From under-the-radar museums to architecture havens and exquisite hotels, the Modern Luxury editorial team has curated the ultimate list for luxury travel in and around the Windy City.
BEST COMEDY SHOW
This comedy mega-institution in the Piper’s Alley entertainment complex grew out of the Compass Players in 1959 and has launched the careers of countless comics, from Alan Arkin and John Belushi to Bill Murray and Tina Fey, and now encompasses seven different venues. Catch current shows Oh, the Places You'll Glow! and Black by Popular Demand. 1616 N. Wells St.
GRANDEST VENUE
Both a National Historic Landmark and one of the city’s most beloved performance venues, this Adler and Sullivan-designed venue boasts 24K gold-leafed ceiling arches and Sullivan’s signature intricate stencil patterns. Just as impressive? The range of performers the 4,000-seat theater has hosted, from President Theodore Roosevelt to Jimi Hendrix and the Joffrey Ballet. 50 E. Ida B. Wells Drive
BEST MUSEUM
Considered one of the world’s finest museums, this prized institution houses more than 300,000 works of art—including Grant Wood’s “American Gothic” and Seurat’s “La Grande Jatte”—and welcomes 1.5 million visitors each year. 111 S. Michigan Ave.
BEST CHICAGO EXPERIENCE
CHICAGO ARCHITECTURE CENTER RIVER CRUISE
Simply put, this is the ultimate way to see Chicago. Hop aboard Chicago’s First Lady, the official cruise line of the Chicago Architecture Foundation for an edifying, informative look at dozens of edifices lining the river, all narrated by a CAF-certified volunteer docent. 112 E. Wacker Drive
BEST UNDER-THE-RADAR MUSEUM
Late philanthropist Richard H. Driehaus’s unparalleled collection of late-19th and early-20th-century fine and decorative art—including treasures by John La Farge and Louis Comfort Tiffany—is showcased in what was formerly the historic Samuel M. Nickerson Mansion. 40 E. Erie St.
BEST DANCE COMPANY
Originally founded in 1956 by Robert Joffrey and Gerald Arpino in New York City, the acclaimed classical-contemporary ballet company has called Chicago home for over two decades. Current artistic director Ashley Wheater MBE champions innovative choreographers, such as Christopher Wheeldon, Alexander Ekman, Yuri Possokhov, Annabelle Lopez Ochoa and Justin Peck. 20 N. Wacker Drive
BEST PUBLIC SPACE
Since its debut 20 years ago, this tribute to contemporary architecture, sculpture and landscape design has become the beating heart of downtown Chicago. The centerpiece is Frank Gehry’s billowing, stainless steel Jay Pritzker Pavilion, which features a distinctive open-air acoustic canopy. Visitors can also stroll through lush gardens dotted with public art, fountains and reflecting pools. Tying it all together is Anish Kapoor’s elliptical sculpture, “Cloud Gate” (aka “The Bean”), which grandly reflects the park and the Chicago skyline. 201 E. Randolph St.
BEST NEW CHICAGO EXPERIENCE
A strikingly rendered love letter to the city of Chicago, this immersive new experience has taken residency at the former IMAX theater at Navy Pier. With a 65-foot spherical screen and special effects such as wind and mist, Flyover surrounds guests as they experience the journey of flight throughout the city. 600 E. Grand Ave.
BEST FAMILY EXPERIENCE
This mind-bending museum offers a sensory immersive experience that transfixes visitors of all ages. Rooms like the Vortex Tunnel and the Rotated Room make for a perspective-skewing walk-through and are complemented by various other psychedelic installations. 25 E. Washington St.
BEST FREE EXPERIENCE
Now celebrating its 90th anniversary season, the Grant Park Music Festival has enthralled Chicagoans with performances from world-class artists like pianist Michelle Cann, violinist Rachel Barton Pine and clarinetist Afendi Yusuf, made even more impressive by the grand setting of Millennium Park’s Pritzker Pavilion. 201 E. Randolph St.
BEST LUXURY TOUR
For a sky-high perspective of the city, nothing touches a helicopter tour along Lake Michigan, and this company’s Shoreline Tour is the ultimate offering out there, giving literal bird’s-eye views of everything from downtown and Navy Pier to the Museum Campus, Montrose Harbor and more. 1339 S. Wood St.
BEST ARCHITECTURE DESTINATION
FRANK LLOYD WRIGHT HOME & STUDIO
This beautifully preserved Oak Park landmark served as Frank Lloyd Wright’s private residence and workplace from 1889 to 1909, the first 20 years of his career. Here, he and his associates developed a new American architecture—the prairie style. Trained interpreters offer insights into Wright’s family life and architectural career through a variety of tours, including interior views and neighborhood walking tours, Unity Temple, Robie House and more. 951 Chicago Ave., Oak Park
BEST HOTEL FOR FITNESS FANATICS
Say sayonara to sad hotel gyms: At this boutique property on the site of Midtown Athletic Club, guests get full access to the location’s pools, tennis courts, yoga studio, boxing gym and more, all just a few miles northwest of downtown. 2444 N. Elston Ave.
BEST DOWNTOWN DIVERSION
This 1.25-mile path from Lake Street to the lakefront has transformed the way locals and visitors alike experience the Chicago River. From lunchtime lounging at the stepped River Theater at LaSalle Street to people-watching at City Winery, this scenic stretch is always abuzz—and a boon to the cityscape.
BEST FAMILY DESTINATION
Chicago’s top attraction, with more than 9 million visitors a year, features rooftop bar Offshore, grand hotel Sable and an all-weather Ferris wheel that soars a towering 196 feet. The latest reason to visit? Flyover, a just-debuted immersive, Chicago-themed flying journey set in the pier’s former IMAX theater. 600 E. Grand Ave.
BEST CHICAGO RIVER ADVENTURE
Gone are the days of waiting to score an invite from that elusive boat-owning friend thanks to this outfit, which rents multiple types of electric boats—Cycleboats, retro boats, even hot tub boats in winter—all of which you can captain yourself, and all BYOB with designated driver. Multiple locations
BEST ROAD TRIP
Whether you’re craving a Vegas vibe, a family getaway, a first-class culinary crawl or (of course) a country music adventure, this booming Southern mecca can do it all—so it’s no wonder it’s become a go-to visitor destination for all seasons.
BEST WINTER FAMILY GETAWAY
Offering pristine white-sand beaches and crystal-clear emerald waters, South Walton offers a blend of family-friendly attractions, charming local culture, and a welcoming atmosphere. Within its 16 distinct neighborhoods, South Walton offers a diverse array of styles curated to suit a family’s vacation preferences. Whether you’re wandering the cobblestone streets of Rosemary Beach or basking in the soothing pastels of Seaside, each locale provides an ideal backdrop for creating family memories.
BEST PUBLIC ART
Downtown Chicago is a treasure trove of public art, but this extraordinary installation takes it to the next level, making the 2.5-acre face of THE MART a vivid canvas for stunning nightly video projections by notable artists from Chicago and beyond. Riverwalk between Orleans and Wells Streets
BEST SUMMER FAMILY GETAWAY
From its car-free streets and horse-drawn carriages to the fudge shops and Grand Hotel’s iconic world’s longest porch, this charmingly old-school destination has been welcoming families for generations.
BEST HOTEL WITH A VIEW
TRUMP INTERNATIONAL HOTEL & TOWER
Premium riverside location—including extraordinary views from both Terrace 16 and Rebar—makes this an unbeatable destination, with amenities including a newly renovated 23,000-square-foot spa and fitness club complete with 75-foot heated indoor swimming pool. 401 N. Wabash Ave.
BEST NEW HOTEL
With stunning design by Jeanne Gang, two must-try restaurants in Miru and Tre Dita, a world-class spa and more, this high-profile hotel south of the Chicago River has deservedly become one of the hottest properties in town. 401 E. Wacker Drive
MOST ARCHITECTURALLY SIGNIFICANT HOTEL
An ideal place to revel in the city, The Langham scores with premium riverfront location, fine dining at Travelle and indulgent spa treatments at the award-winning Chuan Spa, all in a truly iconic Windy City location: Mies van der Rohe’s 1973 IBM Building, whose interiors underwent a dramatic transformation into the poshest of luxury hotels. 330 N. Wabash Ave.
BEST SERVICE
White-glove service has always been the hallmark of this renovated Windy City institution, whether it’s experiencing cocktails in the stunning lobby, dining at upscale destination Torali Italian-Steak or grabbing a workout in the state-of-the-art fitness center. 160 E. Pearson St.
MOST ROMANTIC HOTEL
From intimate nighttime couple’s experiences in the just-renovated spa to exquisite multicourse tasting menus from wildly creative chef Richie Farina—not to mention the option of an in-room visit from the hotel’s mobile martini cart—this grande dame along the Magnificent Mile is peerless when it comes to setting a sultry mood. 120 E. Delaware Place
MOST ELEGANT HOTEL
From its refined lobby and poshly outfitted spa to sophisticated rooftop destination Z Bar, every aspect of this beloved Mag Mile property exudes a hushed dignity, so it’s no surprise that it’s a favorite of A-list celebs and global CEOs. 108 E. Superior St.
Photography by: PHOTO COURTESY OF CHICAGO’S FIRST LADY CRUISES; PHOTO BY: JAMES CAULFIELD; PHOTO BY: STEVE HALL/HEDRICH BLESSING; PHOTO COURTESY OF BRAND; PHOTO COURTESY OF BRAND; PHOTO: BY KEN HAYDEN PHOTOGRAPHY; PHOTO: COURTESY OF THE ST. REGIS CHICAGO; PHOTO COURTESY OF THE PENINSULA CHICAGO
