (ROM) - Chicago, US (CHI)
Aug 21
Aug 21
Aug 31
Sep 1
as low as
$3836
Rome, IT (ROM) - Chicago, US (CHI)
Aug 21
Aug 22
Aug 31
Sep 1
as low as
$4511
Rome, IT (ROM) - Chicago, US (CHI)
Jul 31
Jul 31
Aug 8
Aug 9
as low as
$4579
Rome, IT (ROM) - Chicago, US (CHI)
Jul 31
Jul 31
Aug 8
Aug 9
as low as
$4600
Top Deals on Business Class Flights from Milan to Chicago
Milan, IT (MIL) - Chicago, US (CHI)
Oct 17
Oct 17
Oct 21
Oct 23
as low as
$2568
Milan, IT (MIL) - Chicago, US (CHI)
Jul 22
Jul 23
Jul 26
Jul 27
as low as
$2805
Milan, IT (MIL) - Chicago, US (CHI)
Oct 3
Oct 3
Oct 7
Oct 8
as low as
$3058
Milan, IT (MIL) - Chicago, US (CHI)
Jul 8
Jul 9
Jul 26
Jul 27
as low as
$3187
Milan, IT (MIL) - Chicago, US (CHI)
Jul 25
Jul 26
Aug 15
Aug 16
as low as
$3458
Milan, IT (MIL) - Chicago, US (CHI)
Jul 14
Jul 14
Dec 19
Dec 20
as low as
$3924
Milan, IT (MIL) - Chicago, US (CHI)
Jun 26
Jun 27
Jun 30
Jul 1
as low as
$4200
Milan, IT (MIL) - Chicago, US (CHI)
Oct 17
Oct 17
Oct 21
Oct 22
as low as
$4443
Milan, IT (MIL) - Chicago, US (CHI)
Oct 17
Oct 17
Oct 21
Oct 22
as low as
$4469
Milan, IT (MIL) - Chicago, US (CHI)
Jul 25
Jul 25
Aug 15
Aug 16
as low as
$4511
Milan, IT (MIL) - Chicago, US (CHI)
Jun 26
Jun 26
Jun 30
Jul 1
as low as
$4563
Milan, IT (MIL) - Chicago, US (CHI)
Jun 26
Jun 26
Jun 30
Jul 1
as low as
$4567
Top Deals on Business Class Flights from Venice to Chicago
Venice, IT (VCE) - Chicago, US (CHI)
Sep 15
Sep 15
Nov 3
Nov 5
as low as
$3768
Venice, IT (VCE) - Chicago, US (CHI)
Jun 21
Jun 21
Jul 8
Jul 9
as low as
$4191
Venice, IT (VCE) - Chicago, US (CHI)
Jun 21
Jun 22
Jul 8
Jul 9
as low as
$4560
Venice, IT (VCE) - Chicago, US (CHI)
Sep 15
Sep 15
Nov 3
Nov 4
as low as
$4585
Venice, IT (VCE) - Chicago, US (CHI)
Sep 15
Sep 15
Nov 3
Nov 4
as low as
$4628
Venice, IT (VCE) - Chicago, US (CHI)
Sep 15
Sep 15
Nov 3
Nov 4
as low as
$4630
Venice, IT (VCE) - Chicago, US (CHI)
Sep 15
Sep 15
Nov 3
Nov 4
as low as
$4633
Venice, IT (VCE) - Chicago, US (CHI)
Sep 15
Sep 15
Nov 3
Nov 4
as low as
$4645
Venice, IT (VCE) - Chicago, US (CHI)
Jun 21
Jun 21
Jul 8
Jul 9
as low as
$4794
Venice, IT (VCE) - Chicago, US (CHI)
Jun 21
Jun 21
Jul 8
Jul 9
as low as
$4854
Venice, IT (VCE) - Chicago, US (CHI)
Sep 15
Sep 15
Nov 3
Nov 4
as low as
$4870
Venice, IT (VCE) - Chicago, US (CHI)
Jun 11
Jun 11
Jun 11
Jun 13
as low as
$7177
Top Deals on Business Class Flights from Naples to Chicago
Naples, IT (NAP) - Chicago, US (CHI)
Sep 28
Sep 28
Oct 16
Oct 17
as low as
$2685
Naples, IT (NAP) - Chicago, US (CHI)
Jun 29
Jun 30
Jul 7
Jul 8
as low as
$3487
Naples, IT (NAP) - Chicago, US (CHI)
Sep 28
Sep 29
Oct 2
Oct 3
as low as
$3699
Naples, IT (NAP) - Chicago, US (CHI)
Jun 29
Jun 29
Jul 7
Jul 8
as low as
$3793
Naples, IT (NAP) - Chicago, US (CHI)
Jun 29
Jun 29
Jul 7
Jul 8
as low as
$3841
Naples, IT (NAP) - Chicago, US (CHI)
Jul 8
Jul 8
Jul 15
Jul 16
as low as
$3925
Naples, IT (NAP) - Chicago, US (CHI)
Sep 28
Sep 29
Oct 2
Oct 3
as low as
$4362
Top Deals on Business Class Flights from Florence to Chicago
Florence, IT (FLR) - Chicago, US (CHI)
May 3
May 4
May 10
May 11
as low as
$4720
Florence, IT (FLR) - Chicago, US (CHI)
May 3
May 4
May 7
May 8
as low as
$4923
Florence, IT (FLR) - Chicago, US (CHI)
May 3
May 3
May 10
May 11
as low as
$5325
Florence, IT (FLR) - Chicago, US (CHI)
May 3
May 3
May 10
May 11
as low as
$5325
Florence, IT (FLR) - Chicago, US (CHI)
May 3
May 3
May 10
May 11
as low as
$5329
Florence, IT (FLR) - Chicago, US (CHI)
May 3
May 4
May 10
May 11
as low as
$5485
Florence, IT (FLR) - Chicago, US (CHI)
May 3
May 4
May 10
May 11
as low as
$5498
Florence, IT (FLR) - Chicago, US (CHI)
May 3
May 3
May 7
May 8
as low as
$5729
Florence, IT (FLR) - Chicago, US (CHI)
May 3
May 3
May 10
May 11
as low as
$5741
Florence, IT (FLR) - Chicago, US (CHI)
May 3
May 3
May 7
May 8
as low as
$6014
Florence, IT (FLR) - Chicago, US (CHI)
May 3
May 3
May 10
May 11
as low as
$6469
Top Deals on Business Class Flights from Bologna to Chicago
Bologna, IT (BLQ) - Chicago, US (CHI)
Aug 13
Aug 14
Aug 20
Aug 22
as low as
$3306
Bologna, IT (BLQ) - Chicago, US (CHI)
Aug 13
Aug 13
Aug 20
Aug 21
as low as
$3441
Bologna, IT (BLQ) - Chicago, US (CHI)
Aug 13
Aug 14
Aug 20
Aug 21
as low as
$3811
Bologna, IT (BLQ) - Chicago, US (CHI)
Sep 15
Sep 16
Nov 3
Nov 4
as low as
$3971
Bologna, IT (BLQ) - Chicago, US (CHI)
Aug 13
Aug 13
Aug 20
Aug 21
as low as
$4618
Bologna, IT (BLQ) - Chicago, US (CHI)
Aug 13
Aug 13
Aug 20
Aug 21
as low as
$4622
Bologna, IT (BLQ) - Chicago, US (CHI)
Aug 13
Aug 13
Aug 20
Aug 21
as low as
$4637
Bologna, IT (BLQ) - Chicago, US (CHI)
Aug 13
Aug 13
Aug 20
Aug 21
as low as
$4875
Bologna, IT (BLQ) - Chicago, US (CHI)
Aug 9
Aug 10
Aug 21
Aug 22
as low as
$6327
Bologna, IT (BLQ) - Chicago, US (CHI)
Aug 9
Aug 10
Aug 21
Aug 22
as low as
$6353
Top Deals on Business Class Flights from Catania to Chicago
Catania, IT (CTA) - Chicago, US (CHI)
Jul 18
Jul 18
Aug 4
Aug 5
as low as
$3910
Catania, IT (CTA) - Chicago, US (CHI)
Jul 18
Jul 18
Aug 4
Aug 5
as low as
$3924
Catania, IT (CTA) - Chicago, US (CHI)
Jul 18
Jul 18
Aug 4
Aug 5
as low as
$4240
Catania, IT (CTA) - Chicago, US (CHI)
Jul 18
Jul 19
Aug 4
Aug 5
as low as
$4647
Catania, IT (CTA) - Chicago, US (CHI)
Jul 18
Jul 19
Aug 4
Aug 5
as low as
$4674
Catania, IT (CTA) - Chicago, US (CHI)
Jul 18
Jul 18
Aug 4
Aug 5
as low as
$5465
Catania, IT (CTA) - Chicago, US (CHI)
Jul 18
Jul 18
Aug 4
Aug 5
as low as
$8293
Top Deals on Business Class Flights from Palermo to Chicago
Palermo, IT (PMO) - Chicago, US (CHI)
May 5
May 6
May 12
May 13
as low as
$3822
Palermo, IT (PMO) - Chicago, US (CHI)
May 9
May 9
May 13
May 15
as low as
$5310
Palermo, IT (PMO) - Chicago, US (CHI)
May 9
May 9
May 13
May 15
as low as
$5337
Palermo, IT (PMO) - Chicago, US (CHI)
May 5
May 6
May 12
May 14
as low as
$5376
Palermo, IT (PMO) - Chicago, US (CHI)
May 9
May 9
May 13
May 14
as low as
$5579
Top Deals on Business Class Flights from Pisa to Chicago
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4601
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4601
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 23
May 30
May 31
as low as
$4620
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4620
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4626
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4630
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4630
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4634
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 23
May 30
May 31
as low as
$4645
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4646
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 23
May 30
May 31
as low as
$4646
Pisa, IT (PSA) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4652
Top Deals on Business Class Flights from Bari to Chicago
Bari, IT (BRI) - Chicago, US (CHI)
May 23
May 23
May 30
May 31
as low as
$4491
Bari, IT (BRI) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4783
Bari, IT (BRI) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4794
Bari, IT (BRI) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$4794
Bari, IT (BRI) - Chicago, US (CHI)
May 23
May 23
May 30
May 31
as low as
$4900
Bari, IT (BRI) - Chicago, US (CHI)
May 23
May 23
May 30
May 31
as low as
$5625
Bari, IT (BRI) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$5625
Bari, IT (BRI) - Chicago, US (CHI)
Oct 7
Oct 8
Oct 18
Oct 19
as low as
$6128
Bari, IT (BRI) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$7259
Bari, IT (BRI) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$7259
Bari, IT (BRI) - Chicago, US (CHI)
May 23
May 23
May 30
Jun 1
as low as
$8316
Bari, IT (BRI) - Chicago, US (CHI)
May 23
May 24
May 30
May 31
as low as
$8379
Good to Know
Essential information to help you plan your flight Business Class from Italy to Chicago
Cheapest Flight
$2563
The lowest price we found in the last two weeks, departing Aug 27 and returning Sep 9
1 stop ‧ 13h 30m ‧ businessFastest Flights
$5329
The fastest flight that we found in the last two weeks, departing May 3 and returning May 11
2 stops ‧ 5h 10m ‧ businessCheapest Flight Round-trip
$2563
Cheapest price found in the last 14 days, departing Aug 27 and returning Sep 9
1 stop ‧ 13h 30m ‧ businessCheapest Layover airport
$4630
The cheapest layover airport to Chicago is currently $4630
1 stop ‧ 13h 20m ‧ businessBest Arrival airport
$2563
The best arrival airport to Chicago is currently $2563
1 stop ‧ 13h 30m ‧ businessBest Departure airport
$2563
The best departure airport to Chicago is currently $2563
1 stop ‧ 13h 30m ‧ businessCheapest Airline
$2563
The cheapest airline to Chicago is currently $2563
1 stop ‧ 13h 30m ‧ businessFlights to Chicago
- Flights
- North America
- United States
- Illinois
- Chicago