$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
Round-trip
1 adult, Economy
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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
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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
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Cheapest flights from Pisa to ChicagoExplore 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.
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![American Airlines logo]()
$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![American Airlines logo]()
$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![British Airways logo]()
$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![British Airways logo]()
$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![British Airways logo]()
$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![Multiple Airlines logo]()
$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![KLM logo]()
$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![KLM logo]()
$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![KLM logo]()
$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![Delta logo]()
$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![KLM logo]()
$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![KLM logo]()
$1,999
Best flights from Pisa to ChicagoDiscover carefully curated flight deals from Pisa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 12, 2026.
Discover carefully curated flight deals from Pisa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 12, 2026.
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.
Thu 4/233:30 pm
PSA
- ORD
1 stop27h 50m
American Airlines
Mon 4/278:35 pm
ORD
- PSA
1 stop16h 00m
American Airlines
Deal found 3/7![American Airlines logo]()
$600
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![British Airways logo]()
$637
This United Airlines deal was found by Cheapflights users on 3/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:40 am
PSA
- ORD
2 stops18h 23m
United Airlines
Mon 4/275:55 pm
ORD
- PSA
2 stops17h 05m
United Airlines
Deal found 3/9![United Airlines logo]()
$784
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2910:45 am
PSA
- ORD
2 stops33h 25m
Multiple Airlines
Sun 4/510:52 am
ORD
- PSA
2 stops15h 43m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$857
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![American Airlines logo]()
$605
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![KLM logo]()
$1,257
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![British Airways logo]()
$758
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![Delta logo]()
$1,692
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:30 pm
PSA
- ORD
2 stops27h 34m
British Airways
Tue 4/149:55 am
ORD
- PSA
2 stops18h 15m
British Airways
Deal found 3/10![British Airways logo]()
$796
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![KLM logo]()
$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![KLM logo]()
$1,439
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![KLM logo]()
$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![KLM logo]()
$1,999
Last-minute flights from Pisa to ChicagoDiscover last-minute flight deals from Pisa to Chicago. Data last updated March 12, 2026 and is based on user searches.
Discover last-minute flight deals from Pisa to Chicago. Data last updated March 12, 2026 and is based on user searches.
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![KLM logo]()
$1,802
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![British Airways logo]()
$637
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![Multiple Airlines logo]()
$766
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:30 pm
PSA
- ORD
2 stops27h 34m
British Airways
Tue 4/149:55 am
ORD
- PSA
2 stops18h 15m
British Airways
Deal found 3/10![British Airways logo]()
$796
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![KLM logo]()
$1,257
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![American Airlines logo]()
$600
This United Airlines deal was found by Cheapflights users on 3/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:40 am
PSA
- ORD
2 stops18h 23m
United Airlines
Mon 4/275:55 pm
ORD
- PSA
2 stops17h 05m
United Airlines
Deal found 3/9![United Airlines logo]()
$784
One-way flights from Pisa to ChicagoSearch for one-way flight options from Pisa to Chicago. Find affordable one-way fares based on user searches. Data last updated March 12, 2026.
Search for one-way flight options from Pisa to Chicago. Find affordable one-way fares based on user searches. Data last updated March 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:45 pm
PSA
- ORD
3 stops53h 05m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$343
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/159:10 am
PSA
- ORD
3 stops59h 25m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$358
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2111:30 am
PSA
- ORD
3 stops33h 55m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$430
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:30 pm
PSA
- MDW
3 stops55h 30m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$468
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:30 am
PSA
- ORD
2 stops39h 00m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$475
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:55 pm
PSA
- ORD
1 stop23h 55m
British Airways
Deal found 3/8![British Airways logo]()
$513
This Priceline deal was found by Cheapflights users on 3/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:30 pm
PSA
- ORD
1 stop26h 25m
British Airways
Deal found 3/9![British Airways logo]()
$531
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:30 pm
PSA
- ORD
1 stop28h 00m
American Airlines
Deal found 3/11![American Airlines logo]()
$570
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:15 pm
PSA
- ORD
2 stops34h 35m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$574
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:30 pm
PSA
- MDW
3 stops43h 30m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$672
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:30 pm
PSA
- MDW
3 stops49h 31m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$697
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:55 pm
PSA
- MDW
2 stops57h 26m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$715
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) |
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
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
Showing 1-10 of 27 resultsSorted by cheapest first
- 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.
PSA-CHI
PSA-ORD
PSA-MDW
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
PSA-CHI
PSA-ORD
PSA-MDW
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Alternative routes for Pisa to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on March 12, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Pisa and Chicago flights
Browse other Pisa and Chicago flight options. Last updated on March 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$755 | Average$807 | FlexibilityNo cancel fee | On-time71% |