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$255+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PSA
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap 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 September 17, 2025.

Round-trip from

$449
(British Airways)

One-way from

$255
(Kiwi.com)
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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Find 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 September 17, 2025.

This British Airways deal was found by Cheapflights users on 9/15. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/199:15 pmORD - PSA
1 stop31h 25mBritish Airways
Tue 11/410:20 amPSA - ORD
1 stop34h 30mBritish Airways
Deal found 9/15$449
This British Airways deal was found by Cheapflights users on 9/15. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/99:45 pmORD - PSA
1 stop28h 45mBritish Airways
Sat 11/1511:00 amPSA - ORD
1 stop33h 50mBritish Airways
Deal found 9/15$498
This Booking.com deal was found by Cheapflights users on 9/17. 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.
Wed 10/154:55 pmORD - PSA
1 stop11h 25mBritish Airways
Wed 10/2212:35 pmPSA - ORD
1 stop12h 40mBritish Airways
Deal found 9/17$512
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1510:11 amORD - PSA
2 stops18h 09mAmerican Airlines
Mon 10/208:40 pmPSA - ORD
1 stop22h 10mAmerican Airlines
Deal found 9/15$518
This Booking.com deal was found by Cheapflights users on 9/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3010:45 pmORD - PSA
1 stop29h 25mBritish Airways
Thu 11/612:30 pmPSA - ORD
2 stops33h 00mBritish Airways
Deal found 9/15$520
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 10/1510:11 amORD - PSA
2 stops18h 09mAmerican Airlines
Wed 10/227:40 pmPSA - ORD
2 stops24h 50mAmerican Airlines
Deal found 9/17$527
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/192:41 pmORD - PSA
2 stops13h 54mMultiple Airlines
Tue 11/410:20 amPSA - ORD
2 stops20h 17mMultiple Airlines
Deal found 9/15$531
This KLM deal was found by Cheapflights users on 9/17. 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.
Tue 9/3012:43 pmMDW - PSA
2 stops19h 12mKLM
Fri 10/310:05 pmPSA - MDW
2 stops24h 21mKLM
Deal found 9/17$2,168
This Mytrip deal was found by Cheapflights users on 9/17. 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.
Tue 9/309:20 amMDW - PSA
3 stops31h 35mMultiple Airlines
Fri 10/310:30 amPSA - MDW
3 stops33h 33mMultiple Airlines
Deal found 9/17$2,982

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 September 17, 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

Sun 10/19

9:15 pm-11:40 am

1 stop31h 25m

Pisa Gal Galilei

Tue 11/4

10:20 am-1:50 pm

1 stop34h 30m

$449

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Sun 11/9

9:45 pm-9:30 am

1 stop28h 45m

Pisa Gal Galilei

Sat 11/15

11:00 am-1:50 pm

1 stop33h 50m

$498

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Wed 10/15

10:11 am-11:20 am

2 stops18h 09m

Pisa Gal Galilei

Wed 10/22

7:40 pm-5:00 pm

1 stop28h 20m

$518

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Wed 10/15

10:11 am-11:20 am

2 stops18h 09m

Pisa Gal Galilei

Mon 10/20

8:40 pm-11:50 am

1 stop22h 10m

$518

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Thu 10/30

10:45 pm-10:10 am

1 stop29h 25m

Pisa Gal Galilei

Thu 11/6

12:30 pm-2:30 pm

2 stops33h 00m

$520

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Sun 10/19

2:41 pm-11:35 am

2 stops13h 54m

Pisa Gal Galilei

Tue 11/4

10:20 am-11:37 pm

2 stops20h 17m

$531

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Tue 9/30

12:43 pm-2:55 pm

2 stops19h 12m

Pisa Gal Galilei

Fri 10/3

10:05 pm-3:26 pm

2 stops24h 21m

$2,168

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Tue 9/30

9:20 am-11:55 pm

3 stops31h 35m

Pisa Gal Galilei

Fri 10/3

10:30 am-1:03 pm

3 stops33h 33m

$2,982

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Wed 11/19

6:40 am-7:50 am

3 stops42h 10m

$255

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Wed 1/7

10:15 am-9:55 am

2 stops40h 40m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 20 results
1
2

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 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 September 17, 2025.

It’s typically best to fly out from Chicago to Pisa in the morning. Doing so could potentially save you 17% on the flight price compared to flying in the afternoon, 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 September 17, 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
7,409 reviews

Crew

7.6

Food

6.3

Boarding

7.0

Comfort

6.8

Entertainment

6.4

Overall

6.8

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
7,409 reviews
Lufthansa
6.8
Okay
7,409 reviews

Crew

7.6

Food

6.3

Boarding

7.0

Comfort

6.8

Entertainment

6.4

Overall

6.8

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
7,367 reviews
Lufthansa
6.8
Okay
7,409 reviews

Crew

7.6

Food

6.3

Boarding

7.0

Comfort

6.8

Entertainment

6.4

Overall

6.8

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 19h 12m. Your travel time can differ by up to 12h 13m. The distance between Chicago and Pisa is about 4655 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 $603 on this airline. An additional option worth looking into is Lufthansa, starting at $667.

  • 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.

See more FAQs

Traveling to a place near Pisa?

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

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
British AirwaysCheapest$603Average$1,123FlexibilityNo cancel feeOn-time70%
LufthansaCheapest$667Average$1,089FlexibilityNo cancel feeOn-time76%

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