$297 Find Cheap Flights from Chicago to Portofino - Compare and Save

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 10/4. 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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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$613
Typical prices: $799-$1,288
TAP AIR PORTUGAL
Wed 9/9Wed 9/16
ORD - MXP • 1 stop
Cheapest non-stop
$772
United Airlines
Wed 10/28Thu 11/5
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

Wed, Sep 9 - Wed, Sep 16
TAP AIR PORTUGAL Logo
6:00 pm - 4:25 pm
ORD
-
MXP
15h 25m
1 stop
TAP AIR PORTUGAL Logo
5:30 pm - 12:40 pm
MXP
-
ORD
26h 10m
1 stop
$613TAP AIR PORTUGAL
Sun, Oct 11 - Sat, Oct 24
TAP AIR PORTUGAL Logo
6:00 pm - 11:00 am
ORD
-
MXP
34h 00m
1 stop
TAP AIR PORTUGAL Logo
8:00 pm - 4:30 pm
MXP
-
ORD
27h 30m
1 stop
$614TAP AIR PORTUGAL
Tue, Sep 8 - Tue, Sep 15
Turkish Airlines Logo
11:25 am - 1:15 pm
ORD
-
MXP
18h 50m
1 stop
Turkish Airlines Logo
3:15 pm - 9:40 am
MXP
-
ORD
25h 25m
1 stop
$618Turkish Airlines
Mon, Sep 7 - Mon, Sep 14
Turkish Airlines Logo
8:10 pm - 1:15 pm
ORD
-
MXP
34h 05m
1 stop
Turkish Airlines Logo
7:45 pm - 9:40 am
MXP
-
ORD
20h 55m
1 stop
$626Turkish Airlines
Tue, Sep 8 - Tue, Sep 15
Multiple Airlines Logo
11:25 am - 6:55 pm
ORD
-
MXP
24h 30m
2 stops
Multiple Airlines Logo
3:05 pm - 9:40 am
MXP
-
ORD
25h 35m
2 stops
$652Multiple Airlines
Tue, Sep 8 - Tue, Sep 15
Multiple Airlines Logo
11:25 am - 6:55 pm
ORD
-
MXP
24h 30m
2 stops
Multiple Airlines Logo
3:05 pm - 9:40 am
MXP
-
ORD
25h 35m
2 stops
$653Multiple Airlines
Sun, Oct 11 - Sat, Oct 24
Scandinavian Airlines Logo
7:15 pm - 7:10 pm
ORD
-
MXP
16h 55m
1 stop
Scandinavian Airlines Logo
9:20 am - 4:10 pm
MXP
-
ORD
13h 50m
1 stop
$757Scandinavian Airlines
Fri, Oct 16 - Sat, Oct 24
Scandinavian Airlines Logo
7:15 pm - 7:10 pm
ORD
-
MXP
16h 55m
1 stop
Scandinavian Airlines Logo
9:20 am - 4:10 pm
MXP
-
ORD
13h 50m
1 stop
$757Scandinavian Airlines
Wed, Nov 25 - Sat, Dec 5
Lufthansa Logo
9:50 pm - 4:30 pm
ORD
-
MXP
11h 40m
1 stop
Lufthansa Logo
6:10 am - 6:25 pm
MXP
-
ORD
19h 15m
1 stop
$759Lufthansa
Sun, Nov 8 - Wed, Nov 18
Lufthansa Logo
9:35 pm - 1:15 pm
ORD
-
MXP
8h 40mnonstop
Lufthansa Logo
6:55 am - 1:10 pm
MXP
-
ORD
13h 15m
1 stop
$773Lufthansa
Useful Info

Good to know

Cheapest flight

$297
Flight from Chicago to Bergamo

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 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 5 days, the cheapest one-way ticket between Chicago and Portofino found on KAYAK was with United Airlines for $588. TAP AIR PORTUGAL offered a round-trip connection from $401 and Scandinavian Airlines from $420.

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 7 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 February.

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 1906 reviews
6.8Food
7.7Boarding
8.0Crew
6.8Entertainment
7.3Comfort
Airline reviews

The crew was amazing. Our seats was not very clean and even that was not a full flight but our seats was right beside the WC which did not let us to have a moment of rest.

6.0 Goodkarso, Jul 2026
IAD - CPH
Read more Scandinavian Airlines reviews

The crew was amazing. Our seats was not very clean and even that was not a full flight but our seats was right beside the WC which did not let us to have a moment of rest.

Excellent service, and came on time! Thank you for your dinner that was chicken with salat/, and 🍰 it was good quality food , the breakfast was very good with good cheese , butter,etc and the tea was very good quality. The space where I was seat was nice so I could stretch my legs. I dit not have the bread as I am in a keto died. Have great time everyone in Scandinavia airline.

They lost my luggage and can’t find it. My trip is ruined. Online tracking of lost luggage doesn’t work

Seat was lumpier than I’ve ever remembered it to be although comfortable when tilted back. I don’t recall being that hungry after being served food from SAS before. Flight attendant on the second flight to Aalborg seemed to be having a bad day.

They charge for bottles of water which is crazy period we hit turbulent weather and it's in a good job period

On this shorter leg and with an older plane, just mediocre. On the connecting long haul (Chicago to Copenhagen) everything was great.

My outbound flight was incredible... Milan to Chicago. The crew worked so well together. Each passenger felt spoiled and incredibly valued. The crew on this flight was fine. Nothing to complain specifically about but could not give top rating only because of the superior crew, hospitality, warmth we felt on the first flight. Unfortunately. You managed to lose my luggage ..my only piece checked in. Lost in Copenhagen so I had the added stress, time wasted to file the report. To make things worse, Italian rail decided to strike that Sunday so I could not take the train as planned back to Switzerland. Horrible waiting time and poor communication for boarding substitution bus. The substition bus to the town of Stabio did not run on time and was late about 40 minutes.

Other than a delay that had nothing to do with the staff, it was a very pleasant experience.

The flight was cancelled early on and messed up the whole vacation and hard to get a refund from Kayak as they owned the ticket and of course they did not believe that SAS cancelled the ticket. Definite bad side to third party. SAS had rescheduled but overlapped the connecting flights. That did not work. Flight was cancelled long ago but Kayak still has it. Like it was taken? Bad IT ? Or all assumptions and no follow up which is the whole IT world. It needs to wake up and be more efficient. Especially as the world is going, there will be no freedom to do anything. And we will be living like the Middle Ages. Yeah, go read up on that while you still can.

Boarding the plane outside in the rain was a pain. Very safe flight

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

I love flying with them, the long-haul was fantastic. The short flight from Dublin --> Switzerland was horrible though. Most narrow seats I ever had, first and only time in my life I couldn't even close the seatbelt in seat 1A which was very embarrassing so I had to sit in the middle, because that seatbeld was 20cm longer. No idea why seat 1A would have a much shorter belt, it's just ridicilous. Also I hate the fixed seats, way too narrow.

OK overall. Flight was delayed Crew on flight was good

Late late late. Delayed and arrived an hour late for a 1 hour 45 minute connection. Every time. Poor record for this company. I try to fly any other carrier first.

I flew economy class. Seats were very good and the crew was excellent

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 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.)

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

We couldn't talk to aer lingus we had issues with the flight change and aer lingus made us talk to kayak

Horrible. Garbage airline. Due to the strike we got a replacement plane/crew. I didn't get my exit row seat I paid for. Food was horrible. Plane was hot and didn't have AC vents.

Are Longus was fine. I booked thru Kayak and was unable to get my business class seat early. Sat next to galley. Crew forgot to wake me for breakfast.

They blocked me from checking in online and they charged me lots of money

Everything was good with Tap Air Portugal. It was Logan Airport that was a problem. The fuel system was down and delayed my 10:40 boarding. I wasn't able to board my flight until 2:00 am...after that my flights were great.

Not have my bag forced to be checked when I had a carry on included on my ticket. Staff was very rude to me for asking why they were doing this. I was told there was no more room for carry ons but there was plenty of space in the overhead compartments

The crew was excellent. What I did not enjoy was the food. I have taken many international flights and this was on the low end. Otherwise the trip was fine.

Seats were the most uncomfortable seats i ever experienced on a flight to Europe from Boston. It was a waist of money in buying premium seats for top dollars. I want my money back for what i paid extra for my seats. Awful conditions!

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

As far as I could tell, there was no food service(!) on this flight. Like the attendants were on strike? No entertainment or wifi. Like, I didn't even know where we were unless I looked out the window and tried to recognize landmarks. Never had such a flight. I think you would have had to pay for water but they never offered that service.

Tap air portugal first has you pay for the flight. Then you realize that seats are extra. Had i known that i would have booked emirates instead for a few dollars more

Everything was nearly perfect, and TAP staff were especially helpful when we missed our connecting flights and had to get on the next flight to Rome. The only aspect that could have been better was boarding: it was somewhat disorganized, which created a bit of stress. But in the end, everyone got on the plane, so the less-then-perfect boarding process did not take away from the overall excellent experience.

Two of three flight attendants were not super kind as I would expect. The very kind young lady in my section was wonderful but then lady and man up front were not. Sorry but it makes a difference !

It was okay. Mothers with rowdy children should be invited to sit in front of them.

Good food, overall very comfy. The flight was full so obviously not optimal, but it is what it is.

Flight was delayed by several hours and then cancelled due to weather. But Staff was very helpful getting me on a different flight. United should offer food coupons and tooth brush and paste for stranded passengers

I had a good comfortable seat. There was nearly an hour delay. There was an accident with the champagne, but I was well compensated. These things happen sometimes.

We missed our flight. There was not enough time built into the layover to get through immigration, customs, bagclaim, bag rechecking, and the long trip to another terminal and gate. Kayak really screwed up. We took the bus up to Wisconsin and then were picked up in Brookfield by private car. It was lucky we didnt miss the last bus out.

I tried both on line and by calling the Customer Service line to arrange for a special meal as i have food intolerances. I was under the impression from your service representative that I was successful. I was not. I cannot eat spicy foods and get very ill if i eat bell peppers. I could not eat either menu choice and no special meal was actually ordered. ( your representative tried to order it for a flight that did not have meal service!!! - found this out later). Your wonderful cabin crew managed to put together a fruit, salad, roll and cheese tray for me so I had something to eat. WHY WOULD YOU SERVE SPICY FOOD, WITH NO MILDER OPTION,ON AN INTERNATIONAL FLIGHT???

I liked Quiet people around me. Crew could have helped people with overhead luggage so they aren't moving other peoples bags around and causing problems for people that had there bags there first

The plane was delayed by two hours in Chicago which led to us missing the next flight. Lufthansa rebooked the flight and booked us a hotel for the night in Frankfurt. The level of customer service and getting us taken care of was superb. The flight crew and the service on the ground was superb.

The row of seats were so cramped it was difficult to get in and out of your seat. I even upgraded. A long flight and sad accommodations 😵‍💫 the shorter flight was very comfortable and the seating was spacious

I have flown with many airlines. My first time was several years ago. Now I remember why I avoided them for so long. Lufthanza is the only airline who has ever raised a size/weight issue with my modest standard size carry on. I had to repack three times to meet their carry-on weight criteria. (Apparently the rules of physics apply differently on Lufthansa flight than on other airlines.) In the meantime their staff was quite rude, repeating meaningless phrases like "Rules are Rules." And ignoring the additional fact that weight is also weight, whether it is in found in your carry on or in your suitcase. They eventually acknowledged that customer service and satisfaction is, for them, a low priority. Never choosing Lufthansa again.

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

Complete your trip to Portofino with a hotel stay or car rental