VacationSelector
Cloud Gate in Millennium Park, Chicago
ChicagoCloud Gate in Millennium Park
São Paulo Cathedral, Sao Paulo
Sao PauloSão Paulo Cathedral

Photos: Chicago by Jesus Toledo, Pexels License; Sao Paulo by Webysther Nunes, CC BY-SA 4.0, cropped.

Chicago or Sao Paulo?

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

  • getting around
  • families
  • culture and sights

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

Choose Sao Paulo for

  • prices
  • nightlife
  • day trips

What lies behind each score is written up on Sao Paulo’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, Sao Paulo 42: Chicago leads by 8 points.
Food & drink. Chicago 80, Sao Paulo 84: Sao Paulo leads by 4 points.
Culture & sights. Chicago 78, Sao Paulo 60: Chicago leads by 18 points.
Nightlife. Chicago 77, Sao Paulo 86: Sao Paulo leads by 9 points.
Nature & outdoors. Chicago and Sao Paulo are level on 48.
Day trips. Chicago 42, Sao Paulo 47: Sao Paulo leads by 5 points.
Good for families. Chicago 78, Sao Paulo 52: Chicago leads by 26 points.
Getting around. Chicago 72, Sao Paulo 44: Chicago leads by 28 points.
Shopping & style. Chicago and Sao Paulo are level on 70.
Affordability. Chicago 33, Sao Paulo 62: Sao Paulo leads by 29 points.
Live music & performing arts. Chicago 82, Sao Paulo 76: Chicago leads by 6 points.
Wellness & relaxation. Chicago 33, Sao Paulo 25: Chicago leads by 8 points.
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What lies behind each score is written up on the two cities’ own pages: Chicago and Sao Paulo.

Your match

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

Chicago
Best match
62match

Wins on getting around and families with your weighting.

Sao Paulo
58match

Wins on prices and nightlife 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
No recordsunshine a day
21 °Csea
15 hdaylight a day

Sao Paulo in July

23 °Cdaytime high
13 °Cnight-time low
53 mmrain in the month
6 hsunshine a day
No seasea
11 hdaylight a day

Daytime high, °C

0°10°20°30°JFMAMJJASOND

Rainfall in the month, mm

0100200300JFMAMJJASOND
ChicagoSao Paulo

Temperature and rainfall are climate normals, averaged over the years shown. Chicago: 1991-2020 normals, Chicago Midway Airport (14.5 km from centre). Sao Paulo: 1991-2020 normals, Sao Paulo (5.9 km from centre).

Before you go

MeasureChicagoSao Paulo
Official language-Portuguese
CurrencyUS Dollar (USD)Brazilian Real (BRL)
SocketsAB120 V, 60 HzCN60 Hz
Driving sideRightRight
Time zoneUTC-6, UTC-5 in summerUTC-3
Emergency number911Police 190, ambulance 192, fire 193
Elevation179 m760 m
Main airportChicago O'Hare International Airport (ORD)25 km from centre274 non-stop destinationsSão Paulo/Guarulhos–Governor André Franco Montoro International Airport (GRU)21 km from centre104 non-stop destinations
Public holidays this year13 days15 days

By the numbers

MeasureChicagoSao Paulo
City population2,746,38811,451,999
People per km²4,5297,519
Museums within 10 km4490
UNESCO World Heritage sites within 50 km10
Swim season, months above 21 °C1 month-

Where else could you go?

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