An Aesthete’s Guide to Chicago

Chicago is a hub for design lovers.

Read More

As a cultural capital of the Midwest—and the country’s third-largest city—Chicago is a hub for design lovers. You’ve got Art Deco architecture, world-class museums, high-design restaurants and modern building projects, all in a compact, walkable radius—you’ll want to pack comfy shoes to wander below skyscrapers and step into cool boutiques, museums and restaurants alike. Situated right by Lake Michigan, downtown Chicago’s landscape also includes the Chicago River and plentiful green spaces. Here’s the aesthete’s ultimate guide to the Windy City.

Where to Stay

The Langham, Chicago

  • 330 N. Wabash Ave., Chicago, IL 60611

Tucked into River North, a block north of the Chicago River, the Langham boasts serious architecture cache: it occupies the 13 floors of Ludwig Mies van der Rohe’s last office building design. An orchid scent greets guests at the second-floor check-in, and many of the 316 rooms offer Lake Michigan views. Whimsy and wellness alike can be found here, from the Asian-inspired Chuan Spa (a questionnaire determines one’s ideal oil blend) or the Joyful Expression cocktail at Travelle at The Langham (served in a cat-shaped ceramic urn, paired with dishes inspired by the chef’s global travels). Petal-pink accents throughout the hotel include its courtesy taxi (a London throwback), and the 67-foot-long indoor pool is long enough to swim laps.

The Langham, Chicago. The Langham

The St. Regis Chicago

  • 401 E. Wacker Dr., Chicago, IL 60601

The St. Regis Chicago opened in 2023, inside a Jeanne Gang-designed structure that happens to be the world’s tallest building designed by a woman. This 192-room hotel is three blocks north of Millennium Park in downtown Chicago, where the Chicago River flows into Lake Michigan. The KTGY Simeone Deary Design Group-designed Presidential Suite features abstract sculptures by Denver artist Derrick Velasquez, and charred-wood mantles and a glass-orb chandelier contribute to the lobby’s moody vibe. The firm also designed the 10th-floor spa.

In March 2024, the 8,600-square-foot, two-story Tre Dita, designed by David Collins Studio and led by Evan Funke, debuted, with its own “pasta lab” and wood-fired grill, along with Lake Michigan views. 

The St. Regis Chicago. The St. Regis

Park Hyatt Chicago

  • 800 N. Michigan Ave., Chicago, IL 60611

The Park Hyatt Chicago was the very first Park Hyatt; it debuted in 1980 from the Chicago-based Hyatt brand. In the fall of 2022, this 182-room property completed a $60 million redesign. Thanks to Anderson/Miller Ltd’s design prowess, there are now 23 new suites (including the Wellbeing Suite, stocked with workout equipment) and a new art program focused on Chicago artists. 

A neutral color palette throughout the hotel evokes a sense of calm a block off bustling Michigan Avenue. The hotel’s sushi restaurant, NoMI, ranks among the top in Chicago, and NoMI Garden, an alfresco space on the seventh floor, is a sweet spot to sip cocktails. The hotel also boasts a spa, steam room and indoor pool.

Lake Michigan Suite Bathroom at Park Hyatt Chicago. Park Hyatt

What to Do

The Art Institute of Chicago

  • 111 S. Michigan Ave., Chicago, IL 60603

Flanked by two huge bronze lions at the main entrance along Michigan Avenue, this Beaux-Arts building dates back to 1893, the same year Chicago hosted the World’s Columbian Exposition. The museum owns the largest collection of Claude Monet paintings and drawings (46) outside of Paris. In 2009, the new Renzo Piano-designed Modern Wing expanded the museum’s holdings even more, including a major 2015 donation by Stefan Edlis and Gael Neeson featuring works by Andy Warhol, Jasper Johns, Robert Rauschenberg and Cindy Sherman. On the heels of a Picasso show wrapping up April 8, the museum welcomes two summer shows: “Georgia O’Keeffe: My New Yorks” (June 2 to Sept. 2, 2024) and “Ellsworth Kelly: Spectrum Colors Arranged by Chance” (June 22 to Sept. 9, 2024).

The Art Institute of Chicago: Picasso: Drawing from Life. The Art Institute of Chicago

Chicago Architecture Center River Cruise

  • Northeast corner of Michigan Ave. and E. Wacker Dr.

The river provides the best view of Chicago’s world-class architecture, and this center’s 90-minute floating tour on board the two-tier “Chicago First Lady” boat is narrated, complete with facts and drama about Chicago history, art and, of course, architecture. Multiple departure times throughout the day allow flexibility. On a summer night, book the evening tour to capture golden light in your photos, with a cocktail in hand.

Chicago Architecture Foundation Center River Cruise Aboard Chicago's First Lady. BARRY BUTLER

Millennium Park

Located within the 319-acre Grant Park, there’s a lot of eye candy in this 20-year-old public park in the Loop. It’s anchored by British artist Anish Kapoor’s shimmering mirror-like “Cloud Gate” (locals call it “The Bean”), born out of stainless steel. Crown Fountain, a video-projection tower with a water feature, is another popular art installation. The park spans just under 25 acres and includes the world’s largest rooftop garden. During the summer months, the Jay Pritzker Pavilion—an outdoor bandshell designed by Frank Gehry—hosts free classical music concerts performed by the Grant Park Symphony Orchestra and Chorus on Wednesdays, Saturdays and Sundays.

Jay Pritzker Pavilion. Patrick L. Pyszka

Where to Shop

The Merchandise Mart

  • 222 W. Merchandise Mart Plaza, Chicago, IL 60654

Dubbed “The Mart,” this Art Deco building, which was the world’s largest when it first opened, still proudly displays its 1930 roots. Inside, you’ll find design shops open to both consumer and trade audiences, as well as 250 showrooms retailing wall coverings, carpets, furniture, appliances and more from heavy-hitting design brands like A Rudin, Tai Ping, Miele, Paris Ceramics, Scandinavian Spaces and Scalamandré.

The Merchandise Mart. Bob Grosse

Judy Maxwell Home

  • 1349 N. Wells St., Chicago, IL 60610

Actress Joan Cusack, a Chicago native, dials it back to the general store days with her boutique in Old Town, selling tasteful tchotchkes that are perfect for gifts or dressing up the home. Much of the stock is specific to Chicago. For example, a mug that’s an ode to The Bear, or a hook pillow showing off the Chicago skyline. Cusack’s collection of coffee-table books focused on travel and interior design are alone worth the 15-minute drive north of downtown.

Where to Eat and Drink

Three Dots and a Dash

  • 435 N. Clark St., Chicago, IL 60654

Far from a dive, this upscale Tiki bar in River North straddles classic tropics-inspired drinks (such as the Trader Vic Mai Tai) with innovative concoctions. You’re going to want to have your phone charged, because the presentations are theatrical. Sippopotamus is one example: the tequila and tropical fruit drink is brought to the table in a glass that is propped up in the mouth of a hippopotamus pottery piece, with its jaw hanging open, plus lots of dry ice. Named one of the World’s 50 Best Bars, if you want a more intimate experience with the mixology team, book a seat in the Bamboo Room.

Three Dots and a Dash. Lindsay Eberly x Eberly FIlm Lab

Offshore Rooftop

  • 1000 E. Grand Ave., Chicago, IL 60611

As the country’s largest rooftop bar, this 36,000-square-foot space is open year-round and features a 20,000-square-foot outdoor terrace at the easternmost end of Navy Pier, jutting out into Lake Michigan. This means killer views of the water and skyline. The all-day food menu from chef Michael Shrader focuses on California cuisine, such as fish tacos, salads, salmon poke and the signature skillet-baked Offshore brownie. 

Offshore Rooftop at Chicago's Navy Pier. Tara White

Beatnik on the River

  • 180 N. Wacker Dr., Chicago, IL 60606

Between Memorial Day and Labor Day, Chicago restaurants open up the patios, and that includes this eatery, situated along the Chicago River in the Loop and separated from the water only by a glass wall. Moroccan-style lamps and plant walls are suspended above the seats, offering a perfect pairing to the menu’s Northern African, Mexican, Middle Eastern and Eastern Mediterranean influences. Branzino is served with grilled pineapple, harissa shrimp with couscous and lamb shoulder with cucumber salad. The beverage program is also a hit, including margaritas, tropical standards and zero-proof cocktails.

Beatnik on the River. Beatnik on the River


  • 318 N. Sangamon St., Chicago, IL 60607

Chicago boasts a sea of steakhouses, but many tend to be stuffy. Fioretta, a year-old steakhouse in Fulton Market, however, is far from uptight. The modern and edgy interior design aesthetic of the 8,200-square-foot space extends to the open kitchen, and includes an Italian-marble floor mimicking a chess board, as well as granite-inlay tables and booths born out of green mohair. 

The steak-heavy menu is accented by Italian influences. Prosciutto and meatballs are ideal starters, while the pasta dishes, including king crab linguini, cacio e pepe and truffle mushroom lasagna, are worth an order.

Fioretta. Mark Ballogg

We noticed you're using an ad blocker.

We get it: you like to have control of your own internet experience.
But advertising revenue helps support our journalism.

To read our full stories, please turn off your ad blocker.
We'd really appreciate it.

How Do I Whitelist Observer?

How Do I Whitelist Observer?

Below are steps you can take in order to whitelist on your browser:

For Adblock:

Click the AdBlock button on your browser and select Don't run on pages on this domain.

For Adblock Plus on Google Chrome:

Click the AdBlock Plus button on your browser and select Enabled on this site.

For Adblock Plus on Firefox:

Click the AdBlock Plus button on your browser and select Disable on

Then Reload the Page