From elevated dining experiences to world-class cultural escapes, the Modern Luxury editorial team has curated the ultimate list for luxury travel in and around the Windy City.
Stunning views pair with exquisite Italian cuisine at Tre Dita.
BEST HOTEL RESTAURANT
Tre Dita, The St. Regis Chicago
The first certified Tuscan restaurant in the U.S., this Italian fine dining destination led by L.A.- based chef Evan Funke has made a name for itself with its wood-fired bistecca Fiorentina, braised beef short rib meatballs, seasonal antipasti, handmade pasta and gelati made in-house. Swing by the bar for an extensive list of more than 700 Italian wine offerings— including heritage selections and offerings sourced from Tuscan vintners. 401 E. Wacker Drive, treditarestaurant.com, stregischicago.com
The Art Institute of Chicago’s latest blockbuster exhibit marks Frida Kahlo’s debut at the museum.
BEST MUSEUM
Art Institute of Chicago
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., artic.edu
BEST FAMILY 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, cruisechicago.com
BEST LUXURY TOUR
Fly Heli
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., flyhelitours.com/chicago
BEST DRIVEABLE DESTINATION
Starved Rock State Park, Utica
Less than two hours’ drive from downtown Chicago, this park feels a world away with breathtaking canyons, scenic waterfalls and 13 miles of hiking trails to explore, all in a setting rich with native American history*. Routes 178 and 71, Utica,* dnr.illinois.gov/parks/park.starvedrock.html
BEST HOTEL FOR A STAYCATION
The Peninsula Chicago
From indulging in treatments at the world-class spa to taking in afternoon tea in The Lobby or cocktailing under the stars at sophisticated rooftop destination Z Bar, this poshly outfitted Mag Mile property is the ultimate place to feel like a pampered tourist in your hometown. 108 E. Superior St., peninsula.com/chicago
Cocktails are an art form at Cindy’s Rooftop.
BEST HOTEL BAR
Cindy’s Rooftop
Perched atop the Chicago Athletic Association Hotel with breathtaking views of Millennium Park and Lake Michigan, this always-buzzing hot spot scores with a sophisticated menu of creative cocktails paired with chef Kaleena Bliss’ smart New American cuisine like a must-try chilled king crab and lobster starter. 12 S. Michigan Ave., cindysrooftop.com
BEST SKI GETAWAY
Boyne Mountain, Mich.
With 65 trails, 10 lifts, five terrain parks and 35km of cross-country trails over more than 400 skiable acres, this resort offers top-tier slopes and a lively après-ski scene. When not schussing, you can indulge at the spa, visit the indoor water park or arcade or go winter tubing or ziplining. boynemountain.com
BEST WEEKEND GETAWAY
Door County, Wis.
With its charming waterfront towns, scenic coastal views and abundant outdoor activities, this charming peninsula offers an ideal blend of relaxation and adventure less than five hours’ drive from Chicago. Explore lighthouses, go hiking or hit the beach, then savor local cuisine, boutique shopping and more. doorcounty.com
BEST VISITOR ATTRACTION
Flyover
A strikingly rendered love letter to the city of Chicago, this immersive experience has been an instant hit at the former IMAX theater at Navy Pier since its 2024 debut. 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., flyoverchicagonavypier.com
BEST FAMILY EXPERIENCE
WNDR Museum
With more than 20 immersive art installations that blend art, technology and imagination—from a Yayoi Kusama’s “Love is Calling” and the popular WNDR Light Floor—this West Loop favorite inspires creativity (and yes, wonder) in all ages. New to the museum is Camp WNDR, an immersive retail space with summer camp ambiance, merchandise and food and drink offerings. 1130 W. Monroe St., wndrmuseum.com/chicago
The Auditorium has been one of the city’s most stunning performance venues since it opened its doors in December 1889.
GRANDEST VENUE
The Auditorium
Both a National Historic Landmark and one of the city’s most beloved performance venues, this Adler and Sullivan-designed venue boasts perfect acoustics, unimpaired sightlines, 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 Alvin Ailey American Dance Theater. 50 E. Ida B. Wells Drive, auditoriumtheatre.org
MOST ICONIC HOTEL
The Palmer House
For more than 150 years, this grand Loop property has been renowned for its connection to Chicago business magnate Potter Palmer, for its gorgeous lobby and even for inventing the brownie—and it’s still one of the city’s premier hospitality destinations. 17 E. Monroe St., palmerhousehiltonhotel.com
BEST UNDER-THE-RADAR MUSEUM
The Driehaus 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. Opening this month: Rory McEwan: A New Perspective on Nature, an exhibition of work by the Scottish botanical artist (May 16-Aug. 17). 40 E. Erie St., driehausmuseum.org
MOST ANTICIPATED MUSEUM OPENING
Intuit Art Museum
Set to reopen May 23 after a 1.5-year closure, the reimagined Intuit Art Museum is set to be an international force in the realm of showcasing work by self-taught artists, with a space now encompassing over 18,000 feet over three floors with four exhibition galleries, a dedicated art-making space and more. 756 N. Milwaukee Ave., art.org
BEST DANCE COMPANY
The Joffrey Ballet
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. The troupe closes its season with an extended run of Wheeldon’s fantastical production of Alice’s Adventures in Wonderland (June 5-22). Lyric Opera House, 20 N. Wacker Drive, joffrey.org
See Also: Revealed: Modern Luxury's 2025 Best of Luxury Travel Awards
BEST PUBLIC SPACE
Millennium Park
Since its debut in 2004, 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., millenniumpark.org
BEST FREE EXPERIENCE GRANT PARK
Music Festival
For more than 90 years, 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. This year, the festival welcomes new artistic director and principal conductor Giancarlo Guerrero. 201 E. Randolph St., grantparkmusicfestival.com
BEST HOTEL FOR FITNESS FANATICS
The Hotel at Midtown
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 less than three miles northwest of downtown. 2444 N. Elston Ave., midtownhotelchicago.com
BEST DOWNTOWN DIVERSION
The Riverwalk
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. chicago.gov
BEST FAMILY DESTINATION
Navy Pier
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. One more reason to visit? Flyover, an immersive, Chicago-themed flying journey set in the pier’s former IMAX theater. 600 E. Grand Ave., navypier.com
BEST SUMMER FAMILY GETAWAY
Mackinac Island, Mich.
From its car-free streets and horsedrawn 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. mackinacisland.org
The Frank Lloyd Wright Home and Studio tour draws architecture buffs from Chicago and around the world.
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 guided interior tours and outdoor historic neighborhood walking tours. 951 Chicago Ave., Oak Park, flwright.org
Captaining your own vessel with Chicago Boat Company gives you a refreshing new perspective of the river and city.
BEST CHICAGO RIVER ADVENTURE
Chicago Boat Company
Gone are the days of waiting to score an invite from that elusive boat-owning friend thanks to this popular outfit, which rents multiple types of vessels— yachts, Cycleboats, retro boats, even hot tub boats in winter—many of which you can captain yourself, and all BYOB with a designated driver. Multiple locations, chicagoboatcompany.com
The Second City is classic destination for belly laughs.
BEST COMEDY SHOW
The Second City
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 Best Kept Secret: Tell Everyone, The Best of The Second City: 65 Years of Funny and more. 1616 N. Wells St., secondcity.com
BEST PUBLIC ART
Art On The Mart
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, artonthemart.com
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 recently renovated 23,000-square-foot spa and fitness club complete with a 75-foot heated indoor swimming pool. 401 N. Wabash Ave., trumphotels.com/chicago
Step into Chuan Spa for indulgent treatments and serene vibes.
BEST HOTEL SPA FOR TRAVELERS
Chuan Spa at The Langham, Chicago
With a premium riverfront location and a stunning setting in Mies van der Rohe’s 1973 IBM Building, this award-winning spa is the ultimate destination for an indulgent experience in the heart of the city, from massages and facials to acupuncture and more. 330 N. Wabash Ave., langhamhotels.com/chicago
The lobby of the Ritz-Carlton, Chicago beckons with sophisticated surrounds and five-star service.
BEST WHITE-GLOVE SERVICE
The Ritz-Carlton, Chicago
Impeccable 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., ritzcarlton.com/chicago
BEST HOTEL LOBBY SCENE
Social Lounge at Four Seasons Hotel Chicago
With chic, inviting seating vignettes that make for perfect people-watching and a tempting menu of bar bites like artisanal cheese boards, truffle fries and double cheeseburgers, this sultry space is buzzing yet refined—and an ideal spot to wind down after a day out and about in the city. 120 E. Delaware Place, fourseasons.com/chicago
Photography by: Tre Dita PHOTO BY ERIC WOLFINGER; FRIDA KAHLO, THE FRAME (EL MARCO), 1938, CENTRE POMPIDOU, STATE PURCHASE, 1939/© BANCO DE MÉXICO DIEGO RIVERA FRIDA KAHLO MUSEUMS TRUST, MEXICO, D.F./ADAGP, PARIS, DIGITAL IMAGE ©CNAC/MNAM, DIST. RMN-GRAND PALAIS/ART RESOURCE, NY; Cindy’s Rooftop PHOTO COURTESY OF CINDY’S ROOFTOP; The Auditorium PHOTO COURTESY OF THE AUDITORIUM; The Frank Lloyd Wright Home and Studio PHOTO BY JAMES CAULFIELD/COURTESY OF FRANK LLOYD WRIGHT TRUST; Chicago Boast Company PHOTO COURTESY OF CHICAGO BOAT COMPANY; The Second City PHOTO: BY TODD ROSENBERG; Chuan Spa PHOTO: COURTESY OF THE LANGHAM, CHICAGO; Ritz-Carlton PHOTO: COURTESY OF THE RITZ-CARLTON, CHICAGO;
