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$224+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — FLR
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$536
(KLM)

One-way from

$224
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$741
Provider with most accurate pricing for Chicago (CHI)-Florence Peretola flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Florence Peretola flights.
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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 ($204 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($40 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 3, 2025.

This Delta deal was found by Cheapflights users on 11/3. 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 11/910:47 amMDW - FCO
1 stop14h 08mDelta
Tue 11/2512:40 pmFCO - MDW
1 stop18h 00mDelta
Deal found 11/3$525
This Delta deal was found by Cheapflights users on 11/2. 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 12/21:14 pmMDW - FCO
1 stop11h 41mDelta
Wed 12/1712:40 pmFCO - MDW
1 stop18h 07mDelta
Deal found 11/2$536
This Delta deal was found by Cheapflights users on 11/2. 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 11/101:15 pmMDW - FCO
2 stops15h 30mDelta
Tue 11/186:10 amFCO - MDW
2 stops18h 58mDelta
Deal found 11/2$540
This Delta deal was found by Cheapflights users on 11/1. 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 12/29:59 amMDW - FCO
2 stops14h 56mDelta
Tue 12/166:10 amFCO - MDW
2 stops19h 08mDelta
Deal found 11/1$541
This Delta deal was found by Cheapflights users on 10/31. 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 11/1112:45 pmFCO - MDW
2 stops17h 55mDelta
Deal found 10/31$546
This Trip.com deal was found by Cheapflights users on 11/2. 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.
Sun 11/910:47 amMDW - FCO
1 stop16h 43mKLM
Tue 11/256:10 amFCO - MDW
2 stops18h 58mKLM
Deal found 11/2$559
This Delta deal was found by Cheapflights users on 11/3. 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.
Sat 11/81:06 pmMDW - FCO
1 stop11h 49mDelta
Wed 11/196:10 amFCO - MDW
2 stops19h 08mDelta
Deal found 11/3$586
This Delta deal was found by Cheapflights users on 11/2. 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 12/119:34 amMDW - FCO
1 stop15h 21mDelta
Thu 12/189:20 amFCO - MDW
2 stops21h 27mDelta
Deal found 11/2$591
This Delta deal was found by Cheapflights users on 11/1. 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 11/1910:47 amMDW - FCO
2 stops15h 23mDelta
Mon 12/156:10 amFCO - MDW
2 stops19h 08mDelta
Deal found 11/1$596
This Delta deal was found by Cheapflights users on 11/1. 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 11/239:34 amMDW - FCO
2 stops17h 11mDelta
Fri 12/512:40 pmFCO - MDW
1 stop18h 07mDelta
Deal found 11/1$601
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Sat 11/151:37 pmMDW - FCO
2 stops41h 53mMultiple Airlines
Sat 11/227:10 pmFCO - MDW
1 stop23h 32mMultiple Airlines
Deal found 11/2$612
This Delta deal was found by Cheapflights users on 11/2. 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 12/11:15 pmMDW - FLR
2 stops15h 05mDelta
Mon 12/86:40 amFLR - MDW
2 stops18h 38mDelta
Deal found 11/2$647

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 November 3, 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

Wed 11/26

10:47 am-7:55 am

1 stop14h 08m

Rome Fiumicino

Wed 12/3

12:45 pm-11:47 pm

2 stops18h 02m

$536

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 12/10

12:50 pm-7:55 am

1 stop12h 05m

Rome Fiumicino

Tue 12/23

10:05 am-5:26 pm

1 stop14h 21m

$536

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 12/3

10:49 am-7:55 am

1 stop14h 06m

Rome Fiumicino

Thu 12/11

10:05 am-6:00 pm

1 stop14h 55m

$536

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 12/30

9:50 am-7:55 am

1 stop15h 05m

Rome Fiumicino

Thu 1/15

12:40 pm-10:09 pm

1 stop16h 29m

$536

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 3/2

5:25 pm-5:25 pm

2 stops17h 00m

Rome Fiumicino

Mon 3/9

9:05 am-9:46 pm

1 stop18h 41m

$590

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 1/12

1:28 pm-11:45 am

2 stops15h 17m

Rome Fiumicino

Mon 1/19

6:10 am-5:55 pm

2 stops18h 45m

$625

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 3/11

10:35 am-6:55 am

1 stop14h 20m

Rome Fiumicino

Wed 3/18

6:10 am-6:08 pm

2 stops17h 58m

$646

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Mon 3/9

1:00 pm-11:20 am

2 stops16h 20m

Florence Peretola

Thu 3/19

6:40 am-6:34 pm

2 stops17h 54m

$647

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Mon 1/12

1:28 pm-2:25 pm

2 stops17h 57m

Florence Peretola

Sun 1/18

6:40 am-10:09 pm

2 stops22h 29m

$647

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Mon 12/1

1:15 pm-11:20 am

2 stops15h 05m

Florence Peretola

Mon 12/8

6:40 am-6:18 pm

2 stops18h 38m

$647

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 31 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 14h 06m. Delta provides one of the quickest options available for as low as $536. Airlines will cover a distance of 4810 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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.

See more FAQs

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Alternative routes for Midway to Tuscany

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