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15 Unique Places to Stay in Chicago, Illinois

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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 or Los Angeles.

However, its nickname “Second City” doesn’t mean it’s not a first-class destination – in fact, it earned that nickname when it was rebuilt after the Chicago fire, better than ever. So, whether you’re here for a weekend or a week, Chicago is an excellent place to visit.

As travelers or visitors, we usually tend to gravitate to well-known places, especially when it comes to lodging options in cities we’ve never visited. Many of Chicago’s hotels can be found downtown in The Loop neighborhood, though you shouldn’t discount accommodations in one of the city’s dozens of other neighborhoods either.

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

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

Unique Places to Stay in Chicago, Illinois

1. ACME Hotel

Acme Hotel Hotel entrance in Chicago, Illinois
4kclips / Shutterstock

Address: 15 E Ohio St, Chicago, IL 60611

The ACME Hotel has a long-standing history in the city, dating back to 1924 when it was The Berkshire Hotel. It may not be the oldest among hotels in Chicago (that would be The Palmer House), though it’s certainly one of the most unique. This hotel was voted #1 in Condé Nast Traveler’s 2019 Reader’s Choice and the #2 Hotel in Chicago in 2020.


The ACME Hotel is a chic, modern-looking hotel with a traveler’s budget in mind. Centrally located in River North, you’re just steps from some of Chicago’s biggest crowd-pleasers including Millennium Park. The hotel also has a coffee shop called West Town Bakery, an offsite bowling alley, a fitness center, bicycle rental services, and even a private hot tub area you can rent called Bunny Slope.

What’s surprising is that all these features do not come at a high cost – ACME Hotel is one of the best value boutique hotels in the city. For a local social experience, ACME also has The Berkshire Room – a cocktail lounge named for the former hotel.


The location of ACME is probably one of its best qualities. It sits near the Magnificent Mile, also known as The Mag Mile, which offers countless shopping and recreational opportunities.

What’s unique about the ACME Hotel?

ACME Hotel’s design leans towards a vintage style with a modern twist. It even hosts its own local art initiatives like the eclectic River North Arts Exhibits – a fitting endeavor as the lobby has a mural created by Brian Tull.

There is also an ongoing partnership with the nearby Lincoln Hall and Schubas Tavern for live music events. So, if you’re the young and/or trendy sort and want to be immersed in the culture of the city, this is one of the best places to stay in Chicago.

Planning a trip to Chicago soon? Make sure that your travel is protected before your stay in Chicago. Check out SafetyWing to get the best travel insurance deals.

See Related: Best Boutique Hotels in Chicago for a Unique Experience

2. The Blackstone Hotel

Lobby of The Blackstone Chicago
The Blackstone Hotel /

Address: 636 South Michigan Avenue, Chicago, IL 60605

For a luxury hotel with a history, The Blackstone Hotel is definitely one of the best places to stay in Chicago. This iconic hotel has been in the Windy City for more than a century, making it just as much of a tourist destination as anything else.

From presidents to celebrities, The Blackstone is still a prime destination in downtown Chicago for people who want to have the best experience in the city. There’s a reason its nickname is The Hotel of Presidents. Generations of America’s leaders have stayed here since it opened in 1910.


The Blackstone Hotel offers a luxurious experience to those who want to stay in downtown Chicago in style. It also has an on-site fitness center, a mod-Medittereanean restaurant called Mercat a la Planxa, a bar, and a game room for billiards.


Set within walking distance of some of Chicago’s greatest treasures like Millennium Park and the Art Institute, The Blackstone is an excellent home base for a stay in Chicago. It is especially great for walkers who want to have a more intimate tour around the city. It’s also perfect for biking around the vicinity.

If you’re looking for the best place to stay during the spring or summertime, The Blackstone is one of the best hotels in Chicago to choose from. Not only are you able to walk around downtown with ease, but you can also get a room with a clear view of stunning Lake Michigan — Chicagoans love Lake Michigan.

What’s unique about The Blackstone Hotel?

It is a hotel with a rich history, as it 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 the hotel was launched in April 1910.

Since then, this hotel has bared witness to many historical events. This was where the Republican leaders decided to nominate Warren Harding for president and Al Capone had meetings with his “business associates” — newcomers to Chicago will recognize that Capone is linked to a lot of places all over the city.

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

3. Villa D’ Citta

Villa D'Citta Pool in Chicago
Villa D’ Citta /

Address: 2230 N Halsted St, Chicago, IL 60614

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 in Lincoln Park.

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.


Dubbed Chicago’s “Old World Style” luxury bed and breakfast, Villa D’ Citta offers complimentary breakfast, a jacuzzi, a sun deck, and a sitting area, among other amenities. What’s especially unique about this place is its old European influence in all aspects.


Nestled at the heart of the Lincoln Park neighborhood, Villa D’ Citta lies near the boutique shopping district and Chicago’s beloved Lincoln Park Zoo. This is an excellent place for those who want to walk around the city, as it is located near historic sites such as the Garfield Park Conservatory, Macy’s on State Street, and The Rookery Building. Also in the neighborhood is North Avenue Beach, though you may want to drive there.

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. Typical Chicago-style homes you’ll see around the city are bungalows and two flats.

See Related: Is Chicago Safe for Travelers?

4. Freehand Chicago

Lobby of the Freehand Chicago
Freehand Chicago /

Address: 19 E Ohio St, Chicago, IL 60611

Also on our list of unique places to stay in Chicago is this hotel set inside a refurbished Art Deco building from the 1920s. Freehand Chicago‘s overall aesthetic is a tribute to the cozy Midwestern city with warm wood tones and a historical vibe. If you’re looking for an affordable and different vibe, this is your place to stay in Chicago.


This unique boutique hotel can accommodate groups of all sizes and even offers room service for those times when you really want to be alone. You’ll also have access to the hotel’s cocktail bar, Broken Shaker, and their on-site café as well.


Freehand Hotel is located in downtown Chicago and is only a 2-minute walk away from the Magnificent Mile. It’s also near other Chicago Loop attractions like the shopping district on Michigan Avenue and Water Tower Place.

There are also popular beaches near the hotel as well like Ohio Street Beach and Oak Street Beach. It may not be the ocean, but Chicagoans treat our massive lake as such. Don’t knock our beaches until you try them.

What’s unique about the Freehand Hotel?

Its architecture and style are a standout. As mentioned, the hotel resides in a 1920s Art Deco building and the decor reflects this bygone era. You’ll notice the buildings along the Chicago River reflect the city’s deep love of the Art Deco architectural style. Be sure to check them out during your stay in Chicago.

5. Aloft Chicago Downtown River North

Room at the Aloft Chicago Downtown River North
Aloft Chicago Downtown River North /

Address: 515 N Clark St, Chicago, IL 60654

If you are looking for the best place to stay downtown, the trendy Aloft Chicago Downtown River North may be the spot for you. This unique, contemporary hotel has a glass front and an interior packed with touches of retro designs, colors, and decor.


In general, most guests agree that this hotel provides extremely comfortable beds. The property also boasts an onsite bar called WXYZ, its restaurant Beatrix, a coffee house, a fitness center, and an activity room with a pool table.


Aloft Chicago Downtown River North is within walking distance of many of the city’s top attractions. A tour of the neighborhood will bring you to Chicago’s top attractions, such as The Art Institute of Chicago, the Willis Tower, and the Magnificent Mile. You’re also in the midst of many boutique shops, amazing restaurants, and live music venues in River North as well.

What’s unique about Aloft Chicago Downtown River North?

Aloft Chicago Downtown River North’s design makes it one of the coolest hotels to stay in Chicago. From the outside, you can’t miss the chic glass exterior of the hotel.

Glass exteriors are common for skyscrapers in the massive city, however, that style trend has not carried over to many Chicago hotels yet, so Aloft is quite different. 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

Interior of the Old Chicago Inn
Old Chicago Inn Bed and Breakfast / Expedia

Address: 3222 N Sheffield Ave, Chicago, IL 60657

A quaint and quirky bed and breakfast with gracious hosts that treat customers like family – is this something you’d expect from a small inn, smack dab in the middle of Chicago? It should be. You are in the Midwest after all!

That’s exactly what Old Chicago Inn offers from its home in Lakeview. This 10-room Sheffield Avenue property not only offers an incredible city view but also a home away from home in its 1920s and Prohibition-inspired lodgings.


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

Plus the hotel’s Room 13 speakeasy-style bar in the basement is a hit for members and guests alike. Keep in mind that Room 13 has a cocktail/business casual dress code.

In addition to that, guests receive complimentary breakfast each day as well as one complimentary meal at Trader Todd’s a few doors down during their stay.


The Old Chicago Inn is about 30 minutes away from both Midway International Airport and O’Hare International Airport. With three train lines, it’s also less than 15 minutes away from the Loop too.

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

Apart from its antique furniture and 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 1920s. At the same time, 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

7. The Publishing House Bed and Breakfast

Interior of The Publishing House Bed and Breakfast
Publishing House Bed and Breakfast /

Address: 108 N May St, Chicago, IL 60607

Perhaps one of the most unique boutique hotels one can find in Chicago is The Publishing House Bed and Breakfast in the West Loop neighborhood. This historic building was built in 1909 and once housed the Free Methodist Publishing House. In 2017, the building was reopened as a bed and breakfast with its own distinctive charm.


With furnishings akin to luxury hotels, The Publishing House is defined by its stunning interiors. Guests are treated to a lavish breakfast each morning before they set off for their day of big-city adventures.


Publishing House is in the West Loop, yet very close to the downtown area. West Loop is Chicago’s former meat-packing district, though it has gotten quite a makeover in the past few decades.

The surrounding neighborhood is full of bars and live music, restaurants, boutiques, and galleries. It is also located near top attractions like Willis Tower (locals will forever call it The Sears 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 clearly 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: Things to Do in Cincinnati, Ohio

8. Sophy Hyde Park

Lobby of Sophy Hyde Park Hotel
Sophy Hyde Park /

Address: 1411 E 53rd St, Chicago, IL 60615

Sophy Hyde Park offers luxury accommodations featuring community-inspired works. This suits its Hyde Park home as this neighborhood in Chicago is full of artists, history, and culture. If you want to immerse yourself in Hyde Park’s history, staying at the Sophy Hyde Park would maximize your experience.

Named for the Greek word for wisdom, Sophos, the Sophy is perfectly suited to Hyde Park. Why? Because the neighborhood is widely known for being home to a number of Nobel Prize winners as well as the former home of President Barack Obama.


The aesthetic of the Sophy is fashioned after the many, many cultural icons who called the city and neighborhood home. Flush with color and music, it is meant to curate inspiration around every corner.

It does not have an on-site bar or restaurant like many other hotels in Chicago, though you are certainly not lacking in either around the neighborhood. Get to know the area and you’ll become more acquainted with Chicago.


In Hyde Park, one of the most iconic neighborhoods in Chicago, guests have access to much of what Chicago has to offer. This area is home to the Museum of Science and Industry, the DuSable Black History Museum and Education Center, lots of shopping and eateries, and a couple of public parks. Though outside of the Chicago Loop neighborhood, it’s still close to downtown without staying in downtown.

What’s unique about Sophy Hyde Park?

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

See Related: Chicago CityPASS Review

9. Chicago Athletic Association

Cindy's restaurant on the 13th floor of Chicago Athletic Association
Leonard Zhukovsky / Shutterstock

Address: 12 S Michigan Ave, Chicago, IL 60603

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. This iconic Venetian Gothic-style building looks more cathedral than a hotel from the street. Even so, the city landmark is easily one of the most iconic hotels in Chicago.

Don’t think that this Chicago accommodation is lacking in any modern amenities. Steps away from the Magnificent Mile, the Chicago Athletic Association beckons visitors to seek out its hallowed halls.


Perched upon the 13th floor, Cindy’s is the hotel’s on-site restaurant. With a domed glass ceiling, guests get stunning views of the surrounding city. Not to mention the rooftop bar access via the open-air terrace.

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. As such, this hotel is one of the more fun places to stay in Chicago.


The Chicago Athletic Association is on South Michigan Avenue, nestled within the Chicago Loop. You can easily access the whole city from here by train or simply enjoy walking around downtown.

What’s unique about the Chicago Athletic Association?

The Chicago Athletic Association has a rooftop lounge overlooking Millennium Park and Lake Michigan. But more than the incredible view this hotel provides, its charm lies in its concept of mixing vintage and athletic equipment with modern comforts.

If you want a truly Chicago experience, this is the place to do it. There’s also an eight-seat speakeasy in the hotel that club members used during the Prohibition era.

10. Hotel Versey

Lobby of Hotel Versey Chicago
Hotel Versey /

Address: 644 W Diversey Pkwy, Chicago, IL 60614

Known by several names including the “Rock and Roll Days Inn,” Hotel Versey is one of the coolest hotels you can find in Chicago. The name Versey comes from a shortened name for the street the hotel is located on, Diversey.

It even has 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.

Nestled in Lincoln Park, this funky hotel has been a hot spot for hotshots for decades. Chicago’s history in the music industry can’t be understated. So it makes sense that a place like this solidifies that history.


Local art can be found throughout the hotel, connecting the building’s storied history in the music arts to the Chicago artists of today. Guests have access to a nearby gym as well since the hotel does not have its own fitness center.


Hotel Versey is in Lincoln Park, easily within walking distance of many of the neighborhood’s favorite destinations. From the Lincoln Park Zoo to the Garfield Park Conservatory to the Chicago History Museum, there’s a lot to see in this neighborhood.

What’s unique about Hotel Versey?

To pay tribute to its 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. Being in Lincoln Park as well makes this hotel a great place to stay in Chicago with easy access to the other city neighborhoods.

See Related: Things to Do in Chicago

11. Virgin Hotels Chicago

Rooftop bar at Virgin Hotels Chicago.
Virgin Hotels Chicago /

Address: 203 N Wabash Ave, Chicago, IL 60601

Steps away from the Magnificent Mile, Virgin Hotels Chicago is one of downtown’s trendy, modern hotels. This boutique hotel is just right in the middle of the hustle and bustle of downtown.

This is one of the best hotels to call home, especially if you are seeing a show at The Chicago Theatre which is steps away. From here, too, you can easily see shows of all varieties at a swath of Chicago’s incredible performing arts houses. After all, the city is home to over 200 theater companies, so there truly is something for everyone.


This Chicago hotel features a rooftop bar called Cerise, the Two Zero Three coffeehouse, and Italian eats at Miss Ricky’s. Guests don’t have to wander far from this spot’s rooftop lounge to find a good time or good fun since the location often hosts live music events.

Your best fur friend doesn’t have to miss out on the fun either since this hotel is pet friendly! They can get pampered while the two of you explore the city together.


Being right by the Magnificent Mile, this hotel is in the perfect spot for traversing the city — especially downtown. Guests have easy access to the train system here as well. Plus, Navy Pier is a short drive or bus ride away.

What’s unique about Virgin Hotels Chicago?

With bright and trendy decor combined and multiple dining locations, this boutique hotel is primed for a young or young-at-heart crowd. The modern accommodation has several onsite establishments for guests while remaining an affordable Chicago hotel.

12. Guesthouse Hotel

Sitting area at the Guesthouse.
Guesthouse Hotel /

Address: 4872 N Clark St, Chicago, IL 60640

Up North in Ravenswood or Andersonville or even down in Lincoln Square, this Chicago hotel chain is ready to charm you. A boutique hotel that is more home than vacation living, Guesthouse Hotel is ready to give you a taste of Chicago. These apartment-style units are perfect for families, folks wanting an extended stay, and your pups too!

No matter which location you choose, you’ll be living Chicago-style. With walkable neighborhoods at your disposal, the whole city is your destination.


Because Guesthouse is made up of apartment-style accommodations, there are full kitchens and washers/dryers in each unit. There’s plenty of room to sprawl out and even patios to enjoy the outdoors from the comfort of your home away from home. Dogs are more than welcome.

Guesthouse is one of the best hotels for extended stays since it has the comforts of home. Plus a fitness center will keep you trim even while on vacation or workcation.


All of the locations of Guesthouse are just steps away from tons of food, drink, and shopping options. Although the kinds of eateries you’ll find in Ravenswood may differ from Lincoln Square, you’ll undoubtedly find lots of tasty options anywhere you go.

What’s unique about the Guesthouse Hotel?

Even though it’s a boutique hotel, Guesthouse is an apartment-style accommodation. You have access to laundry at no additional cost from the comfort of your unit and full kitchens in each of the Guesthouse units.

Depending on the location, you may also have roof access and a balcony to enjoy the outdoors. While many hotels have outdoor spaces to utilize, few have the privacy that Guesthouse offers to their visitors.

13. Thompson Chicago

Hotel room with view of the city at the Thompson.
Thompson Chicago /

Address: 21 E Bellevue Pl, Chicago, IL 60611

Back near downtown, the Thompson Chicago is one of the best luxury hotels you’ll find in the Gold Coast. Gold Coast is a stunning neighborhood just North of downtown with incredible views of the lake, as well as some of the city’s finest examples of architecture. Dotted with mansions, the chic Thompson fits right in.

Having long been a Chicago hotel, though with a variety of names, the Thompson is a mainstay in the city. While the Gold Coast neighborhood is gorgeous and near downtown, you’ll probably want a cab or public transit to get to the Magnificent Mile. Even so, you’ll forget the distance when you fall in love with this space.


In-room dining, the hip Italian seafood restaurant Nico Osteria and cocktail lounge Salone Nico may compel you to stay inside. That said, there are also lots of restaurants in the neighborhood to check out even if you fall in love with Nico Osteria’s Heirloom Polenta.

Mid-century modern (MCM) aesthetics envelop guests in that warm Midwestern feeling in a Chicago hotel that is also pet-friendly. You will truly get a sense of the region’s sense of style here between the embrace of the dark tones and MCM vibes.


Although you’re surrounded by luxury homes in this neighborhood, Gold Coast is still remarkably walkable. It may not have as many spots to check out as other parts of the city, but there is still so much to see when staying at the Thompson.

If you want to venture elsewhere in the city, you’re still close to public transit as well. Chicago’s CTA trains and busses are easy to navigate even for first-timers.

What’s unique about the Thompson?

A cozy hotel to give guests a comfortable place to spend their time, the Thompson offers one of the more unique stays in Chicago. Since it’s largely residential, there aren’t a lot of hotels in the Gold Coast neighborhood. Staying here provides visitors with a fascinating neighborhood backdrop for their trip while also giving them proximity to the lake and activities throughout the city.

14. The Robey

The rooftop pool area at The Robey.
The Robey /

Address: 2018 W North Ave, Chicago, IL 60647

A stylish hotel in Wicker Park, Chicago’s hippest neighborhood, The Robey is a chic slice of the city’s history. An Art Deco office building turned hotel, The Robey has gorgeous guestrooms with historic touches. Reminiscent of its past, The Robey embraces what makes it different by highlighting its Art Deco features.


Rooftop bar and pool areas help The Robey stand out among the other hotels in Wicker Park or elsewhere in Chicago. Café Robey provides morning pleasantries for guests in a comfy coffee shop setting.

Not to mention the hotel’s free bike rentals which help you easily get around Chicago. While car traffic might be intimidating for out-of-towners, Chicago is full of biking paths and ways to get around without relying on a car. If you rent a bike, you need to check out the lakefront bike path for unparalleled views of the lake and the city skyline.


Wicker Park is a favorite hotspot in Chicago for good reason. Here is where you will find countless bars, lounges, and restaurants plus arts inclusions that upkeep the area’s vibes. This is where locals and visitors alike flock, so things are also highly walkable.

What’s unique about The Robey?

Since it’s housed in an Art Deco building, The Robey includes lots of historic touches. Rooms reflect the building’s history in their decor aesthetics and guests can truly feel like Jay Gatsby’s party guests while lounging by the rooftop pool.

15. Wicker Park Inn

Bed with floral and bird wallpaper at Wicker Park Inn.
Wicker Park Inn /

Address: 1331 N Wicker Park Ave, Chicago, IL 60622

With nine rooms, the boutique Wicker Park Inn is a chic bed and breakfast in the Wicker Park neighborhood. Housed in a historic home, this B&B is full of homey touches to brighten up every day that guests spend here. The whole house can even be rented for special events or other occasions.


Each room has a skylight and decorative fireplace, giving them each plenty of light and charm. Guests are given breakfast each morning, the perfect start to an adventurous day. Plus the location of the hotel is perfect with easy access to many establishments throughout the neighborhood.

Rooms have either a queen or king-sized bed and the apartment-style room even has a separate single bedroom. The garden-level apartment room also has a queen-sized sleeper sofa as well to accommodate more guests.


The inn is near public transportation and in an easily walkable neighborhood. It should be noted that there are stairs at the inn which some travelers may have trouble with if booking a room that is not on the first floor.

What’s unique about the Wicker Park Inn?

Since the inn is found in a historic neighborhood home, the experience at Wicker Park Inn is authentically Chicago. Each room is vibrant with comfortable accommodations at a reasonable price.

Unique Hotels in Chicago for an Experience to Remember

Unsurprisingly, there are quite a number of interesting and cool places to stay in Chicago. Chicago’s history is fascinating and full of intrigue which makes it a great spot for travelers who love to learn. From budget to luxury, Chicago offers a wide range of hotels with unique qualities that would make your trip to the Windy City one you will never forget.

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.

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