—Stay In Chicago

Chicago: Where Skyline Meets Shore

Discover iconic architecture, lakeside paths, and vibrant neighborhoods shaped by music, art, and flavor.

Discover
— STREET SMART CHICAGO GUIDES

Stay In Chicago helps you find the neighborhoods that fit you

We share Chicago the way locals live it, block by block, so you can plan with real, walkable picks.

From lakefront mornings to late-night bites, we point you to places worth your time, not just the usual highlights.

Come wander, follow your curiosity, and let the city surprise you.

Explore places
The cover and contents of The Chicago City Guide, 2026 edition
Free guide · 2026 edition
The Chicago City Guide

Where to stay, where to eat, when to go and which side of the river to sleep on. The guide reads Chicago in eight territories, from Lincoln Park to Hyde Park, and every address says why it is there. It opens in the browser, and it is free.

  • 102Addresses
  • 22Maps
  • 3Itineraries
Discover the guide
Downtown and Loop Hotels

Skip the Magnificent Mile: where Chicagoans send visitors instead

Skip the Magnificent Mile and base in River North, West Loop or north side neighborhoods instead. A...

Local Concierge City Guides

The Chicago City Guide is out: 102 addresses, 22 maps, three itineraries

Our 2026 Chicago City Guide reads the city territory by territory, from Lincoln Park to Hyde Park: 1...

Hotels with Skyline Views

The rooms where Chicago's skyline does the talking

A local guide to Chicago hotel rooms where the skyline truly matters, from river corridor views to l...

Sports and Game Day Stay Packages

Marathon weekend in Chicago: where to stay and how to move around a city on pause

Planning where to stay Chicago Marathon weekend ? Choose the right neighborhood, navigate closures w...

The journal
Spotlight