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Appealing Chicago hotels that feature boutique vibes and amenities



How do you roll? Are you an art aficionado, history buff, workout fiend, interested in eating your way through a great restaurant city or just want to land in a genuine Chicago neighborhood and enjoy life as a native for a few days? No matter what, these properties dazzle in the details. For a stay that pins the needle at a solid ten on the cool meter,, consider Wicker Park's The Robey, near music venues, dive bars, boutique shopping and stellar restaurants (its own cafe serves excellent brunch seven-days-a-week, too). Publishing House Bed and Breakfast, in the restaurant-heavy West Loop, is ready for its close-up in Architectural Digest. 21C Museum Hotel has its own art museum within the hotel - a cost-free amenity perfect to peruse on a rainy/icy/sweaty day. Spend a day in historic Hyde Park and overnight at Sophy, a boutique hotel steeped in the culture of the south side neighborhood. Lincoln Park has the (still free) Lincoln Park Zoo, Chicago History Museum, Chicago's largest park, nature museum, conservatory, lakefront trail and beaches. Choose Hotel Lincoln (with complimentary bike rentals) or the Neighborhood Hotel - an 1893 classic city walk-up transformed into a residential-style hotel. If your heart is set on nesting near downtown attractions, consider Nobu Hotel Chicago in the busy Fulton Market District; Pendry Chicago, housed in the gleaming 1920's Carbide & Carbon Building, a genuine American Art Deco landmark; the architecturally stunning Radisson Blu Aqua - nirvana for exercise enthusiasts; or Staypineapple, An Iconic Hotel, The Loop which works overtime for the sleep deprived (and isn't that just about all of us these days)? 

 


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Head north into Lincoln Park for this eclectic hotel steps from Lincoln Park Zoo, Chicago History Museum, Steppenwolf Theater and Second City, Chicago's world-renowned improv venue. Among 184 guest rooms you'll find 64 suites and a family suite with bunk beds. It's an easy 10- minute walk to North Avenue beach and two-and-a-half miles to Wrigley Field. The hotel offers complimentary bike rentals to explore the lakefront and neighborhood. Check out the front desk built from more than 30 vintage dresser drawers sourced from antique shops throughout the Midwest. J. Parker, a rooftop lounge with a retractable roof (so it's open year-round) serves handcrafted cocktails and small plates with 360-degree views or go to Sushi Suite 202, a hotel room turned sushi speakeasy with a private chef for a 75-minute, 17-course Omakase experience. The Kennison, named for a legendary Chicago con-man, offers dinner, brunch, dessert and sturdy cocktails.

Recommended for Best Hotels because: This location works for those who want to go to Lincoln Park Zoo or visit the beach and rates are reasonable.

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This modern hotel located near Millennium Park is a gem especially for sport enthusiasts. There's an 8,000 square foot fitness facility that includes a half basketball court and 25-yard lap pool. The outdoor terrace includes the city's largest recreation deck, a running track, 25-foot outdoor lap pool and a wading pool for kids (open Memorial Day to Labor Day), plus a hot tub, sundeck, fire pits, cabanas and a dedicated yoga space. The location is also ideal for biking along Lake Michigan. Families can book suites with two connecting rooms (king connecting to two queens) and dogs are allowed (up to 60 lbs.) The onsite spa helps after all that exercise or look into booking the private movie theater room. Book a room on a Business Class floor for an upcharge, and have access to a free hot breakfast, snacks and refreshments.

Recommended for Best Hotels because: Visitors love this hotel for its amenities, fabulous location and an outdoor terrace with the city's largest recreation deck.

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A hotel can boast walls of modern art and a sexy rooftop bar but where does it land in terms of a great night's sleep? Staypineapple, An Iconic Hotel, The Loop wants guests to "fall in sleep" with "The Naked Experience." Linens are always freshly laundered, so you can sleep au naturel in double duvet European-style bedding, over-the-top luxurious sheets and pillows, thirsty towels and plush signature bathrobes. Those deep zzz's insure energy to explore the city and this hotel is just a short walk to the Chicago Cultural Center (free exhibits and events), Millennium Park, State Street shopping and the theater district. Housed in the Reliance Building, which is on the National Historic Register, Atwood bar and kitchen lists American fare and cocktails in a comfortable space with great views of State St. Look into the Pineapple Pup package to pamper your dog and get a discount on the pet fee or a third-night-free promotion running through Dec., 2022.

Recommended for Best Hotels because: If a great night's sleep is the number one consideration for a hotel stay, Staypineapple is your place in the heart of the Loop.

Read more about Staypineapple, An Iconic Hotel, The Loop →


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If you're keen on staying in a real Chicago neighborhood, consider the Neighborhood Hotel - an 1893 classic city walk-up transformed into a residential-style hotel with 14 suites. There won't be a spa and pricey restaurant on site but you will enjoy a kitchen stocked with local favorites; a trendy MoccaMaster coffee maker and Metric coffee; a collection of books, art and a field guide to all of the cool things to see and do in Lincoln Park. Expect vintage details plus the 21st century conveniences like a mobile-powered security system and key access, Smart TVs, Sonos, YouTubeTV, washers/dryers and enhanced Wi-Fi. Revel in a roster of neighborhood eateries from the famous Wiener's Circle (next door) to places offering vegan empanadas, dim sum, French bakery and Puerto Rican sandwiches. Walk to Lincoln Park, Farmer's Market, the conservatory, beach and zoo.

Recommended for Best Hotels because: A stay at The Neighborhood hotel is akin to renting an Anthropologie-clad apartment in a vibrant 'hood minus the utility bills and nosy landlord.

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Magnificent Mile

Located on Michigan Ave. in between downtown's attractions (like the Art Institute and Millennium Park), the River Walk and all that the Mag Mile offers, Pendry Chicago has location on its side. Housed in the gleaming, iconic 1920's Carbide & Carbon Building, Pendry resides in a genuine American Art Deco landmark. Shop, museum hop, see a show and know that the hotel's amenities insure that you can have a great night inside, too: there's the well-regarded French brasserie and cafe, Venteux (helmed by Chicago's youngest Michelin-starred chef, Don Young); the intimate Bar Pendry for cocktail hour or a nightcap by the double-sided fireplace; The Billiard Gallery to challenge your partner to a friendly game; and a summer rooftop bar 24 stories above Michigan Avenue - Château Carbide. Work it off in the state-of-the-art fitness center or hop on a custom Pendry Chicago bicycle to see Chicago on two wheels.

Recommended for Best Hotels because: In the middle of it all, Pendry Chicago is a smart bet for tourists wanting to see as much of the city as possible.

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Open since July, 2020, Nobu Hotel Chicago is a serene oasis of Japanese minimalism ensconced in the busy Fulton Market District. The 115-room hotel engages the senses from the second you step in - if they could only bottle that enigmatic, dreamy scent that's somewhere between a newborn baby and the best day of your life. Count on impressive skyline views; an indoor tranquility pool; calming, elegant decor; acclaimed dining at Nobu Chicago including a stone sushi bar; and the 11th-floor Rooftop at Nobu for inspiring views of the city, delicate bites and tasty cocktails (you can even have breakfast there when the weather is fine). In-room amenities include Dyson hairdryers, yoga mats, steamers and exclusive Nobu beds.

Recommended for Best Hotels because: Nobu Hotel Chicago is a serene oasis of Japanese minimalism ensconced in the vibrant Fulton Market District.

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This 98-room hotel, which opened in 2018 in Chicago's historic Hyde Park neighborhood, has been wowing visitors with its stunning art collection, Mesler Chicago restaurant and welcoming lobby with fireplace and lounge. Near the site of the future Obama Presidential Center, University of Chicago, the new David Rubenstein Forum, the Museum of Science & Industry and Frank Lloyd Wright's Robie House, the property celebrates intellectual brilliance (the name SOPHY comes from the Greek word "sophia" meaning wisdom). University of Chicago and Hyde Park notables such as Saul Bellow, Mahalia Jackson and Enrico Fermi inspire the hotel's interiors. Consider booking one of the spacious, bright suites that are hallmarks of the Hyde Park boutique hotel. There are frequent package specials such as "Stay Two Nights - Third Night is on Us" so check the website. For fun, trot over to Seven Ten Social, Hyde Park's new bowling alley and cocktail bar.

Recommended for Best Hotels because: Tickle the neurons with a visit to vibrant Hyde Park with the colorful, boutique SOPHY as your home base.

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21c has location in its "plus" column and with 106 suites, guests have more space vs. standard hotel rooms. The eclectic, hip art within the hotel is a cost-free amenity perfect to peruse on a rainy/icy/sweaty day. The gift shop stocks unusual items for adults and children such as miniature versions of the brand's Evergreen Penguin and kids craft kits. No kids? Look into the Pet Lovers Package so you can bring your buddy along. The adjacent Lure Fishbar is one of the best seafood restaurants in Chicago offering spectacular sushi, shellfish towers, lobster rolls, miso-glazed salmon and a very worthy "Bash Burger." Some of Chicago's most popular attractions are nearby and several "unlock" special offers when you show your 21c Museum Hotel Chicago room key card. For example, 21c guests can take advantage of a free TILT experience at 360 Chicago.

Recommended for Best Hotels because: In the heart of lively River North, 21c offers spacious suites, an art museum right in the hotel and an unbeatable location.

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Taking its name from Robey Street that would become Damen Avenue, The Robey enchants in the 1929 Art Deco triangular ediface formerly known as the Northwest Tower. Each of the 89 rooms are steeped in minimalistic, sophisticated design. Have a nightcap in the UP Room, the hotel's 13th floor cocktail lounge, offering views of the unmatched Chicago skyline or visit the 6th floor Cabana Club in the warmer months. The Lounge recently launched a new menu featuring game day bites, sandwiches, and supper. The Blue Line "el" is steps away to whisk you downtown or to O'Hare or explore Wicker Park and Bucktown with free bike rentals. Slip into a comfy banquette as sun seeps through surrounding windows at Café Robey - it serves memorable brunch seven days a week.

Recommended for Best Hotels because: Visitors get a taste of genuine Chicago via The Robey's early 20th-century industrial aesthetic in spunky Wicker Park.

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With just 11 en-suite private rooms inspired by Chicago literary references, Publishing House elevates the traditional bed and breakfast experience by offering stylish interiors, impeccable service and a freshly cooked breakfast each morning. Housed in a century-old building (the former Free Methodist Publishing House was built in 1909, reimagined in 2017), the B & B's common area features an inviting double-sided fireplace (for an always appealing snuggle in the winter), 12-seat dining tables, lounges and a baby grand piano. Forget old-fashioned ideas about busy wallpaper, tons of tacky tchotchke and creaky staircases you may have encountered in other B & B's. Rooms and common areas are beautifully appointed (think subway-style tiles, heated floors, clawfoot tubs and comfy linens). What's more, you're in the heart of the dynamic West Loop's Restaurant Row, music venues, bars and boutique shopping.

Recommended for Best Hotels because: You'll want to live here, not merely visit, for the fabulous food, stylish interiors, luxe amenities and great location in West Loop.

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Meet Jacky Runice

Born in Bucktown when bulletproof was a home safety choice and not a coffee order, Jacky Runice has been knocking around Chicago as a professional print, online and broadcast journalist and...  More About Jacky

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