Sex and the City 2→ Lakeside-lounging season is finally here (BEACHES OPEN 5/28), and you require a suitably sinful beach read. You pick up a copy of LAST NIGHT AT CHATEAU MARMONT (OUT 5/25), by the novelist Lauren Weisberger (The Devil Wears Prada), about—you guessed it—girls getting revenge.

→ You were first in line for the release of SEX AND THE CITY 2 (OPENING 5/28), but after a night with the general public, you want a new cinema strategy. Netflix the original SATC, recruit a few stylish friends, and host a catered private party at THE WIT HOTEL’S SCREEN, a state-of-the-art viewing room outfitted with a 27-foot display and 40 seats. Think Big.

→ Appraising Carrie’s wardrobe, you wonder where fashion comes from. Curious, you sign on for the Chicago History Museum’s WORK SPACES, CHIC PLACES TOUR (6/5), an insider’s jaunt through the underpinnings of the local fashion industry, led by the CHM’s chic curator of costumes, Tim Long.

Chair→ The Tour’s fabulous clothes leave you panting, but summer in Chicago is not a hotbed of retail activity (save for the Hermès opening). It is, however, the prime time for LESLIE HINDMAN’S West Loop auction house, where two Marketplace sales (6/16-17, 8/25-26) mean deals on luxe goods from antiques to paintings. Then RSVP for the Mass Modern auction, 7/10 at WRIGHT.

chocolate semifreddo→ What’s more indulgent than skipping lunch in favor of a drink and dessert? On a break from ogling Matisse’s masterpieces at the Art Institute (the exhibition closes 6/20; for more artistic outings, see Summer Hot List: Arts & Culture), you take a seat at the bar in the Modern Wing’s TERZO PIANO and order a Cava Rosa Carnina (Koval Rose Hip Liqueur, organic sparkling wine, lime juice, and candied beet; $14)—just the thing to wash down a scoop of chocolate semifreddo topped with Spanish-peanut nougat and salted caramel ($9).

See Summer Hot List: Restaurants & Food for more foodie finds.

Frame→ You’re saving bundles with your staycation, so why not spend some like royalty on a personal portrait? THE MASTERPIECE package at the just-opened Hotel Palomar includes in-room massages and facials for two, a hair and makeup session, a Nordstrom spree with a personal shopper, the sitting and finished painting, and a bottle of Dom Pérignon. After posing, you head downstairs to Sable Kitchen & Bar for a five-course dinner with wine pairings.

Starting cost: $18,000

Value of handing your visage down through the generations: priceless

→ The Chicago Yacht Club’s 102nd annual RACE TO MACKINAC on 7/24 presents the perfect opportunity to relive your East Coast prepster youth. No sailboat? Not to worry. You’re among the lucky 42 who snag a spot aboard a 77-foot schooner for VEUVE CLICQUOT’s $85-per-head sail near the starting line’s Parade of Boats.

Sunglasses→ Following a day in the sun, you need some serious buffing and chart a course for the hotel spa in the Gold Coast’s ELYSIAN. After the two-hour cleanse treatment ($335)—including a sea-salt exfoliation and a full-body wrap—it doesn’t matter whether you have a tan or not. You’re glowing.

→ In fact, your future’s so bright you could use a fresh pair of shades. You breeze through the new street-level MARC JACOBS boutique and pick up the design­er’s MJ317 ($275). Gorgeous.



Photography: (Parker) Craig Blankenhorn/New Line Productions, Inc., (pod chair) courtesy of Wright, (semifreddo) Jeff Kauck, (sunglasses) courtesy of Marc Jacobs