The first people to successfully paint the town red spent more time haphazardly assembling scaffolding and arguing over who got to be the "foreman" than enjoying the results. Take the planning out of carousing with today's Groupon: for $1,500, you get a two-hour private-party package at Gilt Bar, in River North (a $3,000 value).

Featured in the Huffington Post, Time Out, and the New York Times, Gilt Bar slings a selection of farm-friendly plates, handcrafted cocktails, and an expansive wine list in an eye-catching modern-yet-rustic atmosphere. Celebrate precious leap-year birthdays in style with an intermediate-level drink package and beginner-level food package that supplies up to 30 friends with enough drinks and appetizers to last until next February 29. Start nights by sampling local sauce with a Death's Door daisy, Wisconsin–distilled vodka infused with Aperol, St. Germain, and lemon. Gilt's old fashioned also pleases palates with demerara sugar, Angostura, and orange bitters, and the Paloma, Lunazul tequila with grapefruit, lime, and soda tastes like summer in a glass. Sip wines from Italy and Spain to enhance the flavors of tenderloin steak tartare or down glasses of pinot grigio alongside bites of foie gras and pork-liver mousse. Dairy devotees can enjoy triple creme délice de bourgogne cheese with fig jam and herb salad, while aromatics aficianados munch on sweet balsamic roasted garlic with olive oil.

Gilt's old-timey speakeasy vibe is just as decadent as its edible offerings. Soft leather couches, artisan light fixtures, and decorative mirrors make the space feel simultaneously rustic and urban. Resident maestro and vinyl tamer Scottie McNiece sets the mood with thoughtful tunes that span a variety of genres. Funk, soul, and alternative rock B-sides bounce off bricks walls as the experienced waitstaff flex tattooed serving muscles.