VacationSelector

Chicago or Boston?

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, 1 point apart

Chicago
56
match

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

Boston
55
match

Wins on nature & day trips and beaches & swimming with your weighting.

What matters to you?

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

The verdict

Choose Boston if the coast and open country matter: 68 beaches within reach, a greener ring of protected land around the city, and more attractions near the centre for children.

Choose Chicago if you want the trip done on foot: roughly twice as many notable places within walking distance of the centre, more restaurants close by and a wider spread of kitchens and bars.

Scoreboard

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

ChicagoBoston
Beaches & swimming. Boston leads by 7 points.7
ChicagoBoston
Score5360
Swim season months10
Beaches 10 km1268
Coast distance10,000 km1 km
Water distance1 km1 km
Places to eat. Chicago leads by 8 points.8
ChicagoBoston
Score8173
Restaurants within 2 km of centre2,1471,452
Effective number of cuisines within 2 km3732
Museums & heritage. Chicago leads by 3 points.3
ChicagoBoston
Score4643
Museums within 10 km4579
Museums within 2 km of centre2027
Share of museums within 2 km %4434
Unesco sites within 50 km10
Nightlife. Chicago leads by 4 points.4
ChicagoBoston
Score6258
Drinking venues within 4 km1,123886
Drinking venues within 2 km of centre728513
Share of drinking venues within 2 km %6558
Nightclubs within 4 km5143
Nature & day trips. Boston leads by 15 points.15
ChicagoBoston
Score3853
Protected land share 50 km %612
Landscape blanket share 50 km %00
Land share of disc %10077
Park area within 2 km118 hectares116 hectares
Good for families. Chicago leads by 2 points.2
ChicagoBoston
Score5553
Tourist attractions within 2 km1828
Park area within 2 km118 hectares116 hectares
Theme parks within 30 km20
Sights concentration. Chicago leads by 12 points.12
ChicagoBoston
Score7058
Notable places within 2 km217111
Min wikipedia languages55
Value for money. Chicago and Boston are level on 43.
ChicagoBoston
Score4343
Price level global100100
Daily budget——
Year-round weather. Chicago leads by 1 points.1
ChicagoBoston
Score5756
Monthly daytime high0.2 °C to 29.4 °C2.9 °C to 28 °C
Monthly rainfall54 mm to 121 mm79 mm to 107 mm
Dry months00
0255075100

Where they differ

Boston is the better base for days out of town: 12% of the surrounding land is protected against 6% around Chicago, and there are 68 beaches nearby against Chicago's 12, though the sea is 1km from both centres.

Chicago concentrates its interest instead. About twice as many notable places sit within walking distance of the centre, and it has somewhat more restaurants near the centre and a wider range of kitchens, so more of a short stay can be done without transport.

Where they are alike

The year has the same shape in both: cold winters and warm summers, with highs of 0-29°C in Chicago and 3-28°C in Boston, and neither gets a month at 40mm of rain or less.

Both are middling for families and heritage. Park space near the centre is much alike; Boston counts more attractions, while Chicago has 2 theme parks within reach. Museum holdings are modest on both sides, Chicago's sitting more tightly around the centre.

Which traveller are you?

A weekend visitor with three days and no car should take Chicago: about twice as many notable places lie within walking distance of the centre, with more restaurants and drinking spots close by, so little time goes on transport.

Families are better served in Boston, which has roughly twice as many attractions near the centre and similar park space, though Chicago answers with 2 theme parks within reach if that is the trip.

Anyone planning to swim or walk should choose Boston: 68 beaches against 12, and 12% of the surrounding land protected against 6%. Chicago's water does get warmer, to 23°C.

What the numbers don't tell you

The value figure is a national price level, identical for both cities by construction, so it is no evidence that they cost the same and no guide to which is dearer. The dataset carries no daily budget for either, so no cost comparison between Boston and Chicago is possible here at all.

Chicago's sunshine figure is missing: no weather station near the city records the hours, so the series is absent rather than low, and its monthly picture rests on temperature, rainfall and sea temperature alone. Treat that side of the weather comparison as unmeasured rather than settled.

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
Boston
3
4
8
14
19
25
28
27
23
17
11
6
Sea temperature, °C
Chicago
3
2
2
4
7
14
21
23
20
15
9
6
Boston
5
3
4
6
10
15
18
19
17
14
10
8
Rainfall, mm
Chicago
58
54
68
105
121
115
102
104
85
98
69
59
Boston
84
79
105
91
83
99
82
80
90
101
93
107
Daylight, hours per day
Chicago
10
11
12
13
15
15
15
14
13
11
10
9
Boston
10
11
12
13
15
15
15
14
13
11
10
9
Sunshine, hours per day
Chicago
No sunshine record
Boston
5
5
6
7
8
8
9
9
7
5
5
4

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). Boston: 1991-2020 normals, Boston Logan International (3.5 km from centre).

WorseBetter

Boston peaks in July and August, when highs reach 27-28°C and the sea reaches 19°C, its warmest. Rain sits near 80mm in those months, no heavier than the rest of its year, so summer is dependable for swimming.

Chicago is the better pick in September, still 25°C with the water at 20°C and rainfall easing to 85mm. Late spring is warm but among its wettest, 121mm in May, and its winter runs colder than Boston's, so the shoulder tips to autumn.

Getting there

Flying fromChicagoBoston
New YorkJFK, EWR, LGA
2 h 5 m
€201-231
ORD · 25 km
1 h 0 m
€192-203
BOS · 4 km
TorontoYYZ, YHM, YTZ
1 h 30 m
€189-423
ORD · 25 km
1 h 30 m
€211-283
1 stop
BOS · 4 km
OrlandoMCO, SFB, ORL
2 h 35 m
€161-221
1 stop
ORD · 25 km
2 h 45 m
no fares
BOS · 4 km
Los AngelesLAX, BUR, SNA, VNY
4 h 0 m
€195-265
1 stop
ORD · 25 km
5 h 35 m
€289-344
1 stop
BOS · 4 km
DenverDEN, APA
2 h 20 m
€113-184
ORD · 25 km
4 h 0 m
no fares
BOS · 4 km
AtlantaATL, PDK
1 h 50 m
€141-200
ORD · 25 km
2 h 25 m
€218-258
1 stop
BOS · 4 km
Punta CanaPUJ
4 h 25 m
no fares
ORD · 25 km
3 h 50 m
no fares
BOS · 4 km
ParisCDG, ORY, BVA
8 h 30 m
no fares
ORD · 25 km
7 h 10 m
no fares
BOS · 4 km
TokyoHND, NRT
12 h 35 m
no fares
ORD · 25 km
13 h 25 m
no fares
BOS · 4 km
Abu DhabiAUH
14 h 25 m
no fares
ORD · 25 km
13 h 15 m
no fares
BOS · 4 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

MeasureChicagoBoston
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 m43 m
Main airportChicago O'Hare International Airport (ORD)25 km from centre272 non-stop destinationsBoston Logan International Airport (BOS)4 km from centre144 non-stop destinations
Public holidays this year13 days12 days

By the numbers

MeasureChicagoBoston
City population2,746,388675,647
People per km²4,5292,910
Museums within 10 km4351
UNESCO World Heritage sites within 50 km10
Distinct cuisines in the centre8774
Swim season, months above 21 °C1 monthNone

Where else could you go?

Every comparison below shares a destination with this one, so you can follow Chicago or Boston 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 2026-09-01. Typical prices can be up to 7 days old. Daily budgets are estimates from country price levels.