VacationSelector
Cloud Gate in Millennium Park, Chicago
ChicagoCloud Gate in Millennium Park
A painted funicular on the hillside, Valparaiso
ValparaisoA painted funicular on the hillside

Photos: Chicago by Jesus Toledo, Pexels License; Valparaiso by Maclemo, CC BY-SA 3.0, cropped.

Chicago or Valparaiso?

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

  • families
  • live music and the arts
  • shopping

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

Choose Valparaiso for

  • prices
  • day trips
  • nature and the outdoors

What lies behind each score is written up on Valparaiso’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, Valparaiso 36: Chicago leads by 14 points.
Food & drink. Chicago 80, Valparaiso 50: Chicago leads by 30 points.
Culture & sights. Chicago 78, Valparaiso 62: Chicago leads by 16 points.
Nightlife. Chicago 77, Valparaiso 56: Chicago leads by 21 points.
Nature & outdoors. Chicago 48, Valparaiso 60: Valparaiso leads by 12 points.
Day trips. Chicago 42, Valparaiso 63: Valparaiso leads by 21 points.
Good for families. Chicago 78, Valparaiso 33: Chicago leads by 45 points.
Getting around. Chicago 72, Valparaiso 44: Chicago leads by 28 points.
Shopping & style. Chicago 70, Valparaiso 30: Chicago leads by 40 points.
Affordability. Chicago 33, Valparaiso 60: Valparaiso leads by 27 points.
Live music & performing arts. Chicago 82, Valparaiso 38: Chicago leads by 44 points.
Wellness & relaxation. Chicago 33, Valparaiso 18: Chicago leads by 15 points.
0255075100

What lies behind each score is written up on the two cities’ own pages: Chicago and Valparaiso.

Your match

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

Chicago
Best match
62match

Wins on families and live music and the arts with your weighting.

Valparaiso
46match

Wins on prices and day trips 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

Valparaiso in July

15 °Cdaytime high
7 °Cnight-time low
71 mmrain in the month
13 °Csea
10 hdaylight a day

Daytime high, °C

0°10°20°30°JFMAMJJASOND

Rainfall in the month, mm

0255075100125JFMAMJJASOND
ChicagoValparaiso

Where the figures come from

Valparaiso 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). Valparaiso: 2010-2025 (rainfall 1991-2020) normals, Viña Del Mar / Montemar (17 km from centre).

Before you go

MeasureChicagoValparaiso
Official language-Spanish
CurrencyUS Dollar (USD)Chilean Peso (CLP)
SocketsAB120 V, 60 HzCL220 V, 50 Hz
Driving sideRightRight
Time zoneUTC-6, UTC-5 in summerUTC-4, UTC-3 in summer
Emergency number911Police 133/134, ambulance 131, fire 132
Elevation179 m21 m
Main airportChicago O'Hare International Airport (ORD)25 km from centre274 non-stop destinationsComodoro Arturo Merino Benítez International Airport (SCL)87 km from centre67 non-stop destinations
Public holidays this year13 days16 days

By the numbers

MeasureChicagoValparaiso
City population2,746,388296,655
People per km²4,5296,180
Museums within 10 km4417
UNESCO World Heritage sites within 50 km11
Swim season, months above 21 °C1 monthNone

Where else could you go?

Every comparison below shares a destination with this one, so you can follow Chicago or Valparaiso 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.