Now Playing

Close Encounters

No matter if you are traveling with kids, gal pals or even solo, we’ve found a dream weekend getaway just for you.

Hotel Red

InterContinental Chicago O’Hare

Pheasant Run Resort’s award-winning, par-72, championship caliber 18-hole course

The Alexander

Townsend Hotel

With Fellow Aesthetes With rotating cutting-edge exhibits, permanent artwork from Chicago’s top galleries and the Montrose Room, an intimate live-music and comedy venue, it’s hard to leave the chic 560-room InterContinental Chicago O’Hare. But we think the neighboring Fashion Outlets of Chicago, the city’s largest and most ambitious retail project in the last decade, might just do the trick. Inside the 530,000-square-foot, two-story space, you’ll find stores from a who’s who of the fashion world, including Gucci, Prada, Ports 1961, Brunello Cucinelli and Michael Kors, plus Bloomingdale’s The Outlet Store, Last Call by Neiman Marcus and Saks Fifth Avenue Off 5th. Shopping till you drop just got a whole lot better. Rooms start at $159. icohare.com

Going Solo If you’re traveling alone, buckle up and hit the road to Motown. Check into suburban Birmingham’s posh Townsend Hotel for Euro-inspired luxury before stepping out the door for a little QT at some of the Midwest’s best boutiques. While Troy’s Somerset Collection offers Michigan Ave.-caliber shopping, make sure to visit burgeoning downtown Detroit to check out hot spots like Michael Symon’s acclaimed Roast, or live jazz in Art Deco inspired environs at Cliff Bell’s. Culture vultures won’t want to miss the Detroit Institute of Arts, Detroit Symphony Orchestra or inimitable 19th century village and the Henry Ford museum. Rooms start at $275. townsendhotel.com

With The Girls Lake Geneva is fondly nicknamed the Hamptons of the Midwest, thanks to Chicago’s society set, which summers at its tony lakefront properties. One of our favorite destinations is the Grand Geneva Resort & Spa (originally built in 1968 as the first Playboy Club Hotel in the United States). For one weekend every month this fall (Oct. 20-23, Nov. 17-20 and Dec. 15-18), enjoy the best of the resort’s luxe accommodations at a nutrition-, spa- and fitness-focused Wellness Retreat, where a customized itinerary completely immerses guests in a weekend of R&R. Offerings include spa treatments (we highly recommend the 90-minute 5 Diamond Pedicure), consultations with a certified nutritionist, cooking lessons with the on-site culinary team and candle-lit yoga. Plus, with its indoor tennis courts, swimming pool and a 35-foot climbing wall, as well as guided horseback-riding trails with scenic views, you’ll more than deserve that 80-minute hot-stone massage. Rooms start at $169. grandgeneva.com

With Your Food-Obsesssed Friends Those living in Madison, Wis., are often boastful of their local food products. And for good reason—you’ll find terrific regional cheeses, beer and sausage in this quaint capital city, plus one of the country’s best farmers markets, which takes place at Capitol Square on Saturdays. Combine all that homegrown goodness with something a little more modern at Hotel Red, Madison’s first stylish boutique hotel. Each of the 48 suites is outfitted with chic furnishings and hip original art. Opt for one of the two-bedroom suites and you’ll also get a private outdoor terrace overlooking Regent Street. No matter which room you stay in, you can be assured the honor bar will feature only the best local goodies. Bon appétit, indeed. Rooms start at $139. hotelred.com

With Your Golf Buddies Tree-lined fairways, pristine lakes, perfectly manicured greens... Pheasant Run Resort’s award-winning, par-72, championship caliber 18-hole course is a golf-lover’s dream. Don’t know your bogey from a birdie? No worries, since the 250-acre St. Charles resort, located an hour from Chicago, features a top-notch golf academy with state-of-the-art equipment, as well as a driving range to practice your swing. Fore! Rooms start at $129. pheasantrun.com

With Your Significant Other There is no place we love more than the five-star American Club in Kohler, Wis. With some of the best restaurants in the country, plus award-winning golf courses and a killer Design Center filled with star Kohler pieces, the charming resort is already a leading luxury retreat for people around the country. Adding to its appeal (and our favorite part!) is the Kohler Waters Spa, located in The Carriage House, an annex with 55 guest rooms where visitors can lounge in their robes from dawn until dusk. Perfect for a weekend of romance, the Carriage House just renovated all its rooms, plus now offers updated treatment rooms for duos. Rooms start at $279. americanclubresort.com

With The Kids Where design meets function, The Alexander in downtown Indianapolis is a vibrant artcentric contemporary hotel that displays more than 40 works of art by some 20 different artists, all curated by the Indianapolis Museum of Art, as well as 12 site-specific works. While in town, take the family to the world’s largest children’s museum, The Children’s Museum of Indianapolis, and explore its five floors of 120,000 artifacts and interactive exhibits. Highlights include the simulated Cretaceous dinosaur habitat, where kids come face to face with 14 full-size dinosaur skeletons, and the museum’s legendary carousel—its whimsical animals make up one of the biggest collections of artifacts in the museum. Rooms start at $249. thealexander.com

With The Guys If there’s one thing men seem to agree on, it’s a mutual love of beer, so what better getaway than to Brew City (aka Milwaukee, Wis.)? Now, guests can stay at the former Pabst brewhouse, which was abandoned in the mid ’90s when the brewery closed. Completely restored and redeveloped into various properties, the LEED-certified, platinum-rated sustainable development complex is home to The Brewhouse Inn & Suites, a 90-room boutique hotel just steps from the city’s famed pub scene. We recommend a Lakefront Brewery tour and Sobelman’s Pub & Grill for the best burger in town. Rooms start at $169. brewhousesuites.com