Although best known for Cloud Gate (aka: the world’s most bananas bean-shaped mirror sculpture), a packed-to-the-max skyline, and wind galore, Chicago is also a city awash in culture, architecture, and delectable eats. Whether you’re looking for a quick weekend getaway or a weeklong family vacay, Chicago offers plenty of goodness to rev everybody’s engines. To get the deets on where to eat, shop, and get inspired (including plenty of kiddo-friendly recs!), we polled a few of the city’s top tastemakers and interior designers. Discover all of their Chicago must-dos, ahead! 

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marble bathroom, peninsula hotel
Photo courtesy of The Peninsula

Where To Stay

The Peninsula. It’s a Chicago classic and the service is impeccable — it never disappoints. There is a great rooftop bar, a beautiful spa, and a little bistro next door that I love. They are also so thoughtful when kids stay. In the winter, they have an outdoor ice rink with a hot chocolate shed set up.” — Sasha Adler

“Soon it will be the new hotel we are designing in Old Town, but until then I love The Langham on the river.  It occupies a Mies Van Der Rohe building, has the best service in town, a great spa, and a pink car to take you around the city. What more do you need?” — Summer Thornton

The Robey is in the heart of urban Chicago located in the Wicker Park/Bucktown neighborhood. They serve brunch, lunch and dinner, and have great cocktails which you can enjoy on their amazing rooftop terrace. We enjoy taking dips in the pool during the summer and showing our friends their one-of-a-kind skyline view of Chicago. Robey is located in the old Northwest Tower building and has fabulous Art Deco architecture.” — Lauren Lozano Ziol and Michelle Jolas of SKIN Interiors

Ambassador Chicago. I love this historic gem of a hotel nestled right in the heart of Chicago’s historic Gold Coast neighborhood (which I call home myself). It’s just footsteps away from all the amazing attractions Chicago has to offer, yet it’s just removed where you can enjoy strolling the neighborhood’s quaint and charming streets. The rooms and atmosphere are absolutely stunning.” — Josh Young

“I always like the Four Seasons. Great location and the nicest doormen & staff around!” — Shelley Johnstone

“I’m tempted to say one of the newer, swaggy boutique hotels in Chicago – of which there are so many great ones – but I always come back to The Peninsula. It’s one of the best hotels in the country for a reason.” — Wendy Labrum

RL restaurant, ralph lauren restaurant
Photo courtesy of RL

Where to Eat & Drink

Avec! The truffle focaccia and bacon-wrapped dates are classics and not to be missed! They have an impressive wine list featuring smaller vineyards and some organic wines. I promise you, everything on the menu is off the charts!” — Sasha Adler

“I love a non-trendy, well-designed and traditional restaurant so RL is my go to spot for classic design, good wine, and yummy french fries.” — Summer Thornton

“One of our favorite restaurants in Chicago is Le Colonial located on the amazing Oak Street. It is a French Vietnamese style restaurant. Our favorite dish is their CA Bam, a Hanoi style monkfish. Mostly we love the decor that takes you right into 1920’s Vietnam, with plants, art, fabrics and “wow factor” wallpaper that evokes the sophistication of a bygone era. You can’t help but feel elegant when you dine there and toast with a ginger martini.” — Lauren Lozano Ziol and Michelle Jolas of SKIN Interiors

RL Restaurant. Hands down. I’ve become a regular and always order the same thing. French 75, escargot, and their famous crab cake. You won’t be disappointed and the atmosphere is so charming and warm.” — Josh Young

“It’s hard to imagine a world without the Gnocchetti Con Pesto from Monteverde. It’s my favorite dish in the city. I may or may not order one to eat there and one to take home.” — Wendy Labrum

millenium park chicago
Photo by Michael Courier

Where to Get Your Culture Fix

“The Art Institute of Chicago. Hands down. A New York transplant myself, I’ve always described the museum as a better curated, paired down version of The MET; and with regards to the amount of notable works, it can easily rival it. Noted by many publications as one of the best museums in the world, this is definitely not one to miss. It also has some of the most beautiful views of the city as well!” — Josh Young

The Art Institute is phenomenal. I could spend days on end there going through the floors of the main building and modern wing. When I go with my children, we stop at the gift shop first to purchase postcards and then we do a treasure hunt to find those pieces in the museum.” — Sasha Adler

Millenium Park with the Art Institute and Cloud Gate by Anish Kapoor are a visual feast in the heart of the city.” — Shelley Johnstone

Pilsen is a fun neighborhood to visit with lots of great street art and new, younger, less stuffy galleries.” — Summer Thornton


Where To Go For Vintage Goodies

“I adore South Loop Loft. The owner, Beth has such a good eye, and she travels the world to curate the fantastic finds at her store. I have never left empty-handed.” — Sasha Adler

“The Randolph Street Antique Market is a fantastic way to find the unique treasures hidden throughout Chicago. It brings together all of the upscale art and antiques we’re often searching for in one location.” — Lauren Lozano Ziol and Michelle Jolas of SKIN Interiors

“I love going north to the Andersonville neighborhood where there are a bunch of cute antique shops with insanely affordable prices. The neighborhood has such a great vibe and feels so ‘old school’ Chicago. Everything is mom and pop and local.” — Josh Young

“It’s definitely not a flea market, but PRIMITIVE is filled with the most beautiful, curated treasures.” — Shelley Johnstone

Pavilion Antiques. It’s around the corner from my house, which is dangerous. Owners Deborah and Neil have curated an impeccable collection of 18th and 19th Century pieces alongside unique contemporary artists and designers.” — Wendy Labrum

Looking for more places to shop? Check out a few of our favorite Chicago-based Chairish Sellers:

Antiques on Old Plank Road
Matthew Rachman Gallery
Vintage Grind House
Studio 6F
Redefined Decor

Where to People Watch

Oak Street Beach. I can’t even begin to express how beautiful Lake Michigan is and during the spring and summer, this part of town is packed with people. My husband and I will pack up a lunch/dinner picnic-style and just sit by the water and enjoy the views of the city directly behind us. It’s breathtaking, honestly.” — Josh Young

Aba in the West Loop has the best rooftop and amazing food and cocktails! Plus, a great scene!” — Sasha Adler

Dove’s Luncheonette in Wicker Park. This is my favorite diner in the city. Sit looking out the windows by the blue line stop in Wicker for good people watching.” — Summer Thornton

Maple and Ash is no doubt the sexiest place to eat, drink, and be seen. It is clearly where people go to see what’s hot in Chicago. The food is amazing and the drinks are to die for, especially their signature vodka cocktail they give you once seated. The ambiance is dark and smokey and the decor is classic mod with old world touches and sexy photography.” — Lauren Lozano Ziol and Michelle Jolas of SKIN Interiors

Cindy’s Rooftop.” — Shelley Johnstone

“The new Le Colonial spot is having a moment. It’s been good for a long time, but its new location perched above Oak Street has propelled it into see-and-be-seen status right now.” — Wendy Labrum

Photo courtesy of the Chicago Botanic Garden

Where to Get Inspired

I absolutely love the Chicago Botanic Garden. It’s a wonderful place to unplug and explore. I go there with my family and spend the day wandering through the various gardens. There is no better source of inspiration than Mother Nature, and I often snap photos to reference later for color inspiration.” — Sasha Adler

“My favorite thing to do in this city is walk around the neighborhoods and admire the architecture from the Turn of the century. Chicago is famous for its skyline but the neighborhoods have equally impressive architecture on a different scale. I can typically be found wandering around Lincoln Park, but the Gold Coast has the most impressive homes—it offers especially great gawking around Christmas.” — Summer Thornton

Museum of Contemporary Art.” — Lauren Lozano Ziol and Michelle Jolas of SKIN Interiors

“There is such a connection between fashion and interiors, and nothing gets my creativity flowing like a little shopping. A couple of hours at Ikram and Blake is sometimes all I need to catch a spark.” — Wendy Labrum

Don’t Leave Town Without…

“Chicago has a fantastic food scene; everything from street food to really elevated dining. It’s a city you definitely want to eat your way through and experience. During the summer months, the Chicago Architecture Tour is my favorite! It’s a great way to spend time on the Chicago River and lakefront, while learning all about the fascinating history behind Chicago’s ever-expanding skyline. ” — Sasha Adler

“Get off the main drag, expand your search beyond Michigan Avenue and see what truly makes this city great; which is it’s neighborhoods. Visit Old Town and hit up The Second City to see who will be next to appear on Saturday Night Live. Visit the Lincoln Park Zoo (Zoo Lights happens after Thanksgiving and is always a hit with kids). Stroll the streets or ride in a horse and carriage through the Gold Coast to look at the Victorian and Gothic mansions. Hit up Bucktown, Wicker Park, West Town or Logan Square for some great restaurants and shopping. Head down to Pilsen for great galleries and yummy food.” — Summer Thornton

“Walking/running or biking on the lakeshore pathway from Belmont Ave to Oak Street Beach.

You can see the city and the lake view is amazing. The vibe of all the people who are enjoying being outside shows you that Chicago has amazing energy.” — Lauren Lozano Ziol and Michelle Jolas of SKIN Interiors

Chicago Botanic Garden. It’s a bit off the beaten path for visitors to the city, but it is completely worth it. You wouldn’t expect it from a city that’s under snow for a good portion of the year, but it’s my respite from the urban grind.” — Wendy Labrum

“Get out and walk the city! Chicago is one of the most walkable cities in the U.S. We are known to have some of the best restaurants, cultural sites, museums, parks, theaters, etc. You’ll never get bored! Start your day at the Art Institute and walk north on Michigan Ave. Take in all of the shopping, sites of Lake Michigan, and enjoy a bike ride through the Gold Coast and Lincoln Park neighborhoods.” — Josh Young


A huge thank you to our Chicago experts! Be sure to check out their amazing work.

Sasha Adler
Summer Thornton
Lauren Lozano Ziol and Michelle Jolas of SKIN Interiors
Josh Young
Shelley Johnstone
Wendy Labrum

Feature Photo courtesy of The Robey Chicago

December 11, 2019

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