Chicago,
a little closer.

A family city break gets easier when you stop treating the map as a checklist. Choose a base that works for the places you most want to see, decide on one main plan for each day, and keep the spaces between plans useful. Chicago can be the setting for exactly that sort of weekend.

Group activities by neighbourhood.

Leave a little room to revisit a favourite spot instead of insisting on something new. There is pleasure in recognising a street, ordering breakfast without studying the map, and feeling briefly at home.