$186 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 1/27. 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.
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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

jeu., janv. 8 - sam., janv. 17
Scandinavian Airlines Logo
7:20 pm - 8:00 pmORD-MXP
17h 40m2 stops
Scandinavian Airlines Logo
11:15 am - 4:45 pmMXP-ORD
12h 30m1 stop
$446Scandinavian Airlines
Find Deal
jeu., janv. 8 - ven., janv. 16
Scandinavian Airlines Logo
7:20 pm - 12:05 pmORD-LIN
33h 45m2 stops
Scandinavian Airlines Logo
12:55 pm - 4:45 pmLIN-ORD
34h 50m2 stops
$446Scandinavian Airlines
Find Deal
mer., nov. 26 - mer., déc. 3
Scandinavian Airlines Logo
7:20 pm - 7:10 pmORD-MXP
16h 50m1 stop
Scandinavian Airlines Logo
1:00 pm - 4:45 pmMXP-ORD
34h 45m2 stops
$448Scandinavian Airlines
Find Deal
mer., nov. 12 - mar., nov. 18
TAP AIR PORTUGAL Logo
7:10 pm - 11:05 amORD-MXP
32h 55m1 stop
TAP AIR PORTUGAL Logo
5:45 pm - 3:00 pmMXP-ORD
28h 15m1 stop
$450TAP AIR PORTUGAL
Find Deal
dim., nov. 9 - mer., nov. 19
TAP AIR PORTUGAL Logo
8:25 pm - 11:35 pmORD-MXP
20h 10m1 stop
TAP AIR PORTUGAL Logo
6:20 am - 3:00 pmMXP-ORD
15h 40m1 stop
$489TAP AIR PORTUGAL
Find Deal
lun., nov. 17 - ven., nov. 21
Aer Lingus Logo
3:50 pm - 11:05 amORD-LIN
12h 15m1 stop
Aer Lingus Logo
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
$492Aer Lingus
Find Deal
lun., déc. 1 - mar., déc. 9
Aer Lingus Logo
3:50 pm - 11:05 amORD-LIN
12h 15m1 stop
Aer Lingus Logo
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
$495Aer Lingus
Find Deal
ven., nov. 14 - lun., nov. 17
Turkish Airlines Logo
11:50 am - 9:05 amORD-MXP
14h 15m1 stop
Turkish Airlines Logo
6:40 pm - 6:25 pmMXP-ORD
30h 45m1 stop
$496Turkish Airlines
Find Deal
mer., nov. 12 - mar., nov. 18
ITA Airways Logo
10:48 am - 10:10 amORD-LIN
16h 22m2 stops
ITA Airways Logo
8:00 pm - 6:10 pmLIN-ORD
29h 10m2 stops
$586ITA Airways
Find Deal
mer., mars 11 - lun., mars 23
ITA Airways Logo
11:00 am - 10:10 amORD-LIN
17h 10m2 stops
ITA Airways Logo
9:30 pm - 6:45 pmLIN-ORD
27h 15m2 stops
$618ITA Airways
Find Deal

Everything you should know

Cheapest round-trip
$446
Overall average: $661
Scandinavian Airlines
jeu. 1/8sam. 1/17
ORD - MXP • 2 stops
Cheapest non-stop
$1,105
United Airlines
mer. 4/1ven. 4/10
ORD - MXP • Non-stop
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We hope you love your trip to Portofino!
Useful Info

Good to know

Cheapest flight$186
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.

  • How long does a flight from Chicago to Portofino take?

    Direct flights cover the 4,526 miles separating Chicago and Portofino in about 12h 15m.

  • How many flights are there between Chicago and Portofino?

    5 direct flights run between Chicago and Portofino on a daily basis. On average, there are about 35 departures each week.

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

    Consider leaving on a Thursday and avoid Saturdays 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 Mondays.

  • 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 Scandinavian Airlines for $272. Scandinavian Airlines offered a round-trip connection from $446 and TAP AIR PORTUGAL from $450.

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 47 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 November, December and January. 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
Scandinavian AirlinesOverall score based on 1548 reviews
6.6Food
8.0Crew
7.3Comfort
7.6Boarding
6.6Entertainment
Airline reviews

No vegetarian option was provided for the regular meal or the pre-landing snack.

2.0 MediocreAnonymous, Oct 2025LAX - CPH
Read more Scandinavian Airlines reviews

No vegetarian option was provided for the regular meal or the pre-landing snack.

The Scandinavian flight was excellent, however the second flight was partnered with TAP Portugal which was not so good. crowded gate area with no chairs, delayed flight, bad boarding process, no entertainment system onboard, and the baggage didn’t get to the carousel until well over an hour which caused our taxi that was waiting to leave. Love SAS, hate TAP.

Great logistics and timeliness as we arrived quite early. Flight smooth and fast. Excellent entertainment. Plane itself was a bit tired and the crew mostly indifferent. Baggage took forever but that’s on CPH. Would use SAS again for sure.

Will not recommend SAS for business travel. Food was so-so. Service was very good. First leg was very good. Second leg from Copenhagen to Barcelona was terrible. We paid a LOT for business class and to have seats worse than most coach seats with no entertainment and no charging available for 1/3rd of the whole trip was not acceptable. Very disappointing. I thought they were coming back in the U.S. with style, NOT YET.

I do not have a problem with the airline but both my two suitcases that were supposed to go from Hawaii to Copenhagen didn’t get on the plane in Seattle. I arrive on Monday the 21st at 10:30 in the morning. I did not get my two suitcases before Friday late afternoon that is unacceptable.

No choice of food. Needed to pay more even for a can of coke!!!

The seats were really close together and hard to get comfortable. The food was okay. The cheese was amazing! I loved the cold towels they gave us.

When my flight was changed from delays they were quick to rebook me.

I really enjoyed how clean and big the aircraft was, as well as how friendly the crew was.

Airline left me stranded in the U.S. gave me an unrequested refund of 40% of booking and canceled my trip back! When I asked why, the said “we don’t have to tell you why”. “But you can rebook”. Never again! Paid 2x and rebooked on Austrian. What a joke!

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

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

The boarding process was not good. From check-in, there was only one desk for check-in, which made for a very long line. I asked to print out my boarding pass for the next leg of my trip, also via Aer Lingus, and they said they couldn't. I was unable to do this on the app or online, either. Many fellow passengers I spoke to had the same issue. Because the plane was delayed taking off by 90 minutes, everyone had to quickly go to a desk for their next boarding pass which was chaos. Overall it wasn't a smooth or happy experience.

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.

I liked the front row seats. A lot of leg room. The check-in window needs to be longer

Too hot. Asked for an extra glass of water and was ignored. Asked to sit in empty seats that were open because it was so hot and crowded and was denied and the seats were empty the entire flight

Terrible leg room - I’m 5’3” and my knees were touching the seat in front of me. When the person sitting in front of me leaned back, there was about 15 inches of space between my head and the TV screen which made it awkward to view movies. Last year they had decent food, but this year the only tasty item on the trip was dessert.

The flight was delayed leaving Philadelphia due to “catering” and consequently arrived in Dublin some 75 minutes later than scheduled. Consequently this caused me to miss my connecting flight to Glasgow and I had to spend the night in Dublin.

The flight from Cincinnati to Philadelphia was satisfactory and uneventful.

It was truly a horrible flight. We were delayed almost 2 hours. The seats were so tiny, my legs were hurting the entire flight. When i finally made it to Ireland i missed my connecting flight because we left Newark late. I will most likely never fly Aer Lingus again

The business class seats were smaller and closer together than other airlines.

Boarding- Good Seat Comfort - OK Crew - Good Food - Mediocre On Time - Very Good

Didn't like much. Wheelchair assistance was almost nonexistent. No one at TAP check in process helpful. On the plane, stewards were not friendly and disorganized. Food was terrible for 8 hr flight. We were skipped at snack time and even though we tried to get attention using overhead call system no one even looked up at us to acknowledge. Being at the back of first section and by the lavatory we only were able to request when they came to pick up everyone else's garbage and they were nonchalant...no apology or even choice. The 1/2 half bread with slice of cheese was a waste. Deplaning was horrible but I'll blame lisbon airport for that. Plane left late at made good time still arrived about 15 behind schedule and for using remote deplaning and bus to terminal took another 20 min to gate. Those with connections were highly stressed. Took us 2 hrs from landing to get to ground transportation and exit airport. And that was with wheelchair assistance.

The person at the checkin was very helpful. We couldn’t check in through the keyosk, but the agent was very helpful.

An old airplane with very uncomfortable seats in the Comfort “class! Small, narrow, and hard seat. Entertainment options are inferior, old movies. Boarding started at the back of the airplane, as we entered the aircraft last instead of after business class, risking the possibility that the comfort section would not have room for carry-on in the overhead bin. The food was ok. White wine was terrible. Overall, the flight felt worse than cheap airliners, and the price was as high as premium carriers.

I will avoid TAP if I can, the ground experience was very poor with bad behaviour from the ground crew and it was only a bit better on the aircraft.

I had a business class ticket from EWR to Madrid with a layover at LIS for 11 hours. It was obvious that I needed to pick up my luggage in Lisbon for 11 hours and check it in again when boarding the second flight to Madrid. Before buying the ticket, I called TAP customer service. Customer service assured me that I could get my luggage in Lisbon. When I arrived at Newark airport, I immediately asked to check my luggage to Lisbon. However, the TAP employee refused me, saying that I should resolve this issue upon arrival in Lisbon. She checked my luggage to Madrid. I asked the TAP employee at the gate to help me when boarding the plane, I asked the flight attendants manager on board the plane to help me. All the employees refused to help me and said that I should resolve this issue in Lisbon. It took me 4 hours to resolve this issue in Lisbon. I arrived at 11am and they didn't give me my luggage until 3pm. As a result, I was so tired after a sleepless night on the plane and 4 hours on my feet at the airport and all my plans were ruined that I couldn't fly to Madrid. It was a terrible experiance,

Check-in guidance for transfer flight, boarding, in-flight service, seat comfort, etc.

The seats were not designed to comfortably see people in coach for more than 10 minutes

We flew TAP last October from Newark to Lisbon. The meal was bad. This flight had good food. Also, this flight was delayed. There were TAP employees waiting at Lisbon to make sure we made our connecting flight. I find the TAP website and app frustrating, but the service once we reached the airport was very good

I don't know about the others but the flight attendant that took care of us had the absolute wrong approach "how do we dare asking for water or anything else for that matter"

Flying on the Boeing 787 from Seattle to London was everything that I expected. Every thing was great.

Not my definition of first class. No leg room and barely any recline. The food was good. The crew was great. The comfort for the price I paid for London to Cairo was highway robbery. The Wi-Fi didn't work for me either.

Seat pitch is not enough to eat comfortably. When seat in front is reclined, your screen comes closer to your face. Ryanair seats are actually more comfortable.

The leg from Portland to Heathrow was great for a business class ticket. The BA leg from Heathrow to Lisbon was terrible. Basically coach seating with an empty seat between you and next passenger. Absolutely no leg room. Should not have been charged for business class and it was a 3 hour flight.

The flat beds. Other than that, the place was not clean.

Moved me away from my family and refused to fix it.

I have always been pleased with their service. Would not change a thing

Seating and food was the worst we have experienced in 35 years of traveling for both personal and busines .

Economy seats felt more cramped than other flights we have taken.7 hr, painful sitting hours 6 and 7. Web site difficult to deal with. Originally put in for 1 special meal due to type 2. Meal was awful. Tried to change selection to standard for return flight, on app and website, unable to complete that action.

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