VacationSelector

Chicago or Portland?

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

Your match

Chicago
✓ Best match
56
match

Wins on beaches & swimming and sights concentration with your weighting.

Portland
42
match

Wins on year-round weather 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.

ChicagoPortland
Beaches & swimming. Chicago leads by 53 points.53
ChicagoPortland
Score530
Swim season months10
Beaches 10 km1227
Coast distance10,000 km69 km
Water distance1 km
Places to eat. Chicago leads by 7 points.7
ChicagoPortland
Score8174
Restaurants within 2 km of centre2,1471,011
Effective number of cuisines within 2 km3744
Museums & heritage. Chicago leads by 11 points.11
ChicagoPortland
Score4635
Museums within 10 km4523
Museums within 2 km of centre2015
Share of museums within 2 km %4465
Unesco sites within 50 km10
Nightlife. Chicago leads by 4 points.4
ChicagoPortland
Score6258
Drinking venues within 4 km1,123942
Drinking venues within 2 km of centre728518
Share of drinking venues within 2 km %6555
Nightclubs within 4 km5132
Nature & day trips. Chicago leads by 3 points.3
ChicagoPortland
Score3835
Protected land share 50 km %613
Landscape blanket share 50 km %03
Land share of disc %100100
Park area within 2 km118 hectares37 hectares
Good for families. Chicago leads by 21 points.21
ChicagoPortland
Score5534
Tourist attractions within 2 km188
Park area within 2 km118 hectares37 hectares
Theme parks within 30 km22
Sights concentration. Chicago leads by 35 points.35
ChicagoPortland
Score7035
Notable places within 2 km21729
Min wikipedia languages55
Value for money. Chicago and Portland are level on 43.
ChicagoPortland
Score4343
Price level global100100
Daily budget
Year-round weather. Portland leads by 8 points.8
ChicagoPortland
Score5765
Monthly daytime high0.2 °C to 29.4 °C7.9 °C to 27.7 °C
Monthly rainfall54 mm to 121 mm13 mm to 145 mm
Dry months03
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
Portland
8
11
13
16
20
23
27
28
25
18
12
8
Sea temperature, °C
Chicago
3
2
2
4
7
14
21
23
20
15
9
6
Portland
No coastline within reach
Rainfall, mm
Chicago
58
54
68
105
121
115
102
104
85
98
69
59
Portland
128
94
101
75
65
41
13
14
39
87
138
145
Daylight, hours per day
Chicago
10
11
12
13
15
15
15
14
13
11
10
9
Portland
9
10
12
14
15
16
15
14
13
11
10
9

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). Portland: 1991-2020 normals, Portland International Airport (9.8 km from centre).

WorseBetter

Getting there

Flying fromChicagoPortland
Los AngelesLAX, BUR, SNA, VNY
4 h 0 m
€195-265
1 stop
ORD · 25 km
2 h 15 m
no fares
PDX · 10 km
New YorkJFK, EWR, LGA
2 h 5 m
€201-231
ORD · 25 km
5 h 20 m
no fares
PDX · 10 km
PhoenixPHX, AZA
3 h 25 m
€182-307
1 stop
ORD · 25 km
2 h 35 m
no fares
PDX · 10 km
DenverDEN, APA
2 h 20 m
€113-184
ORD · 25 km
2 h 30 m
€167-182
PDX · 10 km
MinneapolisMSP, STP
1 h 20 m
no fares
ORD · 25 km
3 h 20 m
no fares
PDX · 10 km
SeattleSEA, BFI
3 h 55 m
€250-272
1 stop
ORD · 25 km
55 m
no fares
PDX · 10 km
DallasDFW, DAL, AFW
2 h 10 m
€187-223
ORD · 25 km
3 h 45 m
no fares
PDX · 10 km
AtlantaATL, PDK
1 h 50 m
€141-200
ORD · 25 km
4 h 45 m
no fares
PDX · 10 km
GuadalajaraGDL
3 h 55 m
no fares
ORD · 25 km
4 h 35 m
no fares
PDX · 10 km
FrankfurtFRA, HHN
8 h 50 m
no fares
ORD · 25 km
10 h 30 m
no fares
PDX · 10 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

MeasureChicagoPortland
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 m152 m
Main airportChicago O'Hare International Airport (ORD)25 km from centre272 non-stop destinationsPortland International Airport (PDX)10 km from centre87 non-stop destinations
Public holidays this year13 days12 days

By the numbers

MeasureChicagoPortland
City population2,746,388652,503
People per km²4,5291,736
Museums within 10 km4317
UNESCO World Heritage sites within 50 km10
Distinct cuisines in the centre8782
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 Portland 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.