VacationSelector
Cloud Gate in Millennium Park, Chicago
ChicagoCloud Gate in Millennium Park
The Winchester Mystery House, San Jose
San JoseThe Winchester Mystery House

Photos: Chicago by Jesus Toledo, Pexels License; San Jose by Roxanna Salceda, CC BY-SA 2.0, cropped.

Chicago or San Jose?

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
  • live music and the arts
  • culture and sights

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

Choose San Jose for

  • day trips
  • nature and the outdoors

What lies behind each score is written up on San Jose’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, San Jose 30: Chicago leads by 20 points.
Food & drink. Chicago 80, San Jose 56: Chicago leads by 24 points.
Culture & sights. Chicago 78, San Jose 36: Chicago leads by 42 points.
Nightlife. Chicago 77, San Jose 33: Chicago leads by 44 points.
Nature & outdoors. Chicago 48, San Jose 72: San Jose leads by 24 points.
Day trips. Chicago 42, San Jose 78: San Jose leads by 36 points.
Good for families. Chicago 78, San Jose 65: Chicago leads by 13 points.
Getting around. Chicago 72, San Jose 30: Chicago leads by 42 points.
Shopping & style. Chicago 70, San Jose 48: Chicago leads by 22 points.
Affordability. Chicago 33, San Jose 20: Chicago leads by 13 points.
Live music & performing arts. Chicago 82, San Jose 38: Chicago leads by 44 points.
Wellness & relaxation. Chicago 33, San Jose 30: Chicago leads by 3 points.
0255075100

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

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 live music and the arts with your weighting.

San Jose
45match

Wins on day trips 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

San Jose in July

27 °Cdaytime high
15 °Cnight-time low
0 mmrain in the month
14 °Csea
15 hdaylight a day

Daytime high, °C

0°10°20°30°JFMAMJJASOND

Rainfall in the month, mm

0255075100125JFMAMJJASOND
ChicagoSan Jose

Temperature and rainfall are climate normals, averaged over the years shown. Chicago: 1991-2020 normals, Chicago Midway Airport (14.5 km from centre). San Jose: 1991-2020 normals, San Jose / Santa Clara Trailer Village (8.2 km from centre).

Before you go

MeasureChicagoSan Jose
CurrencyUS Dollar (USD)US Dollar (USD)
SocketsAB120 V, 60 HzAB120 V, 60 Hz
Driving sideRightRight
Time zoneUTC-6, UTC-5 in summerUTC-8, UTC-7 in summer
Emergency number911911
Elevation179 m25 m
Main airportChicago O'Hare International Airport (ORD)25 km from centre274 non-stop destinationsMineta San Jose International Airport (SJC)8 km from centre38 non-stop destinations
Public holidays this year13 days13 days

By the numbers

MeasureChicagoSan Jose
City population2,746,3881,013,240
People per km²4,5292,167
Museums within 10 km4419
UNESCO World Heritage sites within 50 km10
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 San Jose 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 2026-10-31. Daily budgets are estimates from country price levels.