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$231+ 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
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
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 December 23, 2025.

This Expedia deal was found by Cheapflights users on 12/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:50 pmORD - NAP
1 stop12h 35mLufthansa
Tue 1/63:05 pmNAP - ORD
2 stops36h 00mLufthansa
Deal found 12/23$1,108
This Expedia deal was found by Cheapflights users on 12/22. 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 12/319:50 pmORD - NAP
1 stop12h 35mMultiple Airlines
Tue 1/63:05 pmNAP - ORD
2 stops32h 15mMultiple Airlines
Deal found 12/22$1,109
This oojo deal was found by Cheapflights users on 12/22. 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 12/318:20 pmORD - NAP
1 stop15h 05mTurkish Airlines
Tue 1/67:25 pmNAP - ORD
1 stop30h 00mTurkish Airlines
Deal found 12/22$1,157
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Thu 12/256:50 pmORD - NAP
2 stops20h 50mMultiple Airlines
Sat 12/277:25 pmNAP - ORD
1 stop21h 40mMultiple Airlines
Deal found 12/21$1,199
This Expedia deal was found by Cheapflights users on 12/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:50 pmORD - NAP
2 stops17h 05mMultiple Airlines
Tue 1/63:05 pmNAP - ORD
2 stops36h 00mMultiple Airlines
Deal found 12/23$1,260
This oojo deal was found by Cheapflights users on 12/22. 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 12/269:20 amORD - NAP
2 stops22h 00mITA Airways
Sun 12/286:35 amNAP - ORD
2 stops20h 50mITA Airways
Deal found 12/22$1,363
This Expedia deal was found by Cheapflights users on 12/22. 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.
Fri 12/265:55 pmORD - NAP
2 stops18h 50mMultiple Airlines
Sun 12/288:15 pmNAP - ORD
1 stop24h 45mMultiple Airlines
Deal found 12/22$1,386
This Delta deal was found by Cheapflights users on 12/22. 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.
Wed 12/319:50 amMDW - NAP
2 stops18h 40mDelta
Tue 1/66:15 amNAP - MDW
2 stops19h 17mDelta
Deal found 12/22$2,205
This KLM deal was found by Cheapflights users on 12/22. 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 12/22$2,623
This KLM deal was found by Cheapflights users on 12/21. 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 12/256:08 pmMDW - NAP
2 stops14h 42mMultiple Airlines
Sat 12/276:35 amNAP - MDW
2 stops17h 51mMultiple Airlines
Deal found 12/21$3,264
This Air France deal was found by Cheapflights users on 12/22. 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.
Wed 12/2411:48 amMDW - NAP
2 stops16h 22mAir France
Wed 12/316:35 amNAP - MDW
2 stops17h 51mAir France
Deal found 12/22$3,634
This Air France deal was found by Cheapflights users on 12/21. 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 12/21$3,720

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 December 23, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$475
(KAYAK)

One-way from

$231
(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.
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. 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).
Search Deals
Average for round-trip flights in December 2025
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 December 23, 2025.
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

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 3/18

10:45 pm-3:35 pm

1 stop34h 50m

Naples

Tue 3/31

7:50 am-3:55 pm

1 stop15h 05m

$543

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Tue 3/17

1:56 pm-9:35 am

2 stops13h 39m

Naples

Tue 3/31

4:10 pm-2:30 pm

1 stop29h 20m

$546

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Mon 1/12

6:00 pm-12:30 pm

1 stop11h 30m

Naples

Tue 1/20

11:20 am-3:20 pm

2 stops35h 00m

$547

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 1/11

5:20 pm-9:15 pm

1 stop20h 55m

Naples

Mon 1/26

12:15 pm-3:10 pm

1 stop33h 55m

$554

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 3/18

1:56 pm-9:50 am

2 stops13h 54m

Naples

Wed 4/1

10:40 am-8:14 pm

2 stops16h 34m

$556

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 2/4

12:48 pm-11:30 am

2 stops15h 42m

Naples

Wed 2/11

6:15 am-5:29 pm

2 stops18h 14m

$557

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sat 1/10

2:30 pm-11:30 am

2 stops38h 00m

Naples

Mon 1/19

12:15 pm-6:19 pm

2 stops37h 04m

$575

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Thu 4/9

7:50 pm-7:45 pm

1 stop16h 55m

Naples

Sun 4/19

8:45 pm-6:15 pm

1 stop28h 30m

$582

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 3/18

10:45 pm-3:35 pm

1 stop34h 50m

Naples

Mon 3/30

7:50 am-6:15 pm

1 stop17h 25m

$593

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 1/11

6:25 pm-1:25 pm

1 stop12h 00m

Naples

Sat 1/17

7:05 pm-11:10 am

1 stop23h 05m

$620

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 33 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 December 19, 2025.

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.

What is the cheapest time of day to fly from CHI to C4P?

Find hourly flight availability from Chicago to Capri. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

It’s typically best to fly out from Chicago to Capri in the morning. Doing so could potentially save you 67% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Chicago to Capri?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Capri. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Capri flight should consider departing on Sunday mornings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago to Capri?

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 December 23, 2025.
Get a feel of what it's like to fly with United Airlines, Turkish Airlines, and American 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.
United Airlines
7.4
Good
9,109 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,109 reviews
United Airlines
7.4
Good
9,109 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
Turkish Airlines
7.3
Good
4,112 reviews
United Airlines
7.4
Good
9,109 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
American Airlines
7.2
Good
11,050 reviews
United Airlines
7.4
Good
9,109 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
Aer Lingus
7.2
Good
1,412 reviews
United Airlines
7.4
Good
9,109 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
ITA Airways
6.7
Okay
1,112 reviews
United Airlines
7.4
Good
9,109 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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 12h 50m. United Airlines provides one of the quickest options available for as low as $545. The distance from Chicago to Capri is about 4929 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 $719. On average you can expect to pay $1,049. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $490.

  • 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

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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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$414Average$515FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$496Average$814FlexibilityNo cancel feeOn-time69%
British AirwaysCheapest$497Average$838FlexibilityNo cancel feeOn-time70%
Turkish AirlinesCheapest$530Average$636FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$575Average$796FlexibilityNo cancel feeOn-time76%
SWISSCheapest$602Average$733FlexibilityNo cancel feeOn-time79%
American AirlinesCheapest$630Average$1,113FlexibilityNo cancel feeOn-time71%
Aer LingusCheapest$634Average$857FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$713Average$975FlexibilityNo cancel feeOn-time81%

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