Hip cocktail lounges

LOUNGEsix at Hotel Solamar

Grab a seat at this outdoor rooftop bar in the middle of the Gaslamp and soak up the hopping bar scene, complete with hide-away areas with cozy fire pits and private cabanas. Get carried away with a cocktail made of top-shelf spirits and fresh, organic fruit, and share a few tantalizing small bites (rosemary French fries and house-made charcuterie) from the menu while you enjoy the glam see-and-be-seen scene unfolding before you.

Rivera

Bustling and sleek, this upscale Latin spot has been a downtown hit for cocktails and dining since opening its doors in early 2009. Rivera boasts a tequila bar (with special tequila-tasting chairs) and a long list of custom drinks, making it a great, high-energy post-work spot.

Gitane

Beautifully decorated in fabric and tapestries, Gitane will transport you back to Europe in the 40s. The master mixologist serves up an array of delicious concoctions—try anything from the Vintage cocktail menu and prepare to be wowed.

Anthology

Modeled after the great supper clubs of the 30s and 40s, this sleek entertainment venue has all the ingredients for a sexy night out: delicious cocktails, excellent New American cuisine and live music. Musical acts are eclectic and might include jazz, classic rock, blues, Latin or world music. Want to skip dinner? Grab a drink and appetizers at the bar or head upstairs.

Bondi

Looking for beer with a twist? Bondi’s serves up an Australian riff on the classic beer hall, with a selection of Australian draught beers (sold in Australian sizes: Pony (5oz), Middy (10oz), and Schooner (16oz)). You’ll also find Australian pub classics such as salt-and-pepper calamari and Australian lamb cutlets. The hip open space is cooler than your average bar as well, with accents like sea anemone chandeliers and lava rock walls.

Ivy

Ivy's rooftop bar is a hopping pool scene by day and a sultry lounge by night. Start your evening with a drink or two, while you soak up that gorgeous skyline—then head downstairs to Envy for a night of dancing (assuming, of course, that you care to know whether your colleagues can dance).

Nacional 27

Chicago has its fair share of rock-star mixologists, and Adam Seger of Nacional 27 is certainly one of them. Step into this River North Latin lounge and restaurant, and let yourself be transported somewhere exotic with one of Seger's signature spins on classic cocktails. Whatever you do, don’t miss the Chadwick mojito, a bracing blend of rum, lime, mint, pomegranate, ginger, and habanero.

The Bar at the Peninsula Chicago

A VIP vibe permeates this slick hotel lounge with a gleaming back-lit bar, sumptuous seating and A-list service. The wine list is long and varied, and the tempting cocktail concoctions are worth the extra wait. In no time at all you’ll feel like a mover and shaker yourself.

Rebar

Rebar is the chic cocktail lounge located on the mezzanine level of the Trump International Hotel & Tower, but don't call it a hotel bar—it's so much more than that. A panoramic view of the Chicago River and the Michigan Avenue Bridge creates a sophisticated backdrop for hand-crafted cocktails, champagne, and Rebar's signature punch bowls, along with a selection of sushi and other gourmet light bites. It’s the most elegant place in town to put the workday behind you, so put your BlackBerry away and savor it.

Wilshire

Set beneath twinkle-lit trees on a two-tiered patio designed by favorite Thomas Schoos, Santa Monica's sexiest al-fresco dining is the perfect spot for a romantic rendezvous. Inside, the chic décor, with dark shades and cozy booths, makes this a prime spot for intimate encounters. Andrew Kirschner creates seasonally driven new-urban cuisine with great finesse and style. Ask for one of the booths overlooking the garden if you prefer to be inside.