$689+ 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
PSA — CHI
Aug 28 — Sep 41
Round-trip
1 adult, Economy
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Find cheap flights from Pisa to Chicago with Cheapflights
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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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Last-minute
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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 July 29, 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 July 29, 2026.
This United Airlines deal was found by Cheapflights users on 7/26. 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.
Fri 9/410:35 am
PSA
- ORD
1 stop16h 20m
United Airlines
Tue 9/810:30 pm
ORD
- PSA
1 stop12h 25m
United Airlines
Deal found 7/26![United Airlines logo]()
$802
This KLM deal was found by Cheapflights users on 7/28. 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 8/263:40 pm
PSA
- ORD
1 stop29h 35m
KLM
Sat 9/56:00 pm
ORD
- PSA
2 stops20h 05m
KLM
Deal found 7/28![KLM logo]()
$810
This American Airlines deal was found by Cheapflights users on 7/28. 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 8/2012:15 pm
PSA
- ORD
1 stop31h 15m
American Airlines
Mon 9/288:50 pm
ORD
- PSA
1 stop15h 45m
American Airlines
Deal found 7/28![American Airlines logo]()
$832
This American Airlines deal was found by Cheapflights users on 7/24. 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 9/412:50 pm
PSA
- ORD
2 stops24h 20m
American Airlines
Tue 9/812:54 pm
ORD
- PSA
2 stops15h 16m
American Airlines
Deal found 7/24![American Airlines logo]()
$837
This KLM deal was found by Cheapflights users on 7/26. 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 8/263:40 pm
PSA
- MDW
2 stops31h 35m
KLM
Sat 9/55:45 pm
MDW
- PSA
2 stops20h 20m
KLM
Deal found 7/26![KLM logo]()
$848
This KLM deal was found by Cheapflights users on 7/26. 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.
Thu 8/63:00 pm
PSA
- MDW
2 stops32h 15m
KLM
Mon 8/106:42 pm
MDW
- PSA
2 stops14h 23m
KLM
Deal found 7/26![KLM logo]()
$2,006
This KLM deal was found by Cheapflights users on 7/24. 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.
Mon 8/103:40 pm
PSA
- MDW
2 stops31h 35m
KLM
Thu 8/131:25 pm
MDW
- PSA
2 stops18h 15m
KLM
Deal found 7/24![KLM logo]()
$2,510
This KLM deal was found by Cheapflights users on 7/24. 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 8/114:55 pm
PSA
- MDW
2 stops30h 20m
KLM
Thu 8/131:25 pm
MDW
- PSA
2 stops18h 15m
KLM
Deal found 7/24![KLM logo]()
$2,531
This Trip.com deal was found by Cheapflights users on 7/27. 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 10/3010:05 am
PSA
- MDW
2 stops36h 42m
KLM
Wed 11/1112:30 pm
MDW
- PSA
2 stops37h 45m
KLM
Deal found 7/27![KLM logo]()
$6,134
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 July 29, 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 July 29, 2026.
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Fri 9/410:35 am
PSA
- ORD
1 stop16h 20m
United Airlines
Tue 9/810:30 pm
ORD
- PSA
1 stop12h 25m
United Airlines
Deal found 7/25![United Airlines logo]()
$802
This KLM deal was found by Cheapflights users on 7/25. 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 8/263:40 pm
PSA
- ORD
1 stop29h 35m
KLM
Sat 9/55:18 pm
ORD
- PSA
2 stops20h 47m
KLM
Deal found 7/25![KLM logo]()
$843
This KLM deal was found by Cheapflights users on 7/26. 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 8/263:40 pm
PSA
- MDW
2 stops31h 35m
KLM
Sat 9/55:45 pm
MDW
- PSA
2 stops20h 20m
KLM
Deal found 7/26![KLM logo]()
$848
This KLM deal was found by Cheapflights users on 7/24. 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.
Mon 8/103:40 pm
PSA
- MDW
2 stops31h 35m
KLM
Thu 8/131:25 pm
MDW
- PSA
2 stops18h 15m
KLM
Deal found 7/24![KLM logo]()
$2,510
This KLM deal was found by Cheapflights users on 7/24. 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 8/114:55 pm
PSA
- MDW
2 stops30h 20m
KLM
Thu 8/131:25 pm
MDW
- PSA
2 stops18h 15m
KLM
Deal found 7/24![KLM logo]()
$2,531
This Trip.com deal was found by Cheapflights users on 7/27. 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 10/3010:05 am
PSA
- MDW
2 stops36h 42m
KLM
Wed 11/1112:30 pm
MDW
- PSA
2 stops37h 45m
KLM
Deal found 7/27![KLM logo]()
$6,134
Last-minute flights from Pisa to ChicagoDiscover last-minute flight deals from Pisa to Chicago. Data last updated July 29, 2026 and is based on user searches.
Discover last-minute flight deals from Pisa to Chicago. Data last updated July 29, 2026 and is based on user searches.
This KLM deal was found by Cheapflights users on 7/26. 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.
Thu 8/63:00 pm
PSA
- MDW
2 stops32h 15m
KLM
Mon 8/106:42 pm
MDW
- PSA
2 stops14h 23m
KLM
Deal found 7/26![KLM logo]()
$2,006
This KLM deal was found by Cheapflights users on 7/24. 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.
Mon 8/103:40 pm
PSA
- MDW
2 stops31h 35m
KLM
Thu 8/131:25 pm
MDW
- PSA
2 stops18h 15m
KLM
Deal found 7/24![KLM logo]()
$2,510
This KLM deal was found by Cheapflights users on 7/24. 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 8/114:55 pm
PSA
- MDW
2 stops30h 20m
KLM
Thu 8/131:25 pm
MDW
- PSA
2 stops18h 15m
KLM
Deal found 7/24![KLM logo]()
$2,531
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Mon 8/178:55 pm
PSA
- ORD
1 stop22h 35m
American Airlines
Tue 9/2910:25 pm
ORD
- PSA
1 stop13h 30m
American Airlines
Deal found 7/28![American Airlines logo]()
$918
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Tue 8/1810:35 am
PSA
- ORD
2 stops34h 52m
United Airlines
Mon 9/2812:55 pm
ORD
- PSA
2 stops22h 05m
United Airlines
Deal found 7/28![United Airlines logo]()
$923
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/2011:45 am
PSA
- ORD
1 stop35h 25m
Scandinavian Airlines
Sat 9/267:15 pm
ORD
- PSA
1 stop16h 55m
Scandinavian Airlines
Deal found 7/28![Scandinavian Airlines logo]()
$803
This American Airlines deal was found by Cheapflights users on 7/28. 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 8/2012:15 pm
PSA
- ORD
1 stop31h 15m
American Airlines
Mon 9/288:50 pm
ORD
- PSA
1 stop15h 45m
American Airlines
Deal found 7/28![American Airlines logo]()
$832
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 8/2110:35 am
PSA
- ORD
2 stops31h 23m
United Airlines
Mon 9/281:37 pm
ORD
- PSA
2 stops21h 23m
United Airlines
Deal found 7/28![United Airlines logo]()
$896
This KLM deal was found by Cheapflights users on 7/28. 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 8/263:40 pm
PSA
- ORD
1 stop29h 35m
KLM
Sat 9/56:00 pm
ORD
- PSA
2 stops20h 05m
KLM
Deal found 7/28![KLM logo]()
$810
This KLM deal was found by Cheapflights users on 7/26. 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 8/263:40 pm
PSA
- MDW
2 stops31h 35m
KLM
Sat 9/55:45 pm
MDW
- PSA
2 stops20h 20m
KLM
Deal found 7/26![KLM logo]()
$848
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 July 29, 2026.
Search for one-way flight options from Pisa to Chicago. Find affordable one-way fares based on user searches. Data last updated July 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/164:25 pm
PSA
- MDW
3 stops53h 10m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$689
This KAYAK deal was found by Cheapflights users on 7/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1610:30 am
PSA
- ORD
1 stop34h 30m
Aer Lingus
Deal found 7/27![Aer Lingus logo]()
$746
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/166:20 pm
PSA
- ORD
2 stops54h 55m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$802
This Thrive Travel deal was found by Cheapflights users on 7/26. 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 Thrive Travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/124:55 pm
PSA
- ORD
1 stop26h 30m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$2,390
This Thrive Travel deal was found by Cheapflights users on 7/24. 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 Thrive Travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:05 am
PSA
- ORD
1 stop13h 10m
British Airways
Deal found 7/24![British Airways logo]()
$2,641
This KLM deal was found by Cheapflights users on 7/28. 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.
Sat 9/1210:15 pm
PSA
- MDW
2 stops26h 44m
KLM
Deal found 7/28![KLM logo]()
$5,355
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 July 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $802 (United Airlines) |
One-way from | $689 (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 July 29, 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
Quickest round-trip
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Fri 9/4
10:35 am-7:55 pm
1 stop16h 20m
Chicago O'Hare Intl
Tue 9/8
10:30 pm-5:55 pm
1 stop12h 25m
$802
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Wed 8/26
3:40 pm-2:15 pm
1 stop29h 35m
Chicago O'Hare Intl
Sat 9/5
5:18 pm-9:05 pm
2 stops20h 47m
$843
PisaChicago
PSA - MDW
PSAMDW
Pisa Gal Galilei
Wed 8/26
3:40 pm-4:15 pm
2 stops31h 35m
Chicago Midway
Sat 9/5
5:45 pm-9:05 pm
2 stops20h 20m
$848
PisaChicago
PSA - MDW
PSAMDW
Pisa Gal Galilei
Mon 8/10
3:40 pm-4:15 pm
2 stops31h 35m
Chicago Midway
Thu 8/13
1:25 pm-2:40 pm
2 stops18h 15m
$2,510
PisaChicago
PSA - MDW
PSAMDW
Pisa Gal Galilei
Tue 8/11
4:55 pm-4:15 pm
2 stops30h 20m
Chicago Midway
Thu 8/13
1:25 pm-2:40 pm
2 stops18h 15m
$2,531
PisaChicago
PSA - MDW
PSAMDW
Pisa Gal Galilei
Fri 10/30
10:05 am-4:47 pm
2 stops36h 42m
Chicago Midway
Wed 11/11
12:30 pm-9:15 am
2 stops37h 45m
$6,134
Cheapest one-way
PisaChicago
PSA - MDW
PSAMDW
Pisa Gal Galilei
Sun 8/16
12:10 pm-9:45 am
2 stops52h 35m
$740
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Sun 8/16
10:55 pm-6:15 pm
3 stops50h 20m
$817
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Sat 9/12
11:05 am-9:12 pm
2 stops17h 07m
$2,396
Quickest one-way
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Sat 9/12
11:05 am-5:15 pm
1 stop13h 10m
$2,641
Showing 1-10 of 11 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
No data available for this route at this time. Please check back soon.
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 locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Pisa and Chicago flights
Browse other Pisa and Chicago flight options. Last updated on July 29, 2026.
Popular flight searches
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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 July 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$755 | Average$807 | FlexibilityNo cancel fee | On-time71% |