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Typing a response, and I asked, "What are you looking forward to do in Chicago?". Is that correct, or should I instead ask,

"What are you looking forward to doing in Chicago?"
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Use 'doing'.

Rover
Comments  

The "to", here, is a preposition (not the infinitive particle to) hence the gerund "doing" after it. Infinitives

don't follow prepositions; nouns, pronouns, and verbal nouns (-ing forms) and noun clauses do.