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.

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, luxurious sheets and pillows, thirsty towels and plush bathrobes. Those deep zzz’s insure energy to explore the city and this hotel is just a short walk to the Chicago Cultural Center, Millennium Park, 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 Street and new colossal tv’s to watch the game. Chef David Fingerman traveled to Kentucky to select Staypineapple’s own branded single barrel bourbon from Old Forester. The Pineapple Pup package snags you a discount on the pet fee or a third-night-free promotion running through Dec. 2022.

The Blackstone has hosted royalty, presidents, movie stars, art lovers (it’s four blocks from the Art Institute), sports legends and more Bears’ fans that you can shake an Italian beef sandwich at. Al Capone even held
meetings while getting a haircut in the windowless
barbershop! The historic property’s neoclassical Beaux-Arts architecture lends an air of opulence which continues throughout the lobby and guest rooms. More than 1,600 pieces of original artwork by local artists decorate the common rooms while each of the guest rooms and suites include upgraded marble bath facilities, elegant décor and plush bedding. You might want to book the Suite of Presidents (the master bedroom is inspired by the President and Mrs. Kennedy’s bedroom at the White House) or the luxury three-room “Smoke Filled Suite” – a reference to cigar-puffing politicians circa 1920. Don’t miss an authentic Spanish dining experience at Mercat a la Planxa.

This modern hotel, the first Radisson Blu in the country, is an architectural gem and the bomb 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, running track, outdoor lap pool and wading pool for kids (open Memorial Day to Labor Day), plus a hot tub, sundeck, fire pits and cabanas. Families can book suites with two connecting rooms and dogs are allowed (up to 60 lbs.) Book a room on a Business Class floor and have access to a free hot breakfast, snacks and refreshments or ask for a room with a balcony overlooking the Chicago skyline. FireLake Grill House and Cocktail Bar is known for its wood-fired menu of the Midwest’s best meat, freshwater fish and veg. The Blu was named #10 on U.S. News & World Report’s 2022 Best Hotels in Chicago.

Notice train iconography punctuating the walls at the new Canopy by Hilton Chicago Central Loop? The 117-year-old Landmark status building was once headquarters of the Chicago and North Western Railway and room design and decor harkens back to the golden age of train travel. That’s the original staircase and tile remnants incorporated into the lobby space. Just across the street from Willis Tower in the financial district, the hotel is a smart choice for those who want to be near Union Station and Metra trains. Depot 226 serves as a bistro, bar, market and coffee shop so it’s easy to grab a bite, cup of joe or linger at the lively bar. Snag one of the complimentary Canopy Bikes to explore nearby attractions such as Millennium Park and the Art Institute.

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.

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 “So Cozy” that gets you $50 restaurant credit and admission for two to the Museum of Science & Industry.

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 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.” The “Stay Like a Star” package includes private tours of the current exhibit of Pop Stars! exhibit with wine, exclusive menu items at Lure Fishbar, and 21% off the gift shop during your stay.

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. Clever Coyote cocktail bar serves 80’s and 90’s games like Street Fighter, tiki drinks, wings and steamed buns. 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.

With 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 and tons of tacky tchotchke you may have encountered in other B & B’s. Rooms and common areas are beautifully appointed (think subway-style tiles, heated floors, clawfoot tubs). What’s more, you’re in the heart of the dynamic West Loop’s Restaurant Row, music venues and bars. Enjoy a free beverage during Happy Hour Wednesdays and inquire about cooking classes, wine tastings and other events in the new Print Room space.