Sip in Streeterville
Unassumingly located on the 18th floor of the Northwestern Memorial Hospital office complex in Streeterville, Judson Corrie, concierge at the Waldorf Astoria, says you’ll rejoice in discovering GreenRiver and its sprawling outdoor terrace. Here you’ll find an expansive wrap-around balcony that’s perfect for after-work relaxation, offering sweeping and distinctive views of the urban skyline and Lake Michigan. GreenRiver also boasts one of the top cocktail lists in the entire city—courtesy of the celebrated cocktail duo Sean Muldoon and Jack McGarry of New York’s The Dead Rabbit fame—whose lengthy list of libations is broken down by the main distillate in the base spirit, including tasting notes and even “personality type”.
Concierge can’t get enough of Streeterville Social, the sun-drenched terrace perched atop the third floor of the Loews Chicago Hotel. This sprawling, warm weather retreat features stunning vistas and two lounge areas in addition to a grassy lawn area set for games like giant Jenga, croquet, and pétanque. The elevated “street” food and drink menus pair perfectly with the fun and games—making it the perfect space to soak up the summer sun. The hand-crafted cocktail menu features custom creations like the Streeterville Mai Tai, and old school tiki remixes like the Coconut Batida. Those drawn to a rosier hue can check out the Pink Page, an entire wine selection solely devoted—and rightfully so—to rosé.
If you’re looking for ample seating in addition to good value for creative food and drinks, Suzanne Spring, a concierge at the Sheraton Chicago Hotel & Towers, recommends going to ZED451. Beautifully situated on a quiet corner in River North, this local favorite can always be relied on for an all-around solid Chicago rooftop experience. If you’re here on a weekday, make sure to take advantage of their Happy Hour specials available Monday through Friday from 4:30 p.m. to 7 p.m. featuring deals ranging from $4.51 margaritas and manhattans to half off bottles of wine.
For a laid back afternoon in the sun, corporate concierge Tamika Smith suggests you venture to the South Loop’s beloved rock venue/restaurant/record store (yes, really) and cozy up on their third-floor deck. Dubbed Reggie’s Trainwreck Rooftop Deck, this place has it all: a full bar featuring a great beer selection, full menu, a basketball hoop, a pool table, nine flat-screens, and a pull string shower for those steamy summer days. If you need a break from catching rays on the deck, enjoy live music on the downstairs corner stage
For a view of the Chicago River that is literally impossible to find anywhere else, Philippe Gills, concierge at the Langham Chicago, suggests heading to LH Rooftop. The crown jewel atop the LondonHouse Chicago hotel, snagging a table or couch seat here does require reservations via Tock but you can always opt for a walk-up seat at the bar. With stunning vistas from pretty much every vantage point, make sure to look west at sunset for absolutely show-stopping, no-filter-required views.