Chicago travel guide

Start with the day-by-day plan, then use the supporting guides to pick your month, set a budget, work out how to get around and pack for it. Every guide feeds the same free planner, so you can turn any of it into a real itinerary.

Chicago itineraries

Itinerary

Chicago Itinerary 5 Days: The Ultimate Day-by-Day Plan

A detailed 5-day Chicago itinerary covering the Loop, West Loop, and Gold Coast. Includes costs, transport times, and bookings for the Architecture Tour and Skydeck.

Itinerary

Chicago Itinerary 3 Days: The Essential Loop & Neighbourhoods

Plan a 3-day Chicago trip with this guide to the Loop, River North, and Wicker Park. Includes transport times, daily budgets, and booking requirements.

Chicago travel planning tips

Destination overview

Chicago Travel Guide: Plan Your Trip to the Windy City

Plan a Chicago trip with advice on the best months to visit, neighbourhood guides for Loop and West Loop, daily budgets, and how to use the 'L' train system.