HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$442+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
PSA — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pisa to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 11, 2025.

Round-trip from

$571
(American Airlines)

One-way from

$442
(Kiwi.com)
From Pisa Gal Galilei to Chicago (CHI)
Search Deals
One-way flight from Pisa Gal Galilei to Chicago (CHI)
Search Deals

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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2012:30 pmPSA - ORD
1 stop33h 55mAmerican Airlines
Mon 11/247:24 pmORD - PSA
2 stops57h 11mAmerican Airlines
Deal found 9/10$571
This British Airways deal was found by Cheapflights users on 9/9. 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 11/2012:30 pmPSA - ORD
1 stop13h 15mBritish Airways
Mon 11/246:35 pmORD - PSA
2 stops58h 00mBritish Airways
Deal found 9/9$575
This British Airways deal was found by Cheapflights users on 9/11. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:30 pmPSA - ORD
2 stops34h 06mBritish Airways
Wed 11/511:48 amORD - PSA
2 stops16h 47mBritish Airways
Deal found 9/11$682
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/1812:20 pmPSA - ORD
2 stops25h 56mAmerican Airlines
Mon 9/224:54 pmORD - PSA
2 stops19h 21mAmerican Airlines
Deal found 9/9$697
This lol.travel deal was found by Cheapflights users on 9/11. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1810:35 amPSA - ORD
1 stop15h 25mMultiple Airlines
Mon 9/225:40 pmORD - PSA
1 stop18h 35mMultiple Airlines
Deal found 9/11$748
This Mytrip deal was found by Cheapflights users on 9/9. 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.
Fri 10/247:30 pmPSA - ORD
2 stops32h 30mMultiple Airlines
Fri 10/319:15 pmORD - PSA
2 stops17h 10mMultiple Airlines
Deal found 9/9$806
This lol.travel deal was found by Cheapflights users on 9/9. 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.
Fri 10/246:15 pmPSA - ORD
1 stop25h 40mLufthansa
Fri 10/314:20 pmORD - PSA
1 stop11h 30mLufthansa
Deal found 9/9$832
This British Airways deal was found by Cheapflights users on 9/11. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/111:00 amPSA - ORD
1 stop14h 45mBritish Airways
Wed 11/55:10 pmORD - PSA
1 stop11h 25mBritish Airways
Deal found 9/11$836
This Trip.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/2410:05 pmPSA - MDW
2 stops27h 20mKLM
Fri 10/316:35 pmMDW - PSA
2 stops38h 55mKLM
Deal found 9/9$916
This Trip.com deal was found by Cheapflights users on 9/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3110:05 amPSA - MDW
2 stops29h 40mKLM
Tue 11/45:09 pmMDW - PSA
2 stops57h 11mKLM
Deal found 9/11$1,485

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 September 11, 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 11/20

12:30 pm-11:56 pm

2 stops42h 26m

Chicago O'Hare Intl

Mon 11/24

7:24 pm-11:35 am

2 stops57h 11m

$571

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 11/20

12:30 pm-7:23 pm

2 stops37h 53m

Chicago O'Hare Intl

Mon 11/24

5:40 pm-11:35 am

2 stops58h 55m

$575

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 10/30

12:30 pm-4:36 pm

2 stops34h 06m

Chicago O'Hare Intl

Wed 11/5

5:10 pm-11:35 am

1 stop11h 25m

$682

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 10/30

12:30 pm-4:36 pm

2 stops34h 06m

Chicago O'Hare Intl

Tue 11/4

8:28 pm-11:35 am

2 stops32h 07m

$682

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 10/30

12:30 pm-4:36 pm

2 stops34h 06m

Chicago O'Hare Intl

Mon 11/3

5:40 pm-11:35 am

2 stops58h 55m

$682

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Fri 10/24

7:30 pm-9:00 pm

2 stops32h 30m

Chicago O'Hare Intl

Fri 10/31

9:15 pm-8:25 pm

2 stops17h 10m

$806

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Sat 11/1

11:00 am-7:45 pm

1 stop14h 45m

Chicago O'Hare Intl

Wed 11/5

11:48 am-11:35 am

2 stops16h 47m

$836

PisaChicago

PSA - MDW

PSAMDW

Pisa Gal Galilei

Fri 10/24

10:05 pm-6:25 pm

2 stops27h 20m

Chicago Midway

Fri 10/31

6:35 pm-3:30 pm

2 stops38h 55m

$916

PisaChicago

PSA - MDW

PSAMDW

Pisa Gal Galilei

Fri 10/31

10:05 am-9:45 am

2 stops29h 40m

Chicago Midway

Tue 11/4

5:09 pm-9:20 am

2 stops57h 11m

$1,485

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 10/30

8:25 am-4:15 pm

3 stops37h 50m

$442

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 14 results
1
2

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 September 11, 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
10,000 reviews

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

7.2

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

7.2

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

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 0 different airlines.

  • 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 20m. Your travel time can differ by up to 15h 06m. Airlines will cover a distance of 4655 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, August is the cheapest month in which you can book a flight from Pisa to Chicago (average of $245). Flying from Pisa to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.