VacationSelector

Chicago or San Diego?

Two destinations compared on nine measures of openly sourced data. Weight what matters to you and the verdict follows.

Your match

Too close to call, 2 points apart

Chicago
56
match

Wins on sights concentration and places to eat with your weighting.

San Diego
58
match

Wins on year-round weather and good for families with your weighting.

What matters to you?

Pick a travel style or drag the sliders. The match scores above update as you do.

Scoreboard

Each measure scored 0 to 100. Open a row for the figures behind the score.

ChicagoSan Diego
Beaches & swimming. San Diego leads by 10 points.10
ChicagoSan Diego
Score5363
Swim season months11
Beaches 10 km1242
Coast distance10,000 km1 km
Water distance1 km1 km
Places to eat. Chicago leads by 18 points.18
ChicagoSan Diego
Score8163
Restaurants within 2 km of centre2,147823
Effective number of cuisines within 2 km3727
Museums & heritage. Chicago leads by 2 points.2
ChicagoSan Diego
Score4644
Museums within 10 km4559
Museums within 2 km of centre2030
Share of museums within 2 km %4451
Unesco sites within 50 km10
Nightlife. Chicago leads by 12 points.12
ChicagoSan Diego
Score6250
Drinking venues within 4 km1,123615
Drinking venues within 2 km of centre728408
Share of drinking venues within 2 km %6566
Nightclubs within 4 km5131
Nature & day trips. San Diego leads by 17 points.17
ChicagoSan Diego
Score3855
Protected land share 50 km %66
Landscape blanket share 50 km %00
Land share of disc %10052
Park area within 2 km118 hectares308 hectares
Good for families. San Diego leads by 20 points.20
ChicagoSan Diego
Score5575
Tourist attractions within 2 km1840
Park area within 2 km118 hectares308 hectares
Theme parks within 30 km23
Sights concentration. Chicago leads by 30 points.30
ChicagoSan Diego
Score7040
Notable places within 2 km21740
Min wikipedia languages55
Value for money. Chicago and San Diego are level on 43.
ChicagoSan Diego
Score4343
Price level global100100
Daily budget
Year-round weather. San Diego leads by 31 points.31
ChicagoSan Diego
Score5788
Monthly daytime high0.2 °C to 29.4 °C18.6 °C to 25 °C
Monthly rainfall54 mm to 121 mm0 mm to 56 mm
Dry months09
0255075100

When should you go?

The figures behind each month. Each row is shaded against that destination's own year, so the deepest cell is its best month for that measure and the palest its weakest. Shades are not comparable between the two rows.

J
F
M
A
M
J
J
A
S
O
N
D
Daytime high, °C
Chicago
0
3
9
15
22
27
29
28
25
17
10
3
San Diego
19
19
19
20
21
22
24
25
25
23
21
19
Sea temperature, °C
Chicago
3
2
2
4
7
14
21
23
20
15
9
6
San Diego
15
15
16
16
17
19
20
21
21
19
18
16
Rainfall, mm
Chicago
58
54
68
105
121
115
102
104
85
98
69
59
San Diego
50
56
37
17
7
1
2
0
3
13
20
42
Daylight, hours per day
Chicago
10
11
12
13
15
15
15
14
13
11
10
9
San Diego
10
11
12
13
14
14
14
13
12
11
11
10

Temperature and rainfall are thirty-year climate normals, averaged over the years shown. Chicago: 1991-2020 normals, Chicago Midway Airport (14.5 km from centre). San Diego: 1991-2020 normals, San Diego International Airport (2.8 km from centre).

WorseBetter

Getting there

Flying fromChicagoSan Diego
New YorkJFK, EWR, LGA
2 h 5 m
€201-231
ORD · 25 km
5 h 15 m
€299-455
1 stop
SAN · 3 km
DenverDEN, APA
2 h 20 m
€113-184
ORD · 25 km
2 h 15 m
€64-224
SAN · 3 km
BostonBOS, PSM
2 h 20 m
€220-252
ORD · 25 km
5 h 35 m
no fares
SAN · 3 km
DallasDFW, DAL, AFW
2 h 10 m
€187-223
ORD · 25 km
2 h 55 m
no fares
SAN · 3 km
PhoenixPHX, AZA
3 h 25 m
€182-307
1 stop
ORD · 25 km
1 h 15 m
no fares
SAN · 3 km
Salt Lake CitySLC
3 h 0 m
no fares
ORD · 25 km
1 h 50 m
no fares
SAN · 3 km
Los AngelesLAX, BUR, SNA, VNY
4 h 0 m
€195-265
1 stop
ORD · 25 km
50 m
no fares
SAN · 3 km
TokyoHND, NRT
12 h 35 m
no fares
ORD · 25 km
11 h 15 m
no fares
SAN · 3 km
Mexico CityMEX, NLU, TLC
3 h 50 m
€253
ORD · 25 km
3 h 20 m
no fares
TIJ · 26 km
MunichMUC
9 h 15 m
no fares
ORD · 25 km
12 h 5 m
no fares
SAN · 3 km

The busiest departure cities for these two, with a place kept for each other part of the world. Busiest means arriving passengers where an official count exists, and where none does, the number of non-stop services flown: official route statistics are published by the European reporting countries and by nobody else, so a table ranked on them alone would offer a reader in New York or Tokyo ten European cities. Flying times are estimated from the distance between airports, and every row is a city flown non-stop to both. Where the typical offer connects anyway, the stops are shown. Under each figure is the airport the flight lands at and how far that is from the centre, because the nearest airport is not always the one a route is flown to. Where both columns name the same airport it is one flight, and the difference between the two is the distance printed beside it. Typical return fares for 2026-08 to 2026-10, cached market data up to 7 days old. The figure is the middle half of the offers found, so a single price means they agreed and a range means they did not; for a typical route that middle half spans about a quarter of the median, and for the least settled routes rather more than the median itself.

Before you go

MeasureChicagoSan Diego
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 m129 m
Main airportChicago O'Hare International Airport (ORD)25 km from centre272 non-stop destinationsSan Diego International Airport (SAN)3 km from centre87 non-stop destinations
Public holidays this year13 days13 days

By the numbers

MeasureChicagoSan Diego
City population2,746,3881,386,932
People per km²4,5291,438
Museums within 10 km4326
UNESCO World Heritage sites within 50 km10
Distinct cuisines in the centre8744
Swim season, months above 21 °C1 month1 month

Where else could you go?

Every comparison below shares a destination with this one, so you can follow Chicago or San Diego somewhere new.

Browse every destination we have measured

Sources

© OpenStreetMap contributors, data available under the Open Database Licence. Place counts include data from Overture Maps Foundation (CDLA Permissive 2.0), assembled from Meta, Microsoft, Foursquare and other providers. Notable-place counts from Wikidata (CC0), weighted by Wikipedia language editions. Structured data from Wikidata (CC0). Weather data by Meteostat. Meteorological data provided by NOAA, DWD and others. 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. Typical fares from Travelpayouts (Aviasales data). Route-level air passenger statistics from Eurostat, © European Union, reused under CC BY 4.0.

Scores follow rubric v2; snapshot generated 2026-08-31. Typical prices can be up to 7 days old. Daily budgets are estimates from country price levels.