$208 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 10/30. 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

Tue, Oct 21 - Wed, Oct 29
Scandinavian Airlines Logo
7:15 pm - 10:30 amORD-MXP
32h 15m2 stops
Scandinavian Airlines Logo
7:50 pm - 6:45 pmMXP-ORD
28h 55m2 stops
$418Scandinavian Airlines
Find Deal
Mon, Dec 29 - Mon, Jan 12
Scandinavian Airlines Logo
7:20 pm - 7:10 pmORD-MXP
16h 50m2 stops
Scandinavian Airlines Logo
11:15 am - 4:45 pmMXP-ORD
12h 30m1 stop
$419Scandinavian Airlines
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Wed, Nov 19 - Tue, Nov 25
TAP AIR PORTUGAL Logo
7:10 pm - 4:55 pmORD-MXP
14h 45m1 stop
TAP AIR PORTUGAL Logo
5:45 pm - 3:00 pmMXP-ORD
28h 15m1 stop
$447TAP AIR PORTUGAL
Find Deal
Mon, Sep 22 - Tue, Sep 30
TAP AIR PORTUGAL Logo
6:10 pm - 11:00 amORD-MXP
33h 50m1 stop
TAP AIR PORTUGAL Logo
5:25 pm - 4:10 pmMXP-ORD
29h 45m1 stop
$451TAP AIR PORTUGAL
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Mon, Oct 6 - Fri, Oct 17
Aer Lingus Logo
3:45 pm - 10:40 amORD-LIN
11h 55m1 stop
Aer Lingus Logo
11:20 am - 7:00 pmLIN-ORD
14h 40m1 stop
$620Aer Lingus
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Mon, Oct 6 - Fri, Oct 17
Aer Lingus Logo
5:22 am - 10:40 amORD-LIN
22h 18m2 stops
Aer Lingus Logo
11:20 am - 7:00 pmLIN-ORD
14h 40m1 stop
$625Aer Lingus
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Mon, Aug 11 - Tue, Aug 19
ITA Airways Logo
3:00 pm - 10:10 amORD-LIN
12h 10m1 stop
ITA Airways Logo
7:00 pm - 1:10 pmLIN-ORD
25h 10m1 stop
$669ITA Airways
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Mon, Aug 18 - Tue, Aug 26
ITA Airways Logo
3:00 pm - 11:40 amORD-LIN
13h 40m1 stop
ITA Airways Logo
7:00 pm - 1:10 pmLIN-ORD
25h 10m1 stop
$685ITA Airways
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Wed, Nov 19 - Tue, Dec 2
Delta Logo
9:30 am - 9:05 amMDW-MXP
16h 35m2 stops
Delta Logo
11:05 am - 9:44 pmMXP-MDW
17h 39m1 stop
$834Delta
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Wed, Nov 12 - Wed, Nov 19
Delta Logo
10:35 am - 9:05 amMDW-MXP
15h 30m1 stop
Delta Logo
6:55 am - 6:36 pmMXP-MDW
18h 41m2 stops
$855Delta
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Good to know

Cheapest flight$208
Flight from Chicago Midway 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 14h 45m.

  • How many flights are there between Chicago and Portofino?

    6 direct flights run between Chicago and Portofino on a daily basis. On average, there are about 42 departures each week.

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

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

  • 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 ITA Airways for $243. Scandinavian Airlines offered a round-trip connection from $418 and TAP AIR PORTUGAL from $447.

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 March.

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 8896 reviews
7.7Boarding
6.6Food
7.1Entertainment
7.3Comfort
8.1Crew
Airline reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

10.0 ExcellentAnita, Jul 2025ORD - CMH
Read more United Airlines reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

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!

Painful seats for a 10 hour flight. There’s a very hard flat board in the seat that goes up to half the back and after 7 hours it gets impossible to find the right position to avoid the pain.

I paid for the seat with more leg room but on the day of my departure my seat was changed. I brought it to the airline costumer service and he was able to change it back. The person sitting next to me had the same exact issue.

Great experience. Typically do klm to Amsterdam but may start taking this flight in future - greatxexperience.

The food was wonderful! The blankets and pillows were a nice touch and the staff were very accommodating, making frequent rounds to offer food, drink, etc. We were also told in advance when to expect meals to arrive, which is thoughtful. I liked the early notification about the lack of headphones as well, although unfortunately I'm not sure we received on for the first leg of the trip, which would have been nice to prepare for. The seats are a bit tight, and the bright monitors on the wall were on during an overnight trip, making it difficult to sleep for those close to them. .

The check in not ok! Demanding that we check our carry ons on check in! When there was plenty of available space inside the plane! And the staff at check- in was rude and not helpful and I was traveling with my autistic son and his service dog! Boarding was easy since we were priority boarding! The crew was ok expect from one guy flight attendant that was actually great!

I appteciate the very courteous staff. The flight was good. Something that wasn't good was that my bag was only checked as far as Dublin and I had a connecting flight to Vienna. (That was a mistake the ORD desk made.) Fortunately the desk at DUB was able to re-tag without me having to re-check in (which initially it seemed I might have to do.)

I had an awful experience at the ticketing agent stand. I had purchased three tickets, one of which I had the maiden name of a passenger on the ticket. They refused to help, assist, and actually delayed our process and had us miss an opportunity to purchase a ticket on the same flight. I was sent through multiple phone calls, none of which helped, and the person at the counter was the person who told me to both call Aer Lingus for help and was the person who said they could not fulfill my request that they were privy to from the beginning. My partner is still stuck in Scotland, racking up thousands of dollars in additional fees and tickets. I am very upset and two of my tickets went unused. I will never be using Aer Lingus ever again and I will continue to complain about them.

When I booked the flight, I wasn't aware that this was a "no frills" flight. No wifi, no reclining seat, no complimentary soft drinks.

In business class overhead bins were minuscule. Had to use cabin staff to find a place for my carry-on bag. Boarding process was shambolic, as “passengers who needed assistance in boarding” absorbed an excessive amount of time and attention that Aer Lingus was apparently unprepared for.

Charging for coffee on a business class fare??? And to not even mention it? Inexcusable. Boarding and disembarking was pathetic. Could not use a jetway on either end. Had to use stairs and walk across tarmac at origination and use stairs and be bussed to terminal at destination.

It was excellent! The plane left Chicago early. Arrived in Dublin early. The crew was excellent! It was a great experience.

The food was mediocre, the coffee was terrible. The entertaining selection was plentiful. They lost my checked luggage which put a damper on my 10-day vacation.

Weeeeeeell, you folks know economy class on Airbuses well--you're packed in like sardines. We may actually spring for more expensive seats next time, with a little room to stretch out. NO room to stretch out in Airbus economy class! :-) Apart from this, the food was decent (considering that it's mass-produced, and has severe spatial restrictions of its own), the staff were friendly enough, and there was a wide selection of movies, etc. to watch. Overall, I'd tend to use the word "adequate" rather than "exceptional" for my experience. But really, how could it be otherwise?

Seats were less comfortable and tight from Newark to Dublin, than my second flight ( small segment from Dublin to Lyon). Movie audio was with frying sound overall. Yet the worst was as follows: one male, (dark hair , glasses on) from the crew member was so cold and rough, while I remained with constancy polite and kind. Per exple with the noise level I could not hear him at first for beverages, he rolled his eyes at the third times I finally heard him. From the start, loading my small hand bags , he directly spoke to me and said “ I had to keep my shopping bad by my seat, under , while there was sufficient room and I was among the last to sit. I show him the space , his face was always dull, stoic, not welcoming as the usual crew members from any airline companies are. When I think of my experience I liard w Aer Lingus, this is the image that gets back to me. Needless to say that as a passenger and client, I felt belittled since all this happened in front of the surrendering passengers. It s an affront and not a pleasant feeling especially when being traveling which oftentimes involves stress with carrying, and making it on time. I m not happy with the experience I had to be honest and I fly four times a year. Thank you for allowing me to share this statement with your company.

One cold drinks service. No snacks with drinks. No tomato juice or apple juice, coke - only fanta or sprite then ran out of that. Went to gally after meal service no one there / no self service for water at least. Waited 25 min for cabin crew to assist. No recycling of cardboard/ plastic - all put to garbage. Breakfast was a nutrigrain bar and an orange juice. Also I'm sure I booked a flight with checked luggage allowance but had to buy extra when I had my booking confirmation. Movies were good. Chairs comfy. Pillow and blanket and ac vents.

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

The airport temperature at the airport and on the flight was too warm

Flight being delayed for 35 minutes had me lose the connection to my transport

boarding is so disorganized, i was literally appalled at the boarding experience

Comfortable but not Polaris or Delta comfort Business Class. Overall 7 out of 10

Tap air Portugal was the best I will traveling again with u guys. Thank u.

The long wait at JFK made the trip horrible. Also not having enough buses when we deplaned was annoying

Flight was delayed on 6/20 to miss international connection. Next flight out was 24 hours later. Not acceptable.

Food was edible, not great, and served by attendants who looked like they really were not happy working the flight. The section I was in was too warm making the 11 hour flight uncomfortable. Other areas on the plane were fine.

Checked bG chstgr was extremely high. Over $120. It was s bsit and switch knowing an international passenger would have t9 check a bag.

My experience with British Airways is excellent, thanks for all 🫶🏻✈️

Old tired plane, Uncomfortable business class seat. Breakfast dreadful and meagre. At least flight was on time!

Boarding market okay just because of the delay we had, but not related to the crew in any way…

Safe arrival. Improvement on Time efficiency Effective Communication will be great.

The crew is very friendly and helpful. The food is good for airplane food. The flight is long and hard to sleep. The leg space is great. The plane arrived in plenty of time.

A good flight back to Tampa and thankfully although we had a 90 minute delay because of thunder storms from Charlotte to bottom iof Florida, it was a prudent to avoid these for a comfortable flight as opposed to being tossed around with turbulence.

They removed our booking without telling us. Cost us thousands to book last minute

Enjoyable flight, helpful crew everything was organized to accommodate passengers.

Captain sick. Unable to get replacement so delayed me 30 hours, many others delayed 54 hours. TOTALLY DESTROYED ALL MY PLANS, including lost my rental car which would now cost over 5 times what I paid so stuck with buses n trains... lost hotel reservations.... HORRIBLE!!!

The international flight from PHL to Lisbon was one of the worst I’ve experienced, ever. What was really disappointing was the entire experience of comfort and service in the coach cabin after takeoff. The food was inedible and the wine served with dinner was such low quality - it tasted of petrol. I couldn’t eat more than a bite or two of the chicken entree, being worried it would make me ill. The service took so long to reach the entire coach cabin, I ended up having the lights turned off on me as though I had to rush though dinner (though as I mentioned, it wasn’t as if I ate much - only the salad). Most of the attendants seemed generally annoyed and were not friendly or polite. While there was some turbulence, it wasn’t too uncomfortable and I know that is just a chance. The temperature of the cabin was so warm, even a friend a row or two up and on the other side of the plane felt like this. To top it all off, the seat was so uncomfortable and flattened/overused, I had back pains for DAYS afterward.

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