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Business Class Flight Deals from Milan to Chicago from $1636

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Bundle + Save

Top flight deals from leading airlines:

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... and +100s more

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Stops

  • Up to nonstop
    $4527
  • Up to 1 stop
    $2568

Airlines

  • Aer Lingus
    $2568
  • Air Canada
    $4664
  • Air Dolomiti
    $3924
  • Air SERBIA a.d. Beograd
    $3058
  • American Airlines
    $4506
  • APG Airlines
    $5590
  • Austrian Airlines
    $4548
  • British Airways
    $4618
  • Ethiopian Airlines
    $5871
  • Finnair
    $4598
  • IBERIA
    $4565
  • ITA Airways
    $3458
  • LOT Polish Airlines
    $3002
  • Lufthansa
    $4527
  • Royal Jordanian
    $5337
  • SWISS
    $4455
  • TAP Portugal
    $2797
  • Turkish Airlines
    $3187
  • United Airlines
    $4429

Cabin Class

  • Business
    $2568

Departure Airports

  • Milan Linate Airport
    $2568
  • Milan Malpensa Airport
    $2797

Arrival Airports

  • Chicago O Hare Airport
    $2568

Layover Airports

  • Addis Ababa Bole International Airport
    $5871
  • Belgrade Nikola Tesla Airport
    $3058
  • Dublin Airport
    $2568
  • Frankfurt am Main Airport
    $3924
  • Humberto Delgado Airport (Lisbon Portela Airport)
    $2797
  • Istanbul Airport
    $3187
  • London Heathrow Airport
    $4506
  • New York John F Kennedy Airport
    $4506
  • Queen Alia International Airport
    $5337
  • Rome Fiumicino Airport
    $3458
  • Toronto Pearson Airport
    $4664
  • Vienna International Airport
    $4548
  • Warsaw Chopin Airport
    $3002
  • Zürich Airport
    $4429

Best Price. GUARANTEED.

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Aer Lingus Logo
Aer Lingus

10/17/26

LIN
14h 55m
DUB

10/17/26

ORD
Aer Lingus Logo
Aer Lingus

10/21/26

ORD
30h 40m
DUB

10/23/26

LIN
$2568
TAP Portugal Logo
TAP Portugal

09/12/26

MXP
17h 15m
LIS

09/12/26

ORD
TAP Portugal Logo
TAP Portugal

09/20/26

ORD
15h 25m
LIS

09/21/26

MXP
$2797
LOT Polish Airlines Logo
LOT Polish Airlines

09/17/26

MXP
16h 20m
WAW

09/17/26

ORD
LOT Polish Airlines Logo
LOT Polish Airlines

10/03/26

ORD
14h 5m
WAW

10/04/26

MXP
$3002
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Air SERBIA a.d. Beograd Logo
Air SERBIA a.d. Beograd

10/03/26

MXP
18h 55m
BEG

10/03/26

ORD
Air SERBIA a.d. Beograd Logo
Air SERBIA a.d. Beograd

10/07/26

ORD
20h 25m
BEG

10/08/26

MXP
$3058
Turkish Airlines Logo
Turkish Airlines

07/08/26

MXP
20h 55m
IST

07/09/26

ORD
Turkish Airlines Logo
Turkish Airlines

07/26/26

ORD
14h 15m
IST

07/27/26

MXP
$3187
TAP Portugal Logo
TAP Portugal

10/17/26

MXP
27h
LIS

10/18/26

ORD
TAP Portugal Logo
TAP Portugal

10/21/26

ORD
15h 25m
LIS

10/22/26

MXP
$3240
ITA Airways Logo
ITA Airways

07/25/26

LIN
25h 10m
FCO

07/26/26

ORD
ITA Airways Logo
ITA Airways

08/15/26

ORD
11h 40m
FCO

08/16/26

LIN
$3458
United Airlines Logo
United Airlines

07/14/26

MXP
9h 50m
Direct

07/14/26

ORD
United Airlines Logo
United Airlines

12/19/26

ORD
11h 50m
FRA

12/20/26

LIN
$3924
SWISS Logo
SWISS

10/17/26

MXP
13h 45m
ZRH

10/17/26

ORD
United Airlines Logo
United Airlines

10/21/26

ORD
8h 45m
Direct

10/22/26

MXP
$4429
SWISS Logo
SWISS

10/17/26

MXP
13h 45m
ZRH

10/17/26

ORD
Lufthansa Logo
Lufthansa

10/21/26

ORD
8h 45m
Direct

10/22/26

MXP
$4455
British Airways Logo
British Airways

10/17/26

LIN
13h 35m
LHR

10/17/26

ORD
American Airlines Logo
American Airlines

10/21/26

ORD
12h 22m
JFK

10/22/26

MXP
$4506
United Airlines Logo
United Airlines

06/02/26

MXP
9h 50m
Direct

06/02/26

ORD
Lufthansa Logo
Lufthansa

06/29/26

ORD
8h 40m
Direct

06/30/26

MXP
$4527
SWISS Logo
SWISS

06/02/26

MXP
12h 15m
ZRH

06/02/26

ORD
United Airlines Logo
United Airlines

06/29/26

ORD
8h 40m
Direct

06/30/26

MXP
$4542
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Austrian Airlines Logo
Austrian Airlines

06/02/26

LIN
13h 20m
VIE

06/02/26

ORD
United Airlines Logo
United Airlines

06/29/26

ORD
8h 40m
Direct

06/30/26

MXP
$4548
British Airways Logo
British Airways

10/17/26

MXP
12h 40m
LHR

10/17/26

ORD
IBERIA Logo
IBERIA

10/21/26

ORD
12h 22m
JFK

10/22/26

MXP
$4565
American Airlines Logo
American Airlines

10/17/26

LIN
14h 55m
DUB

10/17/26

ORD
American Airlines Logo
American Airlines

10/21/26

ORD
11h 55m
DUB

10/22/26

LIN
$4570
British Airways Logo
British Airways

10/17/26

MXP
12h 40m
LHR

10/17/26

ORD
American Airlines Logo
American Airlines

10/21/26

ORD
12h 22m
JFK

10/22/26

MXP
$4598
British Airways Logo
British Airways

10/17/26

LIN
11h 55m
LHR

10/17/26

ORD
American Airlines Logo
American Airlines

10/21/26

ORD
12h 22m
JFK

10/22/26

MXP
$4618
Air Canada Logo
Air Canada

10/17/26

MXP
16h 39m
YYZ

10/17/26

ORD
United Airlines Logo
United Airlines

10/21/26

ORD
8h 45m
Direct

10/22/26

MXP
$4664
Air Canada Logo
Air Canada

10/17/26

MXP
16h 39m
YYZ

10/17/26

ORD
Lufthansa Logo
Lufthansa

10/21/26

ORD
8h 45m
Direct

10/22/26

MXP
$4821
Royal Jordanian Logo
Royal Jordanian

07/14/26

MXP
27h 55m
AMM

07/15/26

ORD
Royal Jordanian Logo
Royal Jordanian

12/19/26

ORD
21h 10m
AMM

12/20/26

MXP
$5337
ITA Airways Logo
ITA Airways

09/03/26

LIN
13h 10m
FCO

09/03/26

ORD
ITA Airways Logo
ITA Airways

09/10/26

ORD
12h 10m
FCO

09/11/26

LIN
$5590
Ethiopian Airlines Logo
Ethiopian Airlines

10/03/26

MXP
39h 35m
ADD

10/05/26

ORD
Ethiopian Airlines Logo
Ethiopian Airlines

10/07/26

ORD
36h 35m
ADD

10/09/26

MXP
$5871

Top Deals on flights Business Class from Milan to Chicago

Milan, IT (MIL) - Chicago, US (CHI)

TAP Portugal Logo
TAP Portugal

Sep 16

MXP
23h 40m
LIS

Sep 17

ORD

as low as

$1636

Milan, IT (MIL) - Chicago, US (CHI)

Aer Lingus Logo
Aer Lingus

Jun 12

MXP
22h 45m
DUB

Jun 13

ORD

as low as

$2176

Milan, IT (MIL) - Chicago, US (CHI)

LOT Polish Airlines Logo
LOT Polish Airlines

Sep 16

MXP
16h 20m
WAW

Sep 16

ORD

as low as

$2245

Milan, IT (MIL) - Chicago, US (CHI)

Turkish Airlines Logo
Turkish Airlines

Aug 23

MXP
21h 5m
IST

Aug 24

ORD

as low as

$2261

Milan, IT (MIL) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 20

MXP
17h 14m
LGA

Jul 20

ORD

as low as

$3452

Milan, IT (MIL) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Sep 16

MXP
13h 15m
JFK

Sep 16

ORD

as low as

$3624

Milan, IT (MIL) - Chicago, US (CHI)

British Airways Logo
British Airways

Sep 16

MXP
13h 15m
JFK

Sep 16

ORD

as low as

$3642

Milan, IT (MIL) - Chicago, US (CHI)

IBERIA Logo
IBERIA

Sep 16

MXP
13h 15m
JFK

Sep 16

ORD

as low as

$3642

Milan, IT (MIL) - Chicago, US (CHI)

ITA Airways Logo
ITA Airways

May 15

LIN
23h 10m
FCO

May 16

ORD

as low as

$3686

Milan, IT (MIL) - Chicago, US (CHI)

ITA Airways Logo
ITA Airways

Aug 21

LIN
23h 10m
FCO

Aug 22

ORD

as low as

$3698

Milan, IT (MIL) - Chicago, US (CHI)

ITA Airways Logo
ITA Airways

May 20

LIN
23h 10m
FCO

May 21

ORD

as low as

$3706

Milan, IT (MIL) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Aug 1

MXP
14h 25m
PHL

Aug 1

ORD

as low as

$3759

Good to Know

Essential information to help you plan your flight Business Class from Milan to Chicago

Cheapest Flight

$1636

The lowest price we found in the last two weeks, departing Sep 16 and returning Sep 17

Airline TP1 stop ‧ 23h 40m ‧ business

Fastest Flights

$3924

The fastest flight that we found in the last two weeks, departing Jul 14 and returning Dec 20

Airline EN9h 50m ‧ business

Cheapest Flight Round-trip

$2568

Cheapest price found in the last 14 days, departing Oct 17 and returning Oct 23

Airline EI1 stop ‧ 14h 55m ‧ business

Cheapest Flight One-way

$1636

Cheapest price found in the last 14 days, departing Sep 16

Airline TP1 stop ‧ 23h 40m ‧ business

Cheapest Layover airport

$2245

The cheapest layover airport to Chicago is currently $2245

Airline LO1 stop ‧ 16h 20m ‧ business

Best Arrival airport

$1636

The best arrival airport to Chicago is currently $1636

Airline TP1 stop ‧ 23h 40m ‧ business

Best Departure airport

$1636

The best departure airport to Chicago is currently $1636

Airline TP1 stop ‧ 23h 40m ‧ business

Cheapest Airline

$1636

The cheapest airline to Chicago is currently $1636

Airline TP1 stop ‧ 23h 40m ‧ business

Flights to Chicago