VacationSelector
Cloud Gate in Millennium Park, Chicago
ChicagoCloud Gate in Millennium Park
Cinderella Castle, Magic Kingdom, Orlando
OrlandoCinderella Castle, Magic Kingdom

Photos: Chicago by Jesus Toledo, Pexels License; Orlando by Michael Gray, CC BY-SA 2.0, cropped.

Chicago or Orlando?

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
  • culture and sights
  • live music and the arts

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

Choose Orlando for

  • families
  • day trips
  • prices

What lies behind each score is written up on Orlando’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, Orlando 42: Chicago leads by 8 points.
Food & drink. Chicago 80, Orlando 48: Chicago leads by 32 points.
Culture & sights. Chicago 78, Orlando 22: Chicago leads by 56 points.
Nightlife. Chicago 77, Orlando 40: Chicago leads by 37 points.
Nature & outdoors. Chicago 48, Orlando 46: Chicago leads by 2 points.
Day trips. Chicago 42, Orlando 58: Orlando leads by 16 points.
Good for families. Chicago 78, Orlando 98: Orlando leads by 20 points.
Getting around. Chicago 72, Orlando 8: Chicago leads by 64 points.
Shopping & style. Chicago 70, Orlando 58: Chicago leads by 12 points.
Affordability. Chicago 33, Orlando 36: Orlando leads by 3 points.
Live music & performing arts. Chicago 82, Orlando 40: Chicago leads by 42 points.
Wellness & relaxation. Chicago 33, Orlando 32: Chicago leads by 1 points.
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What lies behind each score is written up on the two cities’ own pages: Chicago and Orlando.

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 culture and sights with your weighting.

Orlando
44match

Wins on families 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

Orlando in July

33 °Cdaytime high
23 °Cnight-time low
189 mmrain in the month
No seasea
14 hdaylight a day

Daytime high, °C

0°10°20°30°40°JFMAMJJASOND

Rainfall in the month, mm

050100150200250JFMAMJJASOND
ChicagoOrlando

Temperature and rainfall are climate normals, averaged over the years shown. Chicago: 1991-2020 normals, Chicago Midway Airport (14.5 km from centre). Orlando: 1991-2020 normals, Orlando Airport (14.2 km from centre).

Before you go

MeasureChicagoOrlando
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 m34 m
Main airportChicago O'Hare International Airport (ORD)25 km from centre274 non-stop destinationsOrlando International Airport (MCO)14 km from centre169 non-stop destinations
Public holidays this year13 days11 days

By the numbers

MeasureChicagoOrlando
City population2,746,388334,854
People per km²4,5291,086
Museums within 10 km4411
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 Orlando 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.