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$523+ Cheap flights from Tuscany to Midway (MDW)

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Tuscany to Midway

Keep the following information in mind while searching for Tuscany to Midway flight deals. Data was last updated September 15, 2025.

Round-trip from

$594
(Delta)

One-way from

$523
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$693
From Tuscany to Chicago Midway
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One-way flight from Tuscany to Chicago Midway
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Highest demand for flights based on searches. 12% potential increase in price ($96 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Tuscany to Midway

Cheapest flights from Tuscany to Midway
Explore the most affordable flight options available from Tuscany to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Delta deal was found by Cheapflights users on 9/13. 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.
Thu 11/1312:45 pmFCO - MDW
2 stops17h 47mDelta
Sun 11/1612:47 pmMDW - FCO
1 stop12h 08mDelta
Deal found 9/13$587
This Delta deal was found by Cheapflights users on 9/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:10 amFCO - MDW
2 stops17h 04mDelta
Wed 11/191:14 pmMDW - FCO
2 stops15h 41mDelta
Deal found 9/12$589
This Delta deal was found by Cheapflights users on 9/13. 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.
Wed 10/16:30 amFCO - MDW
2 stops19h 05mDelta
Mon 10/66:23 pmMDW - FCO
2 stops13h 27mDelta
Deal found 9/13$596
This Delta deal was found by Cheapflights users on 9/13. 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.
Wed 10/16:30 amFCO - MDW
2 stops19h 05mDelta
Wed 10/156:00 amMDW - FCO
1 stop18h 35mDelta
Deal found 9/13$599
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 10/3010:05 amFCO - MDW
2 stops28h 35mDelta
Thu 11/61:08 pmMDW - FCO
2 stops19h 12mDelta
Deal found 9/14$601
This Delta deal was found by Cheapflights users on 9/15. 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.
Fri 10/39:45 amFCO - MDW
1 stop18h 51mDelta
Tue 10/76:23 pmMDW - FCO
2 stops14h 37mDelta
Deal found 9/15$603
This Air France deal was found by Cheapflights users on 9/15. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/39:45 amFCO - MDW
1 stop36h 41mMultiple Airlines
Sun 10/199:20 amMDW - FCO
1 stop20h 25mMultiple Airlines
Deal found 9/15$607
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 11/66:40 amFLR - MDW
2 stops16h 34mDelta
Wed 11/121:14 pmMDW - FLR
2 stops15h 06mDelta
Deal found 9/15$608
This KLM deal was found by Cheapflights users on 9/15. 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 10/159:00 amFCO - MDW
1 stop16h 25mKLM
Thu 10/231:08 pmMDW - FCO
1 stop13h 12mKLM
Deal found 9/15$618
This Delta deal was found by Cheapflights users on 9/13. 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.
Thu 10/26:30 amFLR - MDW
2 stops19h 05mDelta
Mon 10/612:48 pmMDW - FLR
2 stops16h 12mDelta
Deal found 9/13$619
This Delta deal was found by Cheapflights users on 9/15. 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 11/2312:20 pmFLR - MDW
2 stops18h 12mDelta
Sun 11/301:14 pmMDW - FLR
2 stops15h 06mDelta
Deal found 9/15$620
This Trip.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/22:50 pmPSA - MDW
2 stops34h 45mKLM
Mon 10/612:48 pmMDW - PSA
2 stops18h 27mKLM
Deal found 9/15$621

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tuscany to Midway 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 15, 2025.
Use the filters below to find and compare flights from Tuscany to Chicago Midway Airport that are best for you.

Fly from

Tuscany

Fly to

Midway

Route

Depart

Return

Price

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Thu 11/6

6:10 am-4:14 pm

2 stops17h 04m

Chicago Midway

Wed 11/19

1:14 pm-11:55 am

2 stops15h 41m

$589

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Wed 12/3

6:10 am-6:18 pm

2 stops19h 08m

Chicago Midway

Wed 12/17

12:50 pm-7:55 am

1 stop12h 05m

$594

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Wed 10/1

6:30 am-6:35 pm

2 stops19h 05m

Chicago Midway

Mon 10/6

6:23 pm-2:50 pm

2 stops13h 27m

$596

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Fri 10/3

6:30 am-6:35 pm

2 stops19h 05m

Chicago Midway

Sun 10/19

9:20 am-12:45 pm

1 stop20h 25m

$599

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Wed 10/1

6:30 am-6:35 pm

2 stops19h 05m

Chicago Midway

Wed 10/15

6:00 am-7:35 am

1 stop18h 35m

$599

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Thu 10/30

10:05 am-8:40 am

2 stops28h 35m

Chicago Midway

Thu 11/6

1:08 pm-3:20 pm

2 stops19h 12m

$601

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 11/6

6:40 am-4:14 pm

2 stops16h 34m

Chicago Midway

Wed 11/12

1:14 pm-11:20 am

2 stops15h 06m

$608

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Wed 10/15

9:00 am-6:25 pm

1 stop16h 25m

Chicago Midway

Thu 10/23

1:08 pm-9:20 am

1 stop13h 12m

$618

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Wed 10/15

9:00 am-6:25 pm

1 stop16h 25m

Chicago Midway

Thu 10/23

1:08 pm-10:10 am

2 stops14h 02m

$618

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 10/2

6:30 am-6:35 pm

2 stops19h 05m

Chicago Midway

Mon 10/6

12:48 pm-12:00 pm

2 stops16h 12m

$619

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 32 results
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Best time to book a flight from Tuscany to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Tuscany 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 Tuscany to Chicago Midway Airport
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 Tuscany to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Delta and KLM can get you from Tuscany to Chicago Midway Airport in just under 17h 04m. Your travel time can differ by up to 17h 41m. Tuscany and Chicago Midway Airport are separated by a distance of 4810 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Tuscany to Chicago Midway Airport?

    The most popular route from Tuscany to Chicago Midway Airport is Rome Fiumicino - Chicago Midway. You may also consider Florence Peretola - Chicago Midway or Pisa Gal Galilei - Chicago Midway.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Tuscany to Midway 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 Tuscany to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Tuscany to Chicago Midway Airport (average of $160). Flying from Tuscany to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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