Best Boutique Hotels in Chicago, Illinois

12 Cool Boutique Hotels in Chicago

Located on the shores of Lake Michigan, Chicago is an impressively diverse city with no end of things to see and do. Condé Nast Traveler has even listed it as the best large city in the US for four years in a row – and for good reason! From world-class museums to historic architectural landmarks and swanky bars, restaurants, and clubs, Chicago has it all. 

If you’re a sports fan you can catch a Cubs game at the historic Wrigley Field or watch a Bulls game at United Center. For those looking to get cultured, be sure to visit the Art Institute of Chicago, the American Writers Museum, or the Chicago Architecture Center. And if shopping is your thing, look no further than the ritzy stores on Magnificent Mile or the trendy boutiques in the hip Wicker Park and Bucktown neighborhoods!

When it comes to food, you’ll be spoiled for options. Whether you’re a hardcore foodie or just love eating, be sure to visit “Restaurant Row” and Fulton Market in the West Loop neighborhood. You can sample innovative Midwestern cuisine at Blackbird, share a charcuterie board and sip fine wine at The Press Room, or indulge in creative handmade pasta dishes and Italian fare at Monteverde.

Chicago also has some truly opulent historic hotels, incredibly unique bed and breakfasts, and beautiful themed boutique resorts. So many, in fact, that you might have a hard time choosing the perfect one. So we’ve created a list of the 12 best hotels in Chicago to help you plan your perfect getaway!

Where to Stay in Chicago

Where to Stay in Chicago: Cool & Unique Boutique Hotels

As the third most populous city in the US, Chicago is a massive city with 77 different neighborhoods. Luckily, the city boasts excellent public transportation so all of the city’s major attractions are within easy reach. Deciding on where to stay in Chicago largely depends on what you want to see and do during your trip. 

Most hotels are clustered around the city’s major tourist attractions. If you’re visiting for the first time and want to be right in the heart of the action, downtown (also known as the Loop) is the perfect place to base yourself. You’ll be close to iconic landmarks such as Millennium Park, Willis Tower, and the Art Institute of Chicago.

If you’re planning a fun-filled getaway with friends, Wicker Park and Bucktown boast super hip bars, funky boutique shops, and trendy music clubs. Alternately, if you want to stay in one of Chicago’s most upscale areas, the Gold Coast is home to historic homes, the Magnificent Mile, and two lakeside beaches. 

Wrigleyville, on the North Side of Chicago, is the place to be if you’re in town for a Cubs game. And if you’re a foodie, you’ll definitely want to stay near Rudolph Street’s Restaurant Row or the famous Fulton Market in the West Loop area. This part of town also has a buzzing nightlife scene if you want to let loose during your trip!

The 12 Best Hotels in Chicago, Illinois

1. The Publishing House Bed and Breakfast

Cool Hotels in Chicago, Illinois: The Publishing House BnB
Images: The Publishing House Bed and Breakfast

The Publishing House Bed and Breakfast is hands down the most unique boutique hotel in Chicago. Built in 1909, this historic building was once the home of the Free Methodist Publishing House. After three years of renovations, it reopened as a one-of-a-kind bed and breakfast in 2017.

Given the building’s history, it’s fitting that the literature-loving owners dedicated each of the 11 rooms to authors who have written books about Chicago, from Upton Sinclair to Audrey Niffenegger. You’ll even find copies of their books in your room! Each room is different and features vintage decor, heated floors, and clawfoot tubs. 

The friendly owners also just happen to be excellent cooks. Each morning they personally serve guests a lavish breakfast including fresh fruit, homemade granola, and made-to-order options such as corn fritters topped with poached eggs and spinach or veggie frittatas with side salads. If you’re feeling peckish, freshly baked cookies and muffins are served all day long. 

The Publishing House is located in the hip West Loop neighborhood – just minutes away from the foodie haven of Restaurant Row. There are also plenty of live music venues, bars, and boutique shops in the area, so the location can’t be beat!

2. IVY Boutique Hotel

Best Chicago Hotels: IVY Boutique Hotel
Images: IVY Boutique Hotel

With 63 spacious studios and suites, the art-filled IVY Hotel is an excellent option if you’re in town on business or simply want space to spread out during your trip to the Windy City. You can choose from huge studios or opt for the massive king or queen suites, which boast separate bedrooms and living areas. 

Each eco-friendly room features modern gray and purple decor, plush platform beds, and bamboo floors. Floor-to-ceiling windows offer sweeping city views and you can use the automatic window curtains if you want some privacy. You’ll love the luxurious marble bathrooms with rainfall showers, soaking tubs, and complimentary Beekman 1802 bath products.

Start your day off with breakfast and a latte in the lobby’s DiVine Lounge. This hotel is just one block from the bustling Michigan Avenue and walking distance to the lake, so you’ll be right in the heart of the action. After a long day exploring the city, grab a sundowner and some light bites at the rooftop lounge on the 16th story and enjoy the stunning city views.

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3. SOPHY Hyde Park

Cool Hotels in Chicago, Illinois: Sophy Hyde Park
Images: SOPHY Hyde Park

The SOPHY is tucked away in the historic Hyde Park neighborhood near the University of Chicago campus, the Museum of Science & Industry, and the future Barack Obama Presidential Library. To pay tribute to Hyde Park’s unique culture and history, the hotel was designed with the themes of music, science, art, and literature in mind. 

With its original art, funky light fixtures, and vintage posters, this unique boutique hotel feels a lot like a museum. You can wander around the hotel and peruse the locally made artwork, brunch on new American fare at the art-and-book-filled Mesler Kitchen, or enjoy alfresco cocktails on the spacious outdoor patio. 

Each of the rooms has hardwood floors, comfy sitting areas, and luxurious modern bathrooms. You’ll especially love the abstract paintings, which were created by local artist Joey Korom. If you want more space, upgrading to one of the beautiful suites is well worth it for the separate bedrooms.

If you feel like exploring the heart of Chicago, downtown and Millennium Park are a mere 15 minutes away. 

4. The Wheelhouse

Best Chicago Hotels: The Wheel House
Images: The Wheelhouse

If you’re a Cubs fan, you’ll definitely want to stay in The Wheelhouse. Not only is the entire 5-story hotel decked out in vintage baseball-themed decor, but it’s just two blocks from the historic Wrigley Field if you want to catch a game. This is definitely the most unique boutique hotel in Chicago!

Wander around the hotel and you’ll find all sorts of cool features including an art installation made from Louisville Slugger bats and a cute 1950s-style candy store. If you’re in the mood for a tipple, pay a visit to the chic speakeasy in the basement or head up to the rooftop bar for excellent city views. There is also an onsite pizzeria that serves up Detroit-style pies.

This 5-story building has 21 well-appointed rooms with midcentury-modern furniture, sliding barn-style bathroom doors, and vintage signs. With black and white floor tiles, marble countertops, and rain showers, the ensuites are about as stylish as it gets. You’ll love wrapping yourself in the cozy robes – which are made from sweatshirt material – and having a chill movie night on the plush bed.

The Lakeview neighborhood has plenty going on. You can bike along the miles of lakeside beaches, shop at the funky boutiques, and enjoy a live performance at one of the area’s many music venues.

5. The Robey

Best Hotels in Chicago, Illinois: The Robey
Images: The Robey

The Robey is housed in a former 1929 art deco-style office building. Located in between the trendy Wicker Park and Bucktown neighborhoods, this historic building was fully renovated and is now one of the coolest hotels in Chicago. 

Each of the rooms features custom furniture, vintage decor, and soothing maroon and gray tones. You’ll love the luxurious extras like 400-thread-count linens, a Bluetooth sound system, and a smart TV. The comfy bed is the perfect place to kick back and relax after a long day on the town.

During the warmer months you can lounge around the rooftop pool, soaking up the sun and taking in the panoramic views of the Chicago skyline. Head over to the rooftop lounge for summer-inspired Americana dishes at the Cabana Club. If you’re craving a craft cocktail with a view, the hotel’s Up Room rooftop cocktail lounge is the place to be. 

The Robey is located steps away from the Blue Line, which means all of Chicago’s main attractions are easily accessible. Plus, the neighborhood is chock full of hip cafes, delicious eateries, and unique shops.

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6. The Talbott Hotel

Best Chicago Hotels: The Talbott House
Images: The Talbott Hotel

If you’re looking to be right in the center of the action, The Talbott Hotel is arguably one of the best hotels in Chicago. There’s a good reason guests continuously praise this historic boutique hotel! 

Set in a 1927 building, this newly renovated hotel is located in the historic Gold Coast district. All of the ritzy shops and gourmet restaurants that line Magnificent Mile are just steps away. Plus, the Lakefront Trail is a 6-minute walk away and offers unreal views of Lake Michigan. 

Sophisticated boutique hotel rooms feature comfy beds, fine linens, soft bathrobes, and large flat-screens with streaming services for a relaxing movie night. Each room boasts lightning-fast wifi and work desks in case you’re traveling on business. If you need more space, you can easily upgrade to one of the elegant studios or suites. 

If you feel like being lazy after a day of shopping, hiking, and exploring, you can order room service and have a chill night in. Or dine on creative American dishes at the hotel’s restaurant 20 East. After dinner, head over to the trendy onsite bar for a fine glass of wine or an innovative cocktail.

7. Thompson Chicago

Unique Hotels in Chicago, Illinois: Thompson Chicago
Images: Thompson Chicago

Surrounded by tree-lined streets, historic mansions, and luxe boutiques, the Thompson Chicago is yet another architectural gem in the buzzing Gold Coast neighborhood. 

If you want to have a beach day, Oak Street Beach and North Avenue Beach are just minutes away. Or if you’re looking to get a culture fix, the Museum of Contemporary Art and the Chicago History Museum are both nearby.

You can choose from a range of elegant and eclectic rooms and suites, some of which feature floor-to-ceiling windows with city and lake views, velvet mid-century modern couches, and comfy beds with 400-thread-count SFERRA linens. You’ll love the luxurious bathrooms with rain showers, marble counters, and soft French terrycloth robes. You can also upgrade to a room with a lake view or book a suite with a separate bedroom. 

There are plenty of delicious restaurants right outside your door, but if you feel like staying in, Nico Osteria dishes out authentic Italian seafood, homemade pasta, and gourmet sandwiches. The Salone Nico Bar and Lounge mixes up creative craft cocktails and features an excellent list of Italian and Mediterranean wines.

8. Chicago Athletic Association

Chicago Boutique Hotels: Chicago Athletic Association
Images: Chicago Athletic Association

One glance at the facade of this 1890s Gothic building and you’ll be stunned. This historic landmark was the home of an elite sportsmen’s club for 122 years before it was meticulously renovated into one of the most unique hotels in Chicago. The beautiful Chicago Athletic Association Hotel opened its doors in 2015 and is conveniently located right across the street from Millennium Park.

The exposed brick walls, opulent lounges, and vintage sports-themed decor pay homage to the building’s history. Expect to find a mix of old-world Chicago style and modern amenities throughout. There’s also a game room and bar where you can sip whiskey and play billiards, shuffleboard, and poker, just like the good old days!

Each boutique hotel room features plush beds, custom modern leather chairs and chaise lounges, and vintage sports equipment like rollers skates and basketballs. The boxing-style bathrobes, 42-inch flat-screen, and fully stocked minibar with locally sourced snacks are perfect for a relaxing night in. You can even order room service from the Shake Shack!

There are seven bars, restaurants, and lounges at the hotel. Definitely grab a cocktail at Milk Room, an 8-seater speakeasy-style bar once used by club members during prohibition. Or head up to the rooftop bar and restaurant for stunning city and lake views.

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9. Virgin Hotels Chicago

Boutique Hotels in Chicago, Illinois: Virgin Hotels
Images: Virgin Hotel Chicago

This trendy boutique hotel is another great option if you want to be based near Millennium Park. The whole concept was designed to give you the best customer service possible, so expect to be waited on hand and foot!

What makes the Virgin Hotel Chicago unique is that each two-chamber room features sliding privacy doors to create two separate rooms. The spacious dressing room boasts a closet, a luxury bath with a rain shower, and a regal vanity. Doors slide open to the living and sleeping area with an ergonomic lounge bed, a workstation, and a comfy sitting area. 

You’ll love all of the cool extra features such as the Stellé Audio Bluetooth Pillar, the 42-inch smart TV, and the cute red SMEG refrigerator stocked with snacks that aren’t marked up in price. There are even pet-friendly rooms equipped with dog beds for your furry friends!

If you feel like mingling, the staff host evening social hours in the trendy cocktail lounge. This hotel has five restaurants and lounges including an ultra-swanky rooftop bar and nightclub. If you want to explore the area, Millennium Park is just a 7-minute walk away. 

10. Hotel Versey

Best Chicago Hotels: Hotel Versey
Images: Hotel Versey

What is now known as the Hotel Versey might just have the coolest history of any Chicago hotel. Despite the fact that it’s changed ownership a few times over the years, there’s a reason this 1920s building has been dubbed the “Rock and Roll Days Inn.” There were times when Kurt Cobain dyed his hair in one of the bathtubs, Sheryl Crow rollerbladed through the lobby, and the Red Hot Chili Peppers stayed the night while on tour. 

While things might not be quite as raucous these days, but the hotel was fully reinvented in 2017 to pay tribute to its musical roots and storied history. The Chicago-themed decor is all about celebrating the city’s local art scene, jazz and rock history, and unique culture. Expect to find colorful paintings, vintage decor, and graffiti throughout this boutique hotel. 

All rooms feature luxury beds and linens, 50-inch flat-screens with SoniCast, and Nespresso coffeemakers for your morning cup of joe. You can upgrade to more deluxe rooms and suites, which boast mini-fridges, microwaves, and sofa beds if you need extra sleeping space. And you’ll love the hand-painted Chicago-themed murals in each room!

This hip hotel is located in between the trendy Linkon Park and Lakeside neighborhoods so you’ll be surrounded by tons of restaurants, cafes, and live music venues. 

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11. Freehand Chicago

Cool Hotels in Chicago, Illinois: Freehand Chicago
Images: Freehand Chicago

Freehand Chicago is by far one of the coolest hotels in Chicago. Housed in yet another one of the city’s historic 1920s buildings, this ultra-stylish hostel features mixed and female-only dorm rooms, private rooms, and a 2-bedroom duplex. There’s also a communal kitchen in case you want to save on money and prepare your own meals. 

Rooms and dorms are all well-appointed with plush mattresses, stylish decor, and ensuite baths. The shared rooms can sleep up to four people and feature cozy sitting areas, two bunk beds, and privacy curtains. There are also plenty of common areas around the hotel where you can watch TV, catch up on work, or socialize with friends. 

Before hitting the town, start your day with the hotel’s complimentary continental breakfast. Freehand is located two blocks from Magnificent Mile and a mile from Millennium Park so it’s the perfect jumping-off point for visiting the Windy City’s major attractions! After a long day, order a cocktail or two at the hotel’s award-winning bar, Broken Shaker.

12. The Blackstone

Coolest Chicago Hotels: The Blackstone
Images: The Blackstone Hotel

Chicago is chock full of historic hotels and The Blackstone Hotel is no exception. Dating back to 1910, this luxury hotel is located in the Historic Michigan Boulevard District and has been listed on the National Register of Historic Places. Known as the “Hotel of Presidents,” numerous former presidents and celebrities have spent the night in this iconic hotel.  

Each of the sleek guestrooms features modern furniture, 50-inch flat-screens, and luxurious marble baths. Although the building has been fully renovated you can still stay in the famous “presidential suite.” The suite still has its original floors, fireplaces, and architectural features!

This lavish 21-story hotel has all sorts of cool amenities. You can play pool in the game room, work up a sweat in the 24-hour gym, or lounge around in the opulent lobby. If you want to wine and dine at the hotel, Mercat a la Planxa serves up modern interpretations of Catalan and Mediterranean tapas and stiff craft cocktails.

That completes our list of the 12 best Chicago hotels! Did we miss any cool boutique hotels in Chicago? Comment below so we can add them to the list!

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19 days ago

Hotel Lincoln is a cute spot with a great rooftop bar! Amazing views too!

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