The Allegro Royal Sonesta Hotel Chicago Loop

A 27-floor Loop hotel by the Chicago Theatre and Riverwalk, formerly branded a DoubleTree by Hilton and now simply a Hilton Hotel, with no pool on site. Coordinates estimated from the street address.

A landmark Loop hotel in a converted historic bank building, with an indoor pool, in-room refrigerators and connecting room options for families, though breakfast is paid rather than complimentary.

A 191-room boutique hotel in the Loop, in a century-old former hat-factory building, previously Kimpton Hotel Monaco before a 2022 rebrand as L7 Chicago. Coordinates interpolated from nearby known addresses on the same street.

An observation deck atop Willis Tower with glass "Ledge" balconies that jut out over the street, fully stroller- and wheelchair-accessible with family restrooms on site.

Chicago's classic deep-dish pizzeria, with a dedicated kids' menu and a full-service, casual dining room that regularly seats families.

A landmark 1893 athletic-club building across from Millennium Park, now a Hyatt hotel whose old lap pool is a tiled event space rather than a place to swim.