Stories from Chicago
Long-form writing on Chicago and the region beyond it — architecture, blues and jazz culture, neighborhood life and the practicalities of travel around the city.
More stories
Chicago in winter: the season everyone warns you about
Deep-dish versus tavern-style: the pizza fight Chicago doesn't advertise
Is the architecture cruise worth it? A dissenting opinion
Chicago has beaches, and nobody warned me
Milwaukee, the day trip you keep postponing
The real cost of a week in Chicago
Riding the L when nobody needs it
The Bean and the selfie crowd
The Frank Lloyd Wright cult in Oak Park
The Riverwalk, ten years on
The South Side's reputation versus what I actually found there
What guidebooks still get wrong about Chicago
Why Chicago sells its gangsters
Good to know about the Chicago blog
The blog is where Chicago Trip steps back from strict planning logistics and covers the questions that shape how a trip actually feels, written with the same honest, no-fluff approach as the rest of the site. It opens with orientation pieces - what to know before visiting Chicago for the first time, and a direct look at whether booking an architecture cruise weeks ahead is really worth the trouble, which stays qualitative rather than inventing precise figures: for a summer weekend trip it usually is, while a flexible traveler visiting in the shoulder season carries a smaller real risk.
History and culture get their own space: a piece on the Great Fire of 1871 explains how it reshaped the city and gave rise to the modern skyscraper, and a piece on Prohibition-era Chicago covers Al Capone, the speakeasies and the St. Valentine's Day Massacre without romanticizing the violence. Food and craft pieces make up a solid share of the blog: a debate on deep-dish versus tavern-style pizza, a piece on the city's blues and house-music heritage from Chess Records to the Green Mill, and a guide to Wrigley Field's history as one of baseball's oldest ballparks.
A best-time-to-visit piece pulls together the seasonal picture in one place: the comfortable shoulder months, the hot humid summer with its festivals, and the cold snowy winter when cruises and patios close. A safety and etiquette piece covers ordinary caution around winter cold and lakefront currents, plus practical notes on dressing in layers. None of the blog content replaces the destination or guide pages - it's meant to be read for context and reassurance before or during a trip, answering the softer questions a strict itinerary or logistics guide doesn't cover.
Frequently asked questions about the Chicago blog
Is booking an architecture cruise in advance worth it?
For a summer weekend trip, it usually is worth the advance reservation, since popular slots sell out; for a flexible traveler visiting in spring or fall, the real risk of missing out is much smaller. The blog's dedicated piece walks through both scenarios in more detail.
Why does the Great Fire of 1871 still come up on every tour?
It destroyed much of the city center but cleared the way for the modern skyscraper, starting with the Home Insurance Building in 1885, which is why architecture tours treat 1871 as the hinge point of Chicago's skyline.
What's the real story behind Chicago's Prohibition history?
Al Capone's bootlegging empire and the speakeasies of the 1920s are real history, culminating in the 1929 St. Valentine's Day Massacre, and several gangster-themed tours and the Green Mill jazz club, once a Capone haunt, still trade on that period today.
Deep-dish or tavern-style: which pizza should I actually try?
Deep-dish, from places like Lou Malnati's or Giordano's, is the famous 'stuffed' version worth trying once; tavern-style thin crust is what most Chicagoans actually eat day to day, so trying both gives a fuller picture.
How should I handle Chicago's winter cold as a visitor?
Layer up, and expect wind off Lake Michigan to make the temperature feel colder than the forecast, especially downtown and along the Riverwalk; most museums and indoor attractions make a very workable backup plan on the coldest days.
Chicago River architecture and sightseeing cruises on GetYourGuide
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GetYourGuide does not provide a product photo for this activity — the image shows the meeting point, photographed by us.
