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Capri

$224+ Cheap flights from Chicago (CHI) 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Capri are usually found in February or January, booked 52 days in advance, depart on a Tuesday or Monday and return on a Saturday

Cheap flight deals from Chicago to Capri

Cheapest flights from Chicago to Capri
Explore the most affordable flight options available from Chicago to Capri. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.

This oojo deal was found by Cheapflights users on 1/25. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 pm
ORD
-
NAP
1 stop17h 25m
TAP AIR PORTUGAL
Thu 5/147:15 pm
NAP
-
ORD
1 stop27h 45m
TAP AIR PORTUGAL
Deal found 1/25$381
This oojo deal was found by Cheapflights users on 1/26. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 pm
ORD
-
NAP
1 stop34h 40m
TAP AIR PORTUGAL
Thu 4/167:15 pm
NAP
-
ORD
1 stop27h 45m
TAP AIR PORTUGAL
Deal found 1/26$385
This oojo deal was found by Cheapflights users on 1/26. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:15 pm
ORD
-
NAP
1 stop17h 05m
TAP AIR PORTUGAL
Fri 4/2412:30 pm
NAP
-
ORD
1 stop34h 45m
TAP AIR PORTUGAL
Deal found 1/26$388
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 pm
ORD
-
NAP
1 stop17h 25m
TAP AIR PORTUGAL
Fri 4/2412:30 pm
NAP
-
ORD
1 stop34h 45m
TAP AIR PORTUGAL
Deal found 1/27$389
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:15 pm
ORD
-
NAP
1 stop12h 50m
Scandinavian Airlines
Fri 5/811:55 am
NAP
-
ORD
1 stop35h 15m
Scandinavian Airlines
Deal found 1/27$466
This oojo deal was found by Cheapflights users on 1/26. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:00 pm
ORD
-
NAP
1 stop17h 20m
TAP AIR PORTUGAL
Fri 5/112:30 pm
NAP
-
ORD
1 stop34h 45m
TAP AIR PORTUGAL
Deal found 1/26$505
This Trip.com deal was found by Cheapflights users on 1/26. 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 4/67:15 pm
ORD
-
NAP
1 stop16h 30m
Scandinavian Airlines
Fri 4/2411:55 am
NAP
-
ORD
1 stop35h 15m
Scandinavian Airlines
Deal found 1/26$507
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/229:50 pm
ORD
-
NAP
1 stop12h 35m
Multiple Airlines
Tue 3/102:50 pm
NAP
-
ORD
1 stop32h 30m
Multiple Airlines
Deal found 1/26$508
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Mon 3/29:50 pm
ORD
-
NAP
1 stop12h 35m
Lufthansa
Mon 3/96:15 pm
NAP
-
ORD
1 stop31h 10m
Lufthansa
Deal found 1/26$510
This Delta deal was found by Cheapflights users on 1/25. 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.
Sun 2/229:34 am
MDW
-
NAP
2 stops18h 56m
Delta
Tue 3/106:15 am
NAP
-
MDW
2 stops18h 25m
Delta
Deal found 1/25$558
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 KLM deal was found by Cheapflights users on 1/26. 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.
Tue 3/1012:47 pm
MDW
-
NAP
2 stops14h 48m
KLM
Tue 3/176:35 am
NAP
-
MDW
2 stops17h 19m
KLM
Deal found 1/26$608

Find flight deals from Chicago to Capri

Keep the following information in mind while searching for Chicago to Capri flight deals. Data was last updated January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$381
(oojo)

One-way from

$224
(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 (CHI) to Capri
Search Deals
One-way flight from Chicago (CHI) 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 Chicago 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 28, 2026.
Use the filters below to find and compare flights from Chicago to Capri that are best for you.

Fly from

Chicago

Fly to

Capri

Route

Depart

Return

Price

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 2/22

9:34 am-11:30 am

2 stops18h 56m

Naples

Tue 3/10

6:15 am-6:40 pm

2 stops18h 25m

$558

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 2/22

6:30 am-11:30 am

2 stops22h 00m

Naples

Tue 3/10

6:15 am-9:49 pm

2 stops21h 34m

$558

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Thu 5/7

11:25 am-8:25 am

1 stop14h 00m

Naples

Wed 5/13

3:45 pm-9:40 am

1 stop24h 55m

$561

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 2/25

1:26 pm-9:50 am

2 stops13h 24m

Naples

Wed 3/4

6:15 am-5:45 pm

2 stops18h 30m

$565

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Thu 5/7

11:25 am-8:25 am

1 stop14h 00m

Naples

Tue 5/12

9:25 am-6:15 pm

1 stop15h 50m

$594

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 3/10

12:47 pm-9:35 am

2 stops14h 48m

Naples

Tue 3/17

6:35 am-5:54 pm

2 stops17h 19m

$608

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 2/22

6:30 am-11:30 am

2 stops22h 00m

Naples

Mon 3/2

6:15 am-8:44 pm

2 stops21h 29m

$609

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 4/8

9:40 pm-4:45 pm

1 stop12h 05m

Naples

Thu 4/16

6:45 am-5:45 pm

2 stops18h 00m

$697

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 3/25

10:50 pm-5:25 pm

1 stop12h 35m

Naples

Wed 4/1

6:25 am-11:43 pm

2 stops24h 18m

$700

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 5/3

6:00 pm-11:40 am

1 stop34h 40m

Naples

Thu 5/7

7:15 pm-4:00 pm

1 stop27h 45m

$741

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 39 results
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Best time to book a flight from Chicago to Capri

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

How far ahead should I book a flight from Chicago to Capri?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Capri. Price data was last updated on January 23, 2026.

The best time to book flights from Chicago to Capri is 52 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Capri?

Currently, March is the cheapest month in which you can book a flight from Chicago to Capri (average of $496). Flying from Chicago to Capri in June is currently the most expensive (average of $816). 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.

Reviews of airlines servicing Capri

Get insights into the airlines that provide service to Capri. 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 Capri. Reviews last updated January 28, 2026.
Get a feel of what it's like to fly with SWISS, United Airlines, and Turkish Airlines from Chicago to Capri by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
SWISS
7.6
Good
1,863 reviews

Food

7.1

Boarding

7.7

Crew

8.3

Entertainment

6.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Katerina,Sep 2025

GVA - ATH

Although the plane was half empty and the flight was late at night, we were not allowed to change seats/ use empty seats to get ourselves more comfortable, or get some proper sleep. It is really frustrating to see lack of flexibility in such a simple need.
SWISS
7.6
Good
1,863 reviews
SWISS
7.6
Good
1,863 reviews

Food

7.1

Boarding

7.7

Crew

8.3

Entertainment

6.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Katerina,Sep 2025

GVA - ATH

Although the plane was half empty and the flight was late at night, we were not allowed to change seats/ use empty seats to get ourselves more comfortable, or get some proper sleep. It is really frustrating to see lack of flexibility in such a simple need.
United Airlines
7.4
Good
9,211 reviews
SWISS
7.6
Good
1,863 reviews

Food

7.1

Boarding

7.7

Crew

8.3

Entertainment

6.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Katerina,Sep 2025

GVA - ATH

Although the plane was half empty and the flight was late at night, we were not allowed to change seats/ use empty seats to get ourselves more comfortable, or get some proper sleep. It is really frustrating to see lack of flexibility in such a simple need.
Turkish Airlines
7.3
Good
4,209 reviews
SWISS
7.6
Good
1,863 reviews

Food

7.1

Boarding

7.7

Crew

8.3

Entertainment

6.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Katerina,Sep 2025

GVA - ATH

Although the plane was half empty and the flight was late at night, we were not allowed to change seats/ use empty seats to get ourselves more comfortable, or get some proper sleep. It is really frustrating to see lack of flexibility in such a simple need.
American Airlines
7.2
Good
11,201 reviews
SWISS
7.6
Good
1,863 reviews

Food

7.1

Boarding

7.7

Crew

8.3

Entertainment

6.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Katerina,Sep 2025

GVA - ATH

Although the plane was half empty and the flight was late at night, we were not allowed to change seats/ use empty seats to get ourselves more comfortable, or get some proper sleep. It is really frustrating to see lack of flexibility in such a simple need.
Aer Lingus
7.2
Good
1,442 reviews
SWISS
7.6
Good
1,863 reviews

Food

7.1

Boarding

7.7

Crew

8.3

Entertainment

6.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Katerina,Sep 2025

GVA - ATH

Although the plane was half empty and the flight was late at night, we were not allowed to change seats/ use empty seats to get ourselves more comfortable, or get some proper sleep. It is really frustrating to see lack of flexibility in such a simple need.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 to Capri?

    A quick flight from Chicago to Capri can take about 13h 24m. Delta provides one of the quickest options available for as low as $565. The distance from Chicago to Capri is about 4931 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Capri one-way?

    $378 is the cheapest one-way deal found within the past few days, from Turkish Airlines. You may also be able to find cheap deals on Scandinavian Airlines and American Airlines, with prices starting from $430 and $438, respectively.

  • What are the cheapest flights from Chicago to Capri?

    The cheapest flight price from Chicago to Capri is $600. On average you can expect to pay $908. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $381.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago 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.

  • What is the cheapest month to book a flight from Chicago to Capri?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Capri (average of $496). Flying from Chicago to Capri in June is currently the most expensive (average of $816). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Capri

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Naples flights
Midway to Naples flights
St. Louis to Naples flights

Top 9 airlines flying from Chicago to Capri

Discover the top 9 airlines that operate flights from Chicago to Capri. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$414Average$515FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$496Average$821FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$526Average$639FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$543Average$842FlexibilityNo cancel feeOn-time70%
LufthansaCheapest$575Average$812FlexibilityNo cancel feeOn-time76%
SWISSCheapest$602Average$810FlexibilityNo cancel feeOn-time79%
American AirlinesCheapest$625Average$1,086FlexibilityNo cancel feeOn-time71%
Aer LingusCheapest$633Average$856FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$713Average$1,033FlexibilityNo cancel feeOn-time81%

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