CHICAGO

CHICAGO — A CITY OF ARCHITECTURE, WATERFRONTS AND BIG-CITY ENERGY WITHOUT THE CHAOS

Chicago has the energy of a major U.S. city, but without the constant pressure you feel in New York or LA. The skyline rises right against Lake Michigan, the river runs straight through the city with bridges and glass buildings reflecting the water, and the streets feel structured, proud and lived-in. Chicago is a city that knows its identity: culture, sports, architecture and food — all done seriously.

If that balance of scale and comfort appeals to you, we can build a Chicago itinerary around it.

The city’s architecture alone is worth the flight — you see it best from the river on an architecture cruise, or from the Skydeck as the grid stretches in every direction. Museums here are not afterthoughts — the Art Institute and Field Museum are global-level institutions. And when the weather shifts, Chicago shifts with it — summer brings beaches and festivals, winter brings lights, ice rinks and indoor culture.

Outside the landmarks, the city runs on local habit:
– Deep-dish pizza and upscale dining coexisting without competition
– Jazz clubs still working like it’s part of the city’s DNA
– Wrigley Field and United Center pulling crowds for sport and loyalty
– Lakefront trails where people cycle and run with skyline views following them

Chicago doesn’t perform for visitors — it simply continues being itself, and that is exactly what makes it so appealing.

Tell us how you imagine your Chicago trip — museums and theatre, food and neighbourhood exploring, sports-focused, architecture-led, or part of a wider USA journey — and we’ll shape it to your pace and style.

Click here to start planning your Chicago city break — and let us turn the image of the skyline into your actual view.