![\"theWit](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2018\/05\/thewit-chicago-a-doubletree.webp)
<\/picture><\/p>\nDesigned by award-winning architect Jeanne Gang, theWit featured a striking glass fa\u00e7ade and earned LEED Silver certification. Inside, I discovered a light-filled haven of modern art and retro-chic furniture that felt playful yet sophisticated \u2014 a true modernist oasis!<\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n My spacious room had a cozy Scandi-chic design with a fire-engine red Smeg fridge, a street-priced minibar, an ergonomic bed, and I loved the geometric monochrome rugs and wonky-on-purpose lamps – they made the space very Instagram-worthy! The Theater District location and being near the Magnificent Mile was also a huge bonus.<\/p>\n My stay was all about big treats \u2014 from watching La La Land<\/em> in the retro-glam private theater to sipping a Smoke and Mirrors mezcal cocktail on the rooftop and savoring Grilled Asparagus and Burrata with lemon zest at State and Lake Tavern by Chef Michael Taus!<\/p>\n My favorite highlights… <\/em><\/strong><\/p>\n Set in a striking Art Deco building, I was won over by the light-filled interiors which mixed sleek modern design with vintage accents \u2014 snazzy terrazzo floors, calming natural woods, and a chic red, white, and gray palette gave it a cool industrial-chic vibe.<\/p>\n This chic, minimalist vibe continued in my room with trendy custom furniture, warm hardwood floors, oxide-red accents, and sleek glass partitions. I particularly liked the crisp Egyptian cotton linens and those iconic corner windows that gave it a stylish urban observatory feel!<\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n The Wicker Park location, with its cool art scene, indie shops, and boho dining spots, made me feel like a local. Back at the hotel, I enjoyed hearty breakfast burritos with chipotle crema, relaxed at the chic rooftop Cabana Club with its pool and terrace, sipped Smoky Mezcal Margaritas in the retro-modern lounge, and even caught a live jazz performance to end the night.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n My personal highlights…<\/strong><\/em><\/p>\n This party hotspot was such a fun option! Housed in a high-rise with a historic Art Deco fa\u00e7ade, it had tech-driven luxury, hardwood flooring and scarlet velvet sofas that created an upscale yet playful vibe I was in awe of!<\/p>\n My roomy, Scandi-chic guest space was extra-special \u2014 it had funky furniture, a statement red Smeg fridge, street-priced minibar, a generous workspace, a patented ergonomic bed, and a sliding door for extra privacy. I particularly liked the cheeky in-room chalkboard where I left a fun note! The Loop setting was also ideal – it put me very near Millennium Park, the Theater District, and the Magnificent Mile.<\/p>\n From skyline Summer Love Sangrias at the rooftop bar and late-night DJ sets to oat milk flat whites in the coffee shop, workouts in the cutting-edge gym, and standout modern American fare (the Butternut Squash Gnocchi with sage brown butter was a favorite) at Commons Club, this stay was a dream!<\/p>\n My personal highlights… <\/strong><\/em><\/p>\n Set in a sleek glass high-rise with avant-garde design by the Rockwell Group, I discovered a striking space with a captivating design-meets-science theme \u2014 filled with vintage instruments, brass accents, marble walls, and shelves of books \u2014 it felt more like staying in a beautifully curated museum than a hotel!<\/p>\n My social-media friendly guest room had a boutique vintage-chic look with a gel memory foam bed, unique art, organic Malin+Goetz toiletries, a flat-screen TV, and a matte black Nespresso coffeemaker. I adored the Alexa-powered robot butler which delivered towels and extra coffee pods right to my door!<\/p>\n Its Streeterville location was perfect for me \u2014 just steps from the Magnificent Mile, Northwestern University, and plenty of shopping, dining, and cultural spots. I was also a big fan of the state-of-the-art gym and The Albert, where the themed d\u00e9cor and inventive global menu stood out \u2014 my roasted mushroom crostini was especially memorable!<\/p>\n My personal highlights… <\/strong><\/em><\/p>\n I totally fell for this lively, quirky hotel! Its sleek glass-and-steel exterior gave way to Instagrammable, eclectic interiors with striking graffiti art, bright pink accents, and a playful, edgy vibe which I loved.<\/p>\n This stay felt fun and functional \u2014 my funky room had a smart industrial-chic design, luxe bedding, a 49-inch Smart TV, peg walls in place of closets, loads of USB ports, and a bright, minimalist shower room. The cheeky neon sign was a stand-out feature for me!<\/p>\n The River North location was spot-on, with Millennium Park<\/a>, the Riverwalk, shopping, and dining all just steps away. Before heading out, I grabbed a Charred Poblano & Corn Taco at the quirky 24\/7 Zombie Taco counter, sipped on a potent Berry Sexy Mule at the lively bar\/reception, and even squeezed in a workout in the modern gym.<\/p>\n My personal highlights… <\/strong><\/em><\/p>\n I was a big fan of this boutique gem! Set in a 1920s building, it had a welcoming eclectic, boho-meets-hipster vibe with vintage rugs, macram\u00e9 wall hangings, leafy potted plants, mid-century armchairs, and unique local artwork.<\/p>\n This place felt like the best of both worlds \u2014 my Superior King Room had vintage details like hooked rugs and dark wood paired with modern touches like a flat-screen TV and luxe linens. The quirky retro rotary phone was a fun touch too!<\/p>\n The River North location was great too, I was steps from the Magnificent Mile, Navy Pier, and bars and art galleries galore. My favorite moments were grabbing breakfast at Caf\u00e9 Integral, working out at the gym, and ending the night with award-winning Lakeside Lemonade cocktails at Broken Shaker.<\/p>\n My highlights… <\/strong><\/em><\/p>\n In Chicago\u2019s upscale Gold Coast, just steps from Michigan Avenue and The Magnificent Mile, this spot felt perfectly sophisticated. It was also close to Lake Michigan<\/a>, and I loved how designer Tara Bernerd combined industrial fittings with warm woods and mid-century Americana for a chic, loft-like vibe.<\/p>\n This stay felt effortlessly chic \u2014 my spacious room featured wall-to-wall windows framing stunning city views, luxurious sheets, a flat-screen TV, and a rainfall shower that felt like a spa. I especially liked the quirky retro-style record player!<\/p>\n I couldn\u2019t get enough of Nico Osteria\u2019s Italian dishes (I especially loved the handmade ricotta gnudi with wild mushrooms and sage), the sophisticated vibe at the romantic Salone Nico, and the complimentary luxury car service! <\/p>\n My personal highlights… <\/strong><\/em><\/p>\n Overlooking Michigan Avenue in Downtown Chicago, this felt like one of the city\u2019s best-located stays. I was enamored by its gothic architecture, moody lighting, classic furniture, and sporty design touches that nodded to its athletic past \u2014 especially the polished wooden rowing oars and historic basketball memorabilia tucked into stylish corners!<\/p>\n The shared spaces felt like stepping into an upscale English mansion, with rich wood paneling, patterned tile floors, and a refined, historic atmosphere.<\/p>\n My unique room also carried the theme beautifully, styled like a classic athletic clubroom with cozy details and quirky d\u00e9cor \u2014 my favorite touches were the pommel horse benches and old leather boxing gloves! Highlights of my stay were sipping a classic French 75 at the rooftop bar overlooking Millennium Park and curling up by the Drawing Room fireplace with a copy of The Devil in the White City<\/em> on a cozy afternoon!<\/p>\n My highlights… <\/strong><\/em><\/p>\n In my opinion this was the ultimate hub for hipsters and digital nomads! It offered me everything I needed for my digital nomad life – handy co-working spaces, shared kitchens, modern meeting spaces, a cozy library, an upscale spa, zen-like yoga sessions, and bike and scooter rentals. It had an awesome location in the heart of the city, close to the Magnificent Mile, stores, restaurants, and Oak Street Beach.<\/p>\n My boutique-style room was a serene retreat, wrapped in calming cream tones that felt like an oasis from the city buzz and I especially liked the trendy hanging hammock chair!<\/p>\n The public spaces blended sleek contemporary minimalism with a nod to the city\u2019s golden-era grandeur, giving the whole place a unique personality. I enjoyed having the Magnificent Mile\u2019s restaurants just steps away, and the grab-and-go breakfast (I opted for the Hummus & Veggie Bagel) was perfect for my busy day of city exploring.<\/p>\n My personal highlights… <\/strong><\/em><\/p>\n Set in one of Chicago\u2019s finest landmarks, this 4-star hotel felt like the height of opulence. I really admired its Art Deco\u2013inspired design, the 1894 high-rise building, and especially the historic elevators with ornate metalwork and marble.<\/p>\n Just a 12-minute stroll from Millennium Park, this spot boasted some of the best city views around. My gorgeous room felt like a smart little luxury retreat, complete with a yoga mat and my favorite feature – subtle LED strip lighting in unexpected places!<\/p>\n I hung out in the trendy rooftop lounge which had a unique retractable roof and stunning city views, indulged in a soothing aroma-infused hot stone massage in the full-service spa, salon, modern fitness center, nightly wine socials where I sipped on velvety Pinot Noirs, and the free loaner bikes.<\/p>\n My highlights… <\/strong><\/em><\/p>\n This was a creative European brand which I thought brought style to downtown, housed in an industrial brick warehouse, the inside of the pet-friendly abode was a beautifully chic and artful haven with a club-style vibe and gorgeous features. I saw potted greenery, communal tables, and artwork celebrating Chicago\u2019s cultural history. <\/p>\n My favorite part was my vintage-meets-modern guest room with a floor-to-ceiling window, mini-fridge, Nespresso coffee maker, flat-screen TV, and my favorite feature \u2014 the industrial-chic exposed concrete ceilings \u2014 while also being just minutes from Morgan Station and its great dining and shopping.<\/p>\n I spent my time lounging in the bar with a tangy Pisco Sour, enjoying charred mushroom anticuchos at rooftop Cabra and roasted cauliflower with tahini at the Peruvian Restaurant Cira, before unwinding in the intimate cocktail bar and soaking up rooftop pool views.<\/p>\n My personal highlights… <\/strong><\/em><\/p>\n Just a few short steps away from the iconic Magnificent Mile<\/a> on Michigan Avenue, I was a big fan of how it offered well-appointed rooms and effortless style throughout!<\/p>\n I adored the opulent yet edgy interiors \u2014 a mix of retro chic and industrial style \u2014 and my guest room came perfectly equipped with free Wi-Fi, a widescreen TV, Italian linens, a cute Apple Mac Mini, and a deep soaking tub. A fun highlight was discovering a discreet flip-open wall panel that revealed a charming hand-drawn sketch of the neighborhood!<\/p>\n From 20 East\u2019s twisty cocktails and craft beer selection to energizing workouts and breezy patio meals, my stay was something very unique!<\/p>\n My favorite highlights… <\/strong><\/em><\/p>\n I thought this place was really something special! I was immediately taken with the Art Deco lobby and its limestone panels carved by Gwen Lux \u2014 it was a striking showstopper!<\/p>\n My romantic room fused Deco glamour with modern perks like luxe bath products, a Keurig, speedy Wi-Fi, and a massive TV. I was especially charmed by the unique backlit bas-relief panel behind the bed, which cast dramatic sculptural shadows at night!<\/p>\n I spent my evenings dining in style, sipping on hand-crafted cocktails gazing at the striking skyline, and unwinding in the retro-glam lobby lounge, with daytime workouts in the excellent gym. Perfectly positioned off Central Michigan Avenue, I admired how this 5-star gem channeled its 1930s roots with polished brass and show-stopping details! <\/p>\n My highlights… <\/strong><\/em><\/p>\n I really admired that contemporary art was woven into the d\u00e9cor here, with curated exhibitions and cultural programming that made the hotel feel like a cultural hub.<\/p>\n Designed by Deborah Berke Partners, my large art-filled room felt like the perfect city hideaway \u2014 all sleek lines, luxurious d\u00e9cor, and soothing neutrals. I particularly liked the quirky framed artwork that came to life at night with subtle projections that shifted colors and cast moving shadows!<\/p>\n I treated myself to a Detoxifying Bourbon Body Scrub at the Soothe Spa, savored dinner and Dockside Martinis at The Lure Fishbar, and loved having the option of cozy in-room dining on quiet nights. Its awesome Magnificent Mile location made shopping, Millennium Park strolls, and museum-hopping effortless for me!<\/p>\n![\"theWit](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/theWit-Hotel.webp)
<\/picture><\/p>\n![\"My](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2025\/03\/My-photo-of-North-Michigan-Avenue-the-Magnificent-Mile-taken-winter-2025.webp)
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2. The Robey<\/h2>\n
![\"The](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/The-Robey-Hotel.webp)
<\/picture><\/p>\n![\"The](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/The-Robey-Hotel-in-Chicago.webp)
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3. Virgin Hotel<\/h2>\n
![\"Virgin](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Virgin-Hotel-Terrace-in-Chicago.webp)
<\/picture><\/p>\n![\"Virgin](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Virgin-Hotel-Bar-in-Chicago.webp)
<\/picture><\/p>\n![\"Virgin](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Virgin-Hotel-DJ-in-Chicago.webp)
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4. Hotel EMC2<\/h2>\n
![\"Hotel](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2020\/02\/Hotel-EMC2-Chicago.webp)
<\/picture><\/p>\n![\"Hotel](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Hotel-EMC2-Restaurant.webp)
<\/picture><\/p>\n![\"My](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2025\/03\/My-photo-of-Bloomingdales-taken-winter-2025.webp)
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5. Moxy Downtown<\/h2>\n
![\"Moxy](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Moxy-Hotel-in-Chicago.webp)
<\/picture><\/p>\n![\"Moxy](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2020\/02\/Moxy-Chicago-Downtown.webp)
<\/picture><\/p>\n![\"Moxy](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Moxy-Hotel-Chicago-Bedroom.webp)
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6. Freehand<\/h2>\n
![\"Freehand](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Freehand-Chicago.webp)
<\/picture><\/p>\n![\"Freehand](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Freehand-Chicago-Lobby.webp)
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7. Thompson<\/h2>\n
![\"Thompson](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Thompson-Hotel-Chicago.webp)
<\/picture><\/p>\n![\"Thompson](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Thompson-Hotel-Chicago-Lobby.webp)
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8. Chicago Athletic Association<\/h2>\n
![\"Chicago](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Chicago-Athletic-Association.webp)
<\/picture><\/p>\n![\"Chicago](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Chicago-Athletic-Association-Lobby.jpg?resize=716%2C752&ssl=1\" "\\"\\"")
<\/p>\n![\"Chicago](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Chicago-Athletic-Association-Bedroom.webp)
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9. Selina<\/h2>\n
![\"Selina](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2020\/02\/Selina-Chicago.webp)
<\/picture><\/p>\n![\"Selina](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Selina-Hotel-Chicago.webp)
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10. The Kimpton Gray Hotel<\/h2>\n
![\"The](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2018\/05\/Kimpton-Grey.webp)
<\/picture><\/p>\n![\"The](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2018\/05\/kimpton-chicago-5033897895-55x31.webp)
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11. The Hoxton<\/h2>\n
![\"Hoxton](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Hoxton-Hotel-Chicago-Terrace.webp)
<\/picture><\/p>\n![\"Hoxton](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Hoxton-Hotel-in-Chicago.webp)
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12. Talbott Hotel<\/h2>\n
![\"Talbott](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2018\/05\/Talbott-Hotel.webp)
<\/picture><\/p>\n![\"Talbott](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2018\/05\/Talbott-Hotel-Chicago.webp)
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13. The Gwen<\/h2>\n
![\"The](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/The-Gwen-Hotel-Chicago.webp)
<\/picture><\/p>\n![\"Gwen](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/Gwen-Hotel-in-Chicago.webp)
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14. 21c Museum Hotel<\/h2>\n
![\"21c](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/21c-Museum-Hotel-Chicago.webp)
<\/picture><\/p>\n![\"21c](\"https:\/\/i0.wp.com\/globalgrasshopper.com\/wp-content\/uploads\/2023\/12\/21c-Museum-Hotel.webp)
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