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10 Unique Places to Stay in Chicago, Illinois

The Windy City has so much to offer when it comes to culture, arts, and recreation. It is one of the largest cities in the United States, but it’s not as fast-paced and crowded as New York City. Just as there are numerous places to visit in Chicago for those passing through, there are also several unique places to stay in Chicago for those who want to get the best of the city.

As travelers or visitors, we usually tend to gravitate to well-known places, especially when it comes to lodging options.

But if you’re like us and want to have a unique adventure, why not book more interesting places? There are numerous hotels and accommodations in Chicago with rich history and gorgeous designs.

Let us give you a peek into some of the more unique places to stay in Chicago.

What makes Chicago accommodation unique and interesting?

Building with Chicago Sign

Before we list our top picks for the best places to stay in Chicago, it’s better to first lay down our qualifications for choosing these places.

Here are the factors we’re looking for in our bid to let you know about some good places to stay in Chicago:


One of the top factors to consider is the quality of the amenities that come with the place.

Of course, big chain hotels top this category, however, the most significant factor we’re looking at here is comfort. If the hotel offers a clean, comfortable, and well-designed accommodations package, then it is good enough in our book.


Another factor to consider when choosing the accommodation to stay in is the accessibility and location of the hotel.

We have to ask these questions:

  • Is the hotel centrally located?
  • Are the main sights and areas you are planning to visit located near the hotel?
  • Does the hotel have nearby metro lines to airports?

Unique Story or Concept Behind the Hotel

Hotels can be destinations instead of just places to stay.

For instance, there are numerous hotels with rich history, background, or interesting concepts in Chicago.

10 Unique Places to Stay in Chicago

We’ve rounded up the best and most unique places to stay in Chicago. So without further ado, here are some of the hotels you might want to book today!

1.      ACME Hotel

Ocean, Sky, and Cityscape

ACME Hotel is probably one of the first hotels on anyone’s list. This hotel was voted #1 in Condé Nast Traveler’s 2019 Reader’s Choice and #2 Hotel in Chicago in 2020.

·         Amenities

ACME Hotel offers a complete list of in-room amenities to its guests.

The hotel also has a coffee shop, an offsite bowling location, a fitness center, bicycle rental services, and complimentary high-speed internet.

What’s surprising is that all these features do not come at a high cost— ACME Hotel is one of the best budget boutique hotels in the city. For a local social experience, ACME also has The Berkshire Room— a cocktail lounge where the locals meet to socialize.

·         Accessibility

The location of the hotel is probably one of its best qualities. It lies near the Magnificent Mile, one of the leading hospitality destinations in the world.

·         What’s unique about ACME Hotel?

ACME Hotel‘s design leans towards the vintage boutique style that offers the comfort of more modern hotels.

This hotel hosts its own local art initiatives like the Eclectic River North Arts Exhibits. Its lobby has a mural created by the Brian Tull.

It also has an ongoing partnership with the Lincoln Hall and Schubas Tavern for its music events.

So, if you’re the young and/or trendy sort and want to be immersed in the culture of Chicago, this is one of the best and safest places to stay.

Planning a trip to Chicago soon?

Make sure too that your travel is protected before you visit the Windy City. Check out AARDY to get the best travel insurance deals!

See Related: Skiplagged Review

2.      The Blackstone Hotel

Boat Cruising on a Green River

For a luxury hotel with history, The Blackstone Hotel is definitely one of the best places to stay in Chicago.

This iconic hotel has been in Chicago for more than a century, making it just as much of a tourist destination as other Chicago attractions.

From presidents to celebrities, The Blackstone is still a prime destination for people who want to have the best experience in the city. Here are some of the reasons why we chose this hotel:

·         Amenities

The Blackstone Hotel offers a luxurious experience to those who want to stay in Chicago in style. It also has its own fitness center, restaurant, banquet room, conference facilities, bar, and lounge for games like billiards.

·         Accessibility

This hotel is 0.6km away from the center of Chicago’s bustling district. It is great for walkers who want to have a more intimate tour around the city. It is also perfect for those wishing to bike around the vicinity without any issues.

If you’re looking for the best place to stay in Chicago for St Patrick’s Day, we recommend The Blackstone Hotel.

·         What’s unique about The Blackstone Hotel?

It is a hotel with a rich history. This hotel was initially a mansion built for Timothy Blackstone, the president of the Chicago and Alton Railroad and the founding president of the Union Stock Yards.

However, the mansion was sold after his death and was launched in April 1910. Since then, this hotel has laid witness to many historical events.

This was where the Republican leaders held meetings to nominate Warren Harding for president. It was also where the first organized crime convention took place.

Apart from being one of the unique places to stay in Chicago, this hotel was officially declared a historic landmark in 1998. Then, it was relaunched in 2008 as the new Blackstone Hotel.

See Related: Chicago vs Detroit: What’s Better to Visit?

3.      Villa D’ Citta

unique places to stay in Chicago

Experiencing the city of Chicago through its local attractions is exciting, but what if you’re transported to a whole new environment once you step into your hotel? That’s exactly what’s going to happen if you visit Villa D’ Citta!

This bed and breakfast venue offers a stay you’ll never forget. It gives you the chance to experience a European-inspired country castle in the middle of a bustling city.

·         Amenities

Dubbed as Chicago’s “Old World Style” luxury bed and breakfast, Villa D’ Citta offers complimentary breakfast and a sitting area, among others. What’s unique about this place is its old European influence in all aspects, from furniture and flooring to furnishings and décor.

With rates starting at $129 per night, it’s one of the cheaper places to stay in Chicago.

·         Accessibility

Nestled at the heart of the Lincoln Park neighborhood, Villa D’ Citta lies near the boutique shopping district.

This is an excellent place for those who want to walk around to discover the vicinity as it is located near historical sites such as the Garfield Park Conservatory, Macy’s on State Street, and The Rookery Building.

·         What’s unique about Villa D’ Citta?

The most unique aspect of this property is its architecture. It is designed as an old-world luxury property from Italy – a sharp contrast against the modern building designs in Chicago.

Make sure you secure your travel to Chicago by getting a travel insurance package that works for you.

See Related: Is Chicago Safe for Travelers?

4.      Freehand Chicago

Bean Looking Art Piece in a City

Also on our list of unique places to stay in Chicago is this hotel set inside a refurbished art deco building in the 1920s.

Its overall design is a tribute to America’s Midwestern heritage. If you’re looking for a unique but affordable place to stay in Chicago, Freehand Chicago is one of the top options you have.

·         Amenities

This hotel can accommodate groups of all sizes, from single occupants to those who want to bunk together with their friends, family, or other guests. It has its own restaurant, bar, and fitness center.

·         Accessibility

Freehand Hotel is located quite strategically. It’s only a 2-minute walk away from the Magnificent Mile and a few more minutes away from Water Tower Chicago. There are popular beaches near the hotel like the Ohio Street Beach and the Oak Street Beach.

·         What’s unique about Freehand Hotel?

Its architecture and style are a standout. As mentioned, the hotel stands on what was previously a 1920s art deco building and the decor reflects this bygone era.

5.      Aloft Chicago City Centre

Buildings and City Lights at Night

If you are looking for the best place to stay in Chicago Downtown, the hip and trendy Aloft Chicago City Centre is the one for you. This unique contemporary hotel has a glass front and an interior packed with touched of retro designs, colors, and decors.

·         Amenities

In general, most guests agree that this hotel provides extremely comfortable beds.

The property also boasts of an onsite bar, restaurant, coffee house, fitness center, and activity rooms with billiards, as well as dry cleaning and laundry services. There are also rentable meeting and banquet facilities in the hotel.

·         Accessibility

Aloft Chicago City Centre is just three blocks away from the Magnificent Mile and is closest to the Midway International Airport and O’Hare International Airport in our list.

A tour of the neighborhood will bring you to Chicago’s top attractions, such as The Art Institute of Chicago, the Willis Tower, Oak Street Beach, and Ohio Street Beach.

If you’re visiting Chicago in March and want to book the best place to stay in Chicago for St Patrick’s Day, check out Aloft in Chicago Downtown.

·         What’s unique about Aloft Chicago City Centre?

Aloft Chicago City Centre’s design makes it one of the unique places to stay in Chicago. From the outside, you can’t miss the chic glass exterior of the hotel.

Upon checking in, you’ll see the hotel’s contemporary design accented by the colorful furnishings found in the lobby and the individual rooms of the hotel.

6.      Old Chicago Inn Bed and Breakfast

unique places to stay in chicago

A quaint and quirky bed and breakfast with a gracious host that treats customers like family—is this something one should expect from a small inn smack in the middle of Chicago?

Yet, because that’s what exactly Old Chicago Inn offers when you book it for an overnight stay! This 10-room Sheffield Avenue property not only offers an incredible city view but also provides a home away from home in its 1920s-inspired lodgings.

·         Amenities

Stepping into Old Chicago Inn’s rooms isn’t like checking into a clinical and soulless luxury hotel room from one of the big chains. Instead, they offer rooms that look more like home.

·         Accessibility

The Old Chicago Inn is less than 15 minutes away from the Midway Airport and O’Hare International Airport. With three train lines, it’s also less than 15 minutes away from the Loop, the city’s central business district.

·         What’s unique about Old Chicago Inn Bed and Breakfast?

Apart from its antique furniture and its 1920s layout, this bed and breakfast is also known for Room 13, a Prohibition-era-inspired speakeasy.

This bar offers classic cocktails heralding the years when Jazz took over the city’s music culture.

Guests from the Old Chicago Inn can enjoy a Cocktail Flight package featuring samples of various cocktails representative of the era, all while the bartenders explain historical descriptions of each drink and anecdotes that bring back memories from the Prohibition era.

See Related: Best Walking Tours in Chicago, Illinois

7.      The Publishing House Bed and Breakfast

unique places to stay in chicago

Perhaps one of the most unique boutique hotels one can find in Chicago is The Publishing House Bed and Breakfast. This historic building was built in 1909 and once housed the Free Methodist Publishing House.

After 2017, this was reopened as bed and breakfast with its own distinctive charm.

·         Amenities

The hosts are incredible cooks, and each guest is personally served a lavish breakfast to start their day.

·         Accessibility

The Publishing House Bed and Breakfast lie outside the Loop, yet very close to the downtown area.

The neighborhood of this bed and breakfast is surrounded by bars and live music, restaurants, boutiques, and galleries. It is also located near top attractions like the Willis Tower and The Art Institute of Chicago.

If The Art Institute of Chicago is on your list, buy a skip-the-line ticket in advance to save time and money.

·         What’s unique about The Publishing House Bed and Breakfast?

The owners of The Publishing House Bed and Breakfast took inspiration from the publishing history of the building.

They dedicated each room to 11 authors who have written books about Chicago, from Audrey Niffenegger to Upton Sinclair. As a result, each room has unique vintage décor and layouts.

See Related: Fun & Best Things to Do in Cincinnati, Ohio

8.      Sophy Hyde Park

unique places to stay in chicago

The Sophy Hyde Park provides a luxurious accommodation that also features community-inspired works fit for guests who appreciate art. If you want to immerse yourself in Hyde Park’s unique history and culture, staying at the Sophy Hyde Park would maximize your experience.

·         Amenities

All rooms at Sophy Hyde Park have hardwood flooring, marble-tiled bathrooms, and plush lounge seating.

·         Accessibility

This hotel is located in Hyde Park, one of the most iconic neighborhoods in Chicago. This area is home to the Museum of Science and Industry, and it has three main shopping districts and a couple of public parks.

·         What’s unique about Sophy Hyde Park?

This hotel has original art and vintage posters that make the place look more like a gallery than a hotel. It also features abstract paintings made by local artist Joey Korom.

See Related: Chicago CityPASS Review

9.      Chicago Athletic Association

unique places to stay in chicago

Once the home of a leading sportsmen’s club for 122 years, the Chicago Athletic Association is now a converted hotel located near Millennium Park.

·         Amenities

Apart from its elegant and eclectic rooms, the Chicago Athletic Association also has a grand 19th Century style ballroom with stained glass windows and an impressive recreational area.

·         Accessibility

The Chicago Athletic Association is in South Michigan Avenue, nestled within the Chicago Loop. You can easily travel to sights around Chicago since it is near the Millennium Station.

·         What’s unique about Chicago Athletic Association?

The Chicago Athletic Association has a rooftop bar overlooking Millennium Park. But more than the incredible view this hotel covers, its charm lies in its concept of mixing vintage and old-style furniture and athletic equipment with modern comforts.

There’s also an 8-seater speakeasy bar in the hotel that the club members formerly used during the Prohibition era.

10.      Hotel Versey

unique places to stay in chicago

Also called the “Rock and Roll Days Inn,” Hotel Versey is one of the coolest hotels one can find in Chicago, with a history of hosting famous rockers over the years. Imagine sleeping in the same room where Kurt Cobain dyed his hair in a bathtub or walking into the lobby where Sheryl Crow decided to go rollerblading back in the day!

·         Amenities

The hotel is also accessible to people with disabilities since it has visual aids like Braille, wheelchair-accessible areas, and lower bathroom sinks, among others.

·         Accessibility

Hotel Versey is in Lincoln Park, just a few kilometers away from Chicago’s Magnificent Mile.

·         What’s unique about Hotel Versey

To pay tribute to its storied history as the “Rock and Roll Days Inn,” Hotel Versey was reinvented with Chicago-themed décor that integrates jazz and rock history with the local art scene.

The hotel is littered with graffiti, vintage décor, and other paintings guests will enjoy immensely. Each room also has hand-painted Chicago-themed murals that will make you feel the hotel’s vibe even more.

See Related: Best Things to Do in Chicago

Stay in Unique Hotels in Chicago for an Experience to Remember

So you see, there are quite a number of interesting (and safe) places to stay in Chicago. From budget to luxury, Chicago offers a wide range of hotels with unique qualities that would make your trip to the Windy City a memory you will never forget.

When choosing good places to stay in Chicago, always take into consideration the amenities, accessibility, and stand-out quality of the property.

We also recommend securing travel insurance before the actual trip. That way, you know you are protected financially if you ever encounter accidents or inconveniences in Chicago.

Are you ready to plan your Chicago trip? Start booking your flight and accommodation today!