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Flight Deals from Milan to Chicago from $400

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Save an average of $240 per person when bundling your flight and hotel together with Priceline

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Stops

  • Nonstop
    from $688
  • Up to 1 stop
    $400
  • Up to 2 stops
    $597

Airlines

  • Aer Lingus
    $843
  • Air Canada
    $676
  • Air SERBIA a.d. Beograd
    $763
  • American Airlines
    $583
  • Austrian Airlines
    $711
  • British Airways
    $717
  • Brussels Airlines
    $709
  • IBERIA
    $790
  • Icelandair
    $549
  • ITA Airways
    $627
  • LOT Polish Airlines
    $787
  • Lufthansa
    $696
  • SAS Airlines
    $580
  • SWISS
    $719
  • TAP Portugal
    $400
  • United Airlines
    $676

Cabin Class

  • Economy
    $400

Departure Airports

  • Milan Linate Airport
    $597
  • Milan Malpensa Airport
    $400

Arrival Airports

  • Chicago O Hare Airport
    $400

Layover Airports

  • Adolfo Suárez Madrid–Barajas Airport
    $721
  • Belgrade Nikola Tesla Airport
    $763
  • Brussels Airport
    $701
  • Copenhagen Kastrup Airport
    $580
  • Dublin Airport
    $843
  • Frankfurt am Main Airport
    $676
  • General Edward Lawrence Logan International Airport
    $763
  • George Bush Intercontinental Houston Airport
    $734
  • Humberto Delgado Airport (Lisbon Portela Airport)
    $400
  • Kraków John Paul II International Airport
    $824
  • London Heathrow Airport
    $583
  • Montreal Trudeau Airport
    $676
  • Munich Airport
    $681
  • New York John F Kennedy Airport
    $604
  • Philadelphia International Airport
    $583
  • Raleigh Durham International Airport
    $597
  • Reykjavik Keflavik Airport
    $549
  • Rome Fiumicino Airport
    $627
  • Stockholm Arlanda Airport
    $614
  • Vienna International Airport
    $691
  • Warsaw Chopin Airport
    $787
  • Washington Dulles Airport
    $688
  • Zürich Airport
    $681

Best Price. GUARANTEED.

Exclusively for Priceline Members
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BUNDLE & SAVE
Book a flight & hotel together for extra savings.
On average save $240 per traveler
TAP Portugal Logo
TAP Portugal

09/18/25

MXP
23h 5m
LIS

09/19/25

ORD
TAP Portugal Logo
TAP Portugal

09/21/25

ORD
25h 15m
LIS

09/22/25

MXP
$400
Icelandair Logo
Icelandair

09/15/25

MXP
27h 5m
KEF

09/16/25

ORD
Icelandair Logo
Icelandair

09/26/25

ORD
18h 5m
KEF

09/27/25

MXP
$549
SAS Airlines Logo
SAS Airlines

09/26/25

MXP
20h 5m
CPH

09/27/25

ORD
SAS Airlines Logo
SAS Airlines

10/04/25

ORD
18h 55m
CPH

10/05/25

MXP
$580
American Airlines Logo
American Airlines

09/15/25

MXP
9h 19m
PHL

09/15/25

ORD
American Airlines Logo
American Airlines

09/26/25

ORD
26h 20m
LHR

09/27/25

MXP
$583
American Airlines Logo
American Airlines

09/15/25

LIN
22h 30m
LHR
RDU

09/16/25

ORD
American Airlines Logo
American Airlines

09/26/25

ORD
24h 25m
LHR

09/27/25

LIN
$597
American Airlines Logo
American Airlines

09/06/25

LIN
9h 35m
LHR

09/06/25

ORD
American Airlines Logo
American Airlines

09/10/25

ORD
19h 11m
JFK

09/11/25

LIN
$604
SAS Airlines Logo
SAS Airlines

09/26/25

MXP
20h 5m
CPH

09/27/25

ORD
SAS Airlines Logo
SAS Airlines

10/04/25

ORD
22h 20m
CPH
ARN

10/05/25

MXP
$614
ITA Airways Logo
ITA Airways

09/15/25

LIN
6h 10m
FCO

09/15/25

ORD
ITA Airways Logo
ITA Airways

09/26/25

ORD
20h 40m
FCO

09/27/25

LIN
$627
Air Canada Logo
Air Canada

09/05/25

MXP
4h 40m
FRA

09/05/25

ORD
Air Canada Logo
Air Canada

09/07/25

ORD
23h 20m
YUL

09/08/25

MXP
$676
United Airlines Logo
United Airlines

09/23/25

MXP
5h 45m
FRA

09/23/25

ORD
United Airlines Logo
United Airlines

09/30/25

ORD
15h 45m
Direct

10/01/25

MXP
$676
United Airlines Logo
United Airlines

09/13/25

MXP
5h 45m
FRA

09/13/25

ORD
United Airlines Logo
United Airlines

09/20/25

ORD
25h 20m
YUL

09/21/25

MXP
$676
United Airlines Logo
United Airlines

09/20/25

MXP
8h 50m
FRA

09/20/25

ORD
United Airlines Logo
United Airlines

09/27/25

ORD
18h 10m
ZRH

09/28/25

MXP
$681
United Airlines Logo
United Airlines

09/03/25

MXP
4h 35m
FRA

09/03/25

ORD
United Airlines Logo
United Airlines

09/14/25

ORD
20h 30m
MUC

09/15/25

MXP
$681
United Airlines Logo
United Airlines

09/23/25

MXP
2h 50m
Direct

09/23/25

ORD
United Airlines Logo
United Airlines

09/30/25

ORD
15h 45m
Direct

10/01/25

MXP
$688
United Airlines Logo
United Airlines

09/20/25

MXP
4h 55m
FRA

09/20/25

ORD
United Airlines Logo
United Airlines

09/30/25

ORD
25h
IAD
FRA

10/01/25

MXP
$688
Air Canada Logo
Air Canada

09/19/25

MXP
6h 20m
VIE

09/19/25

ORD
Air Canada Logo
Air Canada

09/27/25

ORD
25h 20m
YUL

09/28/25

MXP
$691
Lufthansa Logo
Lufthansa

09/15/25

MXP
5h 20m
FRA

09/15/25

ORD
Lufthansa Logo
Lufthansa

09/26/25

ORD
23h 20m
YUL

09/27/25

MXP
$696
United Airlines Logo
United Airlines

10/02/25

MXP
2h 50m
Direct

10/02/25

ORD
United Airlines Logo
United Airlines

10/06/25

ORD
18h 25m
BRU

10/07/25

MXP
$701
Brussels Airlines Logo
Brussels Airlines

09/18/25

MXP
5h 45m
FRA

09/18/25

ORD
Brussels Airlines Logo
Brussels Airlines

09/21/25

ORD
18h 25m
BRU

09/22/25

MXP
$709
Austrian Airlines Logo
Austrian Airlines

09/18/25

MXP
6h 20m
VIE

09/18/25

ORD
Austrian Airlines Logo
Austrian Airlines

09/21/25

ORD
19h 52m
YUL

09/22/25

MXP
$711
British Airways Logo
British Airways

09/17/25

MXP
6h 13m
JFK

09/17/25

ORD
British Airways Logo
British Airways

09/21/25

ORD
19h 55m
LHR

09/22/25

MXP
$717
SWISS Logo
SWISS

09/15/25

MXP
22h
ZRH

09/16/25

ORD
SWISS Logo
SWISS

09/26/25

ORD
20h
FRA

09/27/25

MXP
$719
American Airlines Logo
American Airlines

09/06/25

LIN
6h 25m
MAD

09/06/25

ORD
American Airlines Logo
American Airlines

09/10/25

ORD
19h 11m
JFK

09/11/25

LIN
$721
United Airlines Logo
United Airlines

09/07/25

MXP
13h 31m
FRA
IAH

09/07/25

ORD
United Airlines Logo
United Airlines

09/24/25

ORD
18h 55m
FRA

09/25/25

MXP
$734
Air SERBIA a.d. Beograd Logo
Air SERBIA a.d. Beograd

09/08/25

MXP
7h 15m
BEG

09/08/25

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

09/13/25

ORD
33h 15m
BEG

09/15/25

MXP
$763
American Airlines Logo
American Airlines

09/06/25

LIN
9h 35m
LHR

09/06/25

ORD
American Airlines Logo
American Airlines

09/10/25

ORD
21h 24m
BOS
JFK

09/11/25

LIN
$763
LOT Polish Airlines Logo
LOT Polish Airlines

09/15/25

MXP
9h 10m
WAW

09/15/25

ORD
LOT Polish Airlines Logo
LOT Polish Airlines

09/26/25

ORD
36h 5m
WAW

09/28/25

MXP
$787
IBERIA Logo
IBERIA

09/06/25

MXP
6h 13m
JFK

09/06/25

ORD
IBERIA Logo
IBERIA

09/10/25

ORD
19h 11m
JFK

09/11/25

MXP
$790
LOT Polish Airlines Logo
LOT Polish Airlines

09/15/25

MXP
19h 40m
WAW

09/16/25

ORD
LOT Polish Airlines Logo
LOT Polish Airlines

09/26/25

ORD
40h 50m
KRK
WAW

09/28/25

MXP
$824
Aer Lingus Logo
Aer Lingus

09/15/25

MXP
15h 45m
DUB

09/16/25

ORD
Aer Lingus Logo
Aer Lingus

09/26/25

ORD
21h 5m
LHR

09/27/25

MXP
$843

Top Deals on flights from Milan to Chicago

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

 Logo

Jul 11

MXP
18h 35m
BOS

Jul 12

ORD

as low as

$525

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

Turkish Airlines Logo
Turkish Airlines

Jul 20

MXP
22h 55m
IST

Jul 21

ORD

as low as

$576

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

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

Jul 13

MXP
19h 40m
BEG

Jul 14

ORD

as low as

$596

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

Aer Lingus Logo
Aer Lingus

Aug 6

MXP
15h 45m
DUB

Aug 7

ORD

as low as

$605

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

Aer Lingus Logo
Aer Lingus

Jul 10

LIN
7h 40m
DUB

Jul 10

ORD

as low as

$666

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

TAP Portugal Logo
TAP Portugal

Jul 10

MXP
9h 5m
LIS

Jul 10

ORD

as low as

$691

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

ITA Airways Logo
ITA Airways

Jul 30

LIN
6h 10m
FCO

Jul 30

ORD

as low as

$845

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

ITA Airways Logo
ITA Airways

Jul 21

LIN
26h 43m
FCO
JFK

Jul 22

ORD

as low as

$857

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

American Airlines Logo
American Airlines

Jul 26

LIN
7h 10m
MAD

Jul 26

ORD

as low as

$859

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

American Airlines Logo
American Airlines

Aug 4

MXP
19h 25m
PHL

Aug 5

ORD

as low as

$864

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

TAP Portugal Logo
TAP Portugal

Jul 18

MXP
20h 49m
LIS
EWR

Jul 19

ORD

as low as

$886

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

American Airlines Logo
American Airlines

Jul 30

LIN
17h 35m
LHR

Jul 31

ORD

as low as

$886

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