VacationSelector
Cloud Gate in Millennium Park, Chicago
ChicagoCloud Gate in Millennium Park
The cathedral from Piazza del Duomo, Milan
MilanThe cathedral from Piazza del Duomo

Photos: Chicago by Jesus Toledo, Pexels License; Milan by Jiuguang Wang, CC BY-SA 3.0, cropped.

Chicago or Milan?

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

  • beaches
  • families
  • nightlife

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

Choose Milan for

  • day trips
  • shopping
  • nature and the outdoors

What lies behind each score is written up on Milan’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, Milan 20: Chicago leads by 30 points.
Food & drink. Chicago 80, Milan 78: Chicago leads by 2 points.
Culture & sights. Chicago and Milan are level on 78.
Nightlife. Chicago 77, Milan 66: Chicago leads by 11 points.
Nature & outdoors. Chicago 48, Milan 65: Milan leads by 17 points.
Day trips. Chicago 42, Milan 91: Milan leads by 49 points.
Good for families. Chicago 78, Milan 55: Chicago leads by 23 points.
Getting around. Chicago 72, Milan 79: Milan leads by 7 points.
Shopping & style. Chicago 70, Milan 92: Milan leads by 22 points.
Affordability. Chicago and Milan are level on 33.
Live music & performing arts. Chicago and Milan are level on 82.
Wellness & relaxation. Chicago 33, Milan 42: Milan leads by 9 points.
0255075100

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

Your match

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

Chicago
62match

Wins on beaches and families with your weighting.

Milan
Best match
65match

Wins on day trips and shopping 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

Milan in July

30 °Cdaytime high
20 °Cnight-time low
70 mmrain in the month
9 hsunshine a day
No seasea
15 hdaylight a day

Daytime high, °C

0°10°20°30°40°JFMAMJJASOND

Rainfall in the month, mm

050100150JFMAMJJASOND
ChicagoMilan

Where the figures come from

Milan 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.

Milan's sunshine is measured 41 km from the centre, at Novara / Cameri.

Temperature and rainfall are climate normals, averaged over the years shown. Chicago: 1991-2020 normals, Chicago Midway Airport (14.5 km from centre). Milan: 1991-2020 normals, Milano / Linate (8 km from centre).

Before you go

MeasureChicagoMilan
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 m138 m
Main airportChicago O'Hare International Airport (ORD)25 km from centre274 non-stop destinationsMilan Malpensa International Airport (MXP)40 km from centre208 non-stop destinations
Public holidays this year13 days13 days

By the numbers

MeasureChicagoMilan
City population2,746,3881,354,196
People per km²4,5297,453
Museums within 10 km4488
UNESCO World Heritage sites within 50 km14
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 Milan 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 2026-11-01. Daily budgets are estimates from country price levels.