The City of Big Shoulders is bursting with international dining, spas and nightlife to engage a women’s tour group

America’s third-largest city can be an overwhelming experience for out-of-town groups. Consisting of 77 neighborhoods, Chicago is a diverse collection of ethnic communities, cutting-edge industry and beautiful greenspace. Innumerable spa, nightclub and outdoor adventure options await your women’s group tour experience, so we’ve highlighted the best the Windy City has to offer female travelers.


Summer House Santa Monica

Summer House Santa Monica. credit

The airy dining room of Summer House Santa Monica will transport your group to Southern California with beach-inspired fare and an extensive wine list. A favorite for girls day brunches, the restaurant integrates fresh avocados and jalapeños into its hearty omelets and breakfast sandwiches. For sophisticated Mexican cuisine inspired by seasonal produce, Mercadito (Spanish for “little market”) in the hip River North neighborhood is an inspired choice. Groups are surrounded by Aztec-inspired art and can try dishes perfect for sharing such as tacos, ceviche and margarita pitchers. Across the street is Untitled Supper Club, a tribute to Chicago’s Prohibition era and host to acclaimed jazz and bluegrass artists in a speakeasy setting. Your group can savor Italian-inspired entrees and imbibe a cocktail or champagne flight like the city’s famous Great Depression gangsters.

Pair a view of Chicago’s famous skyline with an excellent meal on one of Odyssey Lake Michigan’s ships. The fleet departs from Navy Pier and can offer historic architecture tours along the Chicago River or beautiful views of the Gold Coast neighborhood from the deck. Groups can book a variety of prix fixe dinners that include a three-course plated meal, unlimited coffee and hot tea and music played by a DJ. Your women’s group might also be interested in Odysseys’ brunch or cocktail cruises.



City Winery

City Winery. Credit

Vino-lovers in your group will want to include City Winery in the tour. The cellar-inspired building in the West Loop is a fully-functioning winery that offers wine-making tours, tastings and meals of Mediterranean-inspired cuisine. The winery also includes a performance area and bar where your group can listen to musical acts in an intimate setting. For a more raucous music venue, venture to Buddy Guy’s Legends. Founded by Rock and Roll Hall of Famer Buddy Guy, this juke-joint-inspired space hosts bands seven days a week and features an authentic Cajun menu that brings a taste of the Bayou to the Windy City. Your group might even catch a performance by Guy himself. Another throwback venue popular with groups is Howl at the Moon, which hosts nightly dueling piano shows and sing-alongs. Tip the musicians enough and you can even hear your favorite song performed. Leave the cellars and juke-joints behind in ROOF, a nightclub found 27 stories high atop the theWit Hotel. Boasting a retractable roof and late-night DJ, it’s the perfect club for a nightcap and view of the Chicago River.


Magnificent Mile Shopping Festival 10

Magnificent Mile Shopping Festival

Shoppers should beeline to the 450 retail stores that line the Magnificent Mile, one of the largest shopping districts in the nation. Upscale brands such as Cartier and Louis Vuitton are intermixed with more budget-friendly options like Nordstrom Rack, and your group can also admire iconic buildings such as the Drake Hotel and the neo-Gothic Tribune Tower. Farther south is State Street, the major commercial artery for Chicago’s Loop and home to one of the largest department stores in the world: Macy’s on State Street. Originally the flagship location for Marshall Field and Company, the building retains many of its opulent Gilded Age touches and features extensive women’s clothing, home goods and perfumes.

Surrounding the city are several outlet mall options, including Chicago Premium Outlets in Aurora. A massive draw for bargain hunters, this massive 120-store facility features savings of up to 65 percent off brands that include Ann Taylor, Banana Republic, Michael Kors and Armani. Minutes from O’Hare International Airport is the Fashion Outlets of Chicago, which specialize in more upscale designers such as Prada, Hugo Boss and Tory Burch. Groups can then explore the surrounding Rosemont restaurant and nightlife scene that caters to convention travelers and includes the candy store-inspired Sugar Factory cocktail bar and Joe’s Live music venue.


The Peninsula Chicago Spa

The Peninsula Chicago Spa

Every girlfriend getaway to a city as vibrant as Chicago requires some stress-free R&R, and the city is populated with spas that can revitalize every sense. A favorite for groups is the Bliss Spa, found in the W Chicago-Lakeshore and home to the famous movie-while-you-manicure station. Other treatments offered include facials, a foot-tension-fighting facility and an innovative vitamized oxygen spray, and a brownie buffet is offered to indulge your taste buds. Luxurious pampering can also be found at the Peninsula Spa, which features shoulder-melting massages and a half-Olympic lap pool. Inspired by Ayurvedic and Asian holistic health philosophies, the facility offers hot stone massages, aromatic ESPA oils and relaxation lounge complete with fireplace. Or book an afternoon at the Waldorf Astoria Spa & Health Club. Amenities include a mosaic-tiled pool, whirlpool tubs, dry saunas and eucalyptus steam rooms, and an adjoining fitness facility features a Pilates and Gyrotonics studio.


Millennium Park

Millennium Park. Credit

While known for its museums and nightlife, Chicago is bursting with outdoor activities and parks to explore that allow your group to wander and stimulate their senses. Part sculpture garden, part arboretum, Millennium Park is a 25-acre complex that is home to iconic art pieces such as the Crown Fountain (a 50-foot video display of faces that spit water on passersby) and Cloud Gate (nicknamed “The Bean”). Cross the BP Pedestrian Bridge to Maggie Daley Park, which includes enjoyable group activities such as rock climbing and roller skating. To explore the Lake Michigan shoreline, rent a fleet of four-wheeled canopy bicycles and ride down the 18-mile Lakefront Trail, which includes stops at Oak Street Beach and Lincoln Park Zoo, a free attraction ideal for day trips.

One of the largest collections of Art Deco architecture and skyscrapers in the world, Chicago’s best experienced on the Chicago River, which cuts through downtown and offers a unique perspective on the city’s buildings and bridges. If your group is further interested in Chicago history, embark on a Shoreline Sightseeing Tour, which includes beautiful views of the Wrigley Building, Marina City Towers and Trump Tower. Another river cruise option is offered by the Chicago Architecture Center. The organization just opened its new visitors center this September, and its cruise guides will explain the design significance of landmarks like Merchandise Mart, River City and Willis Tower.

by Miles Dobis