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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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Capri are usually found in January or February, booked 52 days in advance, depart on a Monday or Tuesday and return on a Saturday

Cheap flight deals from Chicago to Capri

Keep the following information in mind while searching for Chicago to Capri flight deals. Data was last updated November 6, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$491
(Mytrip)

One-way from

$231
(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 (CHI) to Capri
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One-way flight from Chicago (CHI) to Capri
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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 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 November 6, 2025.

This United deal was found by Cheapflights users on 11/6. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/86:25 pmORD - NAP
1 stop12h 25mMultiple Airlines
Mon 12/153:00 pmNAP - ORD
1 stop32h 20mMultiple Airlines
Deal found 11/6$495
This Orbitz deal was found by Cheapflights users on 11/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/259:50 pmORD - NAP
1 stop12h 35mMultiple Airlines
Mon 12/16:15 pmNAP - ORD
2 stops30h 33mMultiple Airlines
Deal found 11/6$497
This lol.travel deal was found by Cheapflights users on 11/5. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/249:50 pmORD - NAP
1 stop12h 35mMultiple Airlines
Mon 12/83:00 pmNAP - ORD
1 stop32h 20mMultiple Airlines
Deal found 11/5$527
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/306:50 pmORD - NAP
1 stop12h 20mSWISS
Sun 12/73:00 pmNAP - ORD
1 stop32h 20mSWISS
Deal found 11/4$567
This Trip.com deal was found by Cheapflights users on 11/5. 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 03mKLM
Mon 12/81:15 pmNAP - MDW
2 stops34h 19mKLM
Deal found 11/5$573
This Expedia deal was found by Cheapflights users on 11/4. 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.
Sun 11/307:20 pmORD - NAP
2 stops42h 55mScandinavian Airlines
Sun 12/77:25 pmNAP - ORD
1 stop28h 20mScandinavian Airlines
Deal found 11/4$574
This FlightHub deal was found by Cheapflights users on 11/5. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/19:50 pmORD - NAP
1 stop12h 35mMultiple Airlines
Sun 12/73:00 pmNAP - ORD
1 stop32h 20mMultiple Airlines
Deal found 11/5$580
This oojo deal was found by Cheapflights users on 11/6. 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 11/1210:48 amORD - NAP
2 stops16h 47mITA Airways
Wed 11/196:35 amNAP - ORD
2 stops18h 35mITA Airways
Deal found 11/6$586
This FlightHub deal was found by Cheapflights users on 11/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2810:35 pmORD - NAP
1 stop12h 40mMultiple Airlines
Fri 12/510:10 amNAP - ORD
1 stop13h 10mMultiple Airlines
Deal found 11/4$593
This Delta deal was found by Cheapflights users on 11/4. 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 11/306:00 amMDW - NAP
2 stops22h 30mDelta
Tue 12/166:15 amNAP - MDW
2 stops18h 45mDelta
Deal found 11/4$654
This Delta deal was found by Cheapflights users on 11/6. 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 12/81:14 pmMDW - NAP
2 stops19h 36mDelta
Mon 12/156:15 amNAP - MDW
2 stops18h 45mDelta
Deal found 11/6$730
This Delta deal was found by Cheapflights users on 11/4. 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 11/2810:47 amMDW - NAP
2 stops17h 23mDelta
Fri 12/56:15 amNAP - MDW
2 stops18h 45mDelta
Deal found 11/4$786

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 November 6, 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

Mon 12/8

1:00 pm-1:50 pm

2 stops17h 50m

Naples

Mon 12/15

3:00 pm-4:20 pm

1 stop32h 20m

$495

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Mon 11/24

12:00 pm-1:50 pm

2 stops18h 50m

Naples

Mon 12/8

3:00 pm-4:20 pm

1 stop32h 20m

$548

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 1/16

6:30 pm-9:45 pm

2 stops20h 15m

Naples

Sat 1/24

10:25 pm-5:20 pm

2 stops25h 55m

$578

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Mon 12/1

9:50 pm-5:25 pm

1 stop12h 35m

Naples

Sun 12/7

3:00 pm-4:20 pm

1 stop32h 20m

$580

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 1/16

11:50 am-6:25 pm

1 stop23h 35m

Naples

Sat 1/24

7:25 pm-6:25 pm

1 stop30h 00m

$584

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 11/28

10:35 pm-6:15 pm

1 stop12h 40m

Naples

Fri 12/5

10:10 am-4:20 pm

1 stop13h 10m

$593

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 11/30

6:00 am-11:30 am

2 stops22h 30m

Naples

Tue 12/16

6:15 am-6:00 pm

2 stops18h 45m

$654

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 1/16

11:52 am-2:10 pm

2 stops19h 18m

Naples

Sat 1/24

6:15 am-2:55 pm

1 stop15h 40m

$657

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 2/12

1:28 pm-9:45 am

2 stops13h 17m

Naples

Thu 2/19

6:15 am-5:37 pm

2 stops18h 22m

$660

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 11/28

1:29 pm-3:50 pm

2 stops19h 21m

Naples

Fri 12/5

6:15 am-9:39 pm

2 stops22h 24m

$705

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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 October 31, 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 November 6, 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.

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 November 6, 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
9,007 reviews

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,007 reviews
United Airlines
7.4
Good
9,007 reviews

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Turkish Airlines
7.3
Good
4,032 reviews
United Airlines
7.4
Good
9,007 reviews

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,040 reviews
United Airlines
7.4
Good
9,007 reviews

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Aer Lingus
7.2
Good
1,365 reviews
United Airlines
7.4
Good
9,007 reviews

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
ITA Airways
6.7
Okay
1,081 reviews
United Airlines
7.4
Good
9,007 reviews

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 17m. Turkish Airlines provides one of the quickest options available for as low as $660. 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 flights from Chicago to Capri?

    The cheapest flight price from Chicago to Capri is $626. On average you can expect to pay $871. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $487.

  • 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$414Average$522FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$496Average$814FlexibilityNo cancel feeOn-time69%
British AirwaysCheapest$497Average$838FlexibilityNo cancel feeOn-time70%
Turkish AirlinesCheapest$524Average$623FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$575Average$744FlexibilityNo cancel feeOn-time76%
SWISSCheapest$602Average$890FlexibilityNo cancel feeOn-time79%
American AirlinesCheapest$631Average$1,114FlexibilityNo cancel feeOn-time71%
Aer LingusCheapest$634Average$858FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$713Average$1,011FlexibilityNo cancel feeOn-time81%

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