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$226+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Nov 12 — Nov 191
Wed 11/12
Wed 11/19
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Capri are usually found in January or March, booked 52 days in advance, depart on a Monday or Tuesday and return on a Tuesday

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 October 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$551
(United Airlines)

One-way from

$226
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$824
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. 22% potential increase in price ($261 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 13, 2025.

This Expedia deal was found by Cheapflights users on 10/12. 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 11/239:50 pmORD - NAP
1 stop12h 35mMultiple Airlines
Tue 12/96:15 pmNAP - ORD
2 stops30h 33mMultiple Airlines
Deal found 10/12$553
This FlightHub deal was found by Cheapflights users on 10/12. 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.
Wed 11/57:05 amORD - NAP
2 stops28h 10mMultiple Airlines
Wed 11/126:15 pmNAP - ORD
1 stop31h 10mMultiple Airlines
Deal found 10/12$558
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/109:50 pmORD - NAP
1 stop12h 35mLufthansa
Mon 11/246:15 pmNAP - ORD
2 stops25h 55mLufthansa
Deal found 10/12$559
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:20 pmORD - NAP
2 stops13h 10mMultiple Airlines
Fri 11/710:10 amNAP - ORD
1 stop13h 10mMultiple Airlines
Deal found 10/12$561
This Mytrip deal was found by Cheapflights users on 10/13. 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.
Wed 11/512:50 pmORD - NAP
2 stops22h 25mMultiple Airlines
Thu 11/136:15 pmNAP - ORD
2 stops25h 55mMultiple Airlines
Deal found 10/13$563
This Expedia deal was found by Cheapflights users on 10/12. 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 11/239:50 pmORD - NAP
1 stop12h 35mLufthansa
Tue 12/96:15 pmNAP - ORD
2 stops25h 55mLufthansa
Deal found 10/12$567
This oojo deal was found by Cheapflights users on 10/11. 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 11/87:20 pmORD - NAP
1 stop16h 15mScandinavian Airlines
Sun 11/167:25 pmNAP - ORD
1 stop28h 20mScandinavian Airlines
Deal found 10/11$569
This Booking.com deal was found by Cheapflights users on 10/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1010:00 amORD - NAP
2 stops24h 25mMultiple Airlines
Tue 12/166:15 pmNAP - ORD
2 stops25h 55mMultiple Airlines
Deal found 10/11$571
This United Airlines deal was found by Cheapflights users on 10/12. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/103:35 pmORD - NAP
2 stops39h 15mUnited Airlines
Mon 11/242:15 pmNAP - ORD
2 stops36h 15mUnited Airlines
Deal found 10/12$572
This FlightHub deal was found by Cheapflights users on 10/12. 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.
Sun 10/2610:50 pmORD - NAP
1 stop12h 35mMultiple Airlines
Sun 11/93:00 pmNAP - ORD
1 stop32h 20mMultiple Airlines
Deal found 10/12$581
This oojo deal was found by Cheapflights users on 10/13. 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.
Sun 10/267:50 pmORD - NAP
1 stop12h 20mSWISS
Sun 11/93:00 pmNAP - ORD
1 stop32h 20mSWISS
Deal found 10/13$588
This Delta deal was found by Cheapflights users on 10/12. 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 11/109:34 amMDW - NAP
2 stops23h 16mDelta
Mon 11/246:15 amNAP - MDW
2 stops18h 53mDelta
Deal found 10/12$681

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 October 13, 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

Sun 1/11

7:30 am-1:25 pm

2 stops22h 55m

Naples

Mon 1/19

2:15 pm-6:51 pm

2 stops35h 36m

$571

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Tue 4/7

11:25 am-2:50 pm

1 stop20h 25m

Naples

Wed 4/22

9:25 am-6:15 pm

1 stop15h 50m

$572

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 10/26

10:50 pm-5:25 pm

1 stop12h 35m

Naples

Sun 11/9

3:00 pm-4:20 pm

1 stop32h 20m

$581

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 10/26

7:50 pm-2:10 pm

1 stop12h 20m

Naples

Sun 11/9

3:00 pm-4:20 pm

1 stop32h 20m

$588

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 11/12

7:20 pm-6:40 pm

1 stop16h 20m

Naples

Sun 11/16

7:25 pm-4:45 pm

1 stop28h 20m

$594

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sat 4/4

7:00 am-3:05 pm

2 stops25h 05m

Naples

Thu 4/23

7:35 pm-4:10 pm

1 stop27h 35m

$594

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Thu 1/8

8:45 pm-3:35 pm

1 stop11h 50m

Naples

Fri 1/16

6:20 am-5:42 pm

2 stops18h 22m

$597

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 1/7

4:20 pm-5:25 pm

2 stops18h 05m

Naples

Wed 3/4

6:15 pm-1:10 pm

2 stops25h 55m

$598

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 3/27

9:20 pm-1:50 pm

1 stop34h 30m

Naples

Sun 4/5

8:45 pm-6:15 pm

1 stop28h 30m

$602

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 12/5

11:50 am-6:25 pm

1 stop23h 35m

Naples

Sun 12/14

9:15 am-6:25 pm

1 stop16h 10m

$602

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 36 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 10, 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 $861). 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 October 13, 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.

Weekly flight availability from Chicago to Capri

Explore weekly flight availability from Chicago to Capri. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 13, 2025.

The most flights from CHI to C4P are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 October 13, 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
8,971 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,971 reviews
United Airlines
7.4
Good
8,971 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
Turkish Airlines
7.3
Good
4,005 reviews
United Airlines
7.4
Good
8,971 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
American Airlines
7.2
Good
11,046 reviews
United Airlines
7.4
Good
8,971 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
Lufthansa
6.8
Okay
7,476 reviews
United Airlines
7.4
Good
8,971 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
ITA Airways
6.7
Okay
1,064 reviews
United Airlines
7.4
Good
8,971 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 20m. United Airlines provides one of the quickest options available for as low as $588. 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 flights from Chicago to Capri?

    The cheapest flight price from Chicago to Capri is $441. On average you can expect to pay $716. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $499.

  • 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 $861). 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 October 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$414Average$522FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$496Average$818FlexibilityNo cancel feeOn-time69%
British AirwaysCheapest$497Average$838FlexibilityNo cancel feeOn-time70%
Turkish AirlinesCheapest$517Average$622FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$591Average$809FlexibilityNo cancel feeOn-time76%
SWISSCheapest$602Average$919FlexibilityNo cancel feeOn-time79%
American AirlinesCheapest$630Average$1,129FlexibilityNo cancel feeOn-time71%
Aer LingusCheapest$634Average$860FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$713Average$1,011FlexibilityNo cancel feeOn-time81%

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