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$401+ Cheap flights from Midway (MDW) 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PSA
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Midway to Pisa

Cheapest flights from Midway to Pisa
Explore the most affordable flight options available from Midway to Pisa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This KLM deal was found by Cheapflights users on 1/20. 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 5/52:12 pm
MDW
-
PSA
2 stops17h 43m
KLM
Tue 5/193:00 pm
PSA
-
MDW
2 stops32h 25m
KLM
Deal found 1/20$1,077
This KLM deal was found by Cheapflights users on 1/20. 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 5/95:59 pm
MDW
-
PSA
2 stops37h 41m
KLM
Tue 5/193:00 pm
PSA
-
MDW
2 stops32h 25m
KLM
Deal found 1/20$1,084
This KLM deal was found by Cheapflights users on 1/18. 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 9/42:00 pm
MDW
-
PSA
2 stops18h 05m
KLM
Sat 9/1210:15 pm
PSA
-
MDW
2 stops25h 12m
KLM
Deal found 1/18$1,653
This KLM deal was found by Cheapflights users on 1/21. 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 6/22:00 pm
MDW
-
PSA
2 stops17h 55m
KLM
Sun 6/78:45 am
PSA
-
MDW
2 stops16h 20m
KLM
Deal found 1/21$2,578
This KLM deal was found by Cheapflights users on 1/21. 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 6/302:00 pm
MDW
-
PSA
2 stops18h 35m
KLM
Wed 7/84:25 pm
PSA
-
MDW
2 stops31h 02m
KLM
Deal found 1/21$2,813
This KLM deal was found by Cheapflights users on 1/21. 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 6/302:00 pm
MDW
-
PSA
2 stops18h 35m
KLM
Thu 7/93:00 pm
PSA
-
MDW
2 stops32h 27m
KLM
Deal found 1/21$3,105

Find flight deals from Midway to Pisa

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) 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 January 21, 2026.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$1,077
(KLM)

One-way from

$401
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Pisa Gal Galilei flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Pisa Gal Galilei flights.
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From Chicago Midway to Pisa Gal Galilei
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One-way flight from Chicago Midway to Pisa Gal Galilei
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 January 21, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Pisa that are best for you.

Fly from

Midway

Fly to

Pisa

Route

Depart

Return

Price

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Tue 5/5

2:12 pm-2:55 pm

2 stops17h 43m

Pisa Gal Galilei

Tue 5/19

3:00 pm-4:25 pm

2 stops32h 25m

$1,077

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Sat 5/9

5:59 pm-2:40 pm

2 stops37h 41m

Pisa Gal Galilei

Tue 5/19

3:00 pm-4:25 pm

2 stops32h 25m

$1,084

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Tue 6/2

2:00 pm-2:55 pm

2 stops17h 55m

Pisa Gal Galilei

Sun 6/7

8:45 am-6:05 pm

2 stops16h 20m

$2,578

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Tue 6/30

2:00 pm-3:35 pm

2 stops18h 35m

Pisa Gal Galilei

Tue 7/7

4:55 pm-4:27 pm

2 stops30h 32m

$2,813

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Tue 6/30

2:00 pm-3:35 pm

2 stops18h 35m

Pisa Gal Galilei

Wed 7/8

4:25 pm-4:27 pm

2 stops31h 02m

$2,813

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Tue 6/30

2:00 pm-3:35 pm

2 stops18h 35m

Pisa Gal Galilei

Thu 7/9

3:00 pm-4:27 pm

2 stops32h 27m

$3,105

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Thu 3/5

7:30 am-4:35 pm

3 stops26h 05m

$401

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Sun 2/15

4:13 pm-7:55 pm

2 stops20h 42m

$766

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Best time to book a flight from Midway to Pisa

Have a flexible travel schedule? Discover the best time to fly to Pisa from Midway 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.

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Midway?

    Pisa Gal Galilei (PSA) is the airport you will fly into if you book a flight from Chicago Midway to Pisa. You should not have trouble finding flights to Gal Galilei from Chicago Midway; the airport handles an average of 0 inbound flights from Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Pisa airport from Chicago Midway. It is only a 2.7 mi journey from Gal Galilei (PSA) to Pisa’s city center.

  • How long is the flight from Chicago Midway Airport to Pisa?

    There are many flights that can get you from Chicago Midway Airport to Pisa in 17h 43m. Fly via KLM to get the fastest option. Chicago Midway Airport and Pisa are separated by a distance of 4655 mi.

  • Can I find deals for flights from Midway to Pisa that include hotel bookings?

    Yes. In addition to deals on Midway to Pisa flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Pisa?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Pisa.

  • Can I find deals for business class flights from Midway to Pisa?

    Yes. Cheapflights offers flight deals from Midway 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
La Spezia
Livorno
Monterosso al Mare

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