$488+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
PSA — CHI
May 29 — Jun 51
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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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 April 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 April 29, 2026.
This American Airlines deal was found by Cheapflights users on 4/28. 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 9/33:30 pm
PSA
- ORD
1 stop28h 00m
American Airlines
Sun 9/61:15 pm
ORD
- PSA
2 stops23h 45m
American Airlines
Deal found 4/28![American Airlines logo]()
$663
This American Airlines deal was found by Cheapflights users on 4/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:30 pm
PSA
- ORD
1 stop27h 55m
American Airlines
Mon 5/118:35 pm
ORD
- PSA
1 stop16h 00m
American Airlines
Deal found 4/27![American Airlines logo]()
$664
This British Airways deal was found by Cheapflights users on 4/27. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:15 pm
PSA
- ORD
1 stop13h 00m
British Airways
Sun 9/65:28 pm
ORD
- PSA
2 stops19h 32m
British Airways
Deal found 4/27![British Airways logo]()
$667
This British Airways deal was found by Cheapflights users on 4/25. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:30 pm
PSA
- ORD
2 stops26h 25m
British Airways
Tue 6/1612:47 pm
ORD
- PSA
2 stops15h 23m
British Airways
Deal found 4/25![British Airways logo]()
$671
This British Airways deal was found by Cheapflights users on 4/29. 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 5/79:20 pm
PSA
- ORD
2 stops25h 45m
British Airways
Mon 5/114:40 pm
ORD
- PSA
2 stops19h 55m
British Airways
Deal found 4/29![British Airways logo]()
$676
This British Airways deal was found by Cheapflights users on 4/29. 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.
Wed 8/267:50 pm
PSA
- ORD
1 stop29h 25m
British Airways
Sat 9/54:27 pm
ORD
- PSA
2 stops18h 38m
British Airways
Deal found 4/29![British Airways logo]()
$799
This KLM deal was found by Cheapflights users on 4/27. 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 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 47m
KLM
Sat 9/55:59 pm
MDW
- PSA
2 stops20h 06m
KLM
Deal found 4/27![KLM logo]()
$866
This KLM deal was found by Cheapflights users on 4/29. 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 5/72:50 pm
PSA
- MDW
2 stops32h 22m
KLM
Mon 5/111:22 pm
MDW
- PSA
2 stops17h 53m
KLM
Deal found 4/29![KLM logo]()
$932
This KLM deal was found by Cheapflights users on 4/25. 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.
Tue 6/93:00 pm
PSA
- MDW
2 stops32h 16m
KLM
Tue 6/161:16 pm
MDW
- PSA
2 stops18h 39m
KLM
Deal found 4/25![KLM logo]()
$1,579
This Delta deal was found by Cheapflights users on 4/29. 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 20m
Delta
Thu 7/2311:05 am
MDW
- PSA
2 stops20h 35m
Delta
Deal found 4/29![Delta logo]()
$1,583
This KLM deal was found by Cheapflights users on 4/29. 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 6/1310:15 pm
PSA
- MDW
2 stops25h 01m
KLM
Sat 6/206:55 pm
MDW
- PSA
2 stops36h 45m
KLM
Deal found 4/29![KLM logo]()
$2,044
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 April 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 April 29, 2026.
This British Airways deal was found by Cheapflights users on 4/27. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:15 pm
PSA
- ORD
1 stop13h 00m
British Airways
Sun 9/65:28 pm
ORD
- PSA
2 stops19h 32m
British Airways
Deal found 4/27![British Airways logo]()
$667
This KLM deal was found by Cheapflights users on 4/29. 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
2 stops30h 18m
KLM
Sat 9/55:45 pm
ORD
- PSA
2 stops20h 20m
KLM
Deal found 4/29![KLM logo]()
$865
This Mytrip deal was found by Cheapflights users on 4/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1110:35 am
PSA
- ORD
2 stops16h 20m
Multiple Airlines
Thu 6/182:15 pm
ORD
- PSA
3 stops20h 05m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$940
This Delta deal was found by Cheapflights users on 4/25. 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 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 13m
Delta
Thu 7/239:20 am
MDW
- PSA
2 stops22h 20m
Delta
Deal found 4/25![Delta logo]()
$1,583
This British Airways deal was found by Cheapflights users on 4/29. 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.
Wed 8/267:50 pm
PSA
- ORD
1 stop29h 25m
British Airways
Sat 9/54:27 pm
ORD
- PSA
2 stops18h 38m
British Airways
Deal found 4/29![British Airways logo]()
$799
This KLM deal was found by Cheapflights users on 4/27. 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 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 47m
KLM
Sat 9/55:59 pm
MDW
- PSA
2 stops20h 06m
KLM
Deal found 4/27![KLM logo]()
$866
This KLM deal was found by Cheapflights users on 4/25. 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.
Tue 6/93:00 pm
PSA
- MDW
2 stops32h 16m
KLM
Tue 6/161:16 pm
MDW
- PSA
2 stops18h 39m
KLM
Deal found 4/25![KLM logo]()
$1,579
Last-minute flights from Pisa to ChicagoDiscover last-minute flight deals from Pisa to Chicago. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Pisa to Chicago. Data last updated April 29, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/73:30 pm
PSA
- ORD
1 stop27h 55m
American Airlines
Mon 5/118:35 pm
ORD
- PSA
1 stop16h 00m
American Airlines
Deal found 4/29![American Airlines logo]()
$663
This British Airways deal was found by Cheapflights users on 4/29. 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 5/79:20 pm
PSA
- ORD
2 stops25h 45m
British Airways
Mon 5/114:40 pm
ORD
- PSA
2 stops19h 55m
British Airways
Deal found 4/29![British Airways logo]()
$676
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Thu 5/710:40 am
PSA
- ORD
2 stops35h 15m
United Airlines
Mon 5/111:06 pm
ORD
- PSA
2 stops21h 54m
United Airlines
Deal found 4/25![United Airlines logo]()
$827
This KLM deal was found by Cheapflights users on 4/29. 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 5/72:50 pm
PSA
- MDW
2 stops32h 22m
KLM
Mon 5/111:22 pm
MDW
- PSA
2 stops17h 53m
KLM
Deal found 4/29![KLM logo]()
$932
This Booking.com deal was found by Cheapflights users on 4/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:20 am
PSA
- ORD
2 stops18h 55m
Multiple Airlines
Mon 5/117:05 pm
ORD
- PSA
3 stops20h 25m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$1,327
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:05 am
PSA
- ORD
1 stop14h 10m
British Airways
Thu 6/47:05 pm
ORD
- PSA
1 stop12h 20m
British Airways
Deal found 4/28![British Airways logo]()
$1,378
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 April 29, 2026.
Search for one-way flight options from Pisa to Chicago. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:20 pm
PSA
- ORD
1 stop24h 40m
British Airways
Deal found 4/27![British Airways logo]()
$488
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Fri 7/107:55 pm
PSA
- ORD
2 stops46h 55m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$509
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Mon 7/133:05 pm
PSA
- ORD
2 stops33h 45m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 7/129:50 pm
PSA
- ORD
3 stops53h 00m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$566
This Cheapflightsfares deal was found by Cheapflights users on 4/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/612:35 pm
PSA
- ORD
1 stop12h 40m
British Airways
Deal found 4/24![British Airways logo]()
$568
This Cheapflightsfares deal was found by Cheapflights users on 4/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:20 pm
PSA
- ORD
1 stop24h 40m
British Airways
Deal found 4/25![British Airways logo]()
$609
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 7/1210:55 pm
PSA
- MDW
3 stops41h 45m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$628
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Mon 7/136:20 am
PSA
- MDW
3 stops58h 20m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$630
This KLM deal was found by Cheapflights users on 4/26. 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.
Mon 7/133:40 pm
PSA
- MDW
2 stops31h 35m
KLM
Deal found 4/26![KLM logo]()
$1,189
This KLM deal was found by Cheapflights users on 4/27. 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 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 stops25h 12m
KLM
Deal found 4/27![KLM logo]()
$8,566
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 April 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $663 (American Airlines) |
One-way from | $488 (Cheapflightsfares) |
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 April 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
Thu 9/3
12:15 pm-6:15 pm
1 stop13h 00m
Chicago O'Hare Intl
Sun 9/6
5:28 pm-8:00 pm
2 stops19h 32m
$667
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Wed 8/26
7:50 pm-6:15 pm
1 stop29h 25m
Chicago O'Hare Intl
Sat 9/5
4:27 pm-6:05 pm
2 stops18h 38m
$799
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Wed 8/26
3:40 pm-2:58 pm
2 stops30h 18m
Chicago O'Hare Intl
Sat 9/5
5:45 pm-9:05 pm
2 stops20h 20m
$865
PisaChicago
PSA - MDW
PSAMDW
Pisa Gal Galilei
Wed 8/26
3:40 pm-4:27 pm
2 stops31h 47m
Chicago Midway
Sat 9/5
5:59 pm-9:05 pm
2 stops20h 06m
$866
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Thu 6/11
10:35 am-7:55 pm
2 stops16h 20m
Chicago O'Hare Intl
Thu 6/18
2:15 pm-5:20 pm
3 stops20h 05m
$940
PisaChicago
PSA - MDW
PSAMDW
Pisa Gal Galilei
Tue 6/9
3:00 pm-4:16 pm
2 stops32h 16m
Chicago Midway
Tue 6/16
1:16 pm-2:55 pm
2 stops18h 39m
$1,579
PisaChicago
PSA - MDW
PSAMDW
Pisa Gal Galilei
Sun 7/19
3:05 pm-6:18 pm
2 stops34h 13m
Chicago Midway
Thu 7/23
9:20 am-2:40 pm
2 stops22h 20m
$1,583
Cheapest one-way
Quickest one-way
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Thu 9/24
9:20 pm-3:00 pm
1 stop24h 40m
$488
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Fri 7/10
8:05 pm-11:50 am
3 stops46h 45m
$520
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Mon 7/13
7:45 pm-5:50 pm
3 stops29h 05m
$569
Showing 1-10 of 16 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
Hammond
Porter
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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 April 29, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Pisa to Chicago by cabin class
Find flights from Pisa to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Pisa and Chicago flights
Browse other Pisa and Chicago flight options. Last updated on April 29, 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 April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$755 | Average$807 | FlexibilityNo cancel fee | On-time71% |