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Capri

$356+ Cheap flights from Midway (MDW) to Capri, 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Midway to Capri

Cheapest flights from Midway to Capri
Explore the most affordable flight options available from Midway to Capri. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This KLM deal was found by Cheapflights users on 12/17. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:08 pmMDW - NAP
2 stops14h 42mMultiple Airlines
Fri 1/26:35 amNAP - MDW
2 stops17h 51mMultiple Airlines
Deal found 12/17$2,770
This KLM deal was found by Cheapflights users on 12/16. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:48 amMDW - NAP
2 stops16h 22mMultiple Airlines
Thu 1/16:15 amNAP - MDW
2 stops18h 04mMultiple Airlines
Deal found 12/16$3,204
This Air France deal was found by Cheapflights users on 12/17. 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.
Sun 12/2112:45 pmMDW - NAP
2 stops15h 45mAir France
Wed 12/316:35 amNAP - MDW
2 stops17h 51mAir France
Deal found 12/17$3,388
This KLM deal was found by Cheapflights users on 12/16. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:08 pmMDW - NAP
2 stops14h 42mMultiple Airlines
Mon 12/226:35 amNAP - MDW
2 stops17h 51mMultiple Airlines
Deal found 12/16$3,719
This Air France deal was found by Cheapflights users on 12/17. 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.
Sun 12/2812:45 pmMDW - NAP
2 stops15h 45mAir France
Sat 1/36:35 amNAP - MDW
2 stops17h 51mAir France
Deal found 12/17$3,720
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:26 pmMDW - NAP
2 stops20h 49mDelta
Wed 12/316:15 amNAP - MDW
2 stops18h 04mDelta
Deal found 12/17$3,916

Find flight deals from Midway to Capri

Keep the following information in mind while searching for Midway to Capri flight deals. Data was last updated December 18, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$557
(Delta)

One-way from

$356
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$932
Provider with most accurate pricing for Chicago (CHI)-Naples flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Naples flights.
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From Chicago Midway to Capri
Search Deals
One-way flight from Chicago Midway to Capri
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($243 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Capri 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 December 18, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Capri that are best for you.

Fly from

Midway

Fly to

Capri

Route

Depart

Return

Price

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 2/23

6:40 pm-9:15 pm

2 stops19h 35m

Naples

Thu 3/5

6:15 am-10:42 pm

2 stops23h 27m

$557

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 2/22

9:34 am-11:30 am

2 stops18h 56m

Naples

Wed 3/4

6:15 am-5:37 pm

2 stops18h 22m

$606

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 1/11

9:32 am-11:30 am

2 stops18h 58m

Naples

Mon 1/26

6:15 am-5:55 pm

2 stops18h 40m

$656

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 1/30

9:50 am-3:50 pm

2 stops23h 00m

Naples

Fri 2/6

6:15 am-5:55 pm

2 stops18h 40m

$656

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 1/30

1:49 pm-3:50 pm

2 stops19h 01m

Naples

Fri 2/6

6:35 am-10:22 pm

2 stops22h 47m

$681

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 2/11

12:48 pm-11:30 am

2 stops15h 42m

Naples

Wed 2/18

6:15 am-5:45 pm

2 stops18h 30m

$683

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 2/12

1:28 pm-9:45 am

2 stops13h 17m

Naples

Mon 2/16

6:15 am-5:45 pm

2 stops18h 30m

$768

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 4/29

5:59 pm-6:15 pm

2 stops17h 16m

Naples

Thu 5/14

10:15 am-9:45 pm

2 stops18h 30m

$849

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 4/1

5:38 pm-6:15 pm

2 stops17h 37m

Naples

Fri 4/10

6:10 am-5:55 pm

2 stops18h 45m

$857

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 4/7

6:35 pm-6:15 pm

2 stops16h 40m

Naples

Mon 4/27

6:10 am-4:25 pm

2 stops17h 15m

$917

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 12 results
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Best time to book a flight from Midway to Capri

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

    For as low as $557, Delta can have you in Capri from Chicago Midway Airport in 19h 35m. The distance from Chicago Midway Airport to Capri is about 4931 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Capri 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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