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 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! It’s set in a striking glass building in the heart of the city’s theatre, arts, and shopping district and features eye-popping design, stunning views, and creative culinary delights. 

I love that this hotel is designed with elegance in mind, this modernist oasis in the heart of the city features fabulous city and river views, a private movie theatre, and a luxurious spa.

My sleek and stylish guest room came with an individual design and personality and came with floor-to-ceiling windows with wonderful views, a flat-screen TV, and an iPod dock.

The calm, neutral color palette is highlighted with bright, colorful couches and chaise lounges, throws, and cushions.

My favorite area was the rooftop lounge offers dining and dancing with the city skyline as a backdrop, and the State and Lake Tavern by Chef Michael Tauss has a gastropub-style menu and a welcoming atmosphere. Other amenities include a fitness center and room service.

• To book, check prices or availability for theWit Hotel

2. The Robey

I was a big fan of this trendy and swish spot! This iconic and upmarket Art Deco building is set in the heart of the hippest neighborhood.

You only need to step outside the main entrance to be deep into the streets of Wicker Park and Bucktown, the city’s creative hub. If you can pull yourself away, I highly recommend unsigned bands, boho chic, and vegan eateries on every corner! 

The light-filled interiors and industrial, minimalist-chic design are highlighted with materials like terrazzo and natural woods in a palette of red, pink, white, and gray. Triangular suites—with plenty of tech, sleek wooden floors, custom furniture, and luxe linens—offer extensive views across the city.

Café Robey offers modern American cuisine for breakfast, lunch, and dinner. The Cabana Club with its rooftop pool and terrace has a summertime Americana menu and a tropical feel even here in the Windy City.

Gaze out over the city with a cocktail at The Up Room rooftop lounge, or grab a drink and snack at the second-floor Lounge. Cable TV, free WiFi, and light and airy contemporary rooms are standard! Bonus! 

• To book, check prices or availability for The Robey Hotel

3. Virgin Hotel

I personally think this place has modern sophistication and truckloads of style. Located in the Loop area in Downtown, travelers will be spoilt for choice with so many things to see and do right on their doorstep. It has an upscale ambiance without feeling too highbrow.

Communal areas and my guest bedroom have great attention to detail with plush furnishings and modern ornamental pieces. Like many hotels in the city, the Virgin Hotels has a chilled-out rooftop bar area with breathtaking views of the wider city.

Although closed during the heart of winter, in warmer months you can see a DJ and lively crowd until the early hours! 

• To book, check prices or availability for Virgin Hotel

4. Hotel EMC2

I loved this place! It is part of the prestigious Autograph collection and can be found close to the central Magnificent Mile Shopping District within the vibrant Streeterville neighborhood.

A beautifully decorated luxurious urban refuge, the 4-star, and very highly rated Hotel EMC2 perfectly captures the creative spirit of the city with interiors that are designed to sit at the intersection of art and science.

Think sumptuous velvet furnishings mixed with brass fitments and industrial lighting, dark wood floor, marble walls, and oversized artwork and you have captured the mood of the hotel’s eclectic styling.

The truly gorgeous modern/vintage rooms offer flat-screen TVs, minifridges, coffeemakers, funky glass-enclosed showers, and designer toiletries.

The highly regarded Albert restaurant is a feast for the mind, body, and soul and is the perfect place to enjoy the delights of one of the finest hotels in the city. I thought it was just fabulous darling!

• To book, check prices or availability for Hotel EMC2

5. Moxy Downtown

I totally fell for this lively, quirky hotel right in the heart of the River North neighborhood, close to Millennium Park, art galleries, nightlife, restaurants, and more.

Like the other Moxy hotels, it is geared to millennial tastes and needs and the rooms have an abundance of USB and power outlets and 49-inch Smart TVs for all streaming needs.

In my opinion the vivid artwork in the shared spaces makes this an Insta-worthy hotel perfect for Millennials and Gen Zs. You’ll find more material sustenance at the 24-hour Zombie Taco and custom cocktails at Bar Moxy.

The rooms are comfortable with a restful, muted decor and many have city views. Inner Circle rooms overlook a quirky art installation inspired by the Garden of Eden.

• To book, check prices or availability for Moxy Downtown

6. Freehand

Based in the trendy River North neighborhood, I was a big fan of this boutique gem, which is near central amenities and easily accessible to all areas of the city.

The hotel is set inside a refurbished 1920s art deco building and among the city’s numerous Downtown skyscrapers and high-rises. There’s a stylish, relaxed vibe with modern touches to give extra color and warmth.

Tastefully decorated communal spaces and rooms of different sizes give tribute to America’s Midwest heritage. An award-winning cocktail bar called Broken Shaker is well worth visiting for exotic cocktails, light bites, and fun and games. A fitness center, cheap parking, and a coffee bar are some additional popular amenities.

• To book, check prices or availability for Freehand

7. Thompson

The city’s affluent Gold Coast is full of upscale restaurants and historic mansions and nestled amongst them (very near Michigan Avenue and The Magnificent Mile) is this sophisticated spot.

It’s 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. I suggest booking a table if you can! 

I also enjoyed drinks and cocktails at the smart Salone Nico, one of the city’s most popular downtown wine bars and cocktail lounges. Think it can’t get any better? They even throw in a complimentary luxury car service – not bad at all! 

• To book, check prices or availability for Thompson

8. Chicago Athletic Association

Situated in the Downtown area overlooking Michigan Avenue, this is arguably 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.

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.

The unique bedrooms mirror the traditional clubrooms of athletic associations and provide plenty of comfort for weary travelers.

A rooftop bar lets guests see fantastic views of Millennium Park and the wider city. Head to the Drawing Room to relax with afternoon tea or coffee next to a warm and cozy fireplace!

• To book, check prices or availability for The Chicago Athletic Association

9. Selina

In my opinion, Selina hotels are the ultimate hipster hotels. They offer 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 has 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 is 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’s a grab-and-go option for breakfast, which helped when I was eager to explore! 

• To book, check prices or availability for Selina Hotel

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, the height of opulence. It offers smart, sophisticated, and stylish Art Deco-inspired accommodation throughout.

I loved the ornate high-rise building, which dates from 1894. It is just a 12-minute walk from central Millennium Park and offers some of the finest views in the city.

With quirky amenities like loaner bikes, nightly wine socials, and a yoga mat in every room, you will be staying in a cleverly crafted luxury environment.

The rooftop lounge serves light bites and refreshments, and the day spa, salon, and fitness centers offer all the complimentary facilities you would expect from such an upmarket place! 

• To book, check prices or availability for Kimpton Grey

11. The Hoxton

The creative European brand brings its style to downtown, which is only a few minutes’ walk from Morgan Station and great restaurants and shops.

Housed in an industrial brick warehouse, the inside of the pet-friendly abode is a beautifully chic and artful haven with a club-style vibe and gorgeous features such as potted greenery, communal tables, and design elements fashioned by local artists.

My hotel highlights included my chic and vintage/retro-inspired guest room with floor-to-ceiling window, mini-fridge, coffee maker, flat-screen Ts, and free Wi-Fi.

There is also the 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 offering great city views! 

• To book, check prices or availability for The Hoxton Hotel

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 come with Apple Mac Mini computers and soaking tubs. Enjoy a drink or two in the contemporary chic hotel restaurant 20 East, which offers a thoroughly modern take on traditional American fare and a wide selection of craft beers.

You can always work off those extra calories in the onsite fitness center. Also, I would suggest not missing the chance to eat outside on the patio area! Sublime!

• To book, check prices or availability for The Talbott Hotel

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 include a sophisticated restaurant, a terrace bar offering superb city views, a gym, and a very grand lobby lounge. 

• To book, check prices or availability for The Gwen Hotel

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 are 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.

For those in need of extra pampering, I would suggest booking an appointment at the Soothe Spa. The Lure Fishbar offers the finest seafood and a fresh bar and has the option of in-room dining.

• To book, check prices or availability for 21c Museum Hotel

15. Viceroy

Viceroy hotels are known for reimagining traditional luxury, and in this city, that means 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 looks like Art Deco redone for the 21st century, and the theme is echoed in the interior gold and black accents.

The decor is 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 when you’re ready for some fine dining and nightlife I would highly recommend heading to the rooftop Devereaux Lounge, or the Somerset for classic American food and country club style.

• To book, check prices or availability for Viceroy Hotel