Top 15 Cool And Unique Hotels In Chicago
Chicago is famed for its impressive architecture, hip neighborhoods, skyscraper-dotted skyline, vibrant live music scene, and incredible collection of unique and creative places to stay! From intimate boutiques to sleek high-rises, these are the places that made the ‘Windy City’ truly unforgettable on my many trips.…
1. theWit Hotel
Designed by award-winning architect Jeanne Gang, theWit featured a striking glass façade and earned LEED Silver certification. Inside, I discovered a light-filled haven of modern art and retro-chic furniture that felt playful yet sophisticated — a true modernist oasis!
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.
My stay was all about big treats — from watching La La Land 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!
My favorite highlights…
- Gorging on the creamy Manila Cookie Banana Pudding and the exotic Lychee Dream Cocktails at the trendy State and Lake Tavern.
2. The Robey
Set in a striking Art Deco building, I was won over by the light-filled interiors which mixed sleek modern design with vintage accents — snazzy terrazzo floors, calming natural woods, and a chic red, white, and gray palette gave it a cool industrial-chic vibe.
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!
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.
My personal highlights…
- Relaxing in a deep velvet sofa, surrounded by the warm scent of polished wood, while reading The Coast of Chicago by Stuart Dybek in the cozy Art Deco library!
3. Virgin Hotel
This party hotspot was such a fun option! Housed in a high-rise with a historic Art Deco façade, it had tech-driven luxury, hardwood flooring and scarlet velvet sofas that created an upscale yet playful vibe I was in awe of!
My roomy, Scandi-chic guest space was extra-special — 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.
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!
My personal highlights…
- I thought the handy mobile app which they named ‘Lucy’ was a fun feature – I could adjust the room temperature, control the television, order room service, and I even used it to check out without visiting the front desk!
4. Hotel EMC2
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 — filled with vintage instruments, brass accents, marble walls, and shelves of books — it felt more like staying in a beautifully curated museum than a hotel!
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!
Its Streeterville location was perfect for me — 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 décor and inventive global menu stood out — my roasted mushroom crostini was especially memorable!
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My personal highlights…
- The incredible robot butlers who were named Cleo and Leo – I saw them independently maneuver through the hotel’s hallways and even use the elevators to deliver items for us guests!
5. Moxy Downtown
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.
This stay felt fun and functional — 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!
The River North location was spot-on, with Millennium Park, 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.
My personal highlights…
- Being served a “Zombie Gut Punch” cocktail while being checked in – it was a potent mix of tropical juices, rum, and a splash of grenadine, served over ice!
6. Freehand
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, macramé wall hangings, leafy potted plants, mid-century armchairs, and unique local artwork.
This place felt like the best of both worlds — 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!
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 Café Integral, working out at the gym, and ending the night with award-winning Lakeside Lemonade cocktails at Broken Shaker.
My highlights…
- Gorging on the heavenly Segovia gourmet coffee and blueberry muffins from the Café Integral each morning!
7. Thompson
In Chicago’s upscale Gold Coast, just steps from Michigan Avenue and The Magnificent Mile, this spot felt perfectly sophisticated. It was also close to Lake Michigan, and I loved how designer Tara Bernerd combined industrial fittings with warm woods and mid-century Americana for a chic, loft-like vibe.
This stay felt effortlessly chic — 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!
I couldn’t get enough of Nico Osteria’s 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!
My personal highlights…
- I loved the super-luxurious bespoke 400-thread count Sferra linens on my guest room bed – it felt like I was sinking into a cloud each night!
8. Chicago Athletic Association
Overlooking Michigan Avenue in Downtown Chicago, this felt like one of the city’s best-located stays. I was enamored by its gothic architecture, moody lighting, classic furniture, and sporty design touches that nodded to its athletic past — especially the polished wooden rowing oars and historic basketball memorabilia tucked into stylish corners!
The shared spaces felt like stepping into an upscale English mansion, with rich wood paneling, patterned tile floors, and a refined, historic atmosphere.
My unique room also carried the theme beautifully, styled like a classic athletic clubroom with cozy details and quirky décor — 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 on a cozy afternoon!
My highlights…
- The Games Room with its bocce, billiards, shuffleboard, and chess, as well as a buzzing bar pouring local craft favorites like Goose Island 312 and Half Acre’s Daisy Cutter alongside creative mezcal cocktails.
9. Selina
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.
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!
The public spaces blended sleek contemporary minimalism with a nod to the city’s golden-era grandeur, giving the whole place a unique personality. I enjoyed having the Magnificent Mile’s 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.
My personal highlights…
- I loved the Wellness Workshops, from soothing Hatha yoga set to soft music to guided meditation sessions scented with lavender!
10. The Kimpton Gray Hotel
Set in one of Chicago’s finest landmarks, this 4-star hotel felt like the height of opulence. I really admired its Art Deco–inspired design, the 1894 high-rise building, and especially the historic elevators with ornate metalwork and marble.
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!
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.
My highlights…
- All the thoughtful little details, like the motion-activated HVAC unit that filtered fresh outdoor air. It made my room feel fresh and inviting!
11. The Hoxton
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’s cultural history.
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 — the industrial-chic exposed concrete ceilings — while also being just minutes from Morgan Station and its great dining and shopping.
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.
My personal highlights…
- Dining on a hearty weekend brunch of a honeynut squash and mushroom omelette while gazing at the city skyline on the fun Cabra rooftop restaurant.
12. Talbott Hotel
Just a few short steps away from the iconic Magnificent Mile on Michigan Avenue, I was a big fan of how it offered well-appointed rooms and effortless style throughout!
I adored the opulent yet edgy interiors — a mix of retro chic and industrial style — 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!
From 20 East’s twisty cocktails and craft beer selection to energizing workouts and breezy patio meals, my stay was something very unique!
My favorite highlights…
- Dining on the crispy Yukon potatoes and eggplant mutabel in their trendy Laurel restaurant.
13. The Gwen
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 — it was a striking showstopper!
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!
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!
My highlights…
- I really loved the unique glamping option which was a boho Lotus Belle tent located on the 16th-floor terrace which even included a comfortable queen-sized bed as well as incredible views!
14. 21c Museum Hotel
I really admired that contemporary art was woven into the décor here, with curated exhibitions and cultural programming that made the hotel feel like a cultural hub.
Designed by Deborah Berke Partners, my large art-filled room felt like the perfect city hideaway — all sleek lines, luxurious décor, 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!
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!
My personal highlights…
- I was really taken with the striking life-size bison avant-garde sculpture that stood in the lobby and looked spookily realistic!
15. Viceroy
Viceroy hotels are known for reimagining traditional luxury, and here that meant I got a retro-chic stay in the upscale Gold Coast neighborhood, right on Lake Michigan’s shores.
The shimmering glass exterior gave classic Art Deco a bold 21st-century twist, with glamorous gold-and-black interiors and mid-century modern flair by Kelly Wearstler, Jean-Michel Gathy, and Wimberly Allison Tong & Goo. Floor-to-ceiling windows showcased spectacular views of the city and lake.
My striking room was beautifully appointed, and one standout touch was the built-in “mood mirror” — a full-length mirror that softly shifted ambient lighting and overlaid subtle patterns when toggled! My dreamy city evening began with a Lavender Collins cocktail at the rooftop Devereaux Lounge and ended with a country-club-style dinner at Somerset – the Spring Pea Agnolotti was a stand-out!
My highlights…
- The gorgeously scented Natura Bissé citrus-jasmine body products and ROIL’s bergamot and fig shampoo made my bathroom feel like a spa!
