The 15 best hotels in Chicago for 2026

💎 Best for: Knockout luxury for a special occassion

Appropriately enough for a hotel that shares a building with Tiffany’s, staying at The Peninsula Chicago feels like sleeping in a jewel box. Opened in 2001, the property exudes a sense of sparkling charm, and whenever you walk into a room, it feels as if a massive cleaning crew just finished polishing every surface. While there is a definite sense of formality here—marked by glittering chandeliers and marble accents—it never feels too rigid or fussy. 

The guestrooms offer an ultra-luxe yet low-key aesthetic, feeling more like a high-end Chicago apartment than a flashy hotel. With 339 rooms and suites, the decor leans towards the more traditional with muted earth tones, light blues, and marble bathrooms, often featuring chrysanthemum motifs—the official flower of the city. For dining, the hotel blends East Asian and Midwestern influences. While the contemporary Chinese spot, Shanghai Terrace, was closed during my visit, I enjoyed an excellent dinner at The Lobby, an airy space with 20-foot windows. For a nightcap, the rooftop Z Bar offers unobstructed views of the Magnificent Mile. 

The wellness center occupies the entire top floor, and the views are worth the trip alone. I spent my first morning on a treadmill with a bird’s-eye view of Lake Michigan’s endless blue expanse. The spa is enormous, offering everything from massages to half-day retreats, but the real highlight is the 25-meter swimming pool and sun deck. Outside, you are steps away from high-end shopping and a short walk to the DuSable Bridge for architecture tours. 

Time Out tip: Pierrot Gourmet serves a must-try rotisserie chicken.

Address: 108 E Superior Street, Chicago
Price per night: Prices start at $835 per night
Closest transport link: El stop: Red to Chicago. Bus: 3, 10, 26, 66

📍 Discover the best spa hotels in Chicago

💎 Best for: A cozy, homely place to stay

For a seriously stylish home away from home without sacrificing hotel comforts, look no further than The Guesthouse Hotel. This one-of-a-kind, intentionally residential spot stands out against downtown’s ultra-modern high-rises. Originally intended as luxury condos before the 2008 crash, the property now offers 25 elegant suites that feel sophisticated yet neighborly. The common spaces—like the library and club room—feature cozy touches like wood salvaged from a Wisconsin barn, leather-bound tomes, and board games, creating a quiet, un-stuffy atmosphere that avoids the usual city hotel noise.

The suites are fully self-sufficient, featuring high ceilings, open kitchens with granite counters, and private balconies flooded with natural light. Whether you’re in a single or a triple-bed unit, you’ll find homely essentials like a washer/dryer and an ice machine. During my stay in a two-bedroom suite, I loved the mix of velveteen sofas and the choice between a peaceful view of the St. Boniface cemetery or a glimpse of the city skyline. 

The service is impeccably warm; despite a weather-delayed arrival in the early hours, the local staff had my room ready for a seamless check-in. Facilities are equally thoughtful, including a 24/7 fitness room and in-room wellness rentals like infrared sauna blankets. You can soak up the Windy City from two roof decks or wander a mile to Lake Michigan for a swim.

Time Out tip: Andersonville has a legendary Belgian beer bar called Hopleaf, and it’s only a few blocks away. 

Address: The Guesthouse Hotel, 4872 N Clark St, Chicago, IL 60640, US
Price per night: From $354 per night. 
Closest transport: Ravenswood (10 min walk) and Argyle (15 min walk) Metra stops.

📍 These are Chicago’s most romantic hotels

💎 Best for: A city-spa break hybrid

The Langham is a London-born luxury brand with only a handful of US locations, and The Langham Chicago is the world’s only hotel in a Ludwig Mies Van Der Rohe–designed building, which promises to wrap you in quiet luxury and deliver the rest and thoughtfulness you absolutely deserve.

The best rooms look out over the Chicago River and riverwalk, with panoramic views of Lake Michigan, nearby restaurants, hotels and bridges. Their layout is thoughtful with floor-to-ceiling windows, hardwood floors, punctuated by built-in rugs and have a sleek, high-end feel. Other highlights include a tub, rain shower and double vanities. The Langham nails the nuance of a better home-away-from-home. You can also order his-and-hers pillows from a customizable menu, and take advantage of the Diptyque products.

The Langham Chicago truly elevates the standard hotel experience with a host of wellness experiences. Find your Zen at the five-star Chuan Spa, which has a menu of customized massages, facials, foot therapies, manicures and more. Don’t skip the quiet room, stocked with teas and light snacks. There’s also a large indoor pool and a full schedule of fitness classes to help balance out all that Chicago deep dish.

For a sit-down meal, Travelle offers seasonal American dishes with stunning views of the river. On weekends, afternoon tea is served in the cozy Pavilion.

If you’re craving a luxe-yet-lowkey weekend in Chicago, The Langham delivers. You’re steps from Millennium Park, the Art Institute, and some of the best food in town. After a full day of sightseeing (or hot dog sampling), there’s no better retreat than your plush, quiet suite—with skyline views, soft sheets and Diptyque everything.

Time Out tip: Add on access to The Langham Club, which has everything: a quiet place to cool off, Champagne on demand and plenty of grab-and-go snacks.

Address: 330 North Wabash Avenue, Chicago, IL 60611
Price: From $1,071 per night, depending on dates and accommodations
Closest transport: Millennium Station, six-minute walk

📍 Here are the best budget-friendly hotels in Chicago

One of the most striking features of the Radisson Blu Aqua Hotel are the wave-like balconies that ebb and flow around the blue-glass facade of the building—one of the most stunning contemporary additions to a city known for its architecture. With the Chicago River to the north, Lake Michigan to the east and three pools on premise, you’re surrounded by water every which way.

Opened in 2011, the Radisson Blu Aqua comprises the first 18 floors of the 81-story Aqua Tower in Lakeshore East, a microneighborhood of highrises just north of Millennium Park and east of the Loop, the city’s business district. Don’t expect under-the-sea decor, though. Inside, the nods to the water theme are limited to aqua glass in the bathrooms and blue lights in the hotel bar. Instead, the lobby is all concrete floors and exposed brick columns and shimmery modern chandeliers, accented with printing-press block-letter signage (a nod to Chicago’s Printer’s Row neighborhood). 

The hotel’s 334 rooms are decked out with chrome-legged furniture and blonde wood floors and cabinetry, including floating wardrobes with interior lighting that make unpacking less of a drag. 

The hotel’s restaurant, FireLake, serves breakfast, lunch and dinner in a sultry, sunken dining room just a few steps down from the lobby. The weekends bring special dining experiences such as Boozy Brunch with $25 bottomless mimosas and Afternoon Tea ($59 per person, reservations recommended). 

The third-floor sun deck is lined with rows of lounge chairs as well as six mesh-sided cabanas for shade seekers surrounding a large rectangular pool, plus a shallower wading pool for little ones. During the day, you can see glimpses of Lake Michigan between the surrounding highrises and views of grassy Lakeshore East Park below. Inside, there’s a two-lane lap pool and a hot tub.

Time Out tip: The Michigan Avenue docks for river cruises are just a short walk north (the Chicago Architecture Foundation’s tour is a favorite of locals and visitors alike).

Address: 225 N. Columbus Drive, Chicago, IL 60601
Price: Starting from $290
Closest transport: State/Lake L station, 10-minute walk

Viceroy Chicago immediately stands out with its golden facade glinting against the Chicago sun. Its Art Deco lobby is equally dramatic. Housed in what was once the historic 1920s-era Cedar Hotel (the original brickwork still graces its base), the property blends old-school Chicago character with modern elegance. It’s a visual treat, every hallway, fixture and velvet accent feels curated, and the city views are jaw-dropping.

In the rooms, floor-to-ceiling windows reveal sweeping views of downtown and glimpses of Lake Michigan. The color palette is rich and moody, with emerald and navy touches, brass accents and plush materials. The bathrooms are spa-grade, with walk-in rainfall showers and CORPUS toiletries. There are also suites with deep soaking tubs, separate living spaces and corner views for those looking to go big.

The hotel’s crown jewel is Somerset, the ground-floor restaurant with Mediterranean fare, retro glam interiors and an open-air patio in the summer. Upstairs, there’s Pandan, a cocktail lounge and pool bar with stunning skyline views. Come for the cocktails, stay for the sunset.

From check-in to check-out, the service is five-star without being stiff. The front desk staff will greet you like an old friend and give you a map of their favorite neighborhood spots. There’s a rooftop pool—a rare treat in Chicago, especially during the warmer months, and a fitness center with Peloton bikes and more sweeping city views.

Viceroy Chicago hits the rare sweet spot: it feels indulgent but not out of reach, stylish without trying too hard, and historic without being stuffy. It’s perfect for design lovers, couples on a romantic escape or solo travelers looking for a luxurious home base with personality.

Time Out tip: Book a city-view room for the full experience. If you can swing a mid-week stay, you’ll get better rates and less rooftop pool competition.

Address: 1118 N State St, Chicago, IL 60610
Price: Starting from $330 per room, per night
Closest transport: Clark/Division Red Line, five-minute walk

As the longest continuously operating hotel in North America, Palmer House is something of an institution in Chicago. First opened in 1871, this lavish Grande Dame has a string of bold claims to its name—it’s here the chocolate brownie was invented in 1893—and today it’s an extravagant, 25-storey behemoth of a hotel with more than 1,600 rooms.

At its heart is the gilded lobby, ambiently lit by 24-karat gold candelabras designed by Tiffany. You’ll also find a clutch of restaurants, bars and cafes—alongside an excellent spa, fitness centre and newly renovated pool, all smack-dab in the middle of Chicago’s buzzing downtown ‘Loop’ area. 

Everyone from Ronald Reagan, Bill Clinton and Barack Obama to Charles Dickens, Oscar Wilde and King Charles have stayed at Palmer House, while the likes of Frank Sinatra, Judy Garland and Louis Armstrong have performed in its gold-leafed Empire Room. Today its palatial lobby is the crowning centrepiece, with regular live performers and a bar drawing both guests and non-guests beneath a frescoed ceiling. 

There are 1,641 rooms across the hotel, from Standard Rooms with one or two double beds to Deluxe and Premium Rooms that add a bit of extra space. It’s also home to several larger Suites, which come with a wet bar and living and dining area. 

Lockwood Express, the hotel’s café, sells brownie using the OG recipe—they’re moist and buttery, topped with walnuts and a sweet apricot glaze. The Lockwood Restaurant, meanwhile serves classic American breakfasts and classic lunches and dinners. The Lockwood Bar serves a long list of craft cocktails in the lobby.

The spa and health club are hotel highlights with swanky Precor treadmills, cross trainers, step machines, strength training equipment, free weights and more, plus a yoga room and a Peloton bike room. There’s also a heated indoor pool and the spa offers massages, hydrotherapy treatments, body wraps, foot therapies and facials. 

Time Out tip: Ask the spa’s retreat consultant can help you arrange a full-on, personalised wellness retreat package.

Address: 17 East Monroe Street, Chicago, Illinois, 60603
Price: Standard Rooms start from $160 per night
Closest transport: Monroe station, 4-minute walk

This boutique hotel is located in the heart of the city, just five minutes’ walk from the luxury shops of the Magnificent Mile, right in the epicenter of River North. The rooms are modern and sleek with floor-to-ceiling windows, in-room tech, and a fridge stocked with wines available for purchase (bonus: most are very reasonably priced). In-room spa treatments and 24-hour room service are also available. They each have an industrial-chic style and original artistic touches, from the cement ceiling to the reclaimed wooden floors.

While you stay here, you’ll want to check out the luxe spa with a huge number of treatments available, blending traditional techniques with new wellness trends. Book an energizing ginseng facial, an aromatherapy massage, or a citrus detox wrap, or take some downtime in the Himalayan salt sauna, which helps the body expel toxins, or indulge in one of the color-changing chromotherapy showers. There’s also a fitness centre on site, along with concierge services.

Fuel up at the River North Bistro, a sleek eatery serving classic US dishes made from fresh, local, seasonal ingredients with a spacious bar area, intimate dining room, and an outdoor dining patio, perfect for the warmer months.

If you can even fathom leaving such a nice place, you’ll find you’re really close to great shops and museums, including the Museum of Contemporary Art.

Time Out tip: Look out for special offers with curated extras, perfect for romantic getaways or occasions.

Address: 660 N State St, Chicago, IL 60611
Price: Rooms from approximately $120 per night
Closest transport: Grand station, four-minute walk 

If you’re looking for a posh base while exploring downtown Chicago, check into The Gwen, a Michelin Guide one key hotel located within the historic McGraw-Hill building, one of the rare landmark buildings of Art Deco-infused architecture along the Magnificent Mile.

The rooms are handsomely appointed. Guests are treated to spacious surroundings, soft, plush beds, and Art Deco furnishings in a stylish monochrome colourscheme. While the bathrooms are equipped with marble-topped vanities, over-sized walk-in showers, Molton Brown amenities and plush bathrobes and slippers.

If you’re feeling adventurous, the hotel even offers the city’s first urban glamping experience, where guests can sleep in a swanky, festival-style yurt on the private terrace of the Gwen Lux Suite, with picturesque views of some of the city’s most iconic architecture.

Upstairs at The Gwen is the place for breakfast, small plates, dinner or handcrafted cocktails and snacks, with seats at the communal fire table or out on the rooftop terrace with speeing views of Chicago. Head there between 4pm and 5.30pm on Monday to Thursday for happy hour cocktails, wine, beer, and light bites. There’s also a champagne vending machine in the lobby with chilled mini bottles of Imperial Brut or Imperial Rosé.

Named after Gwen Lux, the female sculptor who created the hotel’s iconic facade, the hotel itself is leans into the artistic connection of its new with dramatic murals in each of the guest rooms and an ‘Artist-in-Residence Program’ throughout the hotel.

The theatre district is a small walk away, and it’s steps away from Michigan Avenue and the Chicago River, and you can access the Shops at North Bridge without even stepping outside.

Time Out tip: For a more lively experience, check out the Gwen’s tipsy tea parties, which feature live DJs and cocktails along with towers of snacks.

Address: 521 N Rush St, Chicago, IL 60611
Price: Prices start from aroun $522 per room per night 
Closest transport: Grand station, six-minute walk 

This hotel is a baseball enthusiast’s dream. Across the street from Wrigley Field, it’s a prime example of the Ricketts family’s efforts to change the face of Wrigleyville since taking over ownership of the Chicago Cubs in 2009. Named after Wrigley Field’s original architect, Zachary Taylor Davis, the seven-story, 173-room Hotel Zachary sits on the northwest corner of Clark and Addison, facing Gallagher Way and the ballpark’s iconic marquee. 

The decor offers plenty of touches to warm Cubs fans’ hearts, but without veering into theme-park vibes. The baseball memorabilia is countered with sophisticated mid-century stylings, think dark green Chesterfield sofas, wood panneling and black-and-white sporting photographs. 

The rooms are equally sophisticated with artwork and amenities inspired by the Wrigleyville neighborhood roots. Each has ivy-green headboards, pinstripe carpet, leather wing chairs and floor-to-ceiling windows overlooking Wrigleyville. Look out for local artwork, historical photographs and rare Wrigley Field memorabilia.

Guests can start the day with hot breakfast at The Alma Room and end with an artfully crafted cocktail at the hotel’s lobby bar, which offers classic American favorites for lunch and dinner. Other nearby food and drink offerings include the new second outpost of Big Star, barbecue from Smoke Daddy and craft cocktails at the in-house Mordecai.

Sports lovers should look out for special offers, which include premier Chicago Cubs club box home plate tickets and complimentary pre-game cocktails in the room rate, and architectural tours of Wrigley Field.

Time Out tip: Check out the hotel’s afternoon tea every Sunday with live entertainment and a selection of teas, bubbles and small plates.

Address: 3630 N Clark St, Chicago, IL 60613
Price: Rooms start from around $534 per night 
Closest transport: Addison station, five-minute 

Part of the Marriott chain’s attempt to appeal to the millennials who flock to playful, Instagram-friendly lodgings, Chicago’s first Moxy—Marriott’s European-bred ‘experiential’ brand—opened in River North in May 2018. The 156-room property replaces the traditional check-in desk with a bar, where you’re greeted with a welcome cocktail.

In place of a lobby, the Moxy has a ‘living room’, which is full of pink neon lights, graffiti-covered walls and corners packed with vinyl records, video games and device-charging nooks, plus the occasional visiting DJ.

The cosy rooms keep the amenities on the basic side but with whimsically industrial finishes—the aim is for the invisible half-step between hostel and grownup hotel. No kidding: The Moxy’s general manager—sorry, its ‘captain’—told the Tribune on opening day that the bar’s happy hour will be known as ‘Adulting Is Hard’. Each of the guest rooms industrial chic concrete walls, with handsome hardwood floors and leather headboards. There are slick concrete basins in the room and walk-in wet rooms. Select rooms feature loft-style bunk beds.

Feeling hungry? Zombie Taco is a fun, casual taco counter with a large menu of Mexican classics, and don't Bar Moxy is the spot for custom cocktails and is a laidback spot to catch up with friends.

You’re also super close to most of the attractions and event-spaces you're in Chicago for. Whether it's the theatre district, nightlife, or Water Tower, it's all within walking distance.

Time Out tip: Get competitive in the lobby with shuffleboard and foosball. 

Address: 530 North LaSalle Drive, Chicago, Illinois, 60654
Price: Rooms range from $340 per night
Closest transport: Grand station, six-minute walk

To say the restored 1890s Chicago Athletic Association is beautiful is putting it mildly. The hotel is a Venetian Gothic landmark dating back to the 19th century. Previously used as a private members club, it honours its history with restored carved stone fireplaces, intricately mosaiced floors and ornate wooden panneling. 

Stay in one of the 240 luxury boutique rooms—throwbacks to the club rooms of athletic associations long gone. Each one has vintage-inspired custom furnishings, including atmospheric brass beds, Faribault Woolen Mill Co blankets and boxing-style robes. Plenty also have views straight out over Millennium Park. The Carrara marble bathrooms also come with premium fixtures, such as rain showerheads and custom C.O. Bigelow bath products. 

Cindy’s rooftop restaurant is a jaw-dropping location for lunch and dinner with its impressive domed glass roof and sweeping views of Lake Michigan. Head up for dishes featuring local wild and seasonal produce and fresh seafood. For a real splash-out affair visit Midōsuji, a tiny eight-seat nouvelle omakase where you can eat meticulously plated sushi, or visit the on-site Shake Shack for a treat burger. 

No matter where you are, you can’t escape the atmosphere of this place, especially in the Drawing Room, which is the perfect spot to sip morning coffee, read a book, or sink back a cocktail in a leather wing-back chair surrounded by the hotel’s three ornate fireplaces. This place puts the Chic in Chicago. 

Time Out tip: Hunt out the Game Room, where you can play bocce, shuffleboard and billiards while sipping a cocktail. 

Address: 12 S Michigan Avenue Chicago, IL 60603
Price: Rooms start at approximately $410 per night 
Closest transport: Millenium station, four-minute walk 

This gorgeous hotel, first opened in 1910, has had an intriguing run so far. Many US presidents have stayed here (including Teddy Roosevelt), it was a favorite hangout of Al Capone and his cronies, and Maharishi Yogi, the Beatles’ personal guru, once owned the building. So Zen vibes are guaranteed. Now it’s part of Marriott’s Autograph Collection boutique imprint and is simply one of the most beautiful hotels in the Loop. It’s also a favorite for bands playing at the nearby Lollapalooza music festival in August.

The centre of the hotel is its gleaming lobby with monochrome floors, an ornate fireplace, handsome wooden panneling, gold accents and original artwork dotted about the space. The rooms are equally splendid. Pick from a range of suites and guest rooms, all of which offer, plush ultra-comfortable beds, local artwork and large windows offering views of the city and Michigan Lake. The decor is light and bright, with a focus on the objet d’ art dotted about the room and the bathrooms all have marble tubs to indulge in. 

There on-site restaurant, Mercat a la Planxa, serves Spanish small-plates offering fresh seafood and cured meats, and the 1600 Club is open for Breakfast and Cocktails & Snacks Monday to Friday. There’s also a 24-hour state-of-the-art gym with stunning views over Lake Michigan and Grant Park. It’s also a spot committed to sustainability with rooftop beehives, smart energy saving programmes and a commitment to serving locally grown produce. 

It’s just a short walk to the Art Institute of Chicago and Magnificent Mile’s shop, and after a day of pacing the streets you can relax at the Leaf Spa which specialises in muscle and joint health, natural immunity, and stress relief. 

Time Out tip: Feeling fit? Join the hotel’s 5km running tour through Chicago city, passing iconic sights and history.

Address: The Blackstone, 636 South Michigan Avenue, IL 60605
Price: Rooms start at approximately $380 per night 
Closest transport: Harold Washington Library, 10-minute walk 

The public spaces are decked out with Italian marble, glittering crystal, and exquisite woodwork; rooms and suites come with classy furnishings, high-end toiletries, and twice-daily maid service. Basically, no glitzy detail is overlooked at Chicago’s Four Seasons Hotel. 

It has 345 elegant accommodations with views either sweeping over the glassy skyline or looking towards Lake Michigan, and they range in size from tastefully decorated hotel rooms to the lavish Luxury Residence (which comes with a kitchen, marble bathroom, and separate powder room, plus a menu of ultra-luxe services like shoe-shining). Oh, and book-lovers should have the Author Suite on their radar—it’s home to the hotel’s private literary collection, with personalised works from the likes of none other than Stephen King and Anne Rice included. 

But it’s not just the rooms that exemplify everything which has made this such a standout global brand. There’s also a roving martini cart which will stop by your room for an in-house cocktail hour, which is a great way to kick things off before paying a visit to the hotel’s Adorn Bar and Restaurant. Keen for some of that signature Chicago Jazz? Be sure to stop by any evening from Thursday through Sunday to enjoy a set from one of the hotel’s resident musicians (which also often incorporates vibey South American guitar). 

And we haven’t even talked about the location. Perched just off the city’s Magnificent Mile, the Four Seasons Hotel is on the doorstep of so much of Chicago’s must-see shops and sights. Bloomingdale’s is just downstairs, Oak Street Beach is within a 10-minute stroll and the Chicago Sports Museum is also not too far away. 

In dire need of some rest and recuperation? Book in for a treatment (such as the decadent Black Diamond Facial), try the night spa experience, or take a dip into the 50-foot indoor pool. 

Time Out tip: The hotel is friends with the Chicago Architecture Center, so speak to the concierge and they’ll help you get involved with a boat tour, journeying past landmarks of the city’s architectural history.

Address: 120 E Delaware Pl, Chicago, IL 60611
Price: Starting from approximately $480 per night
Closest transport: Chicago station on the Red Line

Little expense has been spared at this 182-room Magnificent Mile property, housed in the lower third of a slender, 67-story residential tower. The walls and halls are home to an estimated $23 million worth of artwork (no touching!), and a scent expert created signature smells to waft through the modern lobby. 

It specialises in rest and relaxation, too. Park Hyatt’s NoMI Spa, focuses on treatments including the Hydrafacial, which promises medical-grade results minus the downtime, and a customised massage services. You’ll also find all the classics, including mani-pedis, waxing and full body treatments, so you can step out feeling polished and ready to take on the city.

Wellness goes beyond the spa, with 24-hour access to the 7th-floor fitness centre connected to the spa. Hit the state-of-the-art cardio and strength equipment or upgrade to the private Wellbeing Suite, where you can ride a Peloton bike before recovering with a chef-crafted super juice.

The hotel’s guest rooms and suites are designed with wellness in mind, too. The Bryte Sleep Suites track your sleep data and use Somnify—a multi-sensory relaxation experience that combines sleep-inducing sounds with gentle movements—to help you drift into a deep sleep. Or book the Mindfulness Suite, which comes with an open-air private terrace, a deep soaking tub and yoga equipment for morning downward dogs.

Dining at the Park Hyatt is just as impressive. At NoMI Kitchen, marvel at the sweeping views of Water Tower and Lake Michigan from floor-to-ceiling windows while dining on Midwestern classics with a modern twist. For a showstopper, order the seafood tower which is packed with delicacies including Maine lobster, king crab, jumbo shrimp and, of course, oysters.  In the summer, the NoMI Garden lures guests outdoors with its open-air rooftop terrace with its 30-foot ivory granite bar and panoramic skyline views.

Time Out tip: Splash about in the hotel pool, which is on the hotel’s seventh floor with views of downtown Chicago.

Address: 800 N Michigan Ave, Chicago, IL 60611
Price: Rooms start from approximately $663 per night
Closest transport: Chicago station, three-minute walk 

In a landscape filled with mega-hotels and Airbnb rentals, there’s something extra special about a good old bed and breakfast—just don’t expect to find floral wallpaper and canopy beds at the Publishing House in the West Loop.

The quaint but impressive space houses 11 unique rooms (from cozy to XL) that are outfitted with cowhide rugs, clawfoot tubs and funky vintage furniture. Each room is wildly different inspired by a different figure from Chicago’s literary history, giving guests an excuse to venture back again and again. The Carman Room, for example, has a Westetrn feel with cow-hide hugs and mid-century style leather chairs, while the Everleigh room has a romantic feel with original artwork by Jim Dine and David Bromley, restored vintage sofas and a pink clawfoot tub.

All guest rooms at the bed and breakfast are equipped with a seating area, include a private bathroom with a shower, free toiletries and a hair dryer. Each one is also fitted with a desk and a flat-screen TV.

The vibe is eclectic and cosy. Vintage furniture, original artwork and striking touches like a grand piano and double-sided concrete fireplace. It’s even home to a pair of Pug dogs. The literary theme extends to the second-floor reading nook where you can get lost in one of the reads left in each of the rooms. There’s no bar or restaurant on-site, but if you do need sustenance you can visit the butler’s pantry which is filled with homemade cookies and tea. Guests also receive a  10% off coupon for Solo Salon, in the same building as the hotel, and the West Loop is in walking-distance.

Time Out tip: Don’t pass up the breakfast. Cooked by owners Shawn Uldridge and Kimberly Lowery, it features just-baked pastries, fresh juice and cereal as well as a few daily specials from the kitchen. 

Address: 108 N May St, Chicago, IL 60607
Price: Rooms start at approximately $388 per night 
Closest transport: Morgan station, eight-minute walk