The Leaning Tower of Pisa, the Pisa Cathedral, and the surrounding green park.

$330 Cheap Flights from Chicago (ORD) to Pisa (PSA)

View $330 flight on Tue, Apr 20, 2027Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Galileo Galilei Airport (PSA)

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Cheap Flights from Chicago to Pisa (ORD-PSA)

Prices were available within the past 7 days and start at $330 for one-way flights and $730 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Apr 19 - Fri, Apr 23
ORD
Chicago
PSA
Pisa
$730 Roundtrip, found 2 days ago
$730
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Apr 19 from Chicago to Pisa, returning Fri, Apr 23, priced at $730 found 2 days ago
American Airlines
Mon, Apr 19 - Fri, Apr 23
ORD
Chicago
PSA
Pisa
$732 Roundtrip, found 2 days ago
$732
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Apr 19 from Chicago to Pisa, returning Fri, Apr 23, priced at $732 found 2 days ago
American Airlines
Mon, Apr 19 - Fri, Apr 23
ORD
Chicago
PSA
Pisa
$747 Roundtrip, found 2 days ago
$747
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Apr 19 from Chicago to Pisa, returning Fri, Apr 23, priced at $747 found 2 days ago
American Airlines
Mon, Apr 19 - Fri, Apr 23
ORD
Chicago
PSA
Pisa
$752 Roundtrip, found 2 days ago
$752
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Apr 19 from Chicago to Pisa, returning Fri, Apr 23, priced at $752 found 2 days ago
British Airways
Mon, Apr 19 - Fri, Apr 23
ORD
Chicago
PSA
Pisa
$756 Roundtrip, found 2 days ago
$756
Roundtrip
found 2 days ago
Select British Airways flight, departing Mon, Apr 19 from Chicago to Pisa, returning Fri, Apr 23, priced at $756 found 2 days ago
British Airways
Mon, Apr 19 - Fri, Apr 23
ORD
Chicago
PSA
Pisa
$760 Roundtrip, found 2 days ago
$760
Roundtrip
found 2 days ago
Select British Airways flight, departing Mon, Apr 19 from Chicago to Pisa, returning Fri, Apr 23, priced at $760 found 2 days ago
Scandinavian Airlines
Wed, Apr 21 - Sat, May 1
ORD
Chicago
PSA
Pisa
$761 Roundtrip, found 5 days ago
$761
Roundtrip
found 5 days ago
Select Scandinavian Airlines flight, departing Wed, Apr 21 from Chicago to Pisa, returning Sat, May 1, priced at $761 found 5 days ago
British Airways
Mon, Apr 19 - Fri, Apr 23
ORD
Chicago
PSA
Pisa
$761 Roundtrip, found 2 days ago
$761
Roundtrip
found 2 days ago
Select British Airways flight, departing Mon, Apr 19 from Chicago to Pisa, returning Fri, Apr 23, priced at $761 found 2 days ago
United
Mon, Apr 19 - Fri, Apr 23
ORD
Chicago
PSA
Pisa
$776 Roundtrip, found 2 days ago
$776
Roundtrip
found 2 days ago
Select United flight, departing Mon, Apr 19 from Chicago to Pisa, returning Fri, Apr 23, priced at $776 found 2 days ago
Lufthansa
Mon, Apr 19 - Fri, Apr 23
ORD
Chicago
PSA
Pisa
$799 Roundtrip, found 2 days ago
$799
Roundtrip
found 2 days ago
Select Lufthansa flight, departing Mon, Apr 19 from Chicago to Pisa, returning Fri, Apr 23, priced at $799 found 2 days ago

Alternative airports near Pisa

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Galileo Galilei PSA. Cheapest and Closest option available. Average driving time to city center is 7 minutes. Flights from $1,040
PSA
Galileo Galilei
CheapestClosest
Average driving time to city center7 min
Flights from $1,040

Find the cheapest month to fly from Chicago (ORD) to Pisa (PSA)

February is typically the cheapest month to fly

From $433 - $1,791 per traveler.

What you need to know for your flight from O'Hare Intl. to Galileo Galilei

Chicago (ORD) to Pisa (PSA) at a glance

Travel with a range of airlines offering flights from Chicago O'Hare International Airport (ORD) to Pisa's Galileo Galilei Airport (PSA) on this international long-haul journey. Compare choices from full-service carriers to discover the itinerary that suits your budget, schedule, and travel plans while you delve into Pisa's iconic sights and charming neighborhoods. Check out the essential details for this route from Chicago to Pisa.

  • Fastest flight duration: around 10h 15m in-flight, plus roughly 2 hours layover with one stop
  • Route distance: roughly 4,700 miles (7,560 km)
  • Flights per week: around 8 departures on average
  • Typical fares (one-way): economy tickets often range from $285–$1045, depending on seasonality and how far ahead you book

Flights from O'Hare International Airport (ORD) to Galileo Galilei Airport (PSA)

Based on the latest traveler bookings, we've compiled a list of the top airlines flying from Chicago to Pisa, particularly favored for one-stop and multi-stop flights. Common layovers include Frankfurt International Airport (FRA) with about a 2-hour wait and Heathrow Airport (LHR) with around a 1 hour and 30 minutes layover. These options allow you to customize your journey by balancing price, total travel time, and cabin class for the ideal itinerary.

  • United: This full-service airline provides one-stop flights, boasting one-way fares that usually fall between $360 and $1075. It represents around 38% of departures along this route, with an in-flight duration of 10 hours and 15 minutes, resulting in a total travel time of approximately 12 hours when including layovers.
  • British Airways: Offering one-stop service, British Airways is another full-service option, with one-way ticket prices generally ranging from $285 to $985. Accounting for about 33% of the flights on this route, passengers can expect a flight time of 10 hours and 15 minutes, alongside a total journey time close to 12 hours, factoring in layovers.
  • Lufthansa: As a full-service carrier providing one-stop options, Lufthansa's one-way fares typically range from $475 to $650. It operates about 19% of departures on this route, with a flight time of 10 hours and 15 minutes, leading to an overall travel time of roughly 12 hours, including any layover periods.

Alternative route from Chicago (ORD) to Pisa (PSA)

  • Chicago to Florence (ORD-FLR): Peretola Airport (FLR) is located approximately 41 miles from Galileo Galilei Airport (PSA). One-way economy ticket prices for this route generally vary between $285 and $895, influenced by the season and how far in advance you book. Travelers can choose from both one-stop and multi-stop flight options, with popular layover points including Zürich Airport (ZRH) and Franz Josef Strauss International Airport (MUC). Major airlines operating on this route include United and Swiss International Air Lines. Additionally, business class service is offered for those seeking a more premium experience.

How to find the best prices for flights from Chicago (ORD) to Pisa (PSA)

Getting some of the best deals on flights from Chicago to Pisa is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are typically available when booking 2-8 weeks in advance, although most travelers tend to book at least 2 months ahead. Afternoon departures from 12 PM to 6 PM not only offer lower prices but are also the most popular times to fly. Additionally, traveling on Wednesday can result in both cheaper fares and greater demand.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.* Find Pisa hotel and flight deals.
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Galileo Galilei Airport from O'Hare International Airport

Pisa welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Here's how to reach Pisa efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Pisa, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
  • Car rental: Renting a car from Galileo Galilei Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Galileo Galilei Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Galileo Galilei Airport, Pisa Aeroporto Station, a train station, is located about 0.2 miles away on foot, while Livorno/Pisa Seaport, a seaport, is approximately 2 miles away by car, making it convenient for travelers to access these transport options.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei) cost?
You can find cheap one-way flights from $330 and cheap return flights from $730 Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei) with Expedia. One-way flights usually range from $542 to $4298, and return flights typically cost between $817 and $5272. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei)?
The cheapest month to fly from ORD to PSA is April when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei)?
Enter ORD to PSA and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei)?
Delta is one of the cheapest airlines offering connecting flights from Chicago, IL (ORD) to Pisa (PSA) with a layover in Hartsfield-Jackson Atlanta Intl. (ATL), starting from around $1,214. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei)?
The earliest flight from O'Hare International Airport (ORD) to Galileo Galilei Airport (PSA) usually departs at around 5:15 AM, operated by American Airlines and Aer Lingus. This seasonal service is available in September, helping you get an early start on your Italian adventure. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei)?
The most popular departure times for flights from Chicago, IL (ORD) to Pisa (PSA) are in the late afternoon, from 3pm to 6pm. About 22% of passengers prefer this time window. Many major carriers, including British Airways, United Airlines, and Lufthansa, offer flights during this period, making it a great option for travelers looking to arrive in Pisa in the evening.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei)?
A flight from ORD to PSA with a layover takes around 12 hours 30 minutes, with the route covering approximately 4,657 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei)?
Business class seats are offered on the ORD to PSA route. Airlines that offer business class service on this route include:

  • British Airways
  • American Airlines
  • United Airlines
  • SAS
  • Air Canada
  • Lufthansa

First class is available with Lufthansa.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Pisa from O'Hare Intl. (ORD)?
If you're planning to travel to Pisa from O'Hare Intl. (ORD), you can fly into Galileo Galilei (PSA) Some flights may connect through major hubs like Pearson Intl. (YYZ), Pierre Elliott Trudeau Intl. (YUL), Logan Intl. (BOS) before reaching Pisa. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei) Pisa Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Pisa (PSA-Galileo Galilei) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Galileo Galilei
Airlines serving
Aer Lingus, American Airlines, British Airways, Delta, KLM, Lufthansa, Scandinavian Airlines, United
Roundtrip price
$729
Distance
4656 mi

Book with confidence

Chicago to Pisa Flights

The cheapest times to fly from Chicago to Pisa

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Pisa are during the month of April. You can find some of the cheapest flights from Chicago to Pisa with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Pisa

Sunday is one of the best days to book for cheap flights from Chicago to Pisa: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Pisa

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Pisa in 2026. You can also book with separate airlines for your outbound and return journeys, from $330 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Pisa flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Pisa airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Pisa Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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