BostonChicago
City Stories Index · United States · 2026 edition

Boston vs Chicago

Not opinions, measured walking data. On what we can measure, Chicago leads 3–2 (1 within the tie margin). Character is a different question: Boston is the cradle of revolution; Chicago is the city rebuilt after the fire.

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VS
  • Places with a story

    spots where a route tells you what happened there

    Boston

    46

    Chicago

    94

    Chicago leads

  • How often you pass a story

    metres from one story to the next; fewer is better

    Boston

    299

    Chicago

    293

    Tie

  • Historical figures

    real people you meet in its stories

    Boston

    4

    Chicago

    11

    Chicago leads

  • Instagrammability

    score /100, on the index’s fixed scale

    Boston

    60

    Chicago

    37

    Boston leads

  • Group outings

    of every 100 plays, how many bring a group of 3+

    Boston

    6

    Chicago

    22

    Chicago leads

  • International visitors

    % of player reviews written in a foreign language

    Boston

    3

    Chicago

    2

    Boston leads

Differences under 5% count as ties. Sample sizes and definitions on the methodology page.

What their stories are about

How many places with a story each city has per theme: Boston in orange, Chicago in blue. All bars share one scale, so lengths are comparable everywhere on the chart.

BostonChicago
4 places
arts & culture
33 places
7 places
crime & dark history
16 places
7 places
faith & churches
13 places
10 places
parks & leisure
13 places
3 places
legends & myths
12 places
6 places
guilds & trade
6 places
6 places
industry & modern era
5 places

Boston scorecard

The cradle of revolution

Chicago scorecard

The city rebuilt after the fire

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