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$243+ Cheap flights from Midway (MDW) to Tuscany

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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — FLR
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Midway to Tuscany

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

Round-trip from

$495
(Delta)

One-way from

$243
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$886
From Chicago Midway to Tuscany
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One-way flight from Chicago Midway to Tuscany
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Highest demand for flights based on searches. 17% potential increase in price ($196 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($38 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 Midway to Tuscany

Cheapest flights from Midway to Tuscany
Explore the most affordable flight options available from Midway to Tuscany. 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 9/15. 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 11/99:32 amMDW - FCO
2 stops17h 58mDelta
Tue 11/2512:40 pmFCO - MDW
1 stop17h 52mDelta
Deal found 9/15$495
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.
Tue 10/2112:48 pmMDW - FCO
1 stop15h 17mDelta
Tue 11/46:00 amFCO - MDW
2 stops19h 25mDelta
Deal found 9/14$511
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.
Mon 10/2710:35 amMDW - FCO
1 stop16h 55mDelta
Wed 11/56:10 amFCO - MDW
2 stops17h 05mDelta
Deal found 9/13$513
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.
Tue 10/281:08 pmMDW - FCO
2 stops16h 37mDelta
Tue 11/49:20 amFCO - MDW
2 stops19h 54mDelta
Deal found 9/12$514
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 10/291:08 pmMDW - FCO
2 stops13h 37mDelta
Wed 11/126:00 amFCO - MDW
2 stops19h 18mDelta
Deal found 9/13$516
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 11/239:32 amMDW - FCO
2 stops16h 38mDelta
Fri 12/512:40 pmFCO - MDW
1 stop17h 52mDelta
Deal found 9/15$522
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.
Tue 10/281:08 pmMDW - FCO
2 stops16h 37mDelta
Wed 11/126:00 amFCO - MDW
2 stops19h 18mDelta
Deal found 9/14$530
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.
Tue 10/281:08 pmMDW - FCO
2 stops16h 37mDelta
Wed 11/56:10 amFCO - MDW
2 stops17h 05mDelta
Deal found 9/14$532
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.
Wed 11/510:40 amMDW - FCO
2 stops15h 30mDelta
Fri 11/146:00 amFCO - MDW
2 stops19h 18mDelta
Deal found 9/15$543
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.
Tue 11/49:35 amMDW - FCO
2 stops16h 35mDelta
Tue 11/116:10 amFCO - MDW
2 stops19h 08mDelta
Deal found 9/14$545
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 12/41:14 pmMDW - FLR
2 stops15h 06mDelta
Thu 12/116:50 amFLR - MDW
2 stops18h 28mDelta
Deal found 9/14$693
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.
Tue 9/236:15 pmMDW - FLR
2 stops16h 05mDelta
Wed 10/16:30 amFLR - MDW
2 stops19h 05mDelta
Deal found 9/14$713

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Tuscany 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 Chicago Midway Airport to Tuscany that are best for you.

Fly from

Midway

Fly to

Tuscany

Route

Depart

Return

Price

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 11/9

9:32 am-10:30 am

2 stops17h 58m

Rome Fiumicino

Tue 11/25

12:40 pm-11:32 pm

1 stop17h 52m

$495

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 12/10

6:00 am-7:05 am

2 stops18h 05m

Rome Fiumicino

Tue 12/23

12:40 pm-10:16 pm

1 stop16h 36m

$495

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 10/28

1:08 pm-11:45 am

2 stops16h 37m

Rome Fiumicino

Tue 11/4

9:20 am-10:14 pm

2 stops19h 54m

$514

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 10/26

9:35 am-9:30 am

2 stops17h 55m

Rome Fiumicino

Wed 11/5

6:10 am-5:43 pm

2 stops18h 33m

$517

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 11/5

10:40 am-9:10 am

2 stops15h 30m

Rome Fiumicino

Fri 11/14

6:00 am-6:18 pm

2 stops19h 18m

$543

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 11/4

9:35 am-9:10 am

2 stops16h 35m

Rome Fiumicino

Tue 11/11

6:10 am-6:18 pm

2 stops19h 08m

$545

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 11/10

10:47 am-7:55 am

1 stop14h 08m

Rome Fiumicino

Mon 11/24

12:40 pm-11:32 pm

1 stop17h 52m

$580

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Thu 10/30

10:40 am-9:30 am

1 stop16h 50m

Rome Fiumicino

Thu 11/6

10:05 am-6:25 pm

1 stop15h 20m

$580

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 11/26

10:47 am-7:55 am

1 stop14h 08m

Rome Fiumicino

Tue 12/2

6:10 am-6:00 pm

2 stops18h 50m

$584

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 10/29

9:35 am-8:45 am

2 stops17h 10m

Rome Fiumicino

Fri 11/7

6:00 am-6:25 pm

2 stops19h 25m

$599

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 40 results
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Best time to book a flight from Midway to Tuscany

Have a flexible travel schedule? Discover the best time to fly to Tuscany 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Tuscany
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 Midway to Tuscany. 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 Chicago Midway Airport to Tuscany?

    A quick flight from Chicago Midway Airport to Tuscany can take about 17h 58m. Delta provides one of the quickest options available for as low as $495. Airlines will cover a distance of 4810 mi.

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

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

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Tuscany (average of $763). Flying from Chicago Midway Airport to Tuscany in June is currently the most expensive (average of $1,294). 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

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Alternative routes for Midway to Tuscany

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