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Flight Deals from Chicago to Milan from $268

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Stops

  • Nonstop
    from $724
  • Up to 1 stop
    $409
  • Up to 2 stops
    $416

Airlines

  • Aer Lingus
    $845
  • Air Canada
    $674
  • Air France
    $770
  • Air SERBIA a.d. Beograd
    $589
  • Austrian Airlines
    $722
  • British Airways
    $734
  • Brussels Airlines
    $725
  • Delta Air Lines
    $688
  • KLM
    $734
  • LOT Polish Airlines
    $795
  • Lufthansa
    $696
  • SAS Airlines
    $409
  • SWISS
    $708
  • TAP Portugal
    $499
  • Turkish Airlines
    $640
  • United Airlines
    $688

Cabin Class

  • Economy
    $409

Departure Airports

  • Chicago Midway Airport
    $734
  • Chicago O Hare Airport
    $409

Arrival Airports

  • Milan Linate Airport
    $416
  • Milan Malpensa Airport
    $409

Layover Airports

  • Adolfo Suárez Madrid–Barajas Airport
    $812
  • Amsterdam Airport Schiphol
    $783
  • Belgrade Nikola Tesla Airport
    $589
  • Brussels Airport
    $725
  • Copenhagen Kastrup Airport
    $409
  • Denver International Airport
    $792
  • Detroit Metropolitan Airport
    $783
  • Dublin Airport
    $845
  • Frankfurt am Main Airport
    $696
  • General Edward Lawrence Logan International Airport
    $570
  • Hartsfield Jackson Atlanta International Airport
    $688
  • Humberto Delgado Airport (Lisbon Portela Airport)
    $499
  • Istanbul Airport
    $640
  • Kraków John Paul II International Airport
    $810
  • London Heathrow Airport
    $734
  • Montreal Trudeau Airport
    $674
  • Munich Airport
    $722
  • New York John F Kennedy Airport
    $542
  • Newark Liberty Airport
    $700
  • Oslo Gardermoen Airport
    $452
  • Paris Charles de Gaulle Airport
    $703
  • Stockholm Arlanda Airport
    $416
  • Toronto Pearson Airport
    $789
  • Vienna International Airport
    $722
  • Warsaw Chopin Airport
    $795
  • Washington Dulles Airport
    $738
  • Zürich Airport
    $688

Best Price. GUARANTEED.

Exclusively for Priceline Members
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BUNDLE & SAVE

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On average save $240 per traveler
SAS Airlines Logo
SAS Airlines

11/16/25

ORD
39h 5m
CPH

11/18/25

MXP
SAS Airlines Logo
SAS Airlines

11/23/25

MXP
20h 45m
CPH

11/24/25

ORD
$409
SAS Airlines Logo
SAS Airlines

11/16/25

ORD
40h 45m
CPH
ARN

11/18/25

LIN
SAS Airlines Logo
SAS Airlines

11/23/25

LIN
20h 45m
CPH

11/24/25

ORD
$416
SAS Airlines Logo
SAS Airlines

11/02/25

ORD
37h 5m
CPH

11/04/25

MXP
SAS Airlines Logo
SAS Airlines

11/19/25

MXP
27h 45m
OSL
CPH

11/20/25

ORD
$452
TAP Portugal Logo
TAP Portugal

11/05/25

ORD
21h 45m
LIS

11/06/25

MXP
TAP Portugal Logo
TAP Portugal

11/14/25

MXP
8h 55m
LIS

11/14/25

ORD
$499
SAS Airlines Logo
SAS Airlines

11/24/25

ORD
23h 50m
CPH

11/25/25

MXP
SAS Airlines Logo
SAS Airlines

12/01/25

MXP
45h 36m
CPH
JFK

12/03/25

ORD
$542
SAS Airlines Logo
SAS Airlines

11/08/25

ORD
24h 15m
BOS
CPH

11/09/25

MXP
SAS Airlines Logo
SAS Airlines

11/18/25

MXP
20h 45m
CPH

11/19/25

ORD
$570
Air SERBIA a.d. Beograd Logo
Air SERBIA a.d. Beograd

11/05/25

ORD
20h 50m
BEG

11/06/25

MXP
Air SERBIA a.d. Beograd Logo
Air SERBIA a.d. Beograd

11/14/25

MXP
20h 10m
BEG

11/15/25

ORD
$589
Turkish Airlines Logo
Turkish Airlines

11/05/25

ORD
21h 50m
IST

11/06/25

MXP
Turkish Airlines Logo
Turkish Airlines

11/12/25

MXP
11h 30m
IST

11/12/25

ORD
$640
Air Canada Logo
Air Canada

11/12/25

ORD
22h 45m
YUL

11/13/25

MXP
Air Canada Logo
Air Canada

11/18/25

MXP
7h 20m
YUL

11/18/25

ORD
$674
Delta Air Lines Logo
Delta Air Lines

11/12/25

ORD
23h 35m
ATL

11/13/25

MXP
Delta Air Lines Logo
Delta Air Lines

11/18/25

MXP
9h 31m
JFK

11/18/25

ORD
$688
United Airlines Logo
United Airlines

10/26/25

ORD
14h 20m
Direct

10/27/25

MXP
United Airlines Logo
United Airlines

11/10/25

MXP
17h 40m
ZRH

11/11/25

ORD
$688
Lufthansa Logo
Lufthansa

11/05/25

ORD
18h 30m
YUL

11/06/25

MXP
Lufthansa Logo
Lufthansa

11/12/25

MXP
6h 10m
FRA

11/12/25

ORD
$696
Lufthansa Logo
Lufthansa

11/23/25

ORD
19h 30m
EWR

11/24/25

MXP
Lufthansa Logo
Lufthansa

12/05/25

MXP
8h 35m
FRA

12/05/25

ORD
$700
Delta Air Lines Logo
Delta Air Lines

11/05/25

ORD
21h 46m
ATL

11/06/25

MXP
Delta Air Lines Logo
Delta Air Lines

11/12/25

MXP
8h 15m
CDG

11/12/25

ORD
$703
SWISS Logo
SWISS

11/02/25

ORD
19h 15m
ZRH

11/03/25

MXP
SWISS Logo
SWISS

11/18/25

MXP
3h
Direct

11/18/25

ORD
$708
Austrian Airlines Logo
Austrian Airlines

11/05/25

ORD
24h 10m
VIE

11/06/25

LIN
Austrian Airlines Logo
Austrian Airlines

11/12/25

LIN
3h
Direct

11/12/25

ORD
$722
Lufthansa Logo
Lufthansa

11/19/25

ORD
21h 10m
MUC

11/20/25

LIN
Lufthansa Logo
Lufthansa

12/03/25

LIN
4h 55m
FRA

12/03/25

ORD
$722
United Airlines Logo
United Airlines

10/27/25

ORD
14h 20m
Direct

10/28/25

MXP
United Airlines Logo
United Airlines

11/09/25

MXP
3h
Direct

11/09/25

ORD
$724
Brussels Airlines Logo
Brussels Airlines

11/05/25

ORD
18h 25m
BRU

11/06/25

LIN
Brussels Airlines Logo
Brussels Airlines

11/12/25

LIN
3h
Direct

11/12/25

ORD
$725
British Airways Logo
British Airways

10/26/25

ORD
19h 15m
LHR

10/27/25

LIN
British Airways Logo
British Airways

11/10/25

LIN
20h 20m
LHR

11/11/25

ORD
$734
KLM Logo
KLM

11/05/25

MDW
27h 5m
ATL

11/06/25

MXP
KLM Logo
KLM

11/12/25

MXP
5h 25m
CDG

11/12/25

MDW
$734
Austrian Airlines Logo
Austrian Airlines

11/04/25

ORD
27h 30m
IAD
VIE

11/05/25

LIN
Austrian Airlines Logo
Austrian Airlines

11/18/25

LIN
5h 15m
FRA

11/18/25

ORD
$738
Air France Logo
Air France

11/11/25

ORD
26h 15m
CDG

11/12/25

LIN
Air France Logo
Air France

11/18/25

LIN
8h 15m
CDG

11/18/25

ORD
$770
Delta Air Lines Logo
Delta Air Lines

11/06/25

ORD
27h 5m
DTW
AMS

11/07/25

LIN
Delta Air Lines Logo
Delta Air Lines

11/13/25

LIN
10h 7m
ATL

11/13/25

ORD
$783
Austrian Airlines Logo
Austrian Airlines

11/03/25

ORD
24h 10m
VIE

11/04/25

LIN
Austrian Airlines Logo
Austrian Airlines

11/10/25

LIN
17h 8m
FRA
YYZ

11/11/25

ORD
$789
Austrian Airlines Logo
Austrian Airlines

10/29/25

ORD
23h 10m
VIE

10/30/25

LIN
Austrian Airlines Logo
Austrian Airlines

11/17/25

LIN
10h 18m
FRA
DEN

11/17/25

ORD
$792
LOT Polish Airlines Logo
LOT Polish Airlines

11/05/25

ORD
21h 10m
WAW

11/06/25

MXP
LOT Polish Airlines Logo
LOT Polish Airlines

11/12/25

MXP
9h 35m
WAW

11/12/25

ORD
$795
LOT Polish Airlines Logo
LOT Polish Airlines

11/23/25

ORD
20h 55m
KRK
WAW

11/24/25

MXP
LOT Polish Airlines Logo
LOT Polish Airlines

12/05/25

MXP
9h 35m
WAW

12/05/25

ORD
$810
British Airways Logo
British Airways

11/03/25

ORD
21h 20m
MAD

11/04/25

MXP
British Airways Logo
British Airways

11/22/25

MXP
6h 35m
MAD

11/22/25

ORD
$812
Aer Lingus Logo
Aer Lingus

11/19/25

ORD
19h 10m
DUB

11/20/25

LIN
Aer Lingus Logo
Aer Lingus

12/03/25

LIN
6h 10m
DUB

12/03/25

ORD
$845

Top Deals on flights from Chicago to Milan

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

TAP Portugal Logo
TAP Portugal

Jul 27

ORD
22h 25m
LIS

Jul 28

MXP

as low as

$268

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

Icelandair Logo
Icelandair

Jul 28

ORD
26h 35m
KEF

Jul 29

MXP

as low as

$349

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

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

Aug 2

ORD
33h 15m
BEG

Aug 4

MXP

as low as

$392

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

 Logo

Jul 29

ORD
28h 45m
BOS

Jul 30

MXP

as low as

$488

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

Aer Lingus Logo
Aer Lingus

Jul 16

ORD
18h 55m
DUB

Jul 17

LIN

as low as

$576

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

Air Canada Logo
Air Canada

Jul 15

ORD
19h 53m
YUL

Jul 16

MXP

as low as

$578

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

United Airlines Logo
United Airlines

Jul 30

ORD
15h 45m
Direct

Jul 31

MXP

as low as

$578

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

United Airlines Logo
United Airlines

Jul 8

ORD
18h 25m
YUL

Jul 9

MXP

as low as

$578

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

Delta Air Lines Logo
Delta Air Lines

Jul 14

ORD
25h 28m
JFK

Jul 15

MXP

as low as

$582

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

Delta Air Lines Logo
Delta Air Lines

Jul 7

MDW
20h 42m
ATL

Jul 8

MXP

as low as

$582

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

British Airways Logo
British Airways

Jul 28

ORD
18h 20m
LHR

Jul 29

LIN

as low as

$596

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

British Airways Logo
British Airways

Jul 6

ORD
18h 20m
PHL

Jul 7

MXP

as low as

$596

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