top of page

Top 10 Stylish Things in Chicago

This list could be 10,000 stylish things there are or to do in Chicago... but from our humble opinions- these are pretty good.

The Art Institute of Chicago A triumph for the city. We have some of the most important art in the world here in Chicago. Remember that scene in Ferris Bueller's Day off where they're staring at that at Georges Seurat's "A Sunday Afternoon on the Island of La Grande Jatte?" It's here! Play hooky + come see it! Plus countless other iconic, incredible works of art in every conceivable collecting category. Find us drooling in the Modern Wing!

Museum Of Contemporary Art Chicago The MCA is an innovative and compelling

center of contemporary art where the public can directly experience the work + ideas of exceptional artists. We can't play favorites, but you will literally find your mind blown here.

The Music Box Theatre is a historic movie theater built in 1929. Dress up and see it's a wonderful life during Christmas on a big screen! They host new indie releases plus classics- AND SING A LONGS. Sunday mornings they play silent movies accompanied by an old school organist. Totally fun. Have we mentioned they have a bar, too? Chic!

The Merchandise Mart Merchandise Mart, or the Mart, is a landmark building + the largest resource for custom home furnishings + interior design. It is the home, to make a stylish home in Chicago. Encompassing some 4,200,000 square feet of floor space, the Merchandise Mart spans two city blocks along the Chicago River, rises 25 stories, and was the largest building in the world when it opened in 1930. Today it features retail shops, boutiques, radio and television studios, 10 floors of office space, and 11 floors of permanent showrooms. It hosts dozens of trade shows and community events annually that attract designers, architects, builders, consumers, + style icons. The showrooms are they most condensed STYLISH place in the city. Get inspired.

The Frank Lloyd Wright Home and Studio: Only the most notable architectural tour

that you'll take of an American icon! The FLWS +S served as Wright's private residence and workplace from 1889 to 1909, the first 20 years of his career. Here, Wright developed a new brand of American architecture he called "The Prairie Style." Trained docents offer insights into Wright's family life and architectural career.

Chicago's architectural river boat cruises: Stylish + Educational! Cruise the river + hear expertly narrated tours on the history + the iconic architecture of Chicago.

The Green Mill The Green Mill's stylish, sophisticated informality, warm glowing atmosphere steeped in the heady sounds of the early ’30s and ’40s; is patterned after Clark Monroe’s Uptown House in Harlem (as it was during the ’40s). Uniquely comfortable to all audiences from the sequined Saturday night date to the progressively dressed offbeat student, the magic of the Mill is that the audience co-mingles in its mutual respect for the music. Talk a walk back in time to the best speak easy in Chicago. Live jazz every night. Tuesday + Thursday are nights not to be missed, especially Thursday... 15 piece swing orchestra jazz band. Dancing is encouraged, stylishly or not!

This is a combo of 2 stylish, beautiful places for all 4 seasons

Lincoln Park Conservatory: This is my happy place. A Victorian Era glass house that contains four rooms displaying thousands of plants, from tropical species to seasonal flowers, exotic plants from around the world. The Lincoln Park Conservatory is located right next to the Lincoln Park Zoo, and both are free. LPC is truly stylish!


Peggy Notebaert Nature Museum

The museum's exhibits include displays about the ecological history of the Illinois region, a live butterfly house, and a green home demonstration. The butterfly house features more than 200 species of native and exotic butterflies. Not really a zoo, but has two awe inspiring live exhibits, butterflies and tropical birds. Short walk from the conservatory and across from the gorgeous The Alfred Caldwell Lily Pool (which is beyond gorgeous + happy). It houses the winter farmers market every other Saturday morning from Oct. thru April. Plus, right by North Pond, which is a great birding spot in spring and summer. Walk the trails around the museum!

Another COMBO.....

The Second City Second City is one of the country's premier comedy clubs for sketch and improv comedy. You will not regret getting tickets to any of the shows, and you will most likely leave embarrassed you laughed so hard. And you never know who you might see on stage.....


Steppenwolf Theatre Mind-blowing performances from a world-class theatre

ensemble. Steppenwolf Theatre Company is a Tony Award-winning Chicago theatre company founded in 1974 by Gary Sinise, Terry Kinney, Jeff Perry, and H.E. Baccus in the random church in Deerfield. Boy has it come a long way. It's so major! See a play at Steppenwolf. You will not be disappointed! Great actors came from this theater, John Mahoney, Gary Sinese, John Malkovich, Laurie Metcalf... brilliant staff members as well.

The Hideout The Hideout is a perfect bar, bar. It has been called the Hideout since it opened (legally) in 1934. The Hideout is a 100 year old balloon-frame house, built in two days, still standing a century later. They built it faster than the city could tear it down and it's been claimed ever since. Run by undocumented bootleggers + gin runners, running numbers, racing horses, making deals + the spirit lives on. The Hideout is the place to see music, enjoy the scene or just hideout- literally.

RL Restaurant

Every time I walk into RL Restaurant I feel happy! Ralph Lauren always creates the feeling of nostalgia and elegance. From the decor to the famous guidance from Russell + Kurt, all is perfect thought out! The menu + wine list are both well balanced and well executed + you can't beat mini hot dogs. If you want to feel stylish, head to RL.

9 views0 comments

Recent Posts

See All

To DIY or NOT to DIY

This is a big question: Where do you fall? Yes DIY or NO DIY?


bottom of page