HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Capri

$234+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Jan 8 — Jan 151
Thu 1/8
Thu 1/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Capri with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 9, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Wed 12/109:50 pmORD - NAP
1 stop12h 35mMultiple Airlines
Wed 12/1710:35 pmNAP - ORD
2 stops47h 50mMultiple Airlines
Deal found 12/9$958
This Mytrip deal was found by Cheapflights users on 12/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:30 pmORD - NAP
2 stops17h 25mMultiple Airlines
Sat 12/139:55 amNAP - ORD
2 stops35h 50mMultiple Airlines
Deal found 12/7$987
This oojo deal was found by Cheapflights users on 12/9. 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 12/1011:00 amORD - NAP
2 stops16h 35mITA Airways
Wed 12/176:35 amNAP - ORD
2 stops18h 45mITA Airways
Deal found 12/9$995
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:40 pmORD - NAP
1 stop13h 30mMultiple Airlines
Sun 12/1411:20 amNAP - ORD
2 stops34h 37mMultiple Airlines
Deal found 12/6$1,040
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:50 pmORD - NAP
1 stop12h 25mMultiple Airlines
Fri 12/129:15 amNAP - ORD
1 stop16h 10mMultiple Airlines
Deal found 12/6$1,049
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:50 pmORD - NAP
1 stop12h 35mMultiple Airlines
Fri 12/267:25 pmNAP - ORD
1 stop21h 40mMultiple Airlines
Deal found 12/6$1,065
This Delta deal was found by Cheapflights users on 12/9. 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 12/1012:50 pmMDW - NAP
2 stops15h 40mDelta
Wed 12/176:15 amNAP - MDW
2 stops19h 03mDelta
Deal found 12/9$1,071
This Delta deal was found by Cheapflights users on 12/8. 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 12/1210:49 amMDW - NAP
2 stops17h 21mDelta
Sun 12/1411:50 amNAP - MDW
2 stops18h 57mDelta
Deal found 12/8$1,211
This Trip.com deal was found by Cheapflights users on 12/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:50 pmMDW - NAP
2 stops18h 30mMultiple Airlines
Sun 12/149:35 pmNAP - MDW
2 stops27h 25mMultiple Airlines
Deal found 12/6$1,301
This KLM deal was found by Cheapflights users on 12/9. 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
Sun 12/286:35 amNAP - MDW
2 stops17h 51mMultiple Airlines
Deal found 12/9$1,521
This Air France deal was found by Cheapflights users on 12/7. 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.
Tue 12/236:08 pmMDW - NAP
2 stops14h 42mAir France
Sun 12/286:35 amNAP - MDW
2 stops17h 51mAir France
Deal found 12/7$2,556
This KLM deal was found by Cheapflights users on 12/8. 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 12/8$2,599

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 9, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$426
(KAYAK)

One-way from

$234
(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. 21% potential increase in price ($239 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 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 9, 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

Sat 3/7

7:20 pm-7:05 pm

1 stop16h 45m

Naples

Thu 3/12

7:30 pm-5:55 pm

1 stop28h 25m

$505

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sat 3/7

7:00 am-7:05 pm

2 stops29h 05m

Naples

Sat 3/14

6:30 pm-5:45 pm

1 stop29h 15m

$508

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 1/30

8:20 pm-6:25 pm

1 stop15h 05m

Naples

Fri 2/20

9:15 am-10:05 am

1 stop31h 50m

$519

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 1/11

3:45 pm-1:25 pm

2 stops14h 40m

Naples

Mon 1/26

1:15 pm-2:10 pm

1 stop31h 55m

$520

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 1/11

6:50 pm-2:10 pm

1 stop12h 20m

Naples

Mon 1/26

3:05 pm-3:20 pm

2 stops31h 15m

$542

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 3/8

10:45 pm-11:50 am

1 stop31h 05m

Naples

Tue 3/24

12:40 pm-2:50 pm

1 stop32h 10m

$543

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 3/8

10:45 pm-11:50 am

1 stop31h 05m

Naples

Mon 3/23

1:55 pm-7:45 pm

1 stop35h 50m

$543

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Mon 3/2

12:27 pm-11:30 am

2 stops16h 03m

Naples

Tue 3/17

12:20 pm-3:20 pm

1 stop33h 00m

$546

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 1/14

9:50 pm-5:25 pm

1 stop12h 35m

Naples

Wed 1/21

3:10 pm-6:25 pm

2 stops34h 15m

$548

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 3/2

9:50 am-3:50 pm

2 stops23h 00m

Naples

Tue 3/17

6:15 am-5:55 pm

2 stops17h 40m

$556

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

Showing 1-10 of 35 results
1
2
3
4

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 5, 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 9, 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 December 9, 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
9,089 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,089 reviews
United Airlines
7.4
Good
9,089 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
Turkish Airlines
7.3
Good
4,084 reviews
United Airlines
7.4
Good
9,089 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,043 reviews
United Airlines
7.4
Good
9,089 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
Aer Lingus
7.2
Good
1,389 reviews
United Airlines
7.4
Good
9,089 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
ITA Airways
6.7
Okay
1,098 reviews
United Airlines
7.4
Good
9,089 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 14h 40m. Scandinavian Airlines provides one of the quickest options available for as low as $520. 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 $766. On average you can expect to pay $1,216. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $514.

  • 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 December 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$414Average$515FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$496Average$814FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$530Average$626FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$575Average$744FlexibilityNo cancel feeOn-time76%
SWISSCheapest$602Average$791FlexibilityNo cancel feeOn-time79%
British AirwaysCheapest$612Average$842FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$629Average$1,111FlexibilityNo cancel feeOn-time71%
Aer LingusCheapest$634Average$857FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$713Average$975FlexibilityNo cancel feeOn-time81%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.