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$393+ 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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — FLR
Apr 30 — May 71
Wed 4/30
Wed 5/7
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 April 25, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$807
(Mytrip)

One-way from

$393
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$906
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 ($214 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 25, 2025.

This Delta deal was found by Cheapflights users on 4/24. 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 10/276:00 amMDW - FCO
1 stop18h 55mDelta
Mon 11/36:10 amFCO - MDW
2 stops19h 26mDelta
Deal found 4/24$641
This KLM deal was found by Cheapflights users on 4/24. 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 11/191:05 pmMDW - FCO
1 stop14h 25mKLM
Tue 11/2510:05 amFCO - MDW
1 stop15h 31mKLM
Deal found 4/24$735
This Mytrip deal was found by Cheapflights users on 4/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/59:40 amMDW - FCO
2 stops17h 45mPorter Airlines
Thu 6/1212:15 pmFCO - MDW
2 stops27h 30mPorter Airlines
Deal found 4/24$807
This Delta deal was found by Cheapflights users on 4/25. 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 10/75:59 pmMDW - FLR
2 stops16h 21mDelta
Wed 10/156:30 amFLR - MDW
2 stops19h 06mDelta
Deal found 4/25$836
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/69:40 amMDW - FCO
2 stops16h 35mMultiple Airlines
Tue 6/1011:30 amFCO - MDW
2 stops28h 15mMultiple Airlines
Deal found 4/23$868
This KLM deal was found by Cheapflights users on 4/24. 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.
Thu 5/81:08 pmMDW - FLR
2 stops15h 12mKLM
Sun 5/116:30 amFLR - MDW
2 stops18h 15mKLM
Deal found 4/24$957
This Air France deal was found by Cheapflights users on 4/24. 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 11/181:00 pmMDW - FCO
1 stop11h 55mAir France
Wed 11/2612:45 pmFCO - MDW
1 stop15h 59mAir France
Deal found 4/24$980
This Mytrip deal was found by Cheapflights users on 4/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/89:40 amMDW - FLR
3 stops30h 30mMultiple Airlines
Sun 5/117:30 amFLR - MDW
3 stops40h 24mMultiple Airlines
Deal found 4/24$1,189
This Mytrip deal was found by Cheapflights users on 4/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/89:40 amMDW - PSA
3 stops28h 05mMultiple Airlines
Sun 5/119:55 amPSA - MDW
3 stops38h 50mMultiple Airlines
Deal found 4/25$1,199
This SmartFares deal was found by Cheapflights users on 4/25. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/99:24 amMDW - PSA
2 stops21h 51mKLM
Mon 6/163:25 pmPSA - MDW
2 stops37h 20mKLM
Deal found 4/25$1,298

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 25, 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

Thu 6/5

9:40 am-10:25 am

2 stops17h 45m

Rome Fiumicino

Thu 6/12

12:15 pm-8:45 am

2 stops27h 30m

$807

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Fri 6/6

9:40 am-9:15 am

2 stops16h 35m

Rome Fiumicino

Tue 6/10

11:30 am-8:45 am

2 stops28h 15m

$868

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Thu 5/8

1:08 pm-11:20 am

2 stops15h 12m

Florence Peretola

Sun 5/11

6:30 am-5:45 pm

2 stops18h 15m

$957

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 5/13

12:48 pm-7:35 am

1 stop11h 47m

Rome Fiumicino

Wed 5/21

9:00 am-6:45 pm

1 stop16h 45m

$1,014

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 4/28

9:52 am-7:35 am

1 stop14h 43m

Rome Fiumicino

Wed 5/14

9:00 am-6:45 pm

1 stop16h 45m

$1,047

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Thu 5/8

1:08 pm-11:20 am

2 stops15h 12m

Florence Peretola

Mon 5/19

6:30 am-6:45 pm

2 stops19h 15m

$1,057

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Fri 5/9

10:25 am-7:35 am

1 stop14h 10m

Rome Fiumicino

Fri 5/23

6:05 am-3:20 pm

2 stops16h 15m

$1,100

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Thu 5/8

9:40 am-11:10 pm

3 stops30h 30m

Florence Peretola

Sun 5/11

7:30 am-4:54 pm

3 stops40h 24m

$1,189

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Thu 5/8

9:40 am-8:45 pm

3 stops28h 05m

Pisa Gal Galilei

Sun 5/11

9:55 am-5:45 pm

3 stops38h 50m

$1,199

ChicagoPisa

MDW - PSA

MDWPSA

Chicago Midway

Mon 6/9

9:24 am-2:15 pm

2 stops21h 51m

Pisa Gal Galilei

Mon 6/16

3:25 pm-9:45 pm

2 stops37h 20m

$1,298

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

Showing 1-10 of 20 results
1
2

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

Rainfall in Tuscany by month

Plan your trip to Tuscany by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Tuscany ranges from 1.2 - 3.9 inches per month. October is typically the wettest month, when rainfall can reach 3.9 in. July is typically the driest time to visit Tuscany when rainfall is around 1.2 in.

Temperature in Tuscany by month

Plan your trip to Tuscany by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Tuscany, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 75.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

Reviews of airlines servicing Tuscany

Get insights into the airlines that provide service to Tuscany. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Tuscany. Reviews last updated April 25, 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta and KLM from Chicago to Tuscany by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
285 reviews

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,920 reviews
Porter Airlines
8.0
Very good
285 reviews

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
KLM
7.8
Good
1,333 reviews
Porter Airlines
8.0
Very good
285 reviews

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Transat
7.8
Good
385 reviews
Porter Airlines
8.0
Very good
285 reviews

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air France
7.4
Good
1,444 reviews
Porter Airlines
8.0
Very good
285 reviews

Overall

8.0

Crew

8.8

Entertainment

7.0

Boarding

8.2

Comfort

8.1

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Tuscany one-way?

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Tuscany are Porter Airlines ($604), Delta ($627), and KLM ($632).

  • 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 $766). Flying from Chicago Midway Airport to Tuscany in June is currently the most expensive (average of $1,387). 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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