$245 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 4/21. 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
$508
Overall average: $1,162
Scandinavian Airlines
Fri 8/21Sat 12/12
ORD - MXP • 2 stops
Cheapest non-stop
$1,185
Austrian Airlines, Lufthansa
Wed 4/15Wed 4/22
ORD - MXP • Non-stop
Arrival airport
You can't fly directly to Portofino. It is served by Milan (MIL), located 80.2 miles from Portofino.
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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

Fri, Aug 21 - Sat, Dec 12
Scandinavian Airlines Logo
7:15 pm - 7:50 pm
ORD
-
MXP
17h 35m
2 stops
Scandinavian Airlines Logo
11:15 am - 4:45 pm
MXP
-
ORD
12h 30m
1 stop
$508Scandinavian Airlines
Sat, Apr 18 - Wed, Apr 22
Scandinavian Airlines Logo
7:15 pm - 11:20 am
ORD
-
MXP
33h 05m
2 stops
Scandinavian Airlines Logo
9:20 am - 4:10 pm
MXP
-
ORD
13h 50m
1 stop
$528Scandinavian Airlines
Sat, Apr 18 - Tue, Apr 21
Scandinavian Airlines Logo
7:15 pm - 8:30 am
ORD
-
MXP
30h 15m
1 stop
Scandinavian Airlines Logo
3:55 pm - 4:10 pm
MXP
-
ORD
31h 15m
1 stop
$531Scandinavian Airlines
Sat, Apr 18 - Tue, Apr 21
Scandinavian Airlines Logo
7:15 pm - 6:00 pm
ORD
-
MXP
15h 45m
2 stops
Scandinavian Airlines Logo
3:55 pm - 4:10 pm
MXP
-
ORD
31h 15m
1 stop
$532Scandinavian Airlines
Tue, Apr 28 - Tue, May 26
Turkish Airlines Logo
11:25 am - 6:00 pm
ORD
-
MXP
23h 35m
1 stop
Turkish Airlines Logo
6:50 am - 9:40 am
MXP
-
ORD
33h 50m
1 stop
$553Turkish Airlines
Tue, Apr 14 - Tue, May 19
Turkish Airlines Logo
8:10 pm - 6:00 pm
ORD
-
MXP
14h 50m
1 stop
Turkish Airlines Logo
2:55 pm - 9:40 am
MXP
-
ORD
25h 45m
1 stop
$556Turkish Airlines
Tue, Apr 14 - Tue, Apr 21
Multiple Airlines Logo
7:25 pm - 12:25 am
ORD
-
BGY
22h 00m
2 stops
Multiple Airlines Logo
6:00 am - 6:15 pm
BGY
-
ORD
19h 15m
2 stops
$593Multiple Airlines
Mon, Apr 13 - Mon, Apr 20
Multiple Airlines Logo
4:05 pm - 9:40 pm
ORD
-
BGY
22h 35m
2 stops
Multiple Airlines Logo
10:50 am - 1:20 pm
BGY
-
ORD
33h 30m
2 stops
$595Multiple Airlines
Tue, May 12 - Fri, May 22
Delta Logo
1:59 pm - 11:20 am
MDW
-
LIN
14h 21m
2 stops
Delta Logo
11:00 am - 6:33 pm
LIN
-
MDW
14h 33m
2 stops
$1,252Delta
Sun, May 24 - Wed, Aug 19
Delta Logo
1:22 pm - 11:20 am
MDW
-
LIN
14h 58m
2 stops
Delta Logo
6:40 am - 6:31 pm
LIN
-
MDW
18h 51m
2 stops
$1,362Delta
Useful Info

Good to know

Cheapest flight$245
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 Saturday 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 Wednesdays.

  • 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 $355. TAP AIR PORTUGAL offered a round-trip connection from $401 and Scandinavian Airlines from $403.

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 9431 reviews
7.1Entertainment
6.6Food
8.1Crew
7.3Comfort
7.7Boarding
Airline reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

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. :/

IAH to Istanbul was outstanding across the board. The flight from Istanbul to Male was good, not great.

the cabin was kept too hot. couldn't sleep as a result

It was an amazing experience. Flight crew's service, hospitality, and the food were phenomenal. I don't think I'd want to try any other airline company after this. I would definitely recommend to friends and family. Thank you Turkish Airlines !

Business Class pods are horrible. If you're petite, you might be able to sleep on the uncomfortable seat and bed. Crew and food are fantastic.

I have travelled many times on Turkish, but they always board at least 30-40 minutes past the stated time. If informed properly, passengers can choose to spend more time in the .lounge instead of standing around by the gate waiting to board. The new lounge at DFW was a big disappointment. The aircraft itself was a shock. In the past I have flown this sector with regular business class seating configuration of 1-2-1, The 2-3-2 seating is very disappointing after paying such high prices for tickets. The DFW to Istanbul segment was slightly better, but the Istanbul to Delhi segment was no better than premium economy. I will try to travel more on airlines which give business class passengers more value for their money.

Good overall. Seat spacing a bit tight between IST and ISB.

Excellent staff despite some trying passenger situations. Very impressed with their good attitudes and kindness.

Crew were unfriendly, touch screen for movies didn't work very well, seats were tight and uncomfortable

After arriving in Istanbul, the transit information on the electronic board showed a tight departure time, and the gate changed in the middle, making it difficult to make it on time.

Typically good service onboard but baggage delay in airport was significant

Crew members were excellent. The seat wasn’t the best as well as a food options.

5 of my 7 pieces of luggage are missing and they cant call to find out where it is. I have to fill out a form and wait for them to mail it to me in several days (if they find it). That does not work for my travel itinerary. I need my full ticket cost refunded please.

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!!

The pre-check (passport control) for all US flights from Dublin airport is brilliant, meaning these flights come into the domestic airport in the US - it was so quick and easy getting to my hotel once we landed. The plane itself was great, staff were lovely and food was fine.

Punctual, smooth flight. Crew excellent and cabin very clean. Paid for WiFi but once you close out you cannot get back in even if you paid for entire flight.

Flight crew was superb. Meal was one of the meals at altitude I’ve had

Like getting a bus. No great luxury but will get you there

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.

Absolutely unacceptable level of service for a Business class: lousy drink and food options, disgusting food (inedible meat, watery rice, etc...), pathetic level of attentiveness from staff, Business class restrooms were not accessible for long periods because blocked of by staff...overall extremely disappointing, will NEVER fly Business on TAP again.

First time flying Business with Tap, I think it was a very good experience. It beats many domestic US carriers, the food options were really great, authentic Portuguese food, wines & deserts. Next time will do the free 24-48 hour stopover in Lisbon or Porto for sure.

We upgraded to business class. Nice seat with lots of room but otherwise not impressive.

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

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

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