Bobby Gonzalez, Chef Concierge, Kimpton Gray Hotel
City Winery at the Chicago Riverwalk offers a prime spot to watch the boats mosey up and down the Chicago River. Besides its selection of wines on tap— best paired with a sandwich or charcuterie board—you simply can’t beat having a cold beer under the skyline and on the Riverwalk.
Emily Mayer, Concierge, Viceroy Chicago
Tucked behind a charming old coach house, Waterfront Cafe is a darling spot on Lake Michigan that offers dog-friendly outdoor dining and live music on select evenings. The menu offers uncomplicated favorites like lobster rolls and summer salads in addition to beer, wine, and cocktails.
Judson Corrie, Concierge, Waldorf Astoria Chicago
Shore Club is the natural progression of Chicago’s Lake Shore dinishoreng-scape. It’s both as upscale and casual as you want it to be offering swanky cabanas and outdoor games into a mix of patio, sand, and tented expanse.
Shannon Boland, Chef Concierge, LondonHouse Chicago
Transport yourself to Morocco at Beatnik on the River’s lush and plush waterfront patio. Overlooking the South Branch of the Chicago River, expect a plethora of pillows, rose, beautiful people, and inspired nosh!
Diane Martinez, Concierge, Palmer House Hilton
Still flying somewhat under the radar, Café Michelle boasts an ample and reasonable menu alongside a stunning view of the lake and bobbing boats in DuSable Harbor. It’s also a great spot to see Navy Pier’s fireworks every Wednesday and Saturday night (through Labor Day weekend).