Chicago travel ideas and advice

Chicago consistently ranks as one of America’s most architecturally significant cities, combining world-class skyline views with deep-dish pizza culture, gangster heritage from the Prohibition era, and cultural institutions like the Art Institute of Chicago that rival any global capital. From kayaking the Chicago River to marvel at the city’s architectural innovations from water level, to discovering the Tiffany dome in Preston Bradley Hall or the quirky Tribune Tower that literally stole pieces of buildings from around the world, Chicago rewards travellers who look beyond the obvious Millennium Park selfies and tourist traps.

Whether you’re planning your first visit and need the ten reasons why Chicago might be America’s best city, exploring Frank Lloyd Wright architecture in Oak Park, experiencing different pizza styles in the West Loop, or simply understanding which neighbourhoods deserve your attention beyond the Loop, these articles provide enthusiastic, experience-led guidance from someone who genuinely rates this as a favourite city. From practical details like whether you need Art Institute tickets in advance to deeper explorations of why a third visit to Chicago often proves the best, these guides cover everything from gangster tours and architecture cruises to the unexpected joy of the Shedd Aquarium — all whilst explaining why you really should do both an architecture cruise and walking tour to fully appreciate Chicago’s skyline genius.

• Tribune Tower – the building that stole the world.
• Kayaking along the Chicago River.
• Ten reasons why Chicago is the best city in the US.
• Falling instantly in love with Chicago.
• The joy of visiting Chicago third time round.
• Touring Chicago’s gangster heritage.
• Why you should do a Chicago architecture walking tour as well as a cruise.
• Do I need to buy Art Institute of Chicago tickets in advance?
• The Tiffany dome in Preston Bradley Hall: Chicago’s most underrated attraction?
• The best attractions in Chicago’s Millennium Park – including Cloud Gate.
• The best places in Chicago for Frank Lloyd-Wright architecture.
• Why a guided tour is the best way to see Oak Park in Chicago.
• Experiencing different pizza styles in Chicago’s West Loop.
• A guide to Chicago’s best neighbourhoods for visitors.
• Practical guide to visiting the Shedd Aquarium.
• A guide to parking at the Field Museum.
• What to expect when visiting the Chicago Architecture Center.
• Practical guide to visiting the Chicago Children’s Museum on Navy Pier.

For more Chicago activity and experience ideas, head here.