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$403+ Cheap flights from Chicago (CHI) to Pisa (PSA)

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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PSA
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap flight deals from Chicago to Pisa

Cheapest flights from Chicago to Pisa
Explore the most affordable flight options available from Chicago to Pisa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:40 pmORD - PSA
1 stop18h 55mMultiple Airlines
Sun 12/286:00 amPSA - ORD
2 stops21h 00mMultiple Airlines
Deal found 12/15$1,603
This British Airways deal was found by Cheapflights users on 12/13. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:10 pmORD - PSA
1 stop11h 25mBritish Airways
Tue 1/610:20 amPSA - ORD
2 stops40h 29mBritish Airways
Deal found 12/13$1,628
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:40 pmORD - PSA
1 stop20h 35mMultiple Airlines
Fri 1/210:05 amPSA - ORD
2 stops16h 55mMultiple Airlines
Deal found 12/14$1,941
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:40 pmORD - PSA
1 stop18h 55mMultiple Airlines
Fri 1/210:05 amPSA - ORD
2 stops16h 55mMultiple Airlines
Deal found 12/14$2,045
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/233:50 pmORD - PSA
1 stop15h 10mMultiple Airlines
Fri 1/210:05 amPSA - ORD
2 stops16h 55mMultiple Airlines
Deal found 12/14$2,085
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/167:40 pmORD - PSA
2 stops33h 40mMultiple Airlines
Tue 12/306:05 amPSA - ORD
1 stop40h 00mMultiple Airlines
Deal found 12/16$2,155
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:40 pmORD - PSA
1 stop20h 20mMultiple Airlines
Fri 1/210:05 amPSA - ORD
2 stops16h 55mMultiple Airlines
Deal found 12/14$2,353
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:55 pmORD - PSA
1 stop15h 20mMultiple Airlines
Fri 1/24:10 pmPSA - ORD
2 stops24h 55mMultiple Airlines
Deal found 12/14$2,402

Find flight deals from Chicago to Pisa

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Pisa (PSA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$458
(Mytrip)

One-way from

$403
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Pisa Gal Galilei flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Pisa Gal Galilei flights.
Search Deals
From Chicago (CHI) to Pisa Gal Galilei
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One-way flight from Chicago (CHI) to Pisa Gal Galilei
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Pisa 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 December 16, 2025.
Use the filters below to find and compare flights from Chicago to Pisa that are best for you.

Fly from

Chicago

Fly to

Pisa

Route

Depart

Return

Price

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Tue 1/20

9:45 pm-11:35 am

1 stop30h 50m

Pisa Gal Galilei

Thu 2/5

12:30 pm-1:50 pm

1 stop32h 20m

$538

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Sun 1/18

9:45 pm-9:30 am

1 stop28h 45m

Pisa Gal Galilei

Thu 2/5

12:30 pm-1:50 pm

1 stop32h 20m

$538

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Tue 1/20

9:45 pm-11:35 am

1 stop30h 50m

Pisa Gal Galilei

Tue 2/3

10:20 am-1:50 pm

1 stop34h 30m

$538

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Wed 1/21

5:10 pm-11:35 am

1 stop11h 25m

Pisa Gal Galilei

Tue 2/3

10:20 am-1:50 pm

1 stop34h 30m

$538

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Wed 1/28

9:00 pm-8:45 pm

1 stop16h 45m

Pisa Gal Galilei

Wed 2/4

8:15 am-7:15 pm

1 stop18h 00m

$559

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Thu 1/29

5:10 pm-10:10 am

1 stop34h 00m

Pisa Gal Galilei

Thu 2/5

12:30 pm-1:50 pm

1 stop32h 20m

$563

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Thu 1/15

9:45 pm-10:10 am

1 stop29h 25m

Pisa Gal Galilei

Thu 1/22

12:30 pm-5:44 pm

2 stops36h 14m

$586

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Thu 1/22

5:10 pm-10:10 am

1 stop34h 00m

Pisa Gal Galilei

Thu 2/5

12:30 pm-1:50 pm

1 stop32h 20m

$588

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Thu 1/22

9:45 pm-10:10 am

1 stop29h 25m

Pisa Gal Galilei

Tue 2/3

10:20 am-1:50 pm

1 stop34h 30m

$588

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Tue 1/20

9:45 pm-11:35 am

1 stop30h 50m

Pisa Gal Galilei

Sat 2/7

11:00 am-1:50 pm

1 stop33h 50m

$588

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 17 results
1
2

Compare providers for flights from Chicago to Pisa

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Pisa in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Pisa flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Pisa flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Pisa flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Pisa flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Pisa flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Pisa

Have a flexible travel schedule? Discover the best time to fly to Pisa 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 Pisa

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

Currently, December is the cheapest month in which you can book a flight from Chicago to Pisa (average of $448). Flying from Chicago to Pisa 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.

What is the cheapest time of day to fly from CHI to PSA?

Find hourly flight availability from Chicago to Pisa. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 16, 2025.

It’s typically best to fly out from Chicago to Pisa in the morning. Doing so could potentially save you 16% on the flight price compared to flying at noon, which is usually more expensive.

Reviews of airlines servicing Pisa

Get insights into the airlines that provide service to Pisa. 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 Pisa. Reviews last updated December 16, 2025.
See what other customers who have flown with Lufthansa and British Airways from Chicago to Pisa have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Lufthansa
6.8
Okay
7,631 reviews

Food

6.3

Overall

6.8

Comfort

6.8

Crew

7.6

Boarding

7.0

Entertainment

6.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

SFO - FRA

Convenient flight to my destination. Good entertainment options on board. I was seated close to some people who had noisy children which made sleeping a bit challenging.
Lufthansa
6.8
Okay
7,631 reviews
Lufthansa
6.8
Okay
7,631 reviews

Food

6.3

Overall

6.8

Comfort

6.8

Crew

7.6

Boarding

7.0

Entertainment

6.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

SFO - FRA

Convenient flight to my destination. Good entertainment options on board. I was seated close to some people who had noisy children which made sleeping a bit challenging.
British Airways
6.7
Okay
7,580 reviews
Lufthansa
6.8
Okay
7,631 reviews

Food

6.3

Overall

6.8

Comfort

6.8

Crew

7.6

Boarding

7.0

Entertainment

6.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

SFO - FRA

Convenient flight to my destination. Good entertainment options on board. I was seated close to some people who had noisy children which made sleeping a bit challenging.

Related info for your journey

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

  • What airport do you fly into for flights to Pisa from Chicago?

    Pisa Gal Galilei (PSA), located 2.7 mi from the city center, is the airport you fly into when you book flights from Chicago to Pisa. 2 airlines have flights to Gal Galilei from Chicago on a regular basis. Booking flights from Chicago to Pisa Gal Galilei should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Pisa?

    British Airways and KLM can get you from Chicago to Pisa in just under 30h 50m. Your travel time can differ by up to 6h 51m. The distance between Chicago and Pisa is about 4653 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Pisa round-trip?

    Our cheapest airline available from Chicago to Pisa is British Airways. Our recent data shows that you can find tickets from as low as $556 on this airline. An additional option worth looking into is Lufthansa, starting at $780.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Pisa 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 Pisa?

    Currently, December is the cheapest month in which you can book a flight from Chicago to Pisa (average of $448). Flying from Chicago to Pisa 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

Traveling to a place near Pisa?

Book flights to Pisa if you plan to visit one of these locations
La Spezia
Livorno
Monterosso al Mare

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Top 2 airlines flying from Chicago to Pisa

Discover the top 2 airlines that operate flights from Chicago to Pisa. 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
British AirwaysCheapest$556Average$928FlexibilityNo cancel feeOn-time70%
LufthansaCheapest$780Average$1,161FlexibilityNo cancel feeOn-time76%

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