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A mid-priced Loop option by the river: $75 for one to four nights, $125 for five or more, up to two dogs or cats.
A Hilton-brand Hampton Inn on Wacker Place, a block from Michigan Avenue and the river.
The terms, from Hilton's page for this hotel: a pet fee of $75 for stays of one to four nights and $125 for five nights or more, and up to two pets, dogs or cats only.
Not published: a weight limit, rules on leaving a dog alone in the room, and any pet amenities. Ask when you book if your dog is large.
The fee is charged per stay, not per night, which makes this one of the cheaper ways to bring a dog downtown for a long weekend.
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Hampton Inn Chicago Downtown N Loop Michigan Ave