Find Cheap Flights from Chicago Midway to Milan (MDW - MIL)

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Looking for a cheap flight? 25% of our users found flights on this route for $787 or less.

FAQs for Booking Chicago Midway to Milan Flights

How long does a flight from Chicago Midway to Milan take?
An average nonstop flight takes 13h 55m, covering a distance of 4538 miles.
Which airlines provide the cheapest flights from Chicago Midway to Milan?
In the past 3 days, the cheapest round-trip tickets were found on Air France ($779), KLM ($1362) and Delta ($1426).
Do I need a passport to fly between Chicago Midway and Milan?
Yes.

Book cheap flights from Chicago Midway to Milan (round-trip)

Airports
Origin
Chicago
$779
only
$779
Destination
Milan
$779
only
$779
$913
only
$913
Thu, Mar 1
MDW
MXP
34h 50m
Sat, Mar 3
MXP
MDW
36h 23m
Trip: 3 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
DTW
CDG
Excellent 8.0

The crew was good and very good pilot's

No leg room between seats

CDG
RDU
Excellent 8.0

Friendly staff

Window pane was broken on my side and I couldn't shut it down. As it was a day flight the sun heated my skin badly

CDG
OUA
Excellent 8.6

Absolutely nice friendly and professional crew. Congrats! Nice food, rich and healthy Right in time despite few delay at departure

Just a need to improve entertainment facilities (digital screen, Wi-Fi. ..)

YYZ
CDG
Okay 4.6

Got pillow, blanket, headphone and eye cover

Older plane Very small tv screen Didn't get the bread roll with my dinner. Asked for it but she didn't bring it to me. No usb plug to charge

CDG
ATL
Excellent 10.0

Good service at gate and on board

Tue, Mar 13
MDW
LIN
15h 30m
Fri, Mar 23
LIN
MDW
35h 20m
$1362
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1546 reviews
Overall
8.0
Boarding
8.0
Comfort
7.7
Crew
8.5
Entertainment
7.2
Food
7.5
ATL
CLE
Okay 4.6

old plane, tight and uncomfortable

JNB
AMS
Excellent 9.6

Comfort economy well worth the extra.

SFO
AMS
Excellent 10.0

From pre-boarding, to boarding, to the food, and the attentiveness, everything was top notch! The cleanliness of the plane was only topped by the friendliness of the crew.

The flight was marked at almost 11hrs but ended up being only 9...not a negative other than it meant not spending as much time on board!

JNB
AMS
Excellent 8.0

Good multi media access and content

SFO
AMS
Okay 5.0

Crew was very helpful.food

Food was not upto the mark.

Wed, Jan 17
MDW
MXP
15h 13m
Thu, Jan 25
MXP
MDW
18h 35m
$1426
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14300 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PDX
JFK
Excellent 10.0

really great service, arrived early, as good as it gets.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

JFK
PHX
Good 6.6

The crew was late so we were delayed two hours. I find that extremely infuriating when you are a passenger and have to show up two hours before your flight. I also would lose my job if I was two hours late for a client.

Wed, Feb 14
MDW
LIN
34h 00m
Tue, Feb 20
LIN
MDW
18h 45m
Trip: 7 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
CPH
CDG
Okay 5.0

Nice food Right in time Police and customs formalities easy

Poor comfort in business class No entertainment at all

CDG
ATL
Excellent 10.0

Good service at gate and on board

YYZ
CDG
Okay 4.6

Got pillow, blanket, headphone and eye cover

Older plane Very small tv screen Didn't get the bread roll with my dinner. Asked for it but she didn't bring it to me. No usb plug to charge

CDG
NCE
Good 6.6

Short & easy flight

All ok

CDG
TLV
Mediocre 3.0

Not checking my carry on weight at check in then letting me walk all the way to security to then check my bag and tell me to go back to check in then the counter is closed and they tell me it's too late and that I need to get ride of my things so that my bag is under weight and barely making the flight

Wed, Feb 14
MDW
MXP
16h 00m
Tue, Feb 20
MXP
MDW
20h 55m
Trip: 7 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
YYZ
CDG
Okay 4.6

Got pillow, blanket, headphone and eye cover

Older plane Very small tv screen Didn't get the bread roll with my dinner. Asked for it but she didn't bring it to me. No usb plug to charge

DTW
CDG
Excellent 8.0

The crew was good and very good pilot's

No leg room between seats

MAD
CDG
Okay 4.3

Crew was nice and responsive

The overall experience is regular at best

CDG
BEY
Excellent 8.0

It es a good flight back

Items missing on duty free purchases

CDG
ATL
Excellent 10.0

Good service at gate and on board

Tue, Apr 17
MDW
MXP
15h 36m
Tue, Apr 24
MXP
MDW
20h 08m
$1479
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1546 reviews
Overall
8.0
Boarding
8.0
Comfort
7.7
Crew
8.5
Entertainment
7.2
Food
7.5
AMS
IAH
Excellent 8.6

Old airplane with not really comfy seats. No outlets for charging devices. Very old entertainment screen.

KRK
AMS
Mediocre 3.0

Flight way delayed 3 hours. Staff gave no information and wouldn't help rebook us onto other flights. They gave us food vouchers 2 minutes before we finally boarded, so we couldn't use them. The food on the plane had spoiled so we were all starving on the flight, and we all missed our connections. Horrible experience and wouldn't fly with KLM again.

SFO
AMS
Okay 5.0

Crew was very helpful.food

Food was not upto the mark.

ABZ
AMS
Excellent 10.0

Thankful for coffee being served without charge. Not all airlines do that.

SFO
AMS
Excellent 10.0

From pre-boarding, to boarding, to the food, and the attentiveness, everything was top notch! The cleanliness of the plane was only topped by the friendliness of the crew.

The flight was marked at almost 11hrs but ended up being only 9...not a negative other than it meant not spending as much time on board!

Mon, Apr 2
MDW
MXP
14h 40m
Wed, Apr 11
MXP
MDW
18h 17m
$1294
Trip: 10 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
RUH
CDG
Excellent 10.0

Cabin crew very friendly and caring.

Airport services and lounge are OK.

DTW
CDG
Excellent 8.0

The crew was good and very good pilot's

No leg room between seats

CDG
OUA
Excellent 8.6

Absolutely nice friendly and professional crew. Congrats! Nice food, rich and healthy Right in time despite few delay at departure

Just a need to improve entertainment facilities (digital screen, Wi-Fi. ..)

CDG
ATL
Excellent 10.0

Good service at gate and on board

CPH
CDG
Okay 5.0

Nice food Right in time Police and customs formalities easy

Poor comfort in business class No entertainment at all

Thu, Feb 8
MDW
MXP
13h 55m
Sun, Feb 11
MXP
MDW
16h 29m
$1533
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1546 reviews
Overall
8.0
Boarding
8.0
Comfort
7.7
Crew
8.5
Entertainment
7.2
Food
7.5
FCO
AMS
Excellent 10.0

Flight crew was pleasant and attentive. Seats were comfortable for economy as well. We were allowed to check in extra baggage for free at check in which really helped since we would be catching a connecting flight in Amsterdam

SFO
AMS
Okay 5.0

Crew was very helpful.food

Food was not upto the mark.

JNB
AMS
Excellent 9.6

Comfort economy well worth the extra.

KRK
AMS
Mediocre 3.0

Flight way delayed 3 hours. Staff gave no information and wouldn't help rebook us onto other flights. They gave us food vouchers 2 minutes before we finally boarded, so we couldn't use them. The food on the plane had spoiled so we were all starving on the flight, and we all missed our connections. Horrible experience and wouldn't fly with KLM again.

JFK
AMS
Good 7.6

Two hours delay in the start.

Sat, Mar 24
MDW
MXP
16h 40m
Sat, Mar 31
MXP
MDW
16h 17m
$1710
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14300 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

SEA
SNA
Excellent 8.6

The wifi wasn't strong enough to download the app to watch movies on the plane.

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

Tue, May 8
MDW
MXP
14h 40m
Mon, May 21
MXP
MDW
15h 02m
$1294
Trip: 14 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
CDG
RDU
Excellent 8.0

Friendly staff

Window pane was broken on my side and I couldn't shut it down. As it was a day flight the sun heated my skin badly

CDG
OUA
Excellent 8.6

Absolutely nice friendly and professional crew. Congrats! Nice food, rich and healthy Right in time despite few delay at departure

Just a need to improve entertainment facilities (digital screen, Wi-Fi. ..)

CDG
NCE
Good 6.6

Short & easy flight

All ok

MAD
CDG
Okay 4.3

Crew was nice and responsive

The overall experience is regular at best

DTW
CDG
Excellent 8.0

The crew was good and very good pilot's

No leg room between seats

Tue, May 1
MDW
LIN
19h 35m
Mon, May 7
LIN
MDW
29h 22m
$1305
Trip: 7 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
RUH
CDG
Excellent 10.0

Cabin crew very friendly and caring.

Airport services and lounge are OK.

CDG
TLV
Mediocre 3.0

Not checking my carry on weight at check in then letting me walk all the way to security to then check my bag and tell me to go back to check in then the counter is closed and they tell me it's too late and that I need to get ride of my things so that my bag is under weight and barely making the flight

CDG
RDU
Excellent 8.0

Friendly staff

Window pane was broken on my side and I couldn't shut it down. As it was a day flight the sun heated my skin badly

CPH
CDG
Okay 5.0

Nice food Right in time Police and customs formalities easy

Poor comfort in business class No entertainment at all

CDG
OUA
Excellent 8.6

Absolutely nice friendly and professional crew. Congrats! Nice food, rich and healthy Right in time despite few delay at departure

Just a need to improve entertainment facilities (digital screen, Wi-Fi. ..)

Sat, Dec 30
MDW
MXP
18h 50m
Mon, Jan 8
MXP
MDW
18h 35m
$1806
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14300 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

SEA
AUS
Excellent 9.0

Boarding was not smooth. They got me and my son mixed up as we have same name.

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

JFK
PHX
Good 6.6

The crew was late so we were delayed two hours. I find that extremely infuriating when you are a passenger and have to show up two hours before your flight. I also would lose my job if I was two hours late for a client.

Sun, May 6
MDW
MXP
35h 05m
Fri, May 11
MXP
MDW
16h 37m
$1329
Trip: 6 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
CDG
TLV
Mediocre 3.0

Not checking my carry on weight at check in then letting me walk all the way to security to then check my bag and tell me to go back to check in then the counter is closed and they tell me it's too late and that I need to get ride of my things so that my bag is under weight and barely making the flight

DTW
CDG
Excellent 8.0

The crew was good and very good pilot's

No leg room between seats

CDG
BEY
Excellent 8.0

It es a good flight back

Items missing on duty free purchases

CPH
CDG
Okay 5.0

Nice food Right in time Police and customs formalities easy

Poor comfort in business class No entertainment at all

CDG
RDU
Excellent 8.0

Friendly staff

Window pane was broken on my side and I couldn't shut it down. As it was a day flight the sun heated my skin badly

Sun, May 6
MDW
LIN
19h 35m
Fri, May 11
LIN
MDW
17h 47m
$1378
Trip: 6 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
RUH
CDG
Excellent 10.0

Cabin crew very friendly and caring.

Airport services and lounge are OK.

CDG
RDU
Excellent 8.0

Friendly staff

Window pane was broken on my side and I couldn't shut it down. As it was a day flight the sun heated my skin badly

MAD
CDG
Okay 4.3

Crew was nice and responsive

The overall experience is regular at best

CDG
ATL
Excellent 10.0

Good service at gate and on board

CDG
BEY
Excellent 8.0

It es a good flight back

Items missing on duty free purchases

Wed, Jun 13
MDW
LIN
19h 35m
Wed, Jun 20
LIN
MDW
16h 21m
$1432
Trip: 8 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
DTW
CDG
Excellent 8.0

The crew was good and very good pilot's

No leg room between seats

CDG
BEY
Excellent 8.0

It es a good flight back

Items missing on duty free purchases

CDG
NCE
Good 6.6

Short & easy flight

All ok

CDG
OUA
Excellent 8.6

Absolutely nice friendly and professional crew. Congrats! Nice food, rich and healthy Right in time despite few delay at departure

Just a need to improve entertainment facilities (digital screen, Wi-Fi. ..)

CDG
ATL
Excellent 10.0

Good service at gate and on board

Mon, Apr 16
MDW
LIN
15h 15m
Wed, May 2
LIN
MDW
17h 47m
$1488
Trip: 17 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
MAD
CDG
Okay 4.3

Crew was nice and responsive

The overall experience is regular at best

OUA
CDG
Okay 5.6

Seat comfort in business class Professional and friendly crew

Food not tasty Limited entertainment even in business class (such small and old screen style) Newspapers available to be much more diversified When is the WiFi going to be available?

YYZ
CDG
Okay 4.6

Got pillow, blanket, headphone and eye cover

Older plane Very small tv screen Didn't get the bread roll with my dinner. Asked for it but she didn't bring it to me. No usb plug to charge

CDG
OUA
Excellent 8.6

Absolutely nice friendly and professional crew. Congrats! Nice food, rich and healthy Right in time despite few delay at departure

Just a need to improve entertainment facilities (digital screen, Wi-Fi. ..)

CDG
BEY
Excellent 8.0

It es a good flight back

Items missing on duty free purchases

Fri, Jun 1
MDW
MXP
17h 30m
Sun, Jun 10
MXP
MDW
35h 21m
$1499
Trip: 10 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
DTW
CDG
Excellent 8.0

The crew was good and very good pilot's

No leg room between seats

CDG
RDU
Excellent 8.0

Friendly staff

Window pane was broken on my side and I couldn't shut it down. As it was a day flight the sun heated my skin badly

CDG
BEY
Excellent 8.0

It es a good flight back

Items missing on duty free purchases

YYZ
CDG
Okay 4.6

Got pillow, blanket, headphone and eye cover

Older plane Very small tv screen Didn't get the bread roll with my dinner. Asked for it but she didn't bring it to me. No usb plug to charge

CDG
ATL
Excellent 10.0

Good service at gate and on board

Wed, Jan 17
MDW
LIN
34h 00m
Thu, Jan 25
LIN
MDW
18h 35m
$1509
Trip: 9 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
YYZ
CDG
Okay 4.6

Got pillow, blanket, headphone and eye cover

Older plane Very small tv screen Didn't get the bread roll with my dinner. Asked for it but she didn't bring it to me. No usb plug to charge

CDG
ATL
Excellent 10.0

Good service at gate and on board

MAD
CDG
Okay 4.3

Crew was nice and responsive

The overall experience is regular at best

CPH
CDG
Okay 5.0

Nice food Right in time Police and customs formalities easy

Poor comfort in business class No entertainment at all

DTW
CDG
Excellent 8.0

The crew was good and very good pilot's

No leg room between seats

Tue, Apr 17
MDW
LIN
14h 45m
Tue, Apr 24
LIN
MDW
18h 18m
$3392
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1546 reviews
Overall
8.0
Boarding
8.0
Comfort
7.7
Crew
8.5
Entertainment
7.2
Food
7.5
ATL
CLE
Okay 4.6

old plane, tight and uncomfortable

ABZ
AMS
Excellent 10.0

Thankful for coffee being served without charge. Not all airlines do that.

AMS
IAH
Excellent 8.6

Old airplane with not really comfy seats. No outlets for charging devices. Very old entertainment screen.

JFK
AMS
Good 7.6

Two hours delay in the start.

AMS
PRG
Excellent 10.0

Equally friendly crew and experience. It was complimented by the time we got to spend in the fantastic KLM lounge while we waited for the flight.

Nothing!

Fri, Dec 29
MDW
LIN
15h 12m
Thu, Jan 4
LIN
MDW
18h 20m
$2598
Trip: 7 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 1967 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
OUA
CDG
Okay 5.6

Seat comfort in business class Professional and friendly crew

Food not tasty Limited entertainment even in business class (such small and old screen style) Newspapers available to be much more diversified When is the WiFi going to be available?

CDG
BEY
Excellent 8.0

It es a good flight back

Items missing on duty free purchases

CDG
ATL
Excellent 10.0

Good service at gate and on board

MAD
CDG
Okay 4.3

Crew was nice and responsive

The overall experience is regular at best

DTW
CDG
Excellent 8.0

The crew was good and very good pilot's

No leg room between seats

*
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.