Chicago

$343+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
PSA — CHI
Apr 11 — Apr 181
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Cheap 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 March 12, 2026.

This American Airlines deal was found by Cheapflights users on 3/8. 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 4/233:30 pm
PSA
-
ORD
1 stop33h 05m
American Airlines
Mon 4/278:01 am
ORD
-
PSA
2 stops20h 29m
American Airlines
Deal found 3/8$600
This American Airlines deal was found by Cheapflights users on 3/7. 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.
Fri 5/88:30 pm
PSA
-
ORD
1 stop28h 05m
American Airlines
Tue 6/25:57 pm
ORD
-
PSA
2 stops17h 58m
American Airlines
Deal found 3/7$605
This Booking.com deal was found by Cheapflights users on 3/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2612:30 pm
PSA
-
ORD
2 stops26h 48m
British Airways
Mon 11/305:10 pm
ORD
-
PSA
2 stops59h 25m
British Airways
Deal found 3/8$624
This British Airways deal was found by Cheapflights users on 3/12. 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.
Sun 3/2911:55 am
PSA
-
ORD
1 stop31h 30m
British Airways
Sun 4/53:39 pm
ORD
-
PSA
2 stops21h 21m
British Airways
Deal found 3/12$637
This British Airways deal was found by Cheapflights users on 3/7. 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.
Fri 5/88:30 pm
PSA
-
ORD
1 stop26h 25m
British Airways
Tue 6/25:00 pm
ORD
-
PSA
1 stop18h 55m
British Airways
Deal found 3/7$758
This lol.travel deal was found by Cheapflights users on 3/10. 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.
Tue 4/710:35 am
PSA
-
ORD
1 stop16h 20m
Multiple Airlines
Tue 4/1410:52 am
ORD
-
PSA
2 stops16h 13m
Multiple Airlines
Deal found 3/10$766
This Trip.com deal was found by Cheapflights users on 3/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/73:00 pm
PSA
-
MDW
2 stops38h 31m
KLM
Tue 4/1410:41 am
MDW
-
PSA
2 stops21h 14m
KLM
Deal found 3/10$1,257
This KLM deal was found by Cheapflights users on 3/11. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/243:40 pm
PSA
-
MDW
2 stops31h 45m
KLM
Tue 7/215:59 pm
MDW
-
PSA
2 stops14h 36m
KLM
Deal found 3/11$1,269
This KLM deal was found by Cheapflights users on 3/7. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/810:10 pm
PSA
-
MDW
2 stops25h 02m
KLM
Tue 6/21:22 pm
MDW
-
PSA
2 stops18h 33m
KLM
Deal found 3/7$1,439
This Delta deal was found by Cheapflights users on 3/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/193:05 pm
PSA
-
MDW
2 stops34h 00m
Delta
Thu 7/239:30 am
MDW
-
PSA
2 stops22h 10m
Delta
Deal found 3/11$1,692
This KLM deal was found by Cheapflights users on 3/10. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/278:55 am
PSA
-
MDW
2 stops19h 36m
KLM
Tue 3/311:10 pm
MDW
-
PSA
2 stops18h 45m
KLM
Deal found 3/10$1,802
This KLM deal was found by Cheapflights users on 3/11. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/243:40 pm
PSA
-
MDW
2 stops31h 45m
KLM
Mon 7/205:59 pm
MDW
-
PSA
2 stops15h 06m
KLM
Deal found 3/11$1,999

Find 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 March 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$600
(American Airlines)

One-way from

$343
(Kiwi.com)
Provider with most accurate pricing for Pisa Gal Galilei-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Pisa Gal Galilei-Chicago (CHI) flights.
From Pisa Gal Galilei to Chicago (CHI)
One-way flight from Pisa Gal Galilei to Chicago (CHI)

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 March 12, 2026.
Use the filters below to find and compare flights from Pisa to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 4/23

3:30 pm-12:20 pm

1 stop27h 50m

Chicago O'Hare Intl

Mon 4/27

8:35 pm-7:35 pm

1 stop16h 00m

$600

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Fri 5/8

8:30 pm-5:35 pm

1 stop28h 05m

Chicago O'Hare Intl

Tue 6/2

5:57 pm-6:55 pm

2 stops17h 58m

$605

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Sun 3/29

11:55 am-12:25 pm

1 stop31h 30m

Chicago O'Hare Intl

Sun 4/5

3:39 pm-8:00 pm

2 stops21h 21m

$637

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Fri 5/8

8:30 pm-3:55 pm

1 stop26h 25m

Chicago O'Hare Intl

Tue 6/2

5:00 pm-6:55 pm

1 stop18h 55m

$758
Quickest round-trip

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 4/23

10:40 am-10:03 pm

2 stops18h 23m

Chicago O'Hare Intl

Mon 4/27

5:55 pm-6:00 pm

2 stops17h 05m

$784

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Tue 4/7

8:30 pm-5:04 pm

2 stops27h 34m

Chicago O'Hare Intl

Tue 4/14

9:55 am-11:10 am

2 stops18h 15m

$796

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Sun 3/29

10:45 am-1:10 pm

2 stops33h 25m

Chicago O'Hare Intl

Sun 4/5

10:52 am-9:35 am

2 stops15h 43m

$857

PisaChicago

PSA - MDW

PSAMDW

Pisa Gal Galilei

Tue 4/7

3:00 pm-10:31 pm

2 stops38h 31m

Chicago Midway

Tue 4/14

10:41 am-2:55 pm

2 stops21h 14m

$1,257

PisaChicago

PSA - MDW

PSAMDW

Pisa Gal Galilei

Wed 6/24

3:40 pm-4:25 pm

2 stops31h 45m

Chicago Midway

Tue 7/21

5:59 pm-3:35 pm

2 stops14h 36m

$1,269

PisaChicago

PSA - MDW

PSAMDW

Pisa Gal Galilei

Fri 5/8

10:10 pm-4:12 pm

2 stops25h 02m

Chicago Midway

Tue 6/2

1:22 pm-2:55 pm

2 stops18h 33m

$1,439

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

Showing 1-10 of 27 resultsSorted by cheapest first
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  • Most accurate provider: When it comes to deals on Pisa-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pisa-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 $396). Flying from Pisa to Chicago in June is currently the most expensive (average of $896). 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.

  • How long is the flight from Pisa to Chicago?

    American Airlines, British Airways, and KLM can get you from Pisa to Chicago in just under 27h 50m. Your travel time can differ by up to 10h 41m. Airlines will cover a distance of 4653 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $396). Flying from Pisa to Chicago in June is currently the most expensive (average of $896). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Pisa to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

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 March 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$755Average$807FlexibilityNo cancel feeOn-time71%

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