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Flight Deals from Chicago to Milan from $254

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Stops

  • Up to 1 stop
    $457
  • Up to 2 stops
    $418

Airlines

  • Aer Lingus
    $841
  • Air Canada
    $814
  • Air France
    $881
  • Air SERBIA a.d. Beograd
    $696
  • Austrian Airlines
    $866
  • British Airways
    $766
  • Brussels Airlines
    $867
  • Delta Air Lines
    $849
  • ITA Airways
    $873
  • KLM
    $906
  • LOT Polish Airlines
    $796
  • Lufthansa
    $828
  • SAS Airlines
    $418
  • SWISS
    $841
  • TAP Portugal
    $470
  • Turkish Airlines
    $642

Cabin Class

  • Economy
    $418

Departure Airports

  • Chicago O Hare Airport
    $418

Arrival Airports

  • Milan Linate Airport
    $484
  • Milan Malpensa Airport
    $418

Layover Airports

  • Amsterdam Airport Schiphol
    $886
  • Belgrade Nikola Tesla Airport
    $696
  • Brussels Airport
    $867
  • Cincinnati Northern Kentucky International Airport
    $880
  • Copenhagen Kastrup Airport
    $418
  • Detroit Metropolitan Airport
    $876
  • Dublin Airport
    $841
  • Frankfurt am Main Airport
    $828
  • General Edward Lawrence Logan International Airport
    $418
  • Hartsfield Jackson Atlanta International Airport
    $849
  • Humberto Delgado Airport (Lisbon Portela Airport)
    $470
  • Istanbul Airport
    $642
  • Kraków John Paul II International Airport
    $812
  • London Heathrow Airport
    $766
  • Montreal Trudeau Airport
    $814
  • Munich Airport
    $871
  • New York John F Kennedy Airport
    $488
  • New York LaGuardia Airport
    $868
  • Newark Liberty Airport
    $821
  • Oslo Gardermoen Airport
    $461
  • Paris Charles de Gaulle Airport
    $849
  • Rome Fiumicino Airport
    $873
  • Stockholm Arlanda Airport
    $474
  • Toronto Pearson Airport
    $864
  • Vienna International Airport
    $866
  • Warsaw Chopin Airport
    $796
  • Washington Dulles Airport
    $861
  • Zürich Airport
    $841
SAS Airlines Logo
7:00 am – 10:25 am
Chicago(ORD)Milan(MXP)
ORD - MXP · 27h 25m
24 Feb
27h 25m
24 Feb
2 stops
BOS, CPH
SAS Airlines Logo
11:15 am – 5:45 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 6h 30m
8 Mar
6h 30m
8 Mar
1 stop
CPH
$418
SAS Airlines Logo
7:10 pm – 7:10 pm
Chicago(ORD)Milan(MXP)
ORD - MXP · 24h
1 Feb
24h
1 Feb
1 stop
CPH
SAS Airlines Logo
11:15 am – 4:45 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 5h 30m
2 Mar
5h 30m
2 Mar
1 stop
CPH
$457
SAS Airlines Logo
7:10 pm – 2:55 pm
Chicago(ORD)Milan(MXP)
ORD - MXP · 43h 45m
1 Feb
43h 45m
1 Feb
2 stops
CPH, OSL
SAS Airlines Logo
11:15 am – 4:45 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 5h 30m
2 Mar
5h 30m
2 Mar
1 stop
CPH
$461
TAP Portugal Logo
8:25 pm – 4:55 pm
Chicago(ORD)Milan(MXP)
ORD - MXP · 20h 30m
15 Feb
20h 30m
15 Feb
1 stop
LIS
TAP Portugal Logo
5:45 pm – 3:45 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 22h
7 Mar
22h
7 Mar
1 stop
LIS
$470
SAS Airlines Logo
8:20 pm – 8:00 pm
Chicago(ORD)Milan(MXP)
ORD - MXP · 23h 40m
12 Mar
23h 40m
12 Mar
2 stops
CPH, ARN
SAS Airlines Logo
11:15 am – 5:45 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 6h 30m
16 Mar
6h 30m
16 Mar
1 stop
CPH
$474
SAS Airlines Logo
7:20 pm – 12:05 pm
Chicago(ORD)Milan(LIN)
ORD - LIN · 40h 45m
9 Nov
40h 45m
9 Nov
2 stops
CPH, ARN
SAS Airlines Logo
8:00 pm – 4:45 pm
Milan(LIN)Chicago(ORD)
LIN - ORD · 20h 45m
24 Feb
20h 45m
24 Feb
1 stop
CPH
$484
SAS Airlines Logo
10:35 am – 10:25 am
Chicago(ORD)Milan(MXP)
ORD - MXP · 23h 50m
10 Nov
23h 50m
10 Nov
2 stops
BOS, CPH
SAS Airlines Logo
9:15 am – 12:44 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 27h 29m
24 Feb
27h 29m
24 Feb
2 stops
CPH, JFK
$488
Turkish Airlines Logo
11:50 am – 1:30 pm
Chicago(ORD)Milan(MXP)
ORD - MXP · 25h 40m
13 Nov
25h 40m
13 Nov
1 stop
IST
Turkish Airlines Logo
6:55 am – 6:25 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 11h 30m
24 Feb
11h 30m
24 Feb
1 stop
IST
$642
Air SERBIA a.d. Beograd Logo
5:30 pm – 8:45 am
Chicago(ORD)Milan(MXP)
ORD - MXP · 39h 15m
8 Nov
39h 15m
8 Nov
1 stop
BEG
Air SERBIA a.d. Beograd Logo
8:30 pm – 2:35 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 18h 5m
26 Feb
18h 5m
26 Feb
1 stop
BEG
$696
British Airways Logo
4:25 pm – 8:10 am
Chicago(ORD)Milan(MXP)
ORD - MXP · 39h 45m
23 Feb
39h 45m
23 Feb
1 stop
JFK
British Airways Logo
7:15 am – 3:25 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 8h 10m
26 Feb
8h 10m
26 Feb
1 stop
LHR
$766
LOT Polish Airlines Logo
9:55 pm – 9:45 am
Chicago(ORD)Milan(MXP)
ORD - MXP · 35h 50m
7 Nov
35h 50m
7 Nov
1 stop
WAW
LOT Polish Airlines Logo
10:25 am – 8:00 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 9h 35m
24 Feb
9h 35m
24 Feb
1 stop
WAW
$796
LOT Polish Airlines Logo
9:55 pm – 9:45 am
Chicago(ORD)Milan(MXP)
ORD - MXP · 35h 50m
10 Nov
35h 50m
10 Nov
1 stop
WAW
LOT Polish Airlines Logo
10:25 am – 7:55 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 9h 30m
23 Feb
9h 30m
23 Feb
2 stops
WAW, KRK
$812
Air Canada Logo
12:50 pm – 9:55 am
Chicago(ORD)Milan(MXP)
ORD - MXP · 21h 5m
4 Mar
21h 5m
4 Mar
1 stop
YUL
Air Canada Logo
12:05 pm – 8:00 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 7h 55m
11 Mar
7h 55m
11 Mar
1 stop
YUL
$814
TAP Portugal Logo
11:56 am – 4:55 pm
Chicago(ORD)Milan(MXP)
ORD - MXP · 28h 59m
13 Feb
28h 59m
13 Feb
2 stops
EWR, LIS
TAP Portugal Logo
6:20 am – 3:00 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 8h 40m
18 Feb
8h 40m
18 Feb
1 stop
LIS
$821
Lufthansa Logo
3:35 pm – 9:55 am
Chicago(ORD)Milan(MXP)
ORD - MXP · 18h 20m
4 Mar
18h 20m
4 Mar
1 stop
YUL
Lufthansa Logo
2:40 pm – 9:05 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 6h 25m
11 Mar
6h 25m
11 Mar
1 stop
FRA
$828
Aer Lingus Logo
9:00 pm – 11:05 am
Chicago(ORD)Milan(LIN)
ORD - LIN · 38h 5m
21 Jan
38h 5m
21 Jan
1 stop
DUB
Aer Lingus Logo
11:45 am – 7:15 pm
Milan(LIN)Chicago(ORD)
LIN - ORD · 7h 30m
25 Feb
7h 30m
25 Feb
1 stop
DUB
$841
SWISS Logo
3:35 pm – 9:55 am
Chicago(ORD)Milan(MXP)
ORD - MXP · 18h 20m
10 Feb
18h 20m
10 Feb
1 stop
YUL
SWISS Logo
10:40 am – 4:20 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 5h 40m
20 Feb
5h 40m
20 Feb
1 stop
ZRH
$841
Delta Air Lines Logo
5:20 pm – 5:25 pm
Chicago(ORD)Milan(MXP)
ORD - MXP · 24h 5m
18 Feb
24h 5m
18 Feb
1 stop
CDG
Delta Air Lines Logo
11:05 am – 7:29 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 8h 24m
25 Feb
8h 24m
25 Feb
1 stop
ATL
$849
SWISS Logo
6:50 pm – 2:10 pm
Chicago(ORD)Milan(MXP)
ORD - MXP · 19h 20m
8 Feb
19h 20m
8 Feb
1 stop
ZRH
SWISS Logo
1:05 pm – 11:43 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 10h 38m
18 Feb
10h 38m
18 Feb
2 stops
YUL, IAD
$861
Air Canada Logo
11:15 am – 9:55 am
Chicago(ORD)Milan(MXP)
ORD - MXP · 22h 40m
11 Feb
22h 40m
11 Feb
1 stop
YYZ
Air Canada Logo
6:55 am – 1:10 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 6h 15m
7 Mar
6h 15m
7 Mar
1 stop
FRA
$864
Austrian Airlines Logo
4:20 pm – 4:30 pm
Chicago(ORD)Milan(LIN)
ORD - LIN · 24h 10m
4 Mar
24h 10m
4 Mar
1 stop
VIE
Austrian Airlines Logo
6:10 am – 12:10 pm
Milan(LIN)Chicago(ORD)
LIN - ORD · 6h
11 Mar
6h
11 Mar
1 stop
FRA
$866
Brussels Airlines Logo
5:55 pm – 12:20 pm
Chicago(ORD)Milan(LIN)
ORD - LIN · 18h 25m
8 Feb
18h 25m
8 Feb
1 stop
BRU
Brussels Airlines Logo
9:10 am – 3:20 pm
Milan(LIN)Chicago(ORD)
LIN - ORD · 6h 10m
20 Feb
6h 10m
20 Feb
1 stop
FRA
$867
SWISS Logo
6:50 pm – 2:10 pm
Chicago(ORD)Milan(MXP)
ORD - MXP · 19h 20m
8 Feb
19h 20m
8 Feb
1 stop
ZRH
SWISS Logo
1:05 pm – 9:59 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 8h 54m
18 Feb
8h 54m
18 Feb
2 stops
YUL, LGA
$868
Lufthansa Logo
9:50 pm – 6:50 pm
Chicago(ORD)Milan(LIN)
ORD - LIN · 21h
4 Feb
21h
4 Feb
1 stop
MUC
Lufthansa Logo
6:55 am – 1:10 pm
Milan(LIN)Chicago(ORD)
LIN - ORD · 6h 15m
20 Feb
6h 15m
20 Feb
1 stop
FRA
$871
ITA Airways Logo
8:45 am – 10:10 am
Chicago(ORD)Milan(LIN)
ORD - LIN · 25h 25m
1 Mar
25h 25m
1 Mar
2 stops
IAD, FCO
ITA Airways Logo
1:00 pm – 6:33 pm
Milan(LIN)Chicago(ORD)
LIN - ORD · 29h 33m
14 Mar
29h 33m
14 Mar
2 stops
FCO, IAD
$873
Lufthansa Logo
4:20 pm – 2:05 pm
Chicago(ORD)Milan(LIN)
ORD - LIN · 21h 45m
4 Mar
21h 45m
4 Mar
1 stop
FRA
Lufthansa Logo
6:10 am – 6:21 pm
Milan(LIN)Chicago(ORD)
LIN - ORD · 12h 11m
11 Mar
12h 11m
11 Mar
2 stops
FRA, DTW
$876
British Airways Logo
5:10 pm – 11:30 am
Chicago(ORD)Milan(LIN)
ORD - LIN · 18h 20m
8 Feb
18h 20m
8 Feb
1 stop
LHR
British Airways Logo
12:40 pm – 12:40 pm
Milan(LIN)Chicago(ORD)
LIN - ORD · 24h
20 Feb
24h
20 Feb
2 stops
LHR, CVG
$880
Air France Logo
5:20 pm – 11:40 am
Chicago(ORD)Milan(MXP)
ORD - MXP · 18h 20m
3 Feb
18h 20m
3 Feb
1 stop
CDG
Air France Logo
6:55 am – 3:10 pm
Milan(MXP)Chicago(ORD)
MXP - ORD · 8h 15m
18 Feb
8h 15m
18 Feb
1 stop
CDG
$881
Air France Logo
5:20 pm – 7:35 pm
Chicago(ORD)Milan(LIN)
ORD - LIN · 26h 15m
17 Feb
26h 15m
17 Feb
1 stop
CDG
Air France Logo
6:30 am – 2:20 pm
Milan(LIN)Chicago(ORD)
LIN - ORD · 7h 50m
4 Mar
7h 50m
4 Mar
1 stop
AMS
$886
KLM Logo
4:25 pm – 10:55 pm
Chicago(ORD)Milan(LIN)
ORD - LIN · 30h 30m
9 Feb
30h 30m
9 Feb
1 stop
AMS
KLM Logo
9:20 pm – 2:20 pm
Milan(LIN)Chicago(ORD)
LIN - ORD · 17h
17 Feb
17h
17 Feb
1 stop
AMS
$906

Top Deals on flights from Chicago to Milan

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

 Logo

Nov 17

ORD
28h 20m
JFK
DUB

Nov 18

LIN

as low as

$254

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

TAP Portugal Logo
TAP Portugal

Nov 28

ORD
20h 40m
LIS

Nov 29

MXP

as low as

$268

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

SAS Airlines Logo
SAS Airlines

Feb 2

ORD
33h
BOS
CPH

Feb 3

MXP

as low as

$278

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

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

Mar 28

ORD
39h 5m
BEG

Mar 30

MXP

as low as

$313

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

SAS Airlines Logo
SAS Airlines

Apr 27

ORD
40h 10m
CPH
OSL

Apr 29

MXP

as low as

$382

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

SAS Airlines Logo
SAS Airlines

May 11

ORD
24h 35m
CPH
ARN

May 12

MXP

as low as

$385

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

ITA Airways Logo
ITA Airways

Mar 10

ORD
20h 58m
IAD
FCO

Mar 11

LIN

as low as

$424

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

 Logo

Nov 18

ORD
30h 45m
JFK
MAD

Nov 19

MXP

as low as

$498

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

Turkish Airlines Logo
Turkish Airlines

Feb 4

ORD
25h 20m
IST

Feb 5

MXP

as low as

$513

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

Icelandair Logo
Icelandair

May 20

ORD
29h 40m
BOS
KEF

May 21

MXP

as low as

$550

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

 Logo

Nov 21

ORD
29h 15m
YYC
CDG

Nov 22

LIN

as low as

$574

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

United Airlines Logo
United Airlines

Mar 16

ORD
17h 20m
YUL

Mar 17

MXP

as low as

$583

Frequently Asked Questions

Are there convenient layover flights from Chicago to Milan?
Yes, convenient layover flights include: TAP Portugal for $399, with a layover at Lisbon (27h 10m); SAS Airlines for $457, with a layover at Copenhagen (39h 5m); Turkish Airlines for $642, with a layover at Istanbul (21h 15m); British Airways for $766, with a layover at New York (39h 45m); LOT Polish Airlines for $796, with a layover at Warsaw (35h 50m).
What are the most convenient layover airports for the flight?
For your flight from Chicago to Milan, convenient layover airports include Humberto Delgado (Lisbon), Amsterdam Airport Schiphol, Copenhagen Kastrup, New York John F Kennedy, and Warsaw Chopin.
What is the cheapest and fastest flight from Chicago to Milan?
The cheapest flight is with TAP Portugal for $399, taking 27 hours 10 minutes. The fastest flight is with KLM for $947, taking 16 hours 35 minutes.
What are all possible destination arrival airports?
The possible destination arrival airports include Milan Malpensa Airport and Milan Linate Airport.
What is the time difference between destination and arrival?
The time difference between Chicago and Milan is typically 7 hours, with Milan ahead of Chicago. This may vary during daylight saving time adjustments.
Is there a direct flight from Chicago to Milan?
There is no direct flight from Chicago O Hare Airport to Milan. The available flights are 1 stop flights with airlines such as TAP Portugal at $399 and KLM at $947, along with other options.