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What to Eat, Drink, See, and Wear When You Visit Chicago

Blogger and Chicago Native Jenn Lake shares insider tips on making the most of the Windy City.

By Jenn Lake | Photo Illustration by Yujin Kim

“Chicago is a town, a city that doesn’t ever have to measure itself against any other city. Other places have to measure themselves against it. It’s big, it’s outgoing, it’s tough, it’s opinionated, and everybody’s got a story.” —Anthony Bourdain

I am beyond proud to call myself a lifelong Chicagoan. Growing up in the North Shore suburbs and now having lived in the city for more than 20 years, it’s hard to imagine calling any other place home. In fact, my very first blog, created in 2008, was affectionately titled Third Coast Bride as a small ode to the Windy City. Even though it morphed into Style Charade years later, my content still reflects and champions this wonderful place I get to call home.

Moreover, I have a full-time job as a PR executive at an agency in Chicago, so I’ve been able to see how the city has grown and expanded from the tourism, hospitality, and consumer side of things. These past few decades have brought so many incredible developments, new landmarks, and countless events to experience.

Read on to learn more about my favorite Chicago destinations—and what to wear when you visit them.

Where to Stay

The Langham Chicago, which is situated on the inimitable Chicago riverfront, resides in the very last office building designed by iconic architect Mies van der Rohe. The building dates back to 1971 and was originally IBM’s regional headquarters. In 2008, the building was declared a Chicago landmark and was entered into the National Register of Historic Places in 2010. Then, in 2013, The Langham Chicago opened in the building and features many of the hotel group’s signature amenities such as afternoon tea and one of the best spas in the city. The hotel also provides spacious guest rooms, their Mediterranean restaurant and lounge named Travelle, and a fine art collection featuring almost 150 pieces.

What to Wear: My favorite Chicago hotels all include an approachable yet upscale atmosphere. The Pepper dress is the perfect option to check in with style. Pair it with the ultimate day bag—the M.M.LaFleur x SENREVE Maestra bag—and a sleek pair of Rowan flats, and you’ll be ready for anything and everything the city has to offer.

Other Favorites:
Chicago Athletic Association — Another historic landmark, this hotel is located directly across the street from Chicago’s famed Millenium and Grant Parks. Boasting views of the parks and Lake Michigan, this 1893 Venetian Gothic landmark nods toward its athletic heritage and features an updated and stunning aesthetic by award-winning design firm Roman & Williams. The space and rooms offer an early 20th century design sensibility reimagined for the modern traveler. Best of all, the views and atmosphere from their 13th floor rooftop bar, Cindy’s, are unmatched.

Waldorf Astoria Hotel — Nestled in the heart of Chicago’s Gold Coast neighborhood, the Waldorf Astoria offers all the luxury amenities and experiences you’d expect from the famed hotel brand in a location that’s pretty tough to beat. Here, you’re steps away from Chicago’s best restaurants, shopping, and nightlife. Plus, the food and beverage program at the Waldorf Astoria is so good, you might forget to leave the hotel entirely!

Images: The Langham Hotel

Where to Eat

Top Pick: Andros Taverna

Escape downtown Chicago and head to the northwest neighborhood of Logan Square. There, you’ll find plenty of hipster bars, new developments, farmers’ markets, and one of my favorite restaurants: Andros Taverna. This contemporary Greek restaurant has food lovers flocking to it day and night. Start with the crispy kataifi cheese pie and the spicy whipped feta paired with their wood-fired pitas. For entrees, I love their Mediterranean octopus, Georgie’s gyros, and the lamb-spiced ribs.

What to Wear: Given the casual, hip vibes of Logan Square, the Janie dress in stripe cotton poplin is the perfect choice. Pair it with the Dolly jacket and cognac Carter slides for an elevated yet relaxed look.

Other Favorites:
Rose Mary — Situated in the buzzy Fulton Market district, Rose Mary is chef/owner Joe Flamm’s first restaurant. Flamm is a former Top Chef winner and originally made his culinary mark at the recently-shuttered Spiagga (an almost 40-year landmark Italian restaurant favored by the likes of the Obamas and Lady Gaga). Rose Mary has quickly grown to be one of the hardest reservations to snag in the city—and for good reason. Every dish I’ve ever tried has been nothing less than stellar. My personal favorites include the zucchini fritters, the radiatore ‘cacio e pepe,’ and the tuna crudo.

Sushi Dokku — This West Loop mainstay features cozy vibes, a fantastic drink menu, and some of my favorite sushi and Asian fare in the city. Their tuna truffle nigiri is absolutely heavenly, and I also adore the Godzilla roll and the tuna tatake.

Images: Andros Taverna

Where to Drink

Top Pick: The Aviary

The brainchild of Chef Grant Achatz and Nick Kokonas (the owners of Alinea), this cocktail bar is unlike any other. Less of a bar, more of an experience where they strive to engage all five senses. It’s one of those places that’s near impossible to describe, but anyone who’s been has a story to share. Moreover, they also have a lower-level speakeasy bar affectionately called The Office—a great place to hang before or after a dinner in the West Loop.

What to Wear: A lovely night out in the city is the perfect reason to get a bit dressed up. The Alesia dress paired with the green Merritt jardigan (an M.M.LaFleur bestseller) is the way to go. Pair the look with gold M.M.LaFleur x Sarah Flint Perfect Pumps and classic hoop earrings, and you’ll be ready to enjoy all the libations Chicago has to offer.

Other Favorites:
RL Restaurant — Chicago is home to the very first restaurant created by Ralph Lauren, which is situated next door to the brand’s flagship Michigan Avenue boutique. Although many head to RL for steaks, burgers, and American fare, it’s also a fantastic spot to grab a drink. There, you’ll be surrounded by warm woods, vintage brass, and deep leather booths. RL Restaurant is the perfect spot for people watching while sipping on an ice-cold martini.
The Violet Hour — One of Chicago’s first speakeasy revival bars, it has remained a top cocktail destination in the city for more than 20 years. Their James Beard Award-winning bar program features a rotating cocktail list with something for everyone. To note, the entrance is hidden behind an ever-changing mural on the exterior facade. Inside, you’ll find three interior salons, a gorgeous marble bar, and an overall glow thanks to candlelit tables and a sprawling space.

Images: The Aviary

What to See

Although it’s often considered a bit of a touristy experience, Chicago’s architectural boat tour is a must for residents and visitors alike. Board Chicago’s First Lady on the famed Riverwalk, and discover the history and details behind the city’s most famous buildings. It’s incredible to see the layout of downtown from the perspective of the river. Plus, there are evening tours where you can see downtown all lit up at night. Chicago boasts several boat cruises; you really can’t go wrong with any of them!

What to Wear: A day exploring the city requires comfort. At the same time, there’s no reason to sacrifice style. The Milo jean is an all-time favorite of mine. The refined stretch cotton fabric and adjustable hem make it the most versatile pant in my closet. Pair the Milo with the supersoft stripe Leslie T-shirt, the O’Hara blazer, and comfy white M.M.LaFleur x Koio Capri low-top sneakers.

Other Favorites:
Museum of Contemporary Art — There’s always something new and interesting at the MCA. From over-the-top installations to experiential artwork, it’s one of the world’s largest museums dedicated to contemporary art. Here you will find more than 45,000 square feet boasting gallery upon gallery. Plus, the iconic spiraled north staircase is a sight to behold. Each summer, the MCA hosts “Tuesdays on the Terrace,” where they feature a lovely jazz music program. Guests are welcome to bring picnics and spread out on the lawn; you can also purchase food and beverages at their full bar.

Wrigley Field — Whether you’re a sports fan or not, there’s nothing quite like a warm day of baseball at Wrigley Field. Home to the North Side’s Chicago Cubs, the ballpark was built in 1914 and is the epicenter of the Wrigleyville neighborhood. In recent years, the area surrounding the park has undergone dramatic expansions, and visitors can now experience a host of activities, new restaurants, and even a Wrigley-themed hotel just outside of the park.

Music Box Theater — Built in 1929, two months before the start of the Great Depression, this theater is known for having the best independent, art-house, foreign, cult, and classic films in the city. It’s also home to Chicago movie festivals and has a darling lounge and cocktail bar.

Magnificent Mile and Oak Street — There is no shortage of shopping nor sights to behold along Chicago’s Magnificent Mile and adjoining Oak Street. Start at Michigan Avenue at the Chicago River and work your way north while enjoying iconic architecture, world-class boutiques, restaurants, hotels, and everything in between. Once Michigan Avenue intersects with Oak Street, head west to find all the best luxury brands: Chanel, Hermès, Christian Louboutin, Prada, and more.

Images: MCA Chicago (top) and Marriott Traveler (bottom)

Where to Shop

From now through May 21st, experience all that M.M.LaFleur has to offer in-person at their Chicago Pop-Up location in the iconic River North neighborhood. At this location, you can shop one-on-one with an expert M.M.LaFleur stylist! Try on all of your favorite combos, and receive insightful advice on how to take your Power Casual looks to the next level.

What to Wear: I truly adore a marvelous monochromatic moment. I’ve been wearing the gray Liam sweater combined with the gray Senga skirt on repeat from work to weekend. The texture of the knits is just so luxe. Add a classic black Ginger pump, and you’ll be ready for a day of Chicago shopping.

Other Favorites:
ikram — Looking for the very best in designer women’s fashion, accessories, and gift items? A stop by the inimitable ikram boutique is an absolute must. A shopping destination for more than 20 years, ikram was Michelle Obama’s original Chicago stylist and has continued to dress the most well-heeled women of the city. Hard to find labels like Simone Rocha, Ashish, Rodarte, and Jacquemus co-mingle with the likes of Alexander McQueen, Chanel, and Celine.

Semicolon — Opened in 2019, Semicolon has quickly risen to become a Windy City destination for literary lovers from around the city and world. This Black women-owned bookstore is nestled in the heart of the River West neighborhood and emphasizes their commitment to “nurturing the connection between literature, art, and the pursuit of knowledge; while also using the power of words to better our community.” Moreover, it’s also a gallery and event space!

Jayson Home — Home decor lovers flock to Jayson Home—and for good reason. This Lincoln Park mainstay has been delighting interior designers and enthusiasts since 1997. The creative directors of Jayson Home typically travel upwards of 150,000 miles per year on buying trips to France, Spain, England, Morocco, Malaysia, India, and around the United States. The curated store collections are all hand-picked, and their inventory is second to none. Plus, in warm weather, their garden center is an absolute oasis.

Written By

Jenn Lake

Jenn Lake is a Chicago-based executive and style blogger. Her blog, Style Charade, is a colorful online destination for fashion, travel, home design, and lifestyle content.

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