Chicago is famed for its impressive architecture, hip neighborhoods, skyscraper-dotted skyline, vibrant live music scene, and incredible collection of creative places to stay! From intimate boutiques to sleek high rises, here are some of my favorite spots in the Windy City…
1.theWit Hotel
This place wowed me! I discovered it housed in a striking glass building and inside it was a contemporary and striking design haven with lashings of glass which let in huge swathes of light, trendy, eclectic decor with splashes of bold colors, contemporary art installations, and retro-chic furniture. I found the vibe was playful but still sophisticated and luxurious – it felt like a unique modernist oasis in the heart of the city!
My sleek and stylish guest room came with an individual design with floor-to-ceiling windows, incredible city views, a large plush bed, a flat-screen TV, a coffee maker, air con and a large and very impressive ensuite bathroom with a large soaking tub for relaxation, designer toiletries a bathrobe and more incredible city views!
I found it nestled in the heart of the city’s Theater District so I had iconic theaters, cultural attractions, shopping on the Magnificent Mile, and multiple excellent dining options all on my doorstep!
I also made sure I made use out of the private movie theatre, luxurious full-service spa, state-of-the-art gym and the chic rooftop lounge which served up handcrafted cocktails and wood-fired pizzas! On my last night I dined at the onsite State and Lake Tavern overseen Chef Michael Tauss which had a gastropub-style American cuisine menu and a chilled atmosphere!
My favorite highlights…
- The divine Manilla Cookie Banana Pudding and Lychee Dream Cocktails at the trendy State and Lake Tavern.
2. The Robey
I was a big fan of this Insta-worthy spot! I found it set in a striking Art Deco building and inside I discovered light-filled interiors that beautifully mixed sleek modern designs with vintage accents, featuring soft, natural textures, clean lines, and industrial-chic details and lots of terrazzo and natural woods in a palette of red, pink, white, and gray.
My guest room featured a trendy industrial-chic design with custom-designed furniture, hardwood floors, luxurious linens, and floor-to-ceiling windows where I gazed at the sweeping views of the cityscape.
I really liked its location which was ideally situated in the heart of Wicker Park, a hip neighborhood which had a lively arts scene, boutique shopping, and a fine array of boho-styled bars and restaurants – it felt like a genuine local Chicago experience!
I also enjoyed its modern American breakfast, its onsite cozy café, The Cabana Club which had an incredible rooftop pool and terrace complete with lots of comfy sofas to lounge around in, the cocktails on the second-floor Lounge and I thought the exclusive access to live music performances in the bustling Wicker Park area was a nice touch too!
My personal highlights…
- Relaxing in a deep plush sofa reading the “The Coast of Chicago” by Stuart Dybek in the cozy Art Deco library!
3. Virgin Hotel
I thought this party-hotspot was a fun option! Catering to a trendy crowd, I found a large high-rise hotel with a historic Art Deco façade and inside I found stylish and eclectic decor, with lashings of bold colors, contemporary art and plush velvet sofas. The vibe was upscale but playful and had a youthful spirit which I really loved!
My guest room featured a light but cozy Scandi-chic design, custom-made retro-chic furniture, a hipster-friendly large red Smeg fridge, a minibar stocked with street-priced snacks, plenty of work-space, a patented and super comfy ergonomic bed, a flat-screen TV and a sliding privacy door that separates the dressing area from the sleeping space – it felt like a home away from home!
I found myself based in an awesome location in the Loop, where I had direct access to cultural and business hubs, including the Theater District, Millennium Park, and the Magnificent Mile.
I also thought the live DJs, the stylish rooftop bar (which had really incredible city views), cute little coffee shop and state-of-the-art fitness center was a great addition as well as the Commons Club restaurant which served up contemporary American cuisine with global influences in a trendy and open setting!
My personal highlights…
- I loved the handy mobile app which they named ‘Lucy’ – I could adjust the room temperature, control the television, order room service, and I used it to check out without visiting the front desk!
4. Hotel EMC2
This place was just so striking! I discovered a sleek, glass high-rise with an extraordinary avant-garde design and inside I found the interiors were equally as interesting the theme mixed the worlds of art and science and there was an eclectic mix of both modern art and vintage scientific instruments. There were velvet furnishings, brass fitments, industrial style lighting, dark wood floors, marble walls, and lots of oversized artwork!
My gorgeous guest room featured a boutique vintage-chic decor an extra-large luxurious bed complete with a cool action gel memory foam mattress, unique art pieces, organic toiletries, a flat-screen TV, a designer coffeemaker and organic toiletries.
I found it located in the vibrant Streeterville neighborhood, just steps away from the Magnificent Mile and Northwestern University’s downtown campus so I was in within walking distance of awesome shopping, dining, and superb cultural attractions.
I also really loved its other impressive features which included a state-of-the-art fitness center, the Albert Restaurant which featured both tasteful themed decor and a creative globally menu.
- To book, check prices or availability for Hotel EMC2
My personal highlights…
- The incredible robot butlers who were named Cleo and Leo – I saw them independently manoeuvre through the hotel’s hallways and even use the elevators to deliver items for us. I ordered food and drinks but I also saw them deliver towels and toiletries.
5. Moxy Downtown
I totally fell for the charms of this lively, quirky hotel! Outside I saw a bold medium high-rise building with a sleek urban design which featured lashings of glass and steel. Inside I found bold, eclectic decor with a mix of contemporary and urban punk elements, graffiti artwork adorning the walls, unique colorful furniture, and a playful and edgy vibe with a youthful buzz which I really enjoyed.
My guest room was equally as funky with a smart, space-efficient design and an industrial-chic design, plush bedding, large flat-screen TVs, peg walls instead of traditional closets to maximize space and an all-white shower room. It also had plenty of USB and power outlets for all my tech and 49-inch Smart TVs for all my streaming needs.
I found it was located right in the heart of the buzzing River North neighborhood, so I was close to Millennium Park, the Magnificent Mile and the Chicago Riverwalk as well art galleries, awesome nightlife, and hip restaurants entertainment.
Before leaving I also made full use out the Zombie Taco, which was a unique 24/7 food truck-inspired counter which had a playful and inventive menu, the lively bar that doubled as the check-in area, and the modern 24/7 fitness center!
My personal highlights…
- Being a 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! I entered the classic-looking 1920s building and was instantly impressed with this warm and cozy haven which had an eclectic mix of vintage and modern design details with handcrafted furnishings, rich textiles, and a curated collection of local art. To me, it felt homey but still very artistic and bohemian.
My guest room (a Superior King Room) was also cozy with an extra large plush bed, bold hand-woven textiles, unique artwork and lashings of dark wood which contrasted the off-white walls. I also found thoughtful touches such as the hooked rugs and soft linens as well as the modern-tech such as the flat-screen TV which came complete with cable channels.
Located in the trendy River North neighborhood, it put me within walking distance of Chicago’s best galleries, boutiques, bars, and restaurants, as well as key attractions such as the Magnificent Mile and Navy Pier.
I also really enjoyed the award-winning cocktail bar which called Broken Shaker which served up exotic cocktails, light bites, and even games, the onsite fitness center and the funky Cafe Integral where I drank Nicaraguan gourmet coffee and gorged on creative breakfast dishes each morning!
- To book, check prices or availability for Freehand
My highlights…
- Gorging on the heavenly Segovia gourmet coffee and blueberry muffins from the Café Integral each morning!
7. Thompson
The city’s affluent Gold Coast was full of upscale restaurants and historic mansions and nestled amongst them (very near Michigan Avenue and The Magnificent Mile) is this sophisticated spot.
It was also just a short distance from Lake Michigan and the loft-like, urban interiors have been designed by British design icon Tara Bernerd who has combined industrial fittings with warm woods and mid-century Americana.
My bedroom oozed style, with floor-to-ceiling windows affording fantastic views out across the famous city skyline. It also had all the usual mod cons, such as high-thread-count sheets, a flat-screen TV, and lush rainfall showers.
One of the hottest eateries in the city, Nico Osteria, is located in the hotel and I also enjoyed drinks and cocktails at the smart Salone Nico, one of the city’s most popular downtown wine bars and cocktail lounges. They even threw in a complimentary luxury car service – not bad at all!
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
Situated in the Downtown area overlooking Michigan Avenue, I thought this was one of the best-located spots in the city! This place made an instant impression on me with its gothic architecture, low lighting, a variety of classic furniture, and its sporty past connections and design details.
To me, the interior of communal areas felt like an upscale English mansion house: upmarket yet comfortable, featuring tasteful wood paneling and fascinating floor tiling, giving a historic and elegant vibe.
My unique bedroom mirrored the traditional clubrooms of athletic associations and provided plenty of comfort as well as the very interesting decor! I especially loved how the pommel horses used as benches and other subtle nods to its athletic past.
I also really enjoyed the rooftop bar where I saw fantastic views of Millennium Park and the wider city and the Drawing Room were I relaxed with afternoon next to a warm and cozy fireplace!
My highlights…
- I thought the Games Room which had bocce ball, billiards, shuffleboard, and chess as well as a cool bar which served craft beers and cocktails.
9. Selina
In my opinion this was the ultimate hipster hotels! It offered me everything necessary for digital nomads’ lives and work, such as co-working spaces, shared kitchens, event and meeting spaces, a library, spa, yoga sessions, and bike and scooter rentals.
It had a premium location in the heart of the city, close to the Magnificent Mile, stores, restaurants, and Oak Street Beach.
My room came with restful shades of cream for an oasis of calm amid the city’s noise. Guests have the option to share rooms with bunk beds as well. The decor in the public spaces was an intriguing mix of contemporary minimalism with the grand traditions of the city’s golden years.
I also found a wide range of restaurants on the nearby Magnificent Mile, and there was a grab-and-go option for breakfast, which helped when I was eager to explore!
My personal highlights…
- I loved the onsite Wellness Workshops I especially enjoyed the Hatha Yoga classes and the guided meditation sessions!
10. The Kimpton Gray Hotel
Set in one of the city’s finest landmarks and top hotels, the 4-star spot is, in my opinion, was the height of opulence. It offered smart, sophisticated, and stylish Art Deco-inspired accommodation throughout. I especially adored the historic elevators which had ornate metal detailing and original marble!
I loved the ornate high-rise building, which dates from 1894 and it was just a 12-minute walk from central Millennium Park and offering some of the finest views in the city.
I stayed in a cleverly crafted luxury environment and I found quirky amenities like loaner bikes, nightly wine socials, and a yoga mat in my guest room,.
The rooftop lounge – which had an awesome retractable roof – served light bites and refreshments alongside superb city views, and the day spa, salon, and fitness centers offered all the complimentary facilities I expected from such an upmarket place!
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 beautifully chic and artful haven with a club-style vibe and gorgeous features. I saw potted greenery, communal tables, and design elements fashioned by local artists.
My highlights included my chic and vintage/retro-inspired guest room which had floor-to-ceiling window, a mini-fridge, coffee maker, a flat-screen TV, and free Wi-Fi and I was based only a few minutes’ walk from Morgan Station which had great restaurants and shops.
There was also a hip bar and lounge, two restaurants, a co-working space, an intimate cocktail bar, and an outdoor rooftop pool accompanied by an eatery and bar which had awesome city 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 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 offers well-appointed rooms and effortless style throughout!
Opulent interiors combine retro chic with industrial touches, whilst my elegant room was well thought out and full of modern conveniences, including free Wi-Fi, a widescreen TV, and Italian linens.
Upgraded rooms came with Apple Mac Mini computers and soaking tubs. I enjoyed cocktails in the contemporary chic hotel restaurant 20 East, which offered a modern take on traditional American fare and a wide selection of craft beers.
I also really liked the onsite fitness center and dining on the outside on the patio area too!
My favorite highlights…
- Dining on the divine crispy yukon potatoes and eggplant mutabel in their trendy Laurel restaurant.
13. The Gwen
I thought this place was something special! From the breathtaking Art Deco lobby to the first-floor limestone panels carved by locally-born acclaimed sculptor Gwen Lux, this place won me over!
I also loved that it was a few short steps from Central Michigan Avenue with its collection of shops, restaurants, and bars. With brass features and fittings, the 5-star spot has rediscovered its 1930s origins, and the theatrical styling is displayed throughout the hotel in intricate detail.
My upscale, stylish bedroom came with a sumptuous style of the Deco period but combined with a range of modern conveniences, including luxury toiletries, a Keurig coffeemaker, free Wi-Fi, and an enormous wall-mounted TV.
Other fabulous amenities included a sophisticated restaurant, a terrace bar offering superb city views, a gym, and a very grand lobby lounge.
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 incredible views!
14. 21c Museum Hotel
I loved that contemporary art is part of the decor in this stylish spot there are also curated exhibitions and cultural programming for travelers and residents, making it a cultural hub in itself!
Its location on the Magnificent Mile put me close to everything downtown, including the shopping at Michigan Avenue, Millennium Park, and the city’s famous museums.
My room was designed by the architectural firm of Deborah Berke Partners and has clean, contemporary lines and luxurious furnishings in quiet, neutral shades.
There were 297 rooms and 106 suites and I could always find a quiet retreat to prepare for the next day’s adventures in the Windy City.
I also loved the Soothe Spa and The Lure Fishbar which offered the finest seafood and a bar and had the option of in-room dining.
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 in this city, that meant a retro-chic hotel located in the upscale Gold Coast neighborhood, right on the shores of Lake Michigan.
In my opinion, the glass-fronted building looked like Art Deco redone for the 21st century, and the theme was echoed in the interior gold and black accents.
The decor was mid-century modern glamour, redone by renowned designers and architects Kelly Wearstler, Inc., Jean-Michel Gathy, and Wimberly Allison Tong & Goo, with a backdrop of floor-to-ceiling windows with views of the city and the lake.
My room was luxurious and well-appointed, and I headed to the rooftop Devereaux Lounge for drinks and awesome views and the Somerset for classic American food and country club style.
My highlights…
- The gorgeously-scented complementary Natura Bisse body products and ROIL shampoo in my guest bathroom!
