Find Cheap Flights from Milan to Chicago (MIL - CHI)

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Fri 1/19
Fri 1/26
Any month
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Good to Know

Low Season:
February
Best time to beat the crowds
5%
expected price decrease
High Season:
July
Most popular time to fly
25%
expected price increase
Average Price:
$745
(avg. price over the last 2 weeks)
Good Deal:
$529
or less (round trip)

When to Book Flights from Milan to Chicago

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $529 or less.
The cheapest flight from Milan to Chicago was found 90 days before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
High season is considered to be June, July and August. The cheapest month to fly is February.
Morning departure is around 11% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Milan to Chicago Flights

How long does a flight from Milan to Chicago take?
An average nonstop flight takes 12h 15m, covering a distance of 4529 miles.
Which airlines provide the cheapest flights from Milan to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Multiple Airlines ($433), Finnair ($450) and British Airways ($462).
Do I need a passport to fly between Milan and Chicago?
Yes.
What’s the cheapest day of the week to fly Milan to Chicago?
For Milan to Chicago, Wednesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago back to Milan, the best deals are generally found on Monday, with Tuesday being the most expensive.

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

Airports
Origin
Milan
$433
only
$433
$446
only
$446
Destination
Chicago
$433
only
$433
Wed, Apr 18
MXP
ORD
14h 44m
Wed, Apr 25
ORD
MXP
16h 05m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Apr 20
MXP
ORD
35h 15m
Mon, Apr 30
ORD
MXP
17h 10m
Trip: 11 days
7.7GoodShow reviews
Overall 7.7 Good
Based on 2864 reviews
Overall
7.9
Boarding
8.0
Comfort
7.5
Crew
8.3
Entertainment
7.3
Food
7.2
JFK
HEL
Good 6.3

A330 throne seat (2A) is nice and private.

Flight attendant in business class was quite terse and rude.

JFK
HEL
Mediocre 3.0

The plane landed much later than expected, and I missed my connecting flight to Moscow. While I was given another boarding pass, I had to have another layover in St. Petersburg, and fly to Moscow from there. The flight turned out to be much longer, and much more exhausting. My overall experience was unpleasant.

KAO
HEL
Excellent 8.3

We where really late and they where very helpfull.

HEL
MIA
Okay 4.0

Missed my connecting flight from Helsinki to Miami because the flight from New Delhi, India was delayed by more than 4 hours.

DEL
HEL
Okay 4.0

The flight from India was delayed and as a consequence I missed my connecting flight to Miami. I had to put up in a Hotel at Helsinki and take a flight to Miami the next day via London.

Sat, Feb 24
MXP
ORD
16h 03m
Sat, Mar 3
ORD
MXP
18h 30m
Trip: 8 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 14889 reviews
Overall
7.4
Boarding
7.6
Comfort
7.2
Crew
8.0
Entertainment
7.0
Food
6.9
DUB
LHR
Mediocre 2.0

Nothing I didn’t make the flight

Heathrow security is slower than molasses and rude. They had to check my bags and it took them over an hour. They were condescending and very unprofessional. Also extremely slow.

LHR
AUS
Mediocre 2.0

Nothing it was a nightmare

The rude security staff, my previous British air flight from Dublin was 30’minutes late. Heathrow is terrible for connecting flights even with 2 hour leg room. What a joke. English people suck.

BCN
LHR
Excellent 10.0

Nice, smooth, quick flight.

LHR
ORD
Good 6.6

Flight on time, friendly crew.

Not so good meals. For a 9 long-haul flight only one meal provided, other was a cheap candy bar. Other carriers do offer breakfast. Traveled with child and did not allow priority boarding at LHR. Limited leg room, I assume this already a trend well known by travelers.

GVA
LHR
Excellent 10.0

The 787 aircraft is better

Fri, Feb 9
MXP
ORD
17h 45m
Fri, Feb 16
ORD
MXP
16h 50m
Trip: 8 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 17540 reviews
Overall
8.0
Boarding
7.9
Comfort
7.8
Crew
8.3
Entertainment
8.1
Food
8.0
IST
IAH
Mediocre 2.0

Transfer desk in Istanbul is terrible. Poor customer service. It took 6 hours to get transferred from the airport to the hotel.

IAD
IST
Good 7.6

There was a female attendant who as soon as I got to my seat asked me to stop blocking the aisle. I found this very annoying because I'd only just stopped at my seat. I found her manner disrespectful.

ORD
IST
Excellent 10.0

every think

LAX
IST
Excellent 8.3

Asian Vegetarian meal was good.

Seats with less leg room . No WIfi facility at the gate .

KTM
IST
Mediocre 2.0

I did nit like anything...

I hate kayak..

Mon, Apr 16
LIN
ORD
34h 25m
Thu, Apr 26
ORD
LIN
10h 50m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1656 reviews
Overall
8.0
Boarding
7.9
Comfort
7.7
Crew
8.5
Entertainment
7.1
Food
7.4
EZE
AMS
Good 6.0

una valija se perdió. Eso desató el descontrol que tiene KLM para seguir el equipaje. No hay como hacer tracking. No hay un teléfono a donde hablar, la web está desactualizada y con información equivocada. Direccionan a usar canales de twitter y facebook que no responden. Primer experiencia en KLM y no pienso nunca más usar esta aerolínea. Llevar el equipaje o resolver un problema sobre valijas es de lo más básico de una aerolínea y no lo hacen.

ATL
AMS
Excellent 10.0

Got to Amsterdam on time and everything was great including the staff

JFK
AMS
Good 7.0

Crew was courteous and polite! Entertainment system had some great movies at no additional cost.

Poor communication between delta, KLM and Air France meant that I couldn’t check in online and get a digital boarding pass. Furthermore I couldn’t use the check-in kiosks because my name was listed as Reidmr instead of Reid, which meant that my boarding pass did not match my passport. Overall this caused unnecessary delays that were compounded by the fact that I couldn’t use my TSA precheck. My main problem on the plane was that I had to struggle to get water served to me. It’s always so dry on planes and I would have liked to be able to get more than one tiny glass of water at a time. Also, would have loved a window at my window seat. Plus no WIFI!?

AMS
JNB
Excellent 8.0

The flight was very good, specially considering it was a daylight one. Staff was friendly and servicial. Tue food was above the industry's average.

AMS
MAN
Good 7.0

The flight attendants could not do enough for you.

Business class was pretty empty but again I was not allowed to change my seat selection online. Pathetic check-in.

Wed, Mar 28
MXP
ORD
12h 25m
Sun, Apr 1
ORD
MXP
10h 30m
Trip: 5 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5814 reviews
Overall
8.3
Boarding
8.3
Comfort
7.9
Crew
8.7
Entertainment
7.8
Food
8.0
JFK
ZRH
Excellent 10.0

Courteous Staff Excellent Service and enough concern for the guests.

BCN
ZRH
Excellent 10.0

Friendly service and food

Older plane with no entertainment

ORD
ZRH
Excellent 10.0

Excellent Service. Excellent food.

ZRH
CPH
Excellent 8.6

Swiss service relayable

ZRH
VIE
Good 6.0

on board

12 of January, 2018 Dear Austrian Airlines authority, I address to your kind attention to asist me to get to me the hat qhich I lost on board of the flight 1576 when I arrived to Vienna airport on my way frpom JFK to Lwo. It happened because it was no room above my seat's bin and the steard helped me to get my heat in another bin. Unfortunately I forgot at the moment when I left the board of the plane, a minute later I reminded that I forgot my hat but I was not allowed to go back and get my hat. I tried to communicate with the Lot&Found office in Vienna airport as I had 2h40 minutes in connection time and it was enough time to get me back the hat, unfortunately nothing was really done from the airport staff to get me my hat and made to me possible continue traveling with my hat. I spoke to two managers, the name I could share with you if you need. The Found office registered my black hat and the plastic box under the number F2018/000682. In this situation I ask your offices to deliver my hat and the plastic box to Lviv airport as sson as possible as this is a special hat for my daily prayers. I wish you best and ask for your kind assistance to send the item as soon as possible with the nearest flight. Sincerely, Meylakh Sheykhet

Tue, Jun 19
LIN
ORD
13h 00m
Thu, Jul 5
ORD
LIN
21h 15m
Trip: 17 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 1470 reviews
Overall
7.1
Boarding
7.1
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
TLV
BRU
Good 6.4

The safety instructions movie was entertaining the first time. The crew was friendly overall.

Both my luggage items were lost on the way there and one on the way back. No free food or drink although the flight price is not that low.

ABJ
BRU
Excellent 10.0

Everything

ACC
BRU
Okay 5.6

food

BRU
JFK
Excellent 10.0

Everything

EDI
BRU
Excellent 8.3

It was easy boarding. The flight crew had been been late due to a bad taxi driver. We still arrived on time!

No complaints.

Wed, Jun 20
MXP
ORD
12h 35m
Wed, Jul 4
ORD
MXP
11h 00m
Trip: 15 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 18144 reviews
Overall
8.2
Boarding
8.1
Comfort
7.9
Crew
8.5
Entertainment
7.8
Food
7.7
IAD
FRA
Good 7.6

The food was good.

The seats were not too comfortable and the video screen was small.

DEN
FRA
Excellent 8.3

1 hor 30 minutes instead of 2 hours 15

Worst food ever, and zero entertainment

AMS
MUC
Excellent 8.6

Standing outside of the plane in the freezing hail, when my clothing was completely unequipped for it

FRA
DEL
Good 7.6

Everything went well.

Nothing.

LAX
FRA
Excellent 8.0

Service on board was good.

The walk to the connecting flight was too long and took a lot of time.

Sat, Feb 24
LIN
ORD
14h 00m
Sat, Mar 3
ORD
LIN
13h 20m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Feb 27
MXP
ORD
17h 45m
Thu, Mar 1
ORD
MXP
16h 50m
Trip: 3 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 17540 reviews
Overall
8.0
Boarding
7.9
Comfort
7.8
Crew
8.3
Entertainment
8.1
Food
8.0
SFO
IST
Excellent 10.0

The service was excellent and the staff was so professional and nice

KTM
IST
Mediocre 2.0

I did nit like anything...

I hate kayak..

IAD
IST
Good 7.6

There was a female attendant who as soon as I got to my seat asked me to stop blocking the aisle. I found this very annoying because I'd only just stopped at my seat. I found her manner disrespectful.

IST
BOM
Excellent 8.3

Overall the experience was good. Cabin crew helpful.

while going to US from Mumbai -Wheelchair service at Istanbul was found unsatisfactory. The attendanct was unfriendly adamant and rude. overall the wheel chair persons were neglected by the airlines (even at Boston ) but the cabin crew took care of all wheel chair persons.

IAD
IST
Excellent 10.0

Excellent service with comfort

All was great

Tue, Mar 27
LIN
ORD
13h 45m
Thu, Apr 5
ORD
LIN
12h 15m
Trip: 10 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 14889 reviews
Overall
7.4
Boarding
7.6
Comfort
7.2
Crew
8.0
Entertainment
7.0
Food
6.9
LHR
JFK
Mediocre 3.6

Nothing about wheelchairs

When arrived they don't take wheelchairs

SEA
LHR
Excellent 8.0

Quality of food

GVA
LHR
Excellent 10.0

The 787 aircraft is better

TIA
LGW
Excellent 10.0

Very nice and comfortable

LHR
AUS
Mediocre 2.0

Nothing it was a nightmare

The rude security staff, my previous British air flight from Dublin was 30’minutes late. Heathrow is terrible for connecting flights even with 2 hour leg room. What a joke. English people suck.

Tue, Jun 19
LIN
ORD
14h 10m
Tue, Jul 3
ORD
LIN
12h 15m
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Apr 14
MXP
ORD
32h 15m
Wed, Apr 25
ORD
MXP
16h 05m
Trip: 12 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5814 reviews
Overall
8.3
Boarding
8.3
Comfort
7.9
Crew
8.7
Entertainment
7.8
Food
8.0
ORD
ZRH
Excellent 10.0

Excellent Service. Excellent food.

ZRH
CPH
Excellent 8.6

Swiss service relayable

ZRH
GVA
Excellent 8.4

New aircraft

Lost luggage. Flight delayed.

PRG
ZRH
Good 7.0

Roughest flight ever, many people got sick, too much turbulence to fly

ZRH
AMS
Good 7.0

Service was minimal but sufficient, Food was good

Seats 23A, 23B were extra cramped on the B777-300ER, even though they are sold as "extra comfort"! due to the video screen taking space between the seats. The seats were so cramped that the overhead light kept coming on, unknowingly, when people shifted in their seats.

Wed, Jun 20
LIN
ORD
13h 00m
Thu, Jul 5
ORD
LIN
21h 15m
Trip: 16 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 1470 reviews
Overall
7.1
Boarding
7.1
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
DME
BRU
Good 6.3

You have to pay for any drink and snacks in flight

BRU
KGL
Okay 5.0

Food was bad. Crew was distracted gossiping. They skipped rows during meal times as they were distracted. The seats are the most uncomfortable airline seats I've ever sat in.

EDI
BRU
Excellent 8.3

It was easy boarding. The flight crew had been been late due to a bad taxi driver. We still arrived on time!

No complaints.

TXL
BRU
Excellent 8.0

Also a good airline, though the a la cart...

The a la carte approach that includes charging 3 euros for water. I mean, seriously?

TLV
BRU
Good 6.4

The safety instructions movie was entertaining the first time. The crew was friendly overall.

Both my luggage items were lost on the way there and one on the way back. No free food or drink although the flight price is not that low.

Fri, Feb 9
LIN
ORD
13h 30m
Fri, Feb 16
ORD
LIN
12h 30m
Trip: 8 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 18144 reviews
Overall
8.2
Boarding
8.1
Comfort
7.9
Crew
8.5
Entertainment
7.8
Food
7.7
SJJ
MUC
Excellent 10.0

Many bathrooms, crew constantly came around offering juice and water.

FRA
IAH
Excellent 9.3

food was excellent

no 'breakfast' specifically, other snack items were available

PRG
FRA
Excellent 10.0

Great service as always

DEN
FRA
Excellent 8.3

1 hor 30 minutes instead of 2 hours 15

Worst food ever, and zero entertainment

LOS
FRA
Excellent 9.0

Very hospitable. Really enjoyed the food. Got bumped up to Business class on both legs of the trip.

The boarding could have been better organized at Frankfurt. Was very scattered.

Wed, Feb 7
MXP
ORD
14h 55m
Mon, Feb 26
ORD
MXP
30h 35m
Trip: 20 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1656 reviews
Overall
8.0
Boarding
7.9
Comfort
7.7
Crew
8.5
Entertainment
7.1
Food
7.4
AMS
JNB
Excellent 8.0

The flight was very good, specially considering it was a daylight one. Staff was friendly and servicial. Tue food was above the industry's average.

AMS
ATL
Excellent 9.3

Entertainment was good, and crew was very nice and accommodating. Flight was very comfortable and smooth.

The food was okay, not that great.

AMS
ACC
Okay 4.0

Flight was delayed for three hours and was a very stressful flight

Flight was not on time and got to destination very very late pier management of aircrafts

AMS
MAN
Good 7.0

The flight attendants could not do enough for you.

Business class was pretty empty but again I was not allowed to change my seat selection online. Pathetic check-in.

PIT
ATL
Excellent 10.0

Flight was on time and quick and comfortable

Thu, Apr 26
MXP
ORD
14h 35m
Wed, May 2
ORD
MXP
13h 30m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Mar 27
LIN
ORD
13h 45m
Sun, Apr 8
ORD
LIN
11h 15m
Trip: 13 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 14889 reviews
Overall
7.4
Boarding
7.6
Comfort
7.2
Crew
8.0
Entertainment
7.0
Food
6.9
LHR
AUS
Mediocre 2.0

Nothing it was a nightmare

The rude security staff, my previous British air flight from Dublin was 30’minutes late. Heathrow is terrible for connecting flights even with 2 hour leg room. What a joke. English people suck.

LHR
ORD
Good 6.6

Flight on time, friendly crew.

Not so good meals. For a 9 long-haul flight only one meal provided, other was a cheap candy bar. Other carriers do offer breakfast. Traveled with child and did not allow priority boarding at LHR. Limited leg room, I assume this already a trend well known by travelers.

GVA
LHR
Excellent 10.0

The 787 aircraft is better

BCN
LHR
Excellent 10.0

Nice, smooth, quick flight.

SEA
LHR
Excellent 8.0

Quality of food

Tue, Jun 19
MXP
ORD
12h 15m
Thu, Jul 5
ORD
MXP
19h 45m
Trip: 17 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5814 reviews
Overall
8.3
Boarding
8.3
Comfort
7.9
Crew
8.7
Entertainment
7.8
Food
8.0
ORD
ZRH
Excellent 10.0

Excellent Service. Excellent food.

ZRH
JFK
Okay 5.6

Food was actually really good.

Please let families with small children board early. This is the first flight I remember where I and other families with small children had to board with everyone else, and it's stressful for all involved.

ZRH
GVA
Excellent 8.4

New aircraft

Lost luggage. Flight delayed.

ZRH
VIE
Good 6.0

on board

12 of January, 2018 Dear Austrian Airlines authority, I address to your kind attention to asist me to get to me the hat qhich I lost on board of the flight 1576 when I arrived to Vienna airport on my way frpom JFK to Lwo. It happened because it was no room above my seat's bin and the steard helped me to get my heat in another bin. Unfortunately I forgot at the moment when I left the board of the plane, a minute later I reminded that I forgot my hat but I was not allowed to go back and get my hat. I tried to communicate with the Lot&Found office in Vienna airport as I had 2h40 minutes in connection time and it was enough time to get me back the hat, unfortunately nothing was really done from the airport staff to get me my hat and made to me possible continue traveling with my hat. I spoke to two managers, the name I could share with you if you need. The Found office registered my black hat and the plastic box under the number F2018/000682. In this situation I ask your offices to deliver my hat and the plastic box to Lviv airport as sson as possible as this is a special hat for my daily prayers. I wish you best and ask for your kind assistance to send the item as soon as possible with the nearest flight. Sincerely, Meylakh Sheykhet

BCN
ZRH
Excellent 10.0

Friendly service and food

Older plane with no entertainment

Tue, May 29
LIN
ORD
13h 00m
Tue, Jun 12
ORD
LIN
17h 00m
Trip: 15 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 1470 reviews
Overall
7.1
Boarding
7.1
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
BRU
KGL
Okay 5.0

Food was bad. Crew was distracted gossiping. They skipped rows during meal times as they were distracted. The seats are the most uncomfortable airline seats I've ever sat in.

TXL
BRU
Excellent 8.0

Also a good airline, though the a la cart...

The a la carte approach that includes charging 3 euros for water. I mean, seriously?

EDI
BRU
Excellent 8.3

It was easy boarding. The flight crew had been been late due to a bad taxi driver. We still arrived on time!

No complaints.

TLV
BRU
Good 6.4

The safety instructions movie was entertaining the first time. The crew was friendly overall.

Both my luggage items were lost on the way there and one on the way back. No free food or drink although the flight price is not that low.

ABJ
BRU
Excellent 10.0

Everything

Show more results

Milan to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Milan
Flight Price $433
Distance 4529 miles
Airlines Finnair, British Airways, Turkish Airlines, KLM, SWISS, Brussels Airlines, Lufthansa
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

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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.