VacationSelector
Cloud Gate in Millennium Park, Chicago
ChicagoCloud Gate in Millennium Park
The cathedral facade, Siena
SienaThe cathedral facade

Photos: Chicago by Jesus Toledo, Pexels License; Siena by Raimond Spekking, CC BY-SA 4.0, cropped.

Chicago or Siena?

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
  • families

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

Choose Siena for

  • day trips
  • wellness
  • nature and the outdoors

What lies behind each score is written up on Siena’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, Siena 14: Chicago leads by 36 points.
Food & drink. Chicago 80, Siena 62: Chicago leads by 18 points.
Culture & sights. Chicago and Siena are level on 78.
Nightlife. Chicago 77, Siena 27: Chicago leads by 50 points.
Nature & outdoors. Chicago 48, Siena 65: Siena leads by 17 points.
Day trips. Chicago 42, Siena 94: Siena leads by 52 points.
Good for families. Chicago 78, Siena 38: Chicago leads by 40 points.
Getting around. Chicago 72, Siena 60: Chicago leads by 12 points.
Shopping & style. Chicago 70, Siena 35: Chicago leads by 35 points.
Affordability. Chicago 33, Siena 42: Siena leads by 9 points.
Live music & performing arts. Chicago 82, Siena 36: Chicago leads by 46 points.
Wellness & relaxation. Chicago 33, Siena 55: Siena leads by 22 points.
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What lies behind each score is written up on the two cities’ own pages: Chicago and Siena.

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.

Siena
51match

Wins on day trips and wellness 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

Siena in July

31 °Cdaytime high
17 °Cnight-time low
27 mmrain in the month
No seasea
15 hdaylight a day

Daytime high, °C

0°10°20°30°40°JFMAMJJASOND

Rainfall in the month, mm

050100150JFMAMJJASOND
ChicagoSiena

Where the figures come from

Siena's temperatures are measured 45 km from the centre, at Arezzo.

Siena 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). Siena: 2006-2017 (rainfall 1991-2020) normals, Arezzo (45 km from centre).

Before you go

MeasureChicagoSiena
Official language-Italian
CurrencyUS Dollar (USD)Euro (EUR)
SocketsAB120 V, 60 HzCFL230 V, 50 Hz
Driving sideRightRight
Time zoneUTC-6, UTC-5 in summerUTC+1, UTC+2 in summer
Emergency number911112
Elevation179 m322 m
Main airportChicago O'Hare International Airport (ORD)25 km from centre274 non-stop destinationsFlorence Airport, Peretola (FLR)55 km from centre46 non-stop destinations
Public holidays this year13 days13 days

By the numbers

MeasureChicagoSiena
City population2,746,38852,812
People per km²4,529446
Museums within 10 km4430
UNESCO World Heritage sites within 50 km15
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 Siena 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. Tourism statistics from Eurostat, © European Union, reused under CC BY 4.0. 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.