We seriously adore Chicago in the summertime thanks to its glorious, sunshine-filled beaches and jam-packed weekend schedule. Where do we even begin? Skip the tourist overload on Michigan Avenue and instead opt for a stroll along Armitage Avenue in Lincoln Park for cute boutiques and intimate restaurants galore. Chicago may also be known for its unique deep dish pizza, but its hot dogs are a lesser-known must-taste — The Weiners Circle and Portillo's are two such famous Windy City institutions.
1. Proenza Schouler silk-blend shirt dress, $1,250, Net-a-Porter.
2. 3.1 Phillip Lim sunglasses, $265, Shopbop.
3. Natori beach towel, $30, Neiman Marcus.
4. Rag & Bone wide-brim beach hat, $255, Barneys.
5. Rag & Bone suede espadrille sneakers, $450, SSENSE.