Cool and unusual hotels in Chicago

Top 20 cool and unusual hotels in Chicago 2021

Once called “the pulse of America” the city that was founded in the early 1800s and resides on the mighty Lake Michigan in Illinois, is in many ways one of the USA’s greatest. Due to the sometimes blustery nature of the residents (and politicians!), the fact the city is quite a formidable force and also the strong breezes that blow off Lake Michigan has earned it a nickname of the Windy City.

It’s also famed for its impressive architecture, museums, parks, the skyscraper-punctuated skyline and vibrant live music scene, which includes a phenomenal array of jazz, blues and rock clubs. It’s also becoming increasingly hip with lots of funky emerging neighboring worth exploring, ethnic enclaves serving some of the city’s best food and cool street art telling local historic stories. To complement this cool vibe, Chicago is also home to a growing collection of fantastically unique hotels. Thinking of staying? Here are some of the best cool, unique and just simply beautiful hotels to stay in Chicago…

The Robey – a hip, trendy and very instagrammable Chicago hotel

a hip, trendy and very instagrammable Chicago hotel

A trendy and very instagrammable Chicago hotel

The exceptionally rated Robey Hotel is very trendy and swish! This iconic and upmarket Art Deco building is set in the heart of Chicago’s hippest neighborhood. You only need to step outside the main entrance to be deep into the streets of Wicker Park and Bucktown, the creative hub of the city. Discover unsigned bands, boho chic, and vegan eateries on every corner if you can pull yourself away from the contemporary splendor of this hip Chicago abode.

Triangular suites – with plenty of tech, sleek wooden floors, custom furniture, and luxe linens – offer extensive views out across the city, whilst the fab rooftop terrace with its very own pool and Cabana Club cocktail bar means you can still feel tropical even here in the windy city. Cable TV, free WiFi, and light and airy contemporary rooms come as standard in this uber-chic and very cool Chicago hotel. Wonderful!

  • Prices from $120 per night.
  • To book, check prices or availability for The Robey Chicago

theWit Hotel – a cool upscale Chicago hotel with fabulous views

theWit Hotel - a cool upscale Chicago hotel

theWit Hotel - a cool upscale Chicago hotel with fabulous views

Set in a striking glass building in the heart of Chicago’s theatre, arts, and shopping district, the 4-star exceptionally rated theWit Hotel features eye-popping design, stunning views, and creative culinary delights for you to enjoy during your stay. Designed with elegance in mind, each of the trendy hotels smart and stylish guest rooms have their own look and personality and come with a wonderful spa-style bathroom, floor-to-ceiling windows, river views, flat-screen TVs and iPod docks.

There are many chic and romantic hotels in Chicago but this DoubleTree by Hilton Hotel offers more than just overnight accommodation; it is a destination on its own merit. With a rooftop lounge offering fabulous views across the city, a private movie theatre, an onsite spa, and the delicious, innovative cuisine of the State and Lake Restaurant, The Wit is really quite a fabulous place to stay in the city.

  • Prices from $120 per night.
  • To book, check prices or availability for theWit Hotel

Talbott Hotel – a popular trendy boutique hotel on the Magnificent Mile

Talbott Hotel - a popular Chicago boutique hotel

Talbott Hotel - a trendy boutique hotel on the Magnificent Mile

Talbott Hotel - a popular trendy boutique hotel

Just a few short steps away from the iconic Magnificent Mile on Michigan Avenue, the 4-star exceptionally rated Talbott Hotel offers well-appointed rooms and effortless style throughout. Opulent interiors marry retro chic with industrial touches, whilst the elegant rooms at this cool and unusual Chicago stay are well thought out and full of modern conveniences including free Wifi, widescreen TV’s as well as 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, offering 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 don’t miss the chance to eat alfresco on the streets of Chicago in the hotel’s beautiful patio area! Sublime!

  • Prices from $120 per night.
  • To book, check prices or availability for The Talbott Hotel

Hotel EMC2 – a unique modern/vintage chic design hotel

Hotel EMC2 - a unique modern/vintage chic design hotel

Hotel EMC2 - chic design hotel in Chicago

This unique Chicago hotel which is part of the prestigious Autograph collection 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 hotels 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 epicurean delights of one of the finest hotels in the city. Just fabulous darling!

  • Prices from $110 per night.
  • To book, check prices or availability for Hotel EMC2

Thompson Chicago – a dashing Gold Coast beauty and one of the best modern hotels to stay in Chicago

Thompson Chicago - a dashing Gold Coast beauty

Thompson Chicago - one of the best modern hotels to stay in Chicago

Chicago’s affluent Gold Coast is full of upscale restaurants and historic mansions and nestled in amongst them (very near the Michigan Ave and The Magnificent Mile) is this sophisticated Chicago abode. The 4-star exceptionally rated Thompson Hotel is 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.

This luxury Chicago boutique hotel offers bedrooms that ooze style, with floor to ceiling windows affording fantastic views out across the famous Chicago skyline as well as all the usual mod cons such as high-thread-count sheets, flat-screen TVs and rainfall showers. One of the hottest eateries in the city, Nico Osteria is situated in the hotel, and if you can book a table you are in for a treat.

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

  • Prices from $150 per night.
  • To book, check prices or availability for Thompson Chicago

Chicago Athletic Association – a chic hipster’s paradise set in an 1890s Gothic building that once housed an exclusive sportsmen’s club

A trendy hotel Chicago

Chicago Athletic Association - a chic hipster's paradise

Situated in Chicago’s Downtown area overlooking Michigan Avenue, the Chicago Athletic Association is arguably one of the best-located and coolest hotels in the city. The hip Chicago hotel makes an instant impression with its gothic architecture, subtle lighting, a variety of classic furniture, and its sporty past connections.

The interior of communal areas feel like an upscale English mansion house: upmarket yet comfortable, featuring tasteful wood paneling and fascinating floor tiling, giving a historic and opulent 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!

The Kimpton Gray Hotel – a beautiful upscale Art Deco boutique hotel

The Kimpton Gray Hotel - a beautiful upscale Art Deco boutique hotel

The Kimpton Gray Hotel - an Art Deco boutique hotel in Chicago

Set in one of Chicago’s finest landmarks, the 4-star very highly rated Kimpton Grey is the height of opulence, offering smart, sophisticated, and stylish Art Deco-inspired accommodation throughout. The ornate high-rise building dates from 1894 and the trendsetting Chicago hotel is just is a 12-minute walk from central Millennium Park and offers some of the finest views you can find in the city.

With quirky amenities on offer 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 hotel. Just an all-round beautiful place to stay in Chicago.

Virgin Hotels Chicago – a hip hotel voted #1 Hotel by Conde Nast Reader’s Choice

A trendy hotel in Chicago

Chic hotel in Chicago

A trendy Chicago hotel with modern sophistication and truckloads of style. Located in Chicago’s Loop area in Downtown, travelers will be spoilt for choice with so many things to see and do right on their doorstep. The cool hotel has an upscale ambiance without feeling too highbrow, allowing guests to relax, have fun, and be themselves.

Communal areas and bedrooms have great attention to detail with plush furnishings and modern ornamental pieces. Like many hotels in the city, the 4 star Virgin Hotels’ Chicago has a chilled-out rooftop bar area with breathtaking views of the wider city. Although closed during the heart of winter, warmer months see a DJ and lively crowd until the early hours.

Freehand – funky budget Chicago accommodation housed in a 1927 building 

Hip hotel in Chicago

Unique hotel in Chicago

Based in Chicago’s trendy River North neighborhood, Freehand Chicago is nearby central amenities and within easy access to all areas of the city. The hotel is set inside a refurbished 1920s art deco building and among Chicago’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 plenty of fun and games. A fitness center, cheap parking, and a coffee bar are some additional popular amenities.

  • Prices from $60 per night.
  • To book, check prices or availability for Freehand Chicago

The Versey – a fabulous and reasonably priced hipster boutique hotel

Freehand - funky budget Chicago accommodation

Freehand - funky budget accommodation

The Versey offers a great budget option for those looking to explore the city. Situated in the central Lincoln Park neighborhood in downtown Chicago, a wealth of restaurants, bars, excellent music venues, and boutiques are located right on your doorstep.

With small, but perfectly formed, clean and well-styled funky bedrooms, free Wi-Fi and passes to the nearby LA Fitness gym, this colorful and modern functional highly rated hotel offers fuss-free accommodation for those looking to spend their cash elsewhere during their stay. The Chicago-themed art on the walls, and the brightly colored lobby with its maps and murals, sports memorabilia and records will inspire you to get out there and explore the Windy City for yourself!

The Blackstone Hotel – immaculate classic elegance and a beautifully unique place to stay in Chicago

The Blackstone Hotel - a beautifully unique place to stay in Chicago

The Blackstone Hotel - a beautifully unique place to stay in Chicago

A beautiful design hotel in Chicago

An architectural icon with a legendary past, the 4-star exceptionally rated Blackstone Hotel which is part of the prestigious Autograph collection is located on the Cultural Mile and opposite Grant Park in Down Town Chicago. Housed in a fabulous 1910 beaux-arts building and offering a one-of-a-kind experience for the most discerning of travelers, a stay at the Blackstone is an opportunity to explore Chicago’s former “Hotel of Presidents”.

Every room is completely unique and offers sumptuous sleeping accommodation complete with Wifi, iPod docks, and flat-screen TVs as well as some with gorgeous lake views. The trendy Chicago accommodation is also home to over 1,600 contemporary artworks that are a feast for your eyes, swish club rooms, a gym, and the onsite Mercat a la Planxa restaurant which earns rave reviews for its upscale tapas menu, excellent wines, and upbeat atmosphere as well as craft cocktails with an original 1960s vibe. This place will envelop you in so much sumptuous elegance you won’t want to leave!

ACME Hotel – fun, funky and full of tech

ACME Hotel - fun, funky and full of tech

ACME Hotel - fun and funky Chicago hotel

The exceptionally rated Acme Hotel enjoys a fabulous location the trendy central River North neighborhood (7-minute walk from shops along the Magnificent Mile), surrounded by wine bars, gastropubs and fancy boutiques galore, this hip alternative boutique hotel in Chicago is just a five-minute walk away from the shopping haven of Michigan Avenue.

With a bohemian feel, this unique and funky Chicago hotel oozes quirky indie-cool and is dotted with buzzing neon signs, graffiti-painted stairwells, and a lift with walls made of classic album covers. Perfect for urban hipsters of all ages, the cool hotel even provides cool but comfy, tech-savvy bedrooms with free Wi-Fi ergonomic chairs, wireless sound systems, and smart TVs. You can even rent Apple watches and Google Glasses to use during your stay – now that’s attention to detail! When you are done exploring, settle down and relax in the hot tub, with a craft cocktail at the bar or even grab a pastry at the onsite bakery – a cool and funky city oasis!

  • Prices from $90 per night.
  • To book, check prices or availability for Acme Hotel

The Gwen – a prestigious, trendy and unique Chicago hotel

The Gwen - a prestigious, trendy and unique Chicago hotel

The Gwen - a trendy and unique Chicago hotel

A Luxury Collection Hotel Member and once voted one of the best luxury hotels in Chicago by Travel and Leisure, this place is really something else. From the breathtaking Art Deco lobby through to the first-floor limestone panels carved by Chicago-born acclaimed sculptor Gwen Lux, this chic and trendy Chicago hotel is truly a vision to behold! Just a few short steps from central Michigan Avenue with its collection of shops, restaurants, and bars, you will be sleeping in the heart of the city.

With brass features and fittings, the 5-star exceptionally rated Gwen Hotel has rediscovered its 1930s origins and the provocative and theatrical styling is displayed throughout the hotel in intricate detail. The upscale stylish bedrooms all invoke the sumptuous styles of the Deco period but are combined with a range of modern conveniences including luxury toiletries, Keurig coffeemakers, free Wi-Fi and enormous wall-mounted TV’s.

Other fabulous amenities include a sophisticated restaurant, a terrace bar offering superb city views, a gym, and a very grand lobby lounge. A much-loved Chicago institution! 

Aloft Chicago City Centre – a cool and colorful urban-chic retreat

Aloft Chicago City Centre - a cool and colorful urban-chic retreat

Aloft Chicago City Centre - an urban-chic retreat

Another of the best hotels to visit in the uber-hip River North neighborhood in central Chicago (a 6-minute walk from Michigan Avenue’s high-end shopping) is the popular and exceptionally rated Aloft Chicago. The unique and contemporary glass-fronted hotel is jam-packed with cool retro touches and is only situated a short walk from lots of fabulous restaurants, shops, and vibrant nightlife.

A pool table in the lobby and a gym in the basement are just a few of the quirky additions that transform this hip Chicago hotel from just an overnight stay to an eclectic experience. All rooms offer colorful interiors, dedicated workspaces, and fast and free WiFi – perfect for mixing business with pleasure. Sip a cocktail in the hotels very own WXYZ® bar or recharge in the Re:mix lounge before heading back out to explore the wonderful windy city. Oh and if that’s not enough your furry friend gets a bed, water, and treats too – nice!

Kimpton Hotel Allegro – a modern chic boutique hotel located in the Theater District

Kimpton Hotel Allegro - a modern chic boutique hotel in Chicago

Kimpton Hotel Allegro - a modern chic boutique hotel

The Golden Era of America remains alive and well in this refurbished hotel set in the heart of Chicago’s central Theatre District. A gorgeous chic boutique hotel with a theatrical feel, you will be just moments away from the very best shops, bars, and restaurants the city has to offer. Opulent and elegant,  the 4-star exceptionally rated Allegro Hotel offers bedrooms with in-room spa services, cool retro styling feature, flat-screen TVs, iPod docks and Wi-Fi access, as well as minibars and yoga mats.

In the gorgeous suites, you’ll find sitting areas and some have whirlpool tubs. Other highlights include a fine Italian restaurant, an onsite fitness center, it’s pet-friendliness, and the Bar Allegro offering cocktails and fine wines long into the evening (with daily free sociable wine hours). Transport yourself back to a bygone era with Art Deco luxury to be found throughout, this unique Chicago hotel is the perfect spot to relax after a long day exploring!

FieldHouse Jones – cool, trendy and fun budget Chicago lodging

FieldHouse Jones - cool, trendy and fun budget Chicago lodging

FieldHouse Jones - fun budget Chicago lodging

The very highly rated 3-star FieldHouse Jones offers distinctly unique Chicago accommodation set in the trendy central North River neighborhood (only a 3 minutes’ walk from Chicago subway station). With a hip retro sports-themed hotel and flexible room types, ingenious bed arrangements, and first-of-their-kind vacation-apartments you can tailor your stay to suit your needs.

You can also expect custom-made beds, hand-crafted tiles, wide-plank oak flooring, heritage leather benches and original curated art – FieldHouse Jones offers interiors that are designed to impress and wow you!  There are several cool events always going on and ttheir’DropShot’ coffee bar provides brunches, light lunches, and steaming hot coffee, all served in the industrial style surroundings that the city is so famous for.

A funky vibe, flexible accommodation, and very reasonable prices for every kind of visitor can be found at Fieldhouse Jones! Enjoy!

  • Prices from $40 per night.
  • To book, check prices or availability for FieldHouse Jones

The Ace – a hipster’s hangout and one of the coolest hotels in Chicago

The Ace - one of the coolest hotels in Chicago

The Ace - a hipster's hangout in Chicago

The Ace hotels always have an unbeatable cool vibe and this hipster-magnet Chicago version is no exception. This industrial-looking concrete and glass building in the West Loop of the city houses chic and uber-cool bedrooms, trendy eateries, and funky communal spaces.

At the 4-star exceptionally rated Ace Hotel guest rooms come with skyline views, the City Mouse restaurant, the Waydown bar, and the Stumptown Coffee Roasters Cafe all combine to provide an industrial style hotel that offers everything you need and more, including plenty of fun!

Bedrooms offer organic cotton sheets, DAB radio, and flatscreen TVs alongside retro furnishings, tiled walls, and plenty pipework. Upgrade to a suite and you could even find a turntable or an acoustic guitar tucked away inside, giving you the opportunity to be the Chicago rock star you always dreamed of.

  • Prices from $120 per night.
  • To book, check prices or availability for The Ace Hotel

The Guesthouse Hotel – a chic apartment hotel and an awesome place to stay in Chicago

The Guesthouse Hotel - a chic apartment hotel in Chicago

The Guesthouse Hotel - an awesome place to stay in Chicago

The Guesthouse Hotel pens itself as a luxury home away from home, offering affordable, comfortable accommodation in the Lincoln Park neighborhood of the city. Stop outside this highly rated hip Chicago hotel and you can explore the upscale stores on central Armitage Avenue, or the cafés, restaurants, and sweet shops of Clark Street and the historic

Andersonville neighborhood. The Guesthouse offers one, two and three bedrooms suites that easily offer the same size accommodation as many city apartments do, and are all beautifully appointed throughout with granite kitchens, private balconies or patios with gas grills and some have soaking tubs. 

With chic, modern contemporary decor, and long stays available, The Guesthouse really does offer visitors to the city the perfect crash pad no matter how long they intend to stay. Opt for a penthouse suite if you can as they come with a private rooftop deck offering truly gorgeous skyline views! 

Blackstone Hotel images are copyright of Blackstone hotel. The first image for the Talbott Hotel was taken by 

We also have posts on…


Born in England, with a few family roots from Bavaria, and a heart in Scandinavia I've always been a bit of a restless soul. My first true adventure began as a six month voyage around South East Asia as a fresh faced backpacker and ever since I've lived a semi nomadic existence, clocking up over 40 countries on trips and living in Dublin, South East Asia and Australia. I'm a lover of US Road Trips, deserted beaches bathed in warm glow of a sunset, Cuban mojitos, easy-on-the-eye travel destinations far away from the tourist crowds and all things Scandinavian - from cloudberry liquors to Scandi Noirs. When not wandering the world, you'll find me walking my rescue dog in leafy South West London, strolling around the Brighton Laines on random day trips, hunting for photogenic landscapes or daydreaming about returning to my all time favourite places in the world; Havana, Copenhagen, Italy, Thailand and the frozen landscapes of a wintry Iceland. Follow Becky on Twitter and Google+.

Leave a Reply