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$649+ Cheap flights from Pisa (PSA) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
PSA — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Pisa to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Pisa (PSA) to Chicago (CHI). 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$649
(American Airlines)
Provider with most accurate pricing for Pisa Gal Galilei-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Pisa Gal Galilei-Chicago (CHI) flights.
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From Pisa Gal Galilei to Chicago (CHI)
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Find flight deals from Pisa to Chicago

Cheapest flights from Pisa to Chicago
Explore the most affordable flight options available from Pisa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:30 pmPSA - ORD
1 stop33h 55mAmerican Airlines
Tue 11/181:45 pmORD - PSA
2 stops38h 50mAmerican Airlines
Deal found 10/30$649
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2012:30 pmPSA - ORD
2 stops59h 25mAmerican Airlines
Mon 11/248:40 pmORD - PSA
2 stops55h 55mAmerican Airlines
Deal found 10/29$655
This British Airways deal was found by Cheapflights users on 10/29. 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.
Thu 11/1312:30 pmPSA - ORD
1 stop13h 15mBritish Airways
Tue 11/189:02 pmORD - PSA
2 stops31h 33mBritish Airways
Deal found 10/29$706
This Mytrip deal was found by Cheapflights users on 10/29. 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.
Thu 11/139:25 pmPSA - ORD
3 stops24h 30mMultiple Airlines
Tue 11/186:30 pmORD - PSA
2 stops15h 10mMultiple Airlines
Deal found 10/29$1,412

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pisa to Chicago 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 October 30, 2025.
Use the filters below to find and compare flights from Pisa to Chicago that are best for you.

Fly from

Pisa

Fly to

Chicago

Route

Depart

Return

Price

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 11/13

12:30 pm-3:25 pm

1 stop33h 55m

Chicago O'Hare Intl

Tue 11/18

1:45 pm-11:35 am

2 stops38h 50m

$649

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 11/20

12:30 pm-3:25 pm

1 stop33h 55m

Chicago O'Hare Intl

Mon 11/24

8:40 pm-11:35 am

2 stops55h 55m

$655

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 11/13

12:30 pm-6:45 pm

1 stop13h 15m

Chicago O'Hare Intl

Tue 11/18

9:02 pm-11:35 am

2 stops31h 33m

$706

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Mon 1/12

10:05 pm-7:15 pm

1 stop28h 10m

Chicago O'Hare Intl

Sat 1/17

12:05 pm-11:40 pm

2 stops28h 35m

$925

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 1/1

12:30 pm-7:19 am

2 stops25h 49m

$995

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Compare providers for flights from Pisa to Chicago

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 Pisa to Chicago in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 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 Pisa-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Pisa-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Pisa-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pisa-Chicago 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 Pisa-Chicago 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 Pisa to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Pisa 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 Pisa to Chicago
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 30, 2025.
See what other customers who have flown with American Airlines from Pisa to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,034 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
11,034 reviews
American Airlines
7.2
Good
11,034 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Pisa to Chicago. 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 from for flights from Pisa to Chicago?

    Located just 2.7 mi from the city center, Pisa Gal Galilei is the airport most travelers will use when flying to Chicago from Pisa. Booking flights from Gal Galilei (PSA) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 1 airline.

  • How long is the flight from Pisa to Chicago?

    American Airlines can get you from Pisa to Chicago in just under 33h 55m. Your travel time can differ by up to . Airlines will cover a distance of 4653 mi.

  • What is the cheapest airline to fly from Pisa to Chicago round-trip?

    American Airlines, at $762, was found to be the cheapest airline from Pisa to Chicago..

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

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

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

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

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

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

See more FAQs

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Top airline flying from Pisa to Chicago

Discover the top airline that operate flights from Pisa to Chicago. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$762Average$807FlexibilityNo cancel feeOn-time71%

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