$242 Find Cheap Flights from Chicago to Portofino

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Portofino departing on 4/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$428
Typical prices: $475-$1,134
Scandinavian Airlines
Sat 4/18Sat 4/25
ORD - MXP • 1 stop
Cheapest non-stop
$961
United Airlines
Tue 4/7Wed 4/22
ORD - MXP • Non-stop
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Flight Deals
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Flight Deals

Cheap Flights from Chicago to Portofino (CHI-MIL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Portofino that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Portofino

Sat, Apr 18 - Sat, Apr 25
Scandinavian Airlines Logo
7:15 pm - 8:30 am
ORD
-
MXP
30h 15m
1 stop
Scandinavian Airlines Logo
9:20 am - 4:10 pm
MXP
-
ORD
13h 50m
1 stop
$428Scandinavian Airlines
Wed, Apr 15 - Fri, Apr 24
Scandinavian Airlines Logo
7:15 pm - 7:10 pm
ORD
-
MXP
16h 55m
1 stop
Scandinavian Airlines Logo
11:45 am - 4:10 pm
MXP
-
ORD
35h 25m
2 stops
$430Scandinavian Airlines
Sun, Mar 15 - Wed, Apr 15
Scandinavian Airlines Logo
8:20 pm - 7:10 pm
ORD
-
MXP
16h 50m
1 stop
Scandinavian Airlines Logo
9:20 am - 4:10 pm
MXP
-
ORD
13h 50m
1 stop
$435Scandinavian Airlines
Wed, Feb 25 - Wed, Mar 4
Multiple Airlines Logo
6:30 pm - 12:10 am
ORD
-
BGY
22h 40m
2 stops
Multiple Airlines Logo
6:45 am - 5:20 pm
BGY
-
ORD
17h 35m
2 stops
$484Multiple Airlines
Wed, Feb 25 - Mon, Mar 2
Multiple Airlines Logo
6:30 pm - 9:00 pm
ORD
-
BGY
19h 30m
2 stops
Multiple Airlines Logo
10:10 pm - 5:20 pm
BGY
-
ORD
26h 10m
2 stops
$551Multiple Airlines
Tue, Mar 24 - Tue, Mar 31
ITA Airways Logo
8:50 am - 10:10 am
ORD
-
LIN
19h 20m
2 stops
ITA Airways Logo
7:30 am - 6:39 pm
LIN
-
ORD
18h 09m
2 stops
$564ITA Airways
Wed, Mar 18 - Tue, Mar 31
Delta Logo
12:47 pm - 8:05 am
MDW
-
MXP
13h 18m
1 stop
Delta Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
$831Delta
Thu, Mar 19 - Thu, Mar 26
Delta Logo
9:35 am - 8:05 am
MDW
-
MXP
16h 30m
2 stops
Delta Logo
6:55 am - 5:54 pm
MXP
-
MDW
16h 59m
2 stops
$896Delta
Thu, Mar 19 - Tue, Mar 31
KLM Logo
10:45 am - 8:05 am
MDW
-
MXP
15h 20m
1 stop
KLM Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
$941KLM
Thu, Mar 19 - Wed, Apr 1
KLM Logo
12:47 pm - 8:05 am
MDW
-
MXP
13h 18m
1 stop
KLM Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
$1,063KLM
Useful Info

Good to know

Cheapest flight$242
Flight from Chicago O'Hare Airport to Milan Malpensa Airport

When to book flights from Chicago to Portofino

Are your dates flexible? Find out the best times to travel from Chicago to Portofino based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Portofino

  • Which airports will I be using when flying from Chicago to Portofino?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Portofino does not have its own airport so you’ll be flying into nearby Milan All airports airport, which is 80.2 mi away.

  • What’s the cheapest day of the week to fly between Chicago and Portofino?

    Consider leaving on a Sunday and avoid Wednesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Tuesdays.

  • How does KAYAK find such low prices on flights from Chicago to Portofino?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Portofino.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Portofino?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portofino from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Portofino?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portofino with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Portofino?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portofino from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Portofino?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Portofino found on KAYAK was with Turkish Airlines for $323. TAP AIR PORTUGAL offered a round-trip connection from $398 and Scandinavian Airlines from $410.

Top tips for finding cheap flights from Chicago to Portofino

  • There is no airport in Portofino. Instead, you’ll be flying into Milan All airports when flying between Chicago and Portofino.
  • The cheapest flight from Chicago to Portofino was found 19 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 May, June and July. The cheapest month to fly is January.

Reviews of the top 5 airlines serving Chicago to Portofino

 
Need help choosing which airline to fly with from Chicago to Portofino? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9215 reviews
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
7.3Comfort
Airline reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

8.0 ExcellentAnonymous, Jan 2026
ORD - TPA
Read more United Airlines reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Fantastic. The only thing - out of my six luggage one was lost in Copenhagen, however it was delivered Home 3 Days later so all great..

The crew was friendly, the flight was pleasant. Thank you for your service!

Our trip plan from Kayak stated we were flying SAS. That was not true. The first leg was a Delta flight. We wasted 25 minutes before finding out to check in with the correct airline. Then our SAS flight for the second leg arrived 25 minutes late, and our third leg flight with SAS closed the gate knowing the flight delay was SAS’s fault, and that this flight would only be backed up 5 minutes. The final kicker was that between Delta and SAS, they lost all our checked luggage.

Flight was completely full January 9th? I problem i had the stewardess was bumping into me constantly walking by? very annoying.. on Austrian air I dint have this issue at all...

Amazing! Everyone was so nice and the food was so good!!

Terrible customer service. The flight attendants were rude. We experienced significant turbulence for a large portion of the flight and there was very little check in from the flight deck. The space was extremely limited to the point where it felt like torture. Never again

I was surprised how good an American airline can be - I was really impressed.

Excellent service throughout. Airport process is quick and easy. Very courteous staff. Great service in the plane! Just outstanding punctuality and service overall!!

I have paid for extra legroom on my flight. My seat was broken and did not recline. The crew could not fix it and refused to provide me with another seat

Over all experience was good. However the connection time was too short at CPG. We missed our connecting flight to AMS as the passport control line was too long and by the time we got our passport control done it was too late I wish there were some SAS staff to help us out at the passport control center Though they put us in a KLM flight from CPG to AMS, That flight was also delayed by over two hours

The trip was mostly nice, till the last moment when they had some issue with opening the flight door. The flight arrived late by 10 minutes, which was ok-ish, but then we got stuck on the plane for 35 minutes at the bridge and that costed our connection flight to LAX which left with 12+ passengers still on our flight. It added 2 days to our trip home, and we had to make lots of rearrangements to deal with the ripple effects. Don't book a 1+ stop trip with a layover time less than 2 hours.

Canceled my flight couple hours before takeoff. They could not find a decent re-routing and refused to pay for when i subjected alternative with Lufthansa.

Seats a little to soft on the SFO DUB flight

Well, I think we left close to on time. Crew was “eh”.

Flight takeoff was delayed an hour, but arrival time was not updated at the same time as departure time, so those picking me up at the other end were not alerted to the change in my arrival.

Seats are terribly cramped. I’m only 5’2” and my knees were practically in my face. No room to put a normal size bag under the seat and when the person in front of you reclined their seat your tray table was in your lap. This is the airline’s way of cramming more seats into the plane to make more money. I’ll think twice about taking Aer Lingus again since there are a few other options from Boston to the Emerald Isle.

Couldn’t check In online, message was couldn’t check in until Sunday morning though plane left Saturday night. Checked in okay at airport but caused slot if stress.

Staff was generally friendly and helpful. Attendants collecting trash were somewhat inattentive though.

We left 2 1/2 hours late. It wasn't the airlines fault but they did nothing to help the situation. Even water had a price tag. The next flight was better.

Fast and sensible boarding was absolutely amazing. But extortionate wifi and seats that barely moved, making me unable to sleep, didn't do a lot of favors.

Bad. They gave me a voucher for food to use at the airport but didn’t have time since I had to catch the other plane. No refunds and lack of communication

Late. Lack of updates. Rude hostesses. Terrible food. Lack of headphones.

Negative. Food was awful, seat broken, flight was late, baggage lost and damaged

Flight was delayed but crew gave little to no communication, then “began boarding” but really just had everyone stand up and wait for an hour without any news or updates, as if we were going to start boarding at any second. Total chaos. Seemed like this was their first time boarding a plane. When we arrived at our destination, we waited for over an hour for the baggage claim belt to even turn on. Probably waited at baggage claim for our luggage for close to two hours. Everyone was very confused and of course we all worried that the luggage was lost. Again, zero communication and everyone we asked just said “I don’t know.” So we were left wondering whether to wait, or file a missing baggage claim, or check the other baggage claim belts (which we did every fifteen-twenty minutes because we were just confused). Lack of communication throughout the experience was a huge issue.

The cabin crew were curt, not with me, but observed with other passengers. They were unduly rude and it was unprovoked and when they realized they were wrong, they made no attempt to apologize for their own confusion.

From Casablanca to Lisbon our baggage 2 pound over they want me to pay $120 for 2 pound which unexpected we are two family 8 of us they counters lady her customer service is not good I fly frequently for my business next time fly with TAP Air I will think twice

Booked business with TAP from LAX to Cabo Verde - overall ok, but just doesn’t feel like business class. More of a budget airline

Poor. Our flight was delayed and they told me I would be fine to make my connection in Lisbon, I missed it. Then they told me my bag would be automatically loaded onto my new flight to rome. It wasn’t. It’s been 4 days and I still don’t have it.

I like the price. I dislike the website where I wanted to ask questions about the unusual high prices of the luggage fees. I called the toll free number from the United States and I cannot get through. You should test your own toll free website for info and you will know what I am writing about.

Very borderline, low budget airline without low budget prices There are no counts of soda, everything is dispensed enlarged bottles and poured into tiny cups about 70 mL so in order to keep hydrated you have to take 3-4 cups at a time. Also, there was only one food item offered, pasta, they ran out of chicken right away. Snack was very poor. It was called tuna sandwich, which is truly borderline. The flight attend attendance seemed to be overworked and tired.

I was unable to board this flight because of visa changes that I was not alerted about and I’ve been unable to contact Kayak to obtain a refund / credit anything.

The issue was not with BA it was with the link yoiu sent fopr booking the flight

Loved the boarding option from Business class lounge, experience on flight was excellent, plenty of good food choices

Getting the boarding passes between the BA and AA apps was very clunky.

The airline was not clear about a new departure time so we got to the airport early anyway. The flight left early which was great because of weather. The check in process was very easy and staff were friendly and helpful. The crew was great and our flight was very good.

Awful it always is unfortunately is the only way to fly direct to london

Boarding was efficient and quick, crew was very attentive, seats were comfortable.

The space is tight. Either you sit straight up the whole time, but the minute you relax, your knees hit the back of the seat in front of you. My seat would not recline so I was quite uncomfortable. Didn’t use my tray table bc it was stained and sticky and nasty. I was also seating in one of the last rows and one crew member and people going to the bathroom kept hitting my elbow resting on the armrest.

Had a nice little suite although I couldn’t close the door (but I didn’t ask anyone to help). 5K is a nice seat and very private (you look in on first class). Enjoyable flight and nice crew.

The plane was known to be late in advance of takeoff. My guess is that it was known to be late at 11am or 5 hours before scheduled takeoff time. We were late to leave and with a wheelchair and the a cart, we only made it to gate. We raced! Inside plane, all was great

Everything you need to know for your flight from Chicago to Portofino

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