VacationSelector
Cloud Gate in Millennium Park, Chicago
ChicagoCloud Gate in Millennium Park
Naples Pier over turquoise water, Naples, Florida
Naples, FloridaNaples Pier over turquoise water

Photos: Chicago by Jesus Toledo, Pexels License; Naples, Florida by William “Patrick” Ma…, CC BY-SA 3.0, cropped.

Chicago or Naples, Florida?

Our verdict in twelve categories, each scored against the same fixed benchmark cities, and the climate month by month, so you can choose for your trip.

Choose Chicago for

  • nightlife
  • culture and sights
  • getting around

What lies behind each score is written up on Chicago’s own page.

Choose Naples, Florida for

  • beaches
  • nature and the outdoors
  • wellness

What lies behind each score is written up on Naples, Florida’s own page.

Scoreboard

Twelve categories on one fixed scale from 0 to 100. The shaded stretch is the gap between the two.

Beaches & swimming. Chicago 50, Naples, Florida 87: Naples, Florida leads by 37 points.
Food & drink. Chicago 80, Naples, Florida 46: Chicago leads by 34 points.
Culture & sights. Chicago 78, Naples, Florida 27: Chicago leads by 51 points.
Nightlife. Chicago 77, Naples, Florida 20: Chicago leads by 57 points.
Nature & outdoors. Chicago 48, Naples, Florida 66: Naples, Florida leads by 18 points.
Day trips. Chicago 42, Naples, Florida 43: Naples, Florida leads by 1 points.
Good for families. Chicago 78, Naples, Florida 64: Chicago leads by 14 points.
Getting around. Chicago 72, Naples, Florida 22: Chicago leads by 50 points.
Shopping & style. Chicago 70, Naples, Florida 48: Chicago leads by 22 points.
Affordability. Chicago 33, Naples, Florida 17: Chicago leads by 16 points.
Live music & performing arts. Chicago 82, Naples, Florida 40: Chicago leads by 42 points.
Wellness & relaxation. Chicago 33, Naples, Florida 45: Naples, Florida leads by 12 points.
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What lies behind each score is written up on the two cities’ own pages: Chicago and Naples, Florida.

Your match

Pick a travel style or drag the sliders, and both match scores follow your weighting.

Chicago
Best match
62match

Wins on nightlife and culture and sights with your weighting.

Naples, Florida
44match

Wins on beaches and nature and the outdoors with your weighting.

What matters to you?

When should you go?

Pick your month. The climate figures are measured averages, not a forecast.

Chicago in July

29 °Cdaytime high
20 °Cnight-time low
102 mmrain in the month
21 °Csea
15 hdaylight a day

Naples, Florida in July

32 °Cdaytime high
25 °Cnight-time low
197 mmrain in the month
30 °Csea
14 hdaylight a day

Daytime high, °C

0°10°20°30°40°JFMAMJJASOND

Rainfall in the month, mm

050100150200250JFMAMJJASOND
ChicagoNaples, Florida

Where the figures come from

Naples, Florida has no rain gauge within 25 km of the centre, so its rainfall comes from a gridded climate dataset read at the city rather than from a gauge further away.

Temperature and rainfall are climate normals, averaged over the years shown. Chicago: 1991-2020 normals, Chicago Midway Airport (14.5 km from centre). Naples, Florida: 2002-2020 (rainfall 1991-2020) normals, Naples / East Naples (2.3 km from centre).

Before you go

MeasureChicagoNaples, Florida
CurrencyUS Dollar (USD)US Dollar (USD)
SocketsAB120 V, 60 HzAB120 V, 60 Hz
Driving sideRightRight
Time zoneUTC-6, UTC-5 in summerUTC-5, UTC-4 in summer
Emergency number911911
Elevation179 m-2 m
Main airportChicago O'Hare International Airport (ORD)25 km from centre274 non-stop destinationsSouthwest Florida International Airport (RSW)43 km from centre79 non-stop destinations
Public holidays this year13 days11 days

By the numbers

MeasureChicagoNaples, Florida
City population2,746,38819,115
People per km²4,529450
Museums within 10 km444
UNESCO World Heritage sites within 50 km10
Swim season, months above 21 °C1 month10 months

Where else could you go?

Every comparison below shares a destination with this one, so you can follow Chicago or Naples, Florida somewhere new.

Browse every destination

Sources

Structured data from Wikidata (CC0). Weather data by Meteostat. Meteorological data provided by NOAA, DWD and others. Rainfall where no rain gauge is within 25 km is from the TerraClimate 1991-2020 climatology (Abatzoglou et al. 2018, Scientific Data), read at the city. Sea surface temperature from NOAA OISST v2.1, NOAA Physical Sciences Laboratory. Airport data from OurAirports (public domain). Public holidays from Nager.Date (MIT). Exchange rates via Frankfurter, based on European Central Bank reference rates. Non-stop route lists from the "Airlines and destinations" tables on English Wikipedia airport articles, by Wikipedia contributors, reused under CC BY-SA 4.0. Currency from the ISO 4217 register maintained by SIX, cross-checked against country data from GeoNames (CC BY 4.0). Price level from World Bank open data (PPP conversion factor for private consumption and official exchange rate), CC BY 4.0. Time zones from GeoNames (CC BY 4.0); clock offsets computed from the IANA time zone database. Daylight hours computed from each destination's latitude using the NOAA solar position algorithm.

Category scores are our editorial verdict under rubric v3, each placed against the same fixed benchmark cities; the climate figures are measured. How the scores are set. Snapshot generated 2026-11-01. Daily budgets are estimates from country price levels.