201 N State St, 27th floor (312-239-9501)
TheWit Hotel’s swank rooftop lounge sports a specialty cocktail menu, a well-curated wine list and Mediterranean small plates, but it’s the breezy terrace-with-a-view that draws crowds, all ready to throw elbows to score tables per the seat-yourself policy.
Height: 27th floor
Drink of choice: Sex on the Roof: Ketel 1 Citroen vodka, St. Germain elderflower liqueur, Aperol, freshly squeezed lemon and orange juice
If you eat one thing: Wood-fired mushroom pizza with thyme, mozzarella and chile flakes
Wait for a table: 60 minutes at peak times
Crowd: Visiting celebs, fashionistas, hotel guests, international tourists, and anyone else who wants to see and be seen
201 N State St, 27th floor (312-239-9501). El: Brown, Green, Orange, Pink, Purple (rush hrs) to State. Mon–Thu 3pm–2am; Fri 1pm–2am; Sat 1pm–3am; Sun 1pm–midnight. Average cocktail: $12. Open year-round.
Avenue Ale House | Casey Moran's | Citizen Bar | C-View | Doc Ryan's | Epic Sky | Market | Medici | NoMI | Pegasus | The Plymouth | Rock Bottom Brewery | ROOF | Shanghai Terrace | Sidetrack | The Southern | SushiSamba Rio | The Terrace at the Conrad | Terrace at Trump | Twisted Spoke | Vines on Clark | Vertigo Sky Lounge | Zed451