The Sojourn: The Places That Will Blow You Away In Chicago
Located on the southwestern shores of Lake Michigan, it is the third-largest city in the United States. Chicago, Illinois, otherwise known as the Windy City, is an avowed melting pot of arts and culture, with a legacy as the traditional homeland of numerous Indigenous peoples. Chicago's culture is diverse and reflects a commitment to promoting Native cultural heritage and fostering an inclusive environment.
This city’s multiculturalism is built on a massive hip-hop and dance scene, the Chicago International Film Festival, Black Harvest Film Festival, 250 live music venues, more than 200 theatres, and its reputation as the birthplace of improv comedy, gospel, electric blues, house, juke, footwork, and drill music.
Chicago comprises 77 distinct communities and areas, each with its own flavors and experiences. City center, famously coined ‘The Loop’, is the high-end, corporate and fashion hub of the garden city. The surrounding ‘West Loop’ and ‘South Loop’ offer a more low-key, chilled shopping and dining experience. In contrast, outside areas like Lincoln Park, Wicker Park, Uptown and Pilsen offer boutique shops, coffee shops and a look into suburban life.
Here is how to best spend your time in the Windy City, discovering its hidden and well-known luxuries to live it up on the shores of Lake Michigan truly.
Where to Stay
The Willows Hotel is situated in the quiet Lake View East neighborhood, just blocks away from the lakeside Lincoln Park. Here, you’ll find old-world European style combined with luxurious modern amenities. From Standard Queen to Executive King suites, all guest rooms have a polished and elegant feel with dark wood finishes and earthy tones.
Housed in an exquisite three-story brick building built in 1909 is The Publishing House Bed and Breakfast. Condé Nast Traveler named this one of the top 25 stays in Chicago. Situated at the heart of the West Loop and the transformed historic meatpacking district, The Publishing House is the top-ranked boutique B&B in the Midwest. Each room is dedicated to a renowned Chicago author or a Chicago-based novel, and each is finished with a copy of the novel for your reading. A short walk from downtown and the lakefront, this accommodation sits perfectly in the midrange of prices and perfectly in the center of Chicago’s culture and style.
Fancying something a little closer to The Loop and the shore? The Waldorf Astoria adds a touch of Parisian elegance to your stay, just a ten-minute walk from Oak Street Beach and the Magnificent Mile. The hotel has a Forbes-rated spa, a French-inspired courtyard and garden, and skyline views across 26 floors.
Also delivering international flair to the city center is The Peninsula Hotel, which provides traditional Asian service and warm hospitality. This accommodation has received a Forbes Travel Guide Five-Star rating and was added to La Liste’s ‘World’s Best Hotels for 2025’, tying for the top Hotel in the World. Floral art designs by David Qian decorate each guest room, featuring the chrysanthemum, Chicago's official flower. The rooms are light and spacious, with muted earth tones and blues that create a chic, luxurious feel.
Where to Eat
While at The Peninsula Hotel, you will find some of the best Chinese food in Chicago at the Shanghai Terrace. Led under the direction of Chef de Cuisine Elmo Han, the Shanghai Terrace takes a contemporary approach to traditional Chinese cuisine. The menu showcases creative interpretations of beloved Cantonese classic dishes, including the acclaimed dim sum program.
Kasama is a Filipino bakery by day, a Michelin-starred tasting menu by night, located in the East Ukrainian Village neighborhood. Indulge in a range of Genie Kwon’s professionally baked pastries during the day, from an almond croissant to an ube and coconut ‘ensaymada’, or reserve a table in the evening to taste her husband Tim Flores’ interpretation of Filipino cuisine. The husband-and-wife duo also offers a range of savory Filipino breakfast sandwiches and plates.
Tigist Reda is the genius chef and owner behind Demera, an Ethiopian restaurant in the vibrant Uptown area. Demera Ethiopian Restaurant is one of the top-rated and reviewed Ethiopian restaurants in Chicago for its approach to serving traditional cuisine with only the most authentic ingredients. Enjoy a selection of appetizers, cocktails, meaty dishes, and Messob, the family-style sharing platters encompassing an array of flavors.
Tzuco is a French-Mexican fusion restaurant in River North, headed by Carlos Gaytan, the first Latin American chef to earn a Michelin Star. Carlos Gaytán was born in Huitzuco, Mexico, and uses his heritage and training to create award-winning cuisine. The menus include brunch, dinner, drinks, and ‘Back To My Roots’, an evolving menu inspired by Gaytán’s monthly trips back to Mexico. From a papadzul crepe to a mushroom cazuela, Tzuco’s flavors highlight how the intersection of different cultures can create a culinary masterpiece.
Book Shops to Bookmark
Head down to Milwaukee Avenue to Myopic Books for an experience similar to that found at Arthur Conona Doyle and the Strand Magazine, home to over 70,000 new and ‘gently used’ books. This shop features floor-to-ceiling wooden bookshelves for a classic, timeless bookshop feel.
Exile in Bookville is an indie book shop located in the Fine Arts Building on Michigan Avenue. Owners Kristin and Javier Ramirez believe that books and music are synonymous, so they stock both vinyl and books. Their shop has a punk rock feeling, with hanging disco balls, colorful posters on any empty wall, and merchandise wearing skeletons, and they host music, author, and bookseller events. Exile in Bookville stocks novels about self-help, poetry, romance, politics, nature, and much more. Guests will find floor-to-wall wooden bookshelves, exactly what an avid reader and literature fan wants to see.
Uncharted Books is an independent brick-and-mortar bookstore that sells a selection of rare books, zines, and high-quality second-hand books. Their eclectic selection focuses on local, literary, strange, and adventurous stories, which you can enjoy in their cozy interior.
Skin-Care, Self-Care, Grooming and Beauty
There are at least seven BlueMercury shops spread across Chicago’s neighborhoods, making it effortless for you to get your hands on all of your daily essentials. Equipped with brands like Augustinus Bader, La Mer, Charlotte Tilbury, and Goop across a range of fragrance, makeup, skincare, and body care, BlueMercury has what you need at the price you want.
If you need some more specialized cosmetics and pick-me-ups, then continue down Milwaukee Avenue to Mojo Spa. This woman-owned beauty brand is an emporium of over 200 natural beauty products, handmade in Chicago. Browse gifts for her and him, skincare, makeup, bodycare, candles, and more. Engage in Mojo’s in-store beauty bar and work with their specialists to formulate a custom skincare or body care routine.
Housed in a restored factory from 1902 and a few blocks from the North Branch of the Chicago River is AIRE Ancient Baths. Based in River West, just outside of West Loop, this spa offers the experience of traditional Roman, Greek, and Ottoman public baths. Immerse yourself in the brick tunnel baths and engage your senses with the various aromas and sensations as you float in the candlelight. End your experience with a massage, a Himalayan salt wrap, or a wine-soak.
Chuan Spa, located in The Langham Hotel, is guided in its approach to treatments and products by the five elements. Their on-hand team of experienced therapists takes you on a mental journey of self-discovery, while the wellness treatments will keep you feeling refreshed and revitalized. Based in The Loop, right next to the famous Chicago Riverwalk, this spa is a relief from the surrounding bustling city center.
When your hair needs a refresh, consider booking at Maxine Salon. One of Chicago’s premium salons that offers hair care for men and women, including cuts, color, styling, and extensions. Maxine’s professionals have honed their techniques through international exposure and runway-worthy experience to ensure you feel your absolute best.
George The Salon is another excellent choice for your hair care needs when visiting the Windy City. Offering facials, body and bridal treatments, as well as expert hair extensions and coloring, George is here to help you feel gorgeous. The salon offers products from the ‘I Am Gorgeous’ line, which was created by the salon’s owner, George Gonzalez, in honor of supporting women against domestic violence. The brand is the world’s first exclusively all-inclusive premium hair care line.
For specialized attention to male hair, Merchant & Rhoades has cut the hair of Barack Obama, Vince Vaughn, John Calloway, and Frankie Knuckles. With packages tailored to different needs, you can leave this high-end barber feeling luxurious, with your shoes shined, hair cut, neck shaved, and face trimmed and sculpted.
Alternatively, State Street Barbers offers a step back into the classic styles of barber shops, with hardwood floors, oak barber stations, and throne-like leather barber chairs. The professionals are trained in the time-honored traditions of barbering and modern approaches to deliver a superior barber experience.
Where To Shop
The Magnificent Mile is Chicago’s premier cultural and commercial district along Michigan Avenue and includes 430+ retailers, two shopping centers, including Watertower Place, over 275 restaurants, and historic architecture. All of your favorite department stores, such as Nordstrom, Bloomingdale’s, and Neiman Marcus, can be found near the Mag Mile. There is plenty to do and plenty to see for every taste and preference.
The Gold Coast neighborhood on Chicago's Near North Side is a historic, luxurious area. Here you will find designer boutiques, legendary architecture and historical homes, including the former Playboy Mansion, and illustrious restaurants and bars.
Fulton Market District is in the West Loop and is a growing, hip, and up-and-coming neighborhood. It is a former warehouse district that is now home to indie fashion boutiques, offices, coffee roasteries, bars, restaurants, and live music venues. This area is vibrant and alive during the day and into the evening.
For a more bespoke shopping experience, Space 519 is located just off the Magnificent Mile and offers an exclusive shopping experience. Here you’ll find women’s designer clothing and accessories, fine jewelry, apothecary, inspired home goods and gifts. Spouses Lance Lawson and Jim Wetzel have curated a selection of unique and hard-to-find items across a wide range of categories for your shopping pleasure.
For men, Independence offers the same curation of menswear and accessories, with an emphasis on American-made clothing. The clothing style draws on the idea of old American workwear, with some Japanese influence.
Ikram is another high-end women’s clothing store, but with an art gallery and a cafe on its second floor. This exclusive fashion boutique has a unique mix of designers, jewelry, and vintage accessories, hand-picked from across the globe.
Nightlife
The South Side of Chicago is the birthplace of house music in the early 80s, and for decades, the city has maintained a vibrant underground club and rave scene. Radius is a venue frequented by DJ’s globally, providing space for electronic dance music lovers to unwind and escape with like-minded people.
Three Dots and a Dash is a tropical-inspired craft cocktail bar. Their menu is centered around rum and rhum agricoles, inspired by underrepresented islands, to create the ideal tropical island paradise. With a wide array of both cocktails and mocktails served in fanciful glasses with flavourful embellishments, this bar will get your spirits up.
Julia Momosé is the chef, creative director, and beverage visionary behind Kumiko, a Japanese dining and cocktail bar. Momosé (winner of Michelin’s Exceptional Cocktails Award, 2022) has written a book on The Way of the Cocktail and the Japanese traditions and philosophy behind the drinks. Enjoy food or snack pairings with the expertly crafted drinks in their small, intimate space.
TAO Chicago is an Asian bistro and nightclub that offers bottle service to your table so you can dance without interruption. The smart-casual venue offers a range of signature and luxury cocktails. Dine on a variety of small plates, sushi, tempura, and other specialty Asian cuisine before enjoying a lavish club evening.
One of Chicago’s oldest clubs and music venues is The Mine in West Loop. This venue offers three rooms featuring Latin music (reggaeton, salsa, bachata) for three distinct vibes in a chic, stylish environment. VIP table reservations are available to ensure you have the ultimate, thrilling club experience.
The Best Attractions
For a low-key immersion into history and culture, head to the Art Institute of Chicago. Vast and dynamic exhibitions offer a multitude of artistic experiences. It has been home to some of the world’s most famous pieces, such as Nighthawks by Edward Hopper, American Gothic by Grant Wood, and Water Lilies by Claude Monet. Open every day, make sure to check it out.
The Chicago River Walk is a free 1.25-mile scenic pedestrian path along the south bank of the Chicago River. During the walk, you will see public art, boat rentals, architectural boat tours, and waterfront dining. The path is built around four distinct districts (The Confluence, The Arcade, The Civic, and the Esplanade), each with its own vibe and attractions, similar to the neighborhoods of Chicago.
The Chicago Symphony Orchestra was founded in 1891 and hosts year-round concerts, including live performances of the top soundtracks. The orchestra is considered one of the greatest in the world and tours throughout the USA and the world. Book a ticket to hear classical music boom throughout the glorious hall.
Andersonville is a neighborhood in the North Side of Chicago with roots in Swedish heritage. The area is home to one of Chicago’s largest LGBTQ+ communities, with a welcoming, artisanal vibe, and is considered the “shop local capital” for its independently owned stores and boutiques. There's also plenty of hip bars and restaurants to try and Swedish bakeries to dream about.
Chicago has many names. The Windy City, City of Big Shoulders, and The Second City. Whatever you call it, Chicago is extremely connected to its amalgamation of cultures and history, its green spaces and historic park system, and its accomplishments in art, culture, and lifestyle. It is a lively and luxurious city, with many more attractions and gems to discover.