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Capri

$397+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This KLM deal was found by Cheapflights users on 1/27. 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 2/251:26 pm
MDW
-
NAP
2 stops13h 24m
KLM
Wed 3/46:15 am
NAP
-
MDW
2 stops18h 30m
KLM
Deal found 1/27$565
This Trip.com deal was found by Cheapflights users on 1/28. 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 2/1612:45 pm
MDW
-
NAP
2 stops18h 40m
KLM
Mon 3/21:15 pm
NAP
-
MDW
2 stops35h 30m
KLM
Deal found 1/28$598
This Delta deal was found by Cheapflights users on 1/28. 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 8/610:35 am
MDW
-
NAP
1 stop13h 30m
Delta
Wed 8/199:15 am
NAP
-
MDW
1 stop19h 31m
Delta
Deal found 1/28$617
This Delta deal was found by Cheapflights users on 1/28. 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 8/95:59 pm
MDW
-
NAP
2 stops17h 16m
Delta
Wed 8/199:15 am
NAP
-
MDW
1 stop19h 31m
Delta
Deal found 1/28$621
This Delta deal was found by Cheapflights users on 1/28. 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 8/1110:35 am
MDW
-
NAP
1 stop13h 30m
Delta
Sat 8/226:05 am
NAP
-
MDW
2 stops22h 41m
Delta
Deal found 1/28$629
This Delta deal was found by Cheapflights users on 1/28. 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 8/116:00 am
MDW
-
NAP
1 stop18h 05m
Delta
Mon 8/249:15 am
NAP
-
MDW
1 stop19h 31m
Delta
Deal found 1/28$644
This Delta deal was found by Cheapflights users on 1/28. 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 8/119:30 am
MDW
-
NAP
2 stops14h 35m
Delta
Sun 8/239:15 am
NAP
-
MDW
1 stop19h 31m
Delta
Deal found 1/28$649
This Delta deal was found by Cheapflights users on 1/28. 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 8/1310:35 am
MDW
-
NAP
1 stop13h 30m
Delta
Sun 8/236:05 am
NAP
-
MDW
2 stops17h 22m
Delta
Deal found 1/28$656
This Delta deal was found by Cheapflights users on 1/28. 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 8/1110:35 am
MDW
-
NAP
1 stop13h 30m
Delta
Tue 8/2510:15 am
NAP
-
MDW
2 stops18h 31m
Delta
Deal found 1/28$676
This Delta deal was found by Cheapflights users on 1/27. 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 3/246:34 pm
MDW
-
NAP
2 stops20h 41m
Delta
Wed 4/16:05 am
NAP
-
MDW
2 stops19h 35m
Delta
Deal found 1/27$685
This Air France deal was found by Cheapflights users on 1/28. 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 8/75:25 pm
MDW
-
NAP
1 stop30h 40m
Air France
Wed 8/199:15 am
NAP
-
MDW
1 stop19h 31m
Air France
Deal found 1/28$701

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$565
(KLM)

One-way from

$397
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$622
Provider with most accurate pricing for Chicago (CHI)-Naples flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Naples flights.
Search Deals
From Chicago Midway to Capri
Search Deals
One-way flight from Chicago Midway to Capri
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($231 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Wed 4/8

12:47 pm-11:30 am

2 stops15h 43m

Naples

Thu 4/16

6:05 am-5:58 pm

2 stops18h 53m

$788

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 2/27

9:50 am-11:10 am

2 stops18h 20m

Naples

Fri 3/6

10:35 am-8:54 am

2 stops29h 19m

$847

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 4/29

1:23 pm-3:45 pm

2 stops19h 22m

Naples

Thu 5/14

6:05 am-4:25 pm

2 stops17h 20m

$858

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 4/1

9:30 am-11:30 am

2 stops19h 00m

Naples

Wed 4/8

6:05 am-5:22 pm

2 stops18h 17m

$858

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 5/11

1:00 pm-3:15 pm

2 stops19h 15m

Naples

Wed 5/20

6:05 am-6:05 pm

2 stops19h 00m

$859

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 4/9

9:30 am-11:30 am

2 stops19h 00m

Naples

Sat 4/18

6:05 am-6:36 pm

2 stops19h 31m

$894

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 4/9

9:30 am-11:30 am

2 stops19h 00m

Naples

Sun 4/19

6:05 am-5:58 pm

2 stops18h 53m

$895

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 2/27

10:49 am-11:10 am

2 stops17h 21m

Naples

Fri 3/6

6:15 am-6:40 pm

2 stops19h 25m

$913

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 2/27

10:49 am-11:10 am

2 stops17h 21m

Naples

Mon 3/9

6:15 am-6:40 pm

2 stops18h 25m

$922

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 5/9

2:00 pm-11:30 am

2 stops14h 30m

Naples

Sat 5/16

6:05 am-9:45 pm

2 stops22h 40m

$979

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 20 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 $788, Delta can have you in Capri from Chicago Midway Airport in 15h 43m. 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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