How to Plan a Luxury Weekend in Chicago

With its vibrant arts and culture, iconic architecture, and renowned dining, Chicago is an unmatched destination in the middle of America’s heartland. In the summer months, longer days make it easy to fill an active itinerary of shopping, dining, and sightseeing, balanced by quiet moments of rest to recharge. Read on for ways to design a memorable weekend trip to the city, enjoying the best Chicago has to offer.

Check into a five-star hotel

Upon your arrival in town, check in at one of Chicago’s premier hotels. The St. Regis Chicago, designed by celebrated architect Jeanne Gang, is one of the city’s tallest buildings with captivating views of the skyline and Lake Michigan. Enjoy sushi at Miru or modern Tuscan fare and floor-to-ceiling windows at Tre Dita.

The Waldorf Astoria Chicago is an elegant luxury hotel in the upscale Gold Coast neighborhood. Beloved for its Parisian-inspired design and dining (including brasserie fare at Brass Tack), the hotel is a popular choice for locals and visitors alike.

Dine at Michelin-starred restaurants

Courtesy of Enjoy Illinois

Chicago brims with a multitude of showstopping restaurants and tasting menus abound. Try the one at Sepia, a Michelin-starred restaurant featuring sophisticated, seasonal dishes. At the Chef’s Table at Astor Club, book a front-row seat for chef Trevor Teich’s ingredient-first cooking, and at Class Act, the team presents an evening around carefully crafted dishes and communal dining.
Seek out some of the city’s globally inspired options, too. The Michelin-starred restaurant Indienne, helmed by chef Sujan Sarkar, serves modern Indian dishes rooted in French technique.
Mexican flavors see refined, thoughtful presentation at Tzuco, and Atsumeru is a celebration of Nordic and Japanese culinary philosophies. Opened by James Beard Award finalist Thai Dang, Crying Tiger guides diners through Southeast Asia in noodles, curries, and cocktails. Jōtō wows with its omakase menus and dry-aged fish program.

Book a spa treatment

Courtesy of Enjoy Illinois

Relax with a spa treatment at your hotel. The Waldorf Astoria Spa features signature options such as the Himalayan Salt Stone Massage or the Diamond Glow Facial, while the St. Regis Spa is known for its Performance or Stress Relief massages.

Facials are the specialty at SpaDerma—book an appointment at any of their five locations for an instant glow. In Lincoln Park, spend an afternoon at Kohler Waters Spa, where you can take advantage of their signature thermal suite and hydrotherapy circuit post-treatment. And on the Gold Coast, visit Milk + Honey, an award-winning spa complete with salon services.

See views from the Centennial Wheel and Skydeck Chicago

Enjoy skyline and lakefront views from one of Chicago’s most iconic landmarks: Navy Pier’s Centennial Wheel. With the Centennial Wheel VIP Gondola buyout, guests can board the glass-bottomed vessel for a ride that ascends nearly 200 feet in the air. Another sky-high experience? Expedited, priority entry to Skydeck Chicago, where visitors can stand 103 stories from street-level to take in city views.

Explore the arts and architecture

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Led by the Chicago Architecture Center, Chicago’s First Lady is a 90-minute river cruise centered on the city’s rich architectural history. For more time on the water, book the Four Seasons’ Yacht Experience, a four-hour excursion on Lake Michigan aboard the hotel’s 55-foot yacht. (Available May through September, the outing includes personalized menus and cocktail service underneath Navy Pier fireworks.)

Art lovers will appreciate a visit to the Art Institute of Chicago, a world-renowned museum featuring more than 300,000 works, including famed artwork by Picasso, Cassatt, Seurat, and O’Keeffe. Book a private tour with an expert for more in-depth exploration. And at the Richard H. Driehaus Museum, visitors can explore the art, architecture, and design of the late 19th and early 20th centuries in a historic Chicago mansion.

For theatre-goers, book a show through Broadway in Chicago, then consider upgrading the experience. The Suite Service package includes a full private bar and pre-show suite access.

Enjoy afternoon tea and shopping

Courtesy of Enjoy Illinois

Visit the prized 900 North Michigan Shops for seven levels of premier shopping. Stop at Provenance for custom fragrance consulting with Diana Michelle, then visit Janet Mandell and her rental showroom for a designer fitting appointment. Nearby, you can explore Ikram, a clothing boutique with a gallery and café and a favorite of Michelle Obama when she was First Lady.

Head to the Loop to browse handcrafted hats at Optimo Hats, to Belmont Gardens to peruse the collections at Swoon Living Glass, or to Pilsen for the gallery-like boutique Mashallah, where you can shop for designer Mashallah Ghouleh’s jewelry and handbags along with a tightly edited selection of vintage clothing. All three shops are part of Illinois Made, a program celebrating local businesses.

Afterward, settle in for afternoon tea at the Langham. Offered in their Pavilion, the service features sandwiches and pastries inspired by rotating whimsical themes (including this spring’s “A Tale as Old as Tea,” an homage to Beauty and the Beast).

Discover the city’s nearby festivals, botanical garden, and more

Chicago’s North Shore offers its own charming escapes, all within a train ride or short drive from the city. Check out the concert calendar for Ravinia, an outdoor music festival running June through September and featuring performances this year from Paul Simon, Martina McBride, and more.

Nearby, the Chicago Botanic Garden dazzles with 385 acres and a medley of blooming flora. Spend an afternoon strolling the grounds and taking in the sights of many native plants. Stay the night at the nearby Deer Path Inn, an English-style inn located in the heart of Lake Forest, Illinois. Dine at the Brasserie for modern British cuisine in a recently re-imagined, art-driven space. (Or walk five minutes to Le Colonial, where you can enjoy French-Vietnamese dishes.) Top it off by visiting the Bar for inventive cocktails from beverage director Jorge Centeno.