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$397+ Cheap flights from Pisa (PSA) to Chicago (CHI)

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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
PSA — CHI
Feb 6 — Feb 131
Fri 2/6
Fri 2/13
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 January 7, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$829
(Mytrip)

One-way from

$397
(Kiwi.com)
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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One-way flight 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 January 7, 2026.

This American Airlines deal was found by Cheapflights users on 1/5. 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 9/103:30 pmPSA - ORD
1 stop28h 00mAmerican Airlines
Mon 9/147:05 pmORD - PSA
1 stop17h 10mAmerican Airlines
Deal found 1/5$610
This American Airlines deal was found by Cheapflights users on 1/6. 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 1/1512:30 pmPSA - ORD
2 stops37h 04mAmerican Airlines
Tue 1/203:21 pmORD - PSA
2 stops37h 14mAmerican Airlines
Deal found 1/6$615
This lol.travel deal was found by Cheapflights users on 1/6. 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.
Thu 1/1512:30 pmPSA - ORD
1 stop33h 55mBritish Airways
Tue 1/208:45 pmORD - PSA
1 stop31h 50mBritish Airways
Deal found 1/6$674
This Mytrip deal was found by Cheapflights users on 1/6. 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.
Mon 1/1210:05 pmPSA - ORD
3 stops47h 55mMultiple Airlines
Sat 2/286:50 pmORD - PSA
2 stops19h 40mMultiple Airlines
Deal found 1/6$749
This Mytrip deal was found by Cheapflights users on 1/5. 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.
Mon 1/197:45 amPSA - ORD
3 stops43h 00mMultiple Airlines
Thu 1/2210:48 amORD - PSA
2 stops22h 52mMultiple Airlines
Deal found 1/5$829

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 January 7, 2026.
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

Mon 1/19

7:45 am-7:45 pm

3 stops43h 00m

Chicago O'Hare Intl

Thu 1/22

10:48 am-4:40 pm

2 stops22h 52m

$829

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Fri 2/20

1:10 pm-7:15 pm

2 stops37h 05m

Chicago O'Hare Intl

Fri 2/27

7:20 pm-8:55 am

1 stop30h 35m

$909

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Sun 5/24

11:00 am-5:50 pm

3 stops37h 50m

$397

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Mon 1/19

4:30 pm-8:18 am

2 stops46h 48m

$413

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Mon 4/13

8:40 pm-12:20 pm

1 stop22h 40m

$433

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Mon 4/13

8:55 pm-7:20 pm

2 stops29h 25m

$440

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Sun 5/24

11:55 am-1:50 pm

1 stop32h 55m

$455

PisaChicago

PSA - MDW

PSAMDW

Pisa Gal Galilei

Sun 5/24

6:10 am-8:45 am

3 stops33h 35m

$474

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Sun 5/24

10:25 am-10:28 am

2 stops31h 03m

$641

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Mon 4/13

10:20 am-7:55 pm

3 stops40h 35m

$1,578

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 12 results
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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 January.
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

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

Currently, September is the cheapest month in which you can book a flight from Pisa to Chicago (average of $409). Flying from Pisa to Chicago in June is currently the most expensive (average of $819). 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.

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.

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

    American Airlines, at $755, 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.

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

    Currently, September is the cheapest month in which you can book a flight from Pisa to Chicago (average of $409). Flying from Pisa to Chicago in June is currently the most expensive (average of $819). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 January 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$755Average$807FlexibilityNo cancel feeOn-time71%

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