Tuscany

$408+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — FLR
May 17 — May 241
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Cheap 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 April 17, 2026.

This Delta deal was found by Cheapflights users on 4/16. 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 8/182:00 pm
MDW
-
FCO
1 stop15h 40m
Delta
Tue 8/251:10 pm
FCO
-
MDW
1 stop15h 36m
Delta
Deal found 4/16$758
This Delta deal was found by Cheapflights users on 4/14. 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.
Wed 8/121:00 pm
MDW
-
FCO
2 stops15h 25m
Delta
Wed 8/199:00 am
FCO
-
MDW
1 stop16h 31m
Delta
Deal found 4/14$762
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:30 am
MDW
-
FCO
1 stop24h 00m
Multiple Airlines
Thu 4/237:05 pm
FCO
-
MDW
1 stop24h 55m
Multiple Airlines
Deal found 4/12$764
This Air France deal was found by Cheapflights users on 4/17. 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 4/172:12 pm
MDW
-
FCO
1 stop12h 58m
Multiple Airlines
Tue 4/211:10 pm
FCO
-
MDW
1 stop16h 18m
Multiple Airlines
Deal found 4/17$799
This Air France deal was found by Cheapflights users on 4/14. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:24 pm
MDW
-
FCO
1 stop14h 36m
Air France
Tue 4/211:10 pm
FCO
-
MDW
1 stop16h 18m
Air France
Deal found 4/14$800
This Delta deal was found by Cheapflights users on 4/16. 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 4/166:00 am
MDW
-
FCO
1 stop18h 35m
Delta
Thu 4/236:30 am
FCO
-
MDW
2 stops16h 56m
Delta
Deal found 4/16$808
This Delta deal was found by Cheapflights users on 4/16. 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 10/269:30 am
MDW
-
FCO
1 stop18h 05m
Delta
Mon 11/96:10 am
FCO
-
MDW
2 stops17h 15m
Delta
Deal found 4/16$809
This KAYAK deal was found by Cheapflights users on 4/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:16 pm
MDW
-
FCO
1 stop31h 54m
Scandinavian Airlines
Tue 4/211:10 pm
FCO
-
MDW
1 stop16h 18m
Scandinavian Airlines
Deal found 4/13$812
This Delta deal was found by Cheapflights users on 4/12. 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.
Mon 12/289:30 am
MDW
-
FCO
1 stop17h 05m
Delta
Mon 1/119:55 am
FCO
-
MDW
2 stops18h 50m
Delta
Deal found 4/12$815
This Air France deal was found by Cheapflights users on 4/16. 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.
Sun 8/161:05 pm
MDW
-
FCO
1 stop14h 45m
Air France
Fri 8/219:00 am
FCO
-
MDW
1 stop16h 31m
Air France
Deal found 4/16$827
This Delta deal was found by Cheapflights users on 4/12. 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.
Wed 11/45:59 pm
MDW
-
FLR
2 stops13h 26m
Delta
Wed 11/116:40 am
FLR
-
MDW
2 stops18h 57m
Delta
Deal found 4/12$894
This Air France deal was found by Cheapflights users on 4/13. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:59 am
MDW
-
FLR
2 stops14h 56m
Multiple Airlines
Fri 5/226:30 am
FLR
-
MDW
2 stops19h 03m
Multiple Airlines
Deal found 4/13$972

Find flight deals from Midway to Tuscany

Keep the following information in mind while searching for Midway to Tuscany flight deals. Data was last updated April 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$758
(KLM)

One-way from

$408
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$865
Provider with most accurate pricing for Chicago (CHI)-Florence Peretola flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Florence Peretola flights.
From Chicago Midway to Tuscany
One-way flight from Chicago Midway to Tuscany
Highest demand for flights based on searches. 17% potential increase in price ($200 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($34 potential savings vs. average RT price).
Average for round-trip flights in April 2026

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 April 17, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Tuscany that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 6/8

6:58 pm-4:25 pm

2 stops14h 27m

Rome Fiumicino

Thu 7/2

6:30 am-4:46 pm

2 stops17h 16m

$948

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Wed 5/13

6:36 pm-7:00 pm

2 stops17h 24m

Florence Peretola

Fri 5/22

11:20 am-6:33 pm

2 stops14h 13m

$977

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Thu 7/9

11:05 am-11:00 am

2 stops16h 55m

Rome Fiumicino

Wed 7/15

9:00 am-6:25 pm

1 stop16h 25m

$1,013

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Thu 8/20

8:15 am-3:50 pm

2 stops24h 35m

Rome Fiumicino

Wed 9/2

8:10 am-8:50 pm

2 stops19h 40m

$1,015

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Mon 5/11

1:22 pm-11:30 am

2 stops15h 08m

Florence Peretola

Sat 5/23

6:30 am-5:56 pm

2 stops18h 26m

$1,032

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 5/11

1:22 pm-11:00 am

1 stop14h 38m

Rome Fiumicino

Tue 6/2

10:35 am-6:33 pm

2 stops14h 58m

$1,063

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Tue 5/5

1:24 pm-2:55 pm

2 stops18h 31m

Pisa Gal Galilei

Tue 5/19

3:00 pm-4:12 pm

2 stops32h 12m

$1,075

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Mon 4/27

1:24 pm-11:30 am

2 stops15h 06m

Florence Peretola

Tue 5/12

11:20 am-6:33 pm

2 stops14h 13m

$1,076

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sat 6/13

6:35 pm-4:25 pm

2 stops14h 50m

Rome Fiumicino

Mon 6/22

9:00 am-6:31 pm

1 stop16h 31m

$1,087

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Tue 8/4

6:58 pm-3:35 pm

2 stops13h 37m

Pisa Gal Galilei

Sun 8/16

9:45 pm-4:27 pm

2 stops25h 42m

$1,090

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 46 resultsSorted by cheapest first
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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 27m. Delta provides one of the quickest options available for as low as $948. 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?

  • 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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