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Portofino

$239+ Cheap flights from Chicago (CHI) to Portofino, Italy

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MXP
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Find cheap flights from Chicago to Portofino with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Portofino are usually found in January or March, booked 28 days in advance, depart on a Tuesday or Sunday and return on a Tuesday

Cheap flight deals from Chicago to Portofino

Cheapest flights from Chicago to Portofino
Explore the most affordable flight options available from Chicago to Portofino. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This CrystalTravel deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:20 pm
ORD
-
MXP
1 stop16h 50m
Scandinavian Airlines
Mon 3/211:15 am
MXP
-
ORD
1 stop12h 30m
Scandinavian Airlines
Deal found 1/27$427
This oojo deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:10 pm
ORD
-
MXP
1 stop17h 00m
Scandinavian Airlines
Sun 3/18:00 pm
MXP
-
ORD
1 stop27h 45m
Scandinavian Airlines
Deal found 1/27$428
This oojo deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:15 pm
ORD
-
MXP
1 stop16h 55m
Scandinavian Airlines
Fri 4/2411:45 am
MXP
-
ORD
2 stops35h 25m
Scandinavian Airlines
Deal found 1/28$430
This lol.travel deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/158:20 pm
ORD
-
MXP
1 stop16h 50m
Scandinavian Airlines
Wed 4/159:20 am
MXP
-
ORD
1 stop13h 50m
Scandinavian Airlines
Deal found 1/28$435
This CrystalTravel deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:15 pm
ORD
-
MXP
1 stop16h 55m
Scandinavian Airlines
Mon 4/209:20 am
MXP
-
ORD
1 stop13h 50m
Scandinavian Airlines
Deal found 1/27$436
This oojo deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/47:15 pm
ORD
-
MXP
1 stop30h 15m
Scandinavian Airlines
Thu 4/308:00 pm
MXP
-
ORD
1 stop27h 10m
Scandinavian Airlines
Deal found 1/27$438
This oojo deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:15 pm
ORD
-
MXP
2 stops17h 35m
Scandinavian Airlines
Fri 5/13:55 pm
MXP
-
ORD
1 stop31h 15m
Scandinavian Airlines
Deal found 1/27$439
This oojo deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:15 pm
ORD
-
MXP
2 stops33h 05m
Scandinavian Airlines
Sun 4/198:00 pm
MXP
-
ORD
1 stop27h 10m
Scandinavian Airlines
Deal found 1/27$445
This FlightHub deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:20 pm
ORD
-
MXP
1 stop16h 50m
Scandinavian Airlines
Mon 3/911:15 am
MXP
-
ORD
1 stop12h 30m
Scandinavian Airlines
Deal found 1/28$447
This oojo deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:20 pm
ORD
-
LIN
2 stops33h 45m
Scandinavian Airlines
Wed 3/412:55 pm
LIN
-
ORD
2 stops34h 50m
Scandinavian Airlines
Deal found 1/28$483
This Mytrip deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:30 pm
ORD
-
BGY
2 stops22h 40m
Multiple Airlines
Wed 3/46:45 am
BGY
-
ORD
2 stops17h 35m
Multiple Airlines
Deal found 1/28$484
This KAYAK deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:20 pm
ORD
-
LIN
2 stops33h 45m
Scandinavian Airlines
Sat 11/1412:55 pm
LIN
-
ORD
2 stops34h 50m
Scandinavian Airlines
Deal found 1/27$499

Find flight deals from Chicago to Portofino

Keep the following information in mind while searching for Chicago to Portofino flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$427
(CrystalTravel)

One-way from

$239
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$543
Provider with most accurate pricing for Chicago (CHI)-Milan (MIL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Milan (MIL) flights.
Search Deals
From Chicago (CHI) to Portofino
Search Deals
One-way flight from Chicago (CHI) to Portofino
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($247 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Portofino that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Chicago to Portofino that are best for you.

Fly from

Chicago

Fly to

Portofino

Route

Depart

Return

Price

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 2/23

7:20 pm-12:05 pm

2 stops33h 45m

Milan Malpensa

Thu 2/26

11:15 am-4:45 pm

1 stop12h 30m

$504

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 4/30

11:08 am-3:05 pm

2 stops20h 57m

Milan Malpensa

Sat 5/9

9:20 am-4:10 pm

1 stop13h 50m

$583

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 4/22

9:50 pm-8:05 pm

1 stop15h 15m

Bergamo Orio Al Serio

Wed 4/29

8:45 am-7:50 pm

1 stop18h 05m

$587

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 3/2

9:55 pm-7:55 pm

1 stop15h 00m

Bergamo Orio Al Serio

Thu 3/12

8:25 am-9:00 pm

1 stop18h 35m

$593

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Tue 3/17

10:55 pm-7:55 pm

1 stop15h 00m

Bergamo Orio Al Serio

Tue 3/24

8:25 am-9:00 pm

1 stop18h 35m

$606

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 3/18

10:55 pm-7:55 pm

1 stop15h 00m

Bergamo Orio Al Serio

Wed 4/1

8:45 am-7:50 pm

1 stop18h 05m

$609

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 3/4

9:55 pm-7:55 pm

1 stop15h 00m

Bergamo Orio Al Serio

Thu 3/12

8:25 am-9:00 pm

1 stop18h 35m

$610

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 3/2

3:55 pm-10:45 pm

3 stops23h 50m

Bergamo Orio Al Serio

Sat 3/7

8:10 pm-8:05 pm

2 stops30h 55m

$623

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 3/16

10:50 pm-10:45 pm

2 stops17h 55m

Bergamo Orio Al Serio

Tue 3/31

5:55 am-7:55 pm

2 stops21h 00m

$629

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Sun 4/5

4:20 pm-7:30 pm

2 stops20h 10m

Bergamo Orio Al Serio

Mon 4/13

9:45 pm-12:55 pm

2 stops22h 10m

$630

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Portofino

Have a flexible travel schedule? Discover the best time to fly to Portofino from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Portofino?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Portofino. Price data was last updated on January 23, 2026.

To ensure you get the cheapest price possible for a flight from Chicago to Portofino, you should look to book at least 19 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Portofino?

Currently, February is the cheapest month in which you can book a flight from Chicago to Portofino (average of $398). Flying from Chicago to Portofino in July is currently the most expensive (average of $725). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Chicago to Portofino?

Reviews of airlines servicing Portofino

Get insights into the airlines that provide service to Portofino. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portofino. Reviews last updated January 29, 2026.
Read through reviews of airlines operating flights from Chicago to Portofino, such as United Airlines, Scandinavian Airlines, and Aer Lingus. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,215 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Scandinavian Airlines
7.3
Good
1,674 reviews
United Airlines
7.4
Good
9,215 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Aer Lingus
7.2
Good
1,443 reviews
United Airlines
7.4
Good
9,215 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
TAP AIR PORTUGAL
7.1
Good
2,130 reviews
United Airlines
7.4
Good
9,215 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
British Airways
6.7
Okay
7,705 reviews
United Airlines
7.4
Good
9,215 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Related info for your journey

Find useful and relevant information for your journey from Chicago to Portofino. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Portofino?

    For as low as $686, Scandinavian Airlines can have you in Portofino from Chicago in 11h 20m. Airlines will cover a distance of 4536 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Chicago to Portofino?

    When deciding which route to take from Chicago to Portofino consider Chicago O'Hare Intl - Milan Malpensa, Chicago O'Hare Intl - Milan Linate or Chicago Midway - Milan Malpensa as they are the most popular.

  • What are the most reliable airlines from Chicago to Portofino?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Portofino on time: Air Canada (100%), Austrian Airlines (69%), United Airlines (69%).

  • What are the cheapest flights from Chicago to Portofino?

    Looking at all options, your cheapest flight can be booked for $552. While the most popular route (Chicago O'Hare Intl - Milan Malpensa) can be booked for $381 on average, our data indicates $1,081 when flying from Chicago to Portofino.

  • Can I find deals for flights from Chicago to Portofino that include hotel bookings?

    Yes. In addition to deals on Chicago to Portofino flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Portofino?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Portofino.

  • Can I find deals for business class flights from Chicago to Portofino?

    Yes. Cheapflights offers flight deals from Chicago to Portofino by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Portofino?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Portofino (average of $398). Flying from Chicago to Portofino in July is currently the most expensive (average of $725). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 10 airlines flying from Chicago to Portofino

Discover the top 10 airlines that operate flights from Chicago to Portofino. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$398Average$499FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$410Average$551FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$458Average$836FlexibilityNo cancel feeOn-time70%
Turkish AirlinesCheapest$518Average$745FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$584Average$913FlexibilityNo cancel feeOn-time81%
American AirlinesCheapest$624Average$1,569FlexibilityNo cancel feeOn-time71%
Aer LingusCheapest$626Average$1,052FlexibilityNo cancel feeOn-timeN/A
IberiaCheapest$639Average$1,029FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$780Average$1,210FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$793Average$1,268FlexibilityNo cancel feeOn-time69%

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