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Sorrento

$448+ Cheap flights from Midway (MDW) to Sorrento, Italy

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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Midway to Sorrento

Keep the following information in mind while searching for Midway to Sorrento flight deals. Data was last updated November 3, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$704
(Delta)

One-way from

$448
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$716
Provider with most accurate pricing for Chicago (CHI)-Naples flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Naples flights.
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From Chicago Midway to Sorrento
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One-way flight from Chicago Midway to Sorrento
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Highest demand for flights based on searches. 23% potential increase in price ($262 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($32 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 Sorrento

Cheapest flights from Midway to Sorrento
Explore the most affordable flight options available from Midway to Sorrento. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

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.
Mon 11/2412:47 pmMDW - NAP
2 stops20h 03mMultiple Airlines
Mon 12/812:15 pmNAP - MDW
2 stops35h 19mMultiple Airlines
Deal found 11/2$592
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 11/241:15 pmMDW - NAP
2 stops19h 35mDelta
Mon 12/86:15 amNAP - MDW
2 stops18h 45mDelta
Deal found 11/2$655
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.
Fri 11/289:34 amMDW - NAP
2 stops18h 36mDelta
Fri 12/56:15 amNAP - MDW
2 stops18h 45mDelta
Deal found 11/1$737
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 11/115:34 pmMDW - NAP
2 stops20h 41mDelta
Tue 11/186:15 amNAP - MDW
2 stops18h 53mDelta
Deal found 11/1$806
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/171:05 pmMDW - NAP
2 stops18h 15mKLM
Wed 12/2410:25 amNAP - MDW
2 stops29h 40mKLM
Deal found 11/1$998
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 11/36:23 pmMDW - NAP
2 stops19h 52mDelta
Tue 11/186:15 amNAP - MDW
2 stops18h 53mDelta
Deal found 11/2$1,070
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.
Sat 11/14:23 pmMDW - NAP
2 stops17h 27mDelta
Sat 11/86:15 amNAP - MDW
2 stops22h 59mDelta
Deal found 10/31$1,852
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.
Fri 12/269:50 amMDW - NAP
2 stops18h 20mDelta
Fri 1/26:15 amNAP - MDW
2 stops18h 11mDelta
Deal found 11/1$2,354
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 12/2312:45 pmMDW - NAP
2 stops20h 05mDelta
Thu 1/16:15 amNAP - MDW
2 stops23h 07mDelta
Deal found 11/1$2,655
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 12/181:50 pmMDW - NAP
2 stops19h 00mDelta
Tue 12/306:15 amNAP - MDW
2 stops18h 04mDelta
Deal found 11/2$3,460
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 11/2512:47 pmMDW - NAP
2 stops20h 03mDelta
Wed 12/36:15 amNAP - MDW
2 stops19h 03mDelta
Deal found 11/2$8,570
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 11/2410:47 amMDW - NAP
2 stops22h 03mDelta
Wed 12/36:15 amNAP - MDW
2 stops19h 03mDelta
Deal found 11/2$8,820

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Sorrento 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 Sorrento that are best for you.

Fly from

Midway

Fly to

Sorrento

Route

Depart

Return

Price

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 11/24

1:15 pm-3:50 pm

2 stops19h 35m

Naples

Mon 12/8

6:15 am-6:00 pm

2 stops18h 45m

$655

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 11/28

9:34 am-11:10 am

2 stops18h 36m

Naples

Fri 12/5

6:15 am-6:00 pm

2 stops18h 45m

$737

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 11/11

5:34 pm-9:15 pm

2 stops20h 41m

Naples

Tue 11/18

6:15 am-6:08 pm

2 stops18h 53m

$806

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 1/8

11:21 am-3:50 pm

2 stops21h 29m

Naples

Thu 1/15

6:15 am-10:09 pm

2 stops22h 54m

$815

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 1/16

11:21 am-3:50 pm

2 stops21h 29m

Naples

Sat 1/24

6:15 am-4:16 pm

2 stops17h 01m

$956

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 12/17

1:05 pm-2:20 pm

2 stops18h 15m

Naples

Wed 12/24

10:25 am-9:05 am

2 stops29h 40m

$998

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 12/26

9:50 am-11:10 am

2 stops18h 20m

Naples

Fri 1/2

6:15 am-5:26 pm

2 stops18h 11m

$2,354

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 12/23

12:45 pm-3:50 pm

2 stops20h 05m

Naples

Thu 1/1

6:15 am-10:22 pm

2 stops23h 07m

$2,655

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 12/19

1:14 pm-3:50 pm

2 stops19h 36m

Naples

Tue 12/30

6:15 am-10:22 pm

2 stops23h 07m

$3,460

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 12/18

1:50 pm-3:50 pm

2 stops19h 00m

Naples

Tue 12/30

6:15 am-5:19 pm

2 stops18h 04m

$3,460

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 16 results
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Best time to book a flight from Midway to Sorrento

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

    A quick flight from Chicago Midway Airport to Sorrento can take about 19h 35m. Delta provides one of the quickest options available for as low as $655. Chicago Midway Airport and Sorrento are separated by a distance of 4931 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Sorrento by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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