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$358+ Cheap flights from Naples (NAP) to Chicago (CHI)

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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Naples to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Naples (NAP) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Popular in

November

Cheapest in

January

Round-trip from

$550
(lol.travel)

One-way from

$358
(Kiwi.com)
Provider with most accurate pricing for Naples-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Naples-Chicago (CHI) flights.
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High demand for flights, 38% potential price rise
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Best time to find cheap flights, 31% potential price drop
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From Naples to Chicago (CHI)
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One-way flight from Naples to Chicago (CHI)
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Find flight deals from Naples to Chicago

Cheapest flights from Naples to Chicago
Explore the most affordable flight options available from Naples to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2024.

This lol.travel deal was found by Cheapflights users on 11/20. 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.
Fri 12/67:40 pmNAP - ORD
1 stop25h 15mBritish Airways
Sat 12/146:38 pmORD - NAP
2 stops16h 32mBritish Airways
Deal found 11/20$550
This Booking.com deal was found by Cheapflights users on 11/20. 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.
Fri 12/66:20 amNAP - ORD
1 stop15h 10mMultiple Airlines
Sat 12/144:15 pmORD - NAP
2 stops18h 55mMultiple Airlines
Deal found 11/20$578
This American Airlines deal was found by Cheapflights users on 11/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/66:20 amNAP - ORD
1 stop15h 10mAmerican Airlines
Sat 12/1412:10 pmORD - NAP
2 stops23h 00mAmerican Airlines
Deal found 11/21$587
This Expedia deal was found by Cheapflights users on 11/20. 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 12/66:35 amNAP - MDW
2 stops22h 31mMultiple Airlines
Sat 12/1412:44 pmMDW - NAP
2 stops27h 06mMultiple Airlines
Deal found 11/20$1,062
This Air France deal was found by Cheapflights users on 11/20. 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.
Fri 12/66:35 amNAP - MDW
2 stops22h 31mAir France
Sat 12/149:30 amMDW - NAP
2 stops29h 25mAir France
Deal found 11/20$1,220

Find flights from Naples to Chicago within your budget

Customize your flight search to find flights from Naples to Chicago 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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 12/6

7:40 pm-1:55 pm

1 stop25h 15m

Chicago O'Hare Intl

Sat 12/14

6:38 pm-6:10 pm

2 stops16h 32m

$550

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 12/6

6:20 am-2:30 pm

1 stop15h 10m

Chicago O'Hare Intl

Sat 12/14

4:15 pm-6:10 pm

2 stops18h 55m

$578

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 12/6

6:20 am-2:30 pm

1 stop15h 10m

Chicago O'Hare Intl

Sat 12/14

12:10 pm-6:10 pm

2 stops23h 00m

$587

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 12/6

6:35 am-10:06 pm

2 stops22h 31m

Chicago Midway

Sat 12/14

12:44 pm-10:50 pm

2 stops27h 06m

$1,062

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 12/6

6:35 am-10:06 pm

2 stops22h 31m

Chicago Midway

Sat 12/14

9:30 am-9:55 pm

2 stops29h 25m

$1,220

NaplesChicago

NAP - ORD

NAPORD

Naples

Tue 1/21

10:20 am-12:45 pm

3 stops33h 25m

$358

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 1/20

9:15 am-10:10 am

1 stop31h 55m

$487

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 2/21

11:20 am-3:30 pm

2 stops59h 10m

$577

NaplesChicago

NAP - MDW

NAPMDW

Naples

Wed 11/27

4:40 pm-3:25 pm

2 stops53h 45m

$704

NaplesChicago

NAP - ORD

NAPORD

Naples

Sun 1/19

11:35 am-2:30 pm

1 stop33h 55m

$721

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 17 results
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Compare providers for flights from Naples to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Naples to Chicago in November.
ProviderPrice AccuracyTrust Score*
AranGrantPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Naples-Chicago flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Naples-Chicago flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from Naples-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Naples-Chicago flights, Cheapflights users trust AranGrant the most. AranGrant has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Naples-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Naples to Chicago

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

Travel insights for flights from Naples to Chicago

Get recent, data-driven insights about flights from Naples to Chicago including ideal travel times, pricing trends, and more.

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

Find hourly flight availability from Naples to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2024.

When flying from Naples to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 21, 2024.
Delta
8.0
Very good
8,759 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,759 reviews
Delta
8.0
Very good
8,759 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

KLM
7.8
Good
1,350 reviews
Delta
8.0
Very good
8,759 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air France
7.4
Good
1,525 reviews
Delta
8.0
Very good
8,759 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Turkish Airlines
7.4
Good
3,914 reviews
Delta
8.0
Very good
8,759 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,759 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Naples to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Naples to Chicago?

    Located just 2.9 mi from the city center, Naples is the airport most travelers will use when flying to Chicago from Naples. Booking flights from Naples (NAP) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 1 airline.

  • What are the cheapest airlines flying from Naples to Chicago round-trip?

    According to our current data, British Airways ($550), American Airlines ($587), and Air France ($1,220) offers the cheapest pricing from Naples to Chicago. Users have found that British Airways is 23% cheaper than the other options available to this destination.

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

    To fly one-way, consider booking your trip with Turkish Airlines, which is currently one of the cheapest options available, starting at $487. TAP AIR PORTUGAL flights start at $577 while deals on KLM start at $721 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Naples to Chicago 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 Naples to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Naples to Chicago (average of $232). Flying from Naples to Chicago in June is currently the most expensive (average of $308). 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

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Alternative routes for Naples to Chicago

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

Top airline flying from Naples to Chicago

Discover the top airline that operate flights from Naples to Chicago. 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
ITA AirwaysCheapest$491Average$579FlexibilityNo cancel feeOn-time81%
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