$266 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 9/9. 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 Flight Deals 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.

Recent round-trip flight deals from Chicago to Portofino

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Portofino.
Discover the best prices for you by selecting your travel dates on KAYAK.
Scandinavian Airlines Logo
7:15 pm - 7:15 pmORD-MXP
17h 00m1 stop
Scandinavian Airlines Logo
11:15 am - 4:45 pmMXP-ORD
12h 30m1 stop
$413Scandinavian Airlines
Find Deal
Tue, Oct 14 - Thu, Nov 6
Scandinavian Airlines Logo
7:15 pm - 7:55 pmORD-MXP
17h 40m2 stops
Scandinavian Airlines Logo
11:15 am - 4:45 pmMXP-ORD
12h 30m1 stop
$420Scandinavian Airlines
Find Deal
Tue, Oct 14 - Thu, Nov 6
Scandinavian Airlines Logo
7:15 pm - 2:45 pmORD-MXP
12h 30m1 stop
Scandinavian Airlines Logo
8:05 pm - 4:10 pmMXP-ORD
27h 05m1 stop
$423Scandinavian Airlines
Find Deal
Mon, Oct 6 - Mon, Oct 20
British Airways Logo
4:50 pm - 11:20 amORD-MXP
11h 30m1 stop
British Airways Logo
9:45 pm - 1:50 pmMXP-ORD
23h 05m1 stop
$682British Airways
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Wed, Aug 13 - Thu, Aug 14
ITA Airways Logo
3:00 pm - 8:10 pmORD-LIN
22h 10m1 stop
ITA Airways Logo
7:00 am - 1:10 pmLIN-ORD
13h 10m1 stop
$742ITA Airways
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Wed, Sep 17 - Wed, Sep 24
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
$763Aer Lingus
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Sun, Aug 31 - Wed, Sep 10
United Airlines Logo
10:35 am - 7:30 amORD-MXP
13h 55m1 stop
United Airlines Logo
11:15 am - 11:25 amMXP-ORD
31h 10m2 stops
$775United Airlines
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Wed, Aug 13 - Thu, Aug 14
ITA Airways Logo
3:00 pm - 8:10 pmORD-LIN
22h 10m1 stop
ITA Airways Logo
4:00 pm - 1:10 pmLIN-ORD
28h 10m1 stop
$782ITA Airways
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Fri, Sep 12 - Tue, Sep 16
British Airways Logo
10:45 pm - 5:50 pmORD-LIN
13h 05m1 stop
British Airways Logo
7:15 am - 1:55 pmLIN-ORD
13h 40m1 stop
$804British Airways
Find Deal
Sun, Oct 26 - Thu, Nov 6
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
$814Aer Lingus
Find Deal
Wed, Jul 23 - Wed, Aug 6
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Good to know

Cheapest flight$266
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.

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

    Direct flights cover the 4,526 miles separating Chicago and Portofino in about 11h 30m.

  • 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 Tuesday 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 TAP AIR PORTUGAL for $288. Scandinavian Airlines offered a round-trip connection from $413 and TAP AIR PORTUGAL from $471.

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 November.

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 8696 reviews
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
Airline reviews

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

8.0 ExcellentAnonymous, Apr 2025ORD - SFO
Read more United Airlines reviews

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.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats were really cramped. The high backs on the chairs made you feel claustrophobic.

Boarding was chaotic and the flight left late but arrived at a decent time. This may have been because of the sxsw festival that was going on.

The flight got canceled and you just send an email in the middle of the night and no solution to how to get on the next flight or provide other solutions.

You cost me my time and did not compensate properly. Gfy.

Missed a connecting flight and SAS was at fault. I was awarded a $20 voucher in exchange for 8 hours of my time? Gfy.

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.

All flights were on time! The crew was nice and polite Thank you. Food was awful. They give you terrible pasta or rice dish and make you pay for chicken if you’d like meat. When I asked for water with my tea, they told me, I’d have to pay 3 euros for water. Restrooms were filthy half way through the flight.

The meal offered was fish. I am allergic to fish. When I told her, she just took the box of food back without offering me an alternative.... I had to ask... can I then have a bag of chips? She did give it to me. I am a Euro Bonus gold member. Please just take the time to offer something else. Easy and from a customer service point of view, .... Considerate.

It was ok. Vegan meal was good, however no complimentary alcoholic beverages.

The food service was absolutely rubbish. Very arrogant crew. Does Scandinavian airlines think everyone eats meat??? I paid for my flight but could not eat anything because I am vegetarian!!! I was hungry for 7 hours . I demand for refund! This is absolutely unacceptable!!!! If you want more customers keep an open mind!!! Cater to all meal needs. I have flown many airlines and I never make a special request online never! They always have vegetarian options. SAS has no idea of customer service. Shitty service

It was ok not that much because I always travel with Emirates airlines, Etihad, airlines, Qatar airlines compare to them food and comfortable was too low . Staff was good . Helpful

I believe it was short flight in plane I understand not that much compared to other airlines but weighting for checkin was too long need extra person for checkin or Atleast someone to let the customer knows don’t worry someone will be here shortly.

Noted in last review. Good to know, though air Lingus on European flights does not offer any food or drink, even though we were on the plane for 3 1/2 hours from Naples to Dublin everything you had to purchase even water.

Boarding seemed a bit chaotic and we had to walk outside across the tarmac. Passengers of all ages had to drag carry on luggage up the outside stairway into the aircraft. There was no WiFi. Very uncomfortable crammed seats. Glad in-air time was only an hour!

Booked through Kayak, couldnt take flight, Kayak punted to Orbiz, Orbiz punted to Aer Lingus, Aer Lingus said sorry about your luck, try Kayak/Orbiz. Terrible customer service collecting air fares and not even offering a voucher when customers cant take flight

There was no flight. I booked a flight from Toronto to Bordeaux with a stopover in Dublin. I arrived in Dublin and the flight number I had didn't exist and the flight going to Bordeaux I wasn't on. I had to book a new flight with a different airline for later in the day and pay out of pocket.

Gate agents kind of serious. Had to wait til arriving at gate to choose seats. Thankfully they did give us seats together! And grateful the honored our age, giving us seats at the front.

Very polite and helpful staff. Jet blue…ok, but not as helpful!..

Seat was very uncomfortable. The worst in all of my travels. It sagged in the middle, worse than anything any airline can offer. Not flying aer lingus again.

My Aer Lingus flight (booking ref # 2SU4LF) was the worst travel experience I have ever dealt with. My flight from Paris to Dublin was delayed by over 2 hours which caused me to miss my connecting flight back to the US. I was not able to be rebooked on a new flight for another 3 days. When I finally made it on my rescheduled flight, it was delayed AGAIN, causing me to miss my connecting flight from New York to Boston. At this point I decided to just rent a car since the next flight I would have been able to get in wasn’t for another 5 hours. It was a complete nightmare experience and I will never fly Aer Lingus again. I have requested a refund from the booking company I placed my order with.

We ordered a gluten free meal and never got it!

The seats are horribly uncomfortable. We were in premium economy and paid a premium price yet, the seats were the worst! You could feel every structural bar in the seat, there was no padding, no amenities kit, and the leg rests were broken. Duct tape was holding another seat together. When we arrived at our final destination, Venice, my suitcase was ripped open, and my clothes were about to fall out of the bag. I would’ve been more comfortable if I flew a paper airplane across the Atlantic.

The company tries shamelessly to squeeze every dollar)Euro out of its passengers. During the check-in the force you to go through the seat selection, you can skip it. They will assign you the worst seat available, then show you the other available seats on the map, for a fee. But they won't show you the fee until you click on it. And once you do click, there's no way to unselect it!! You will get stuck and forced to pay for that seat. Cheaters!!

Seats weren’t comfortable. Both of our seat backs were either almost straight vertical or laying back into the laps of the people behind us, which is a weird angle to try to get some sleep even on a plane. No in between. Also, neither seat would spring forward like they should.

There wasn't a time for neither food morning entertainment in a short one hour hop over.

Flight on time, flight assistants super nice, business class very comfortable. The whole experience was very good.

It is the worst ever airline. All employees I spoke with over the phone were pompous asses.

The gate information was never populated on the Delta app or the airport displays or the desk at the Delta lounge. We found at the last minute that we had to switch terminals and just made it to our flight. Even this we found accidentally by asking an employee at another gate. On board service was poor. Seats were very poor. All in all a poor experience. At best like a Premium Economy on other airlines

No online or self check in. Sent emails in Italian language. In general, not recommended airline company.

You idiots…ITA cancelled our flights one month out and we had to buy new tickets at a much higher price. You stiffed us by not refunding the cost of the insurance. I’ll never buy through Kayak again.

Too much long line at the TSA and Security. Prepare for long walk for baggage claim.

The flight from Seattle was delayed, which made me miss my connection to Florence. I was re-booked NINE HOURS LATER!!! That’s basically a vacation day lost. British Airways needs to partner with other airlines when possible to get a more realistic travel time, if delays occur. I realize there aren’t many flights to Florence from London, so I would book differently were I to return. The actual flight from Seattle was very comfortable and the crew was great, no faults there. I enjoy British Airways, this was an anomaly.

The crew could not have been more helpful, my meal was excellent, I slept peacefully until right before landing, and the BA lounge was a godsend. The only negative I encountered was the coffee both on the plane and in the lounge. Not to my taste but that’s a personal preference.

I don’t understand why a reputable airline like BA would delegate their London flights to AA. Makes no sense to me, as most domestic carriers do such a poor job these days. Terminal 3 at LHR is a total dump

The boarding process was quite loud and chaotic. The flight attendants kept barking over the PA system about people needing to only stow large items in the overhead bins. During the one and only service, I was hit by the service cart. At the same time, a passenger was returning from the bathroom and the crew definitely saw him but stopped a few seats short of allowing him to sit down before starting service and made him wait a good 10 minutes before passing his seat and allowing him to sit down, after which he had to ask for his snack and beverage or he would have been passed over. Neither flight attendant thanked passengers as they left; in fact, I did not see them again once the plane door was opened.

Cancelled flight minutes before boarding. Rescheduled flight was two days later

The flight attendants were EXTREMELY personable and appreciated the service, lights going off after dinner (probably the norm, but I haven’t flown evening overnight flights in a while). Thank you!

Business class seats were very dated on my plane. Very little storage, charging ports were not easily accessible, tv screen kept flopping away. Vegetarian food was disappointing: hardly any protein and severely under-seasoned. Crew was lovely.

Very quick boarding. I was surprised we only got a small water and small thing of cookies, everything else was for purchase. No entertainment. Crew was excellent though.

The food was ok, but not great. They delayed boarding in Portland and did not enforce group boarding. But the crew was excellent, went above and beyond.

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

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