The 11 Best Chicago Hotels of 2020

Located in historic Andersonville, The Guesthouse Hotel holds the coveted top spot on TripAdvisor. It offers one, two, and three-bedroom suites, all of which create a unique sense of home. Spread out in the sunlit living room or on your private furnished balcony. There’s a washer and dryer in each apartment, while deluxe suites come with a gas fireplace. Although there’s no eatery on-site, you can cook for yourself in the suite’s gourmet kitchen; or order in from one of the hotel’s partner restaurants.

All members of the family are welcome at The Guesthouse Hotel. Kids benefit from a selection of board games, bath toys, and DVDs (all available at no extra cost), while dogs of all sizes are invited to stay for free. Indulge with an in-room massage or skin care service, or keep fit in the 24-hour gym. There’s an artisan boutique in the lobby for stocking up on last-minute souvenirs. In summer, head up to the rooftop for craft beers and beautiful skyline views. 

Those looking to combine affordability with a prime location near the Magnificent Mile need look no further than Ohio House Motel. There’s nothing fancy about the hotel’s exterior, although its 60s design may be a source of nostalgia for some. The property’s real value, however, is in its rooms — which are clean, comfortable, and surprisingly spacious. Whether you choose a Double, Queen, or King bed, all rooms include free Wi-Fi, free local calls, and cable TV.

Some have a fridge and microwave, while the suite includes a pull-out sofa bed. Free parking is available on a first come, first served basis — a major perk and money-saver in the pricey city center. Those that book directly are entitled to free breakfast — and although there’s no proper restaurant on-site, there are plenty of dining options within a five-minute walk of the hotel. These range from laid-back spots for deep dish pizza to refined New American bistros.

Surrounded by the restaurants and bars of the trendy River North district, ACME Hotel Company Chicago is an ultra-hip sanctuary for those that appreciate unconventional design. From the retro lobby mural to the monochrome guestrooms, this hotel packs a serious decor punch. Rooms feature hardwood floors, Egyptian cotton sheets, and spa-inspired bathrooms. Get online using the high-speed Wi-Fi or via the Smart TV. Suites add another level of sophistication with separate chill rooms and state-of-the-art sound systems.

Wake up to a complimentary coffee thermos delivered to your door each morning. ACME is full of quirky extras, from DIY cocktail kits in your room to Apple Watches for rent at reception. Order gourmet sandwiches from downstairs social spot West Town Bakery or spend the evening sampling craft cocktails and small plates in The Berkshire Room. Additional amenities include a fitness center, a business center, room service, and guest parking. 

Stylish Kimpton Hotel Palomar Chicago is conveniently located in the heart of downtown. Kids are welcomed with a small gift, while the Guppy Love program lets your little ones take care of their own pet fish. Cribs are provided at no extra charge, and heavy items such as strollers are available for rent. Choose interconnecting rooms or book the Artist Suite, which is complete with a master bedroom, bathroom, and living room with a sofa bed.

A same-day laundry service makes your life easy, while the heated indoor pool is perfect for family bonding time. Sable Kitchen & Bar serves fine New American cuisine and Prohibition-era cocktails for Mom and Dad, and provides high-chairs for smaller guests. At the complimentary wine hour, kids receive an alcohol-free “mocktail.” The concierge can arrange accredited babysitting services (or in-room massages for when you need a break).

Located outside the city center in tranquil Oak Park, Harvey House Bed & Breakfast is ideal for a romantic getaway. When you feel like a night out on the town, you can drive to downtown Chicago in just 15 minutes. The hotel has five intimate suites, each one uniquely decorated with silk fabrics and antique furniture. Slip into the Jacuzzi tub for two, ​or snuggle up in front of the cozy fireplace.

Penthouse suites include hardwood floors and a separate kitchenette for added independence. Your room rate includes a gourmet home-cooked breakfast and there are plenty of bars and restaurants within easy walking distance. Upgrade to the Romance Package for champagne and chocolates delivered to your room. The hotel also has Wi-Fi and free parking. 

From the lobby chandelier to the dove gray guestrooms, understated opulence reigns at the Waldorf Astoria Chicago. You’re a few minutes’ walk from the Magnificent Mile and scenic Lake Michigan. All rooms include a deep-soaking tub with an LCD TV set into the bathroom vanity, a surround sound system, and a fully stocked wet bar. Most have fireplaces, while the Presidential Suite boasts 26th-floor views from two private terraces. Enjoy fine dining throughout the day at Bernard’s Bar & Restaurant or make a reservation for afternoon tea. A French restaurant and patisserie by award-winning chef Michael Mina which opened in April 2017. Treat yourself to a massage at the Waldorf Astoria Spa, swim laps at the health club, or make the most of the complimentary Mercedes Benz chauffeur service.

A few minutes' walk from House of Blues Chicago and the bars of River North, The Godfrey Hotel Chicago is the ideal choice for trendsetting partygoers. The highlight is the IO Godfrey Lounge - one of the best rooftop bars in the city. It’s made special by its unique indoor/outdoor design, sultry mood-lighting and stunning skyline views. Expect a hip young crowd drawn by good music and pitcher cocktails. All guestrooms and suites include a wet bar, a 46” HD TV and luxury linens for a good night’s sleep when the party eventually winds down. The next day, recharge with a spa massage or authentic Neapolitan fare at Dolce Italian restaurant. The hotel also has a fitness center and complimentary Wi-Fi. 

Conveniently located near the Loop business district, Wyndham Grand Chicago Riverfront is a 12-minute drive from McCormick Place convention center. There'​​s more than 16,000 square feet of event space on-site — including the Grand Ballroom and the Penthouse Ballroom, both with space for up to 250 guests. In between meetings, get online at the business center or let off steam with a fitness center workout. Whether you opt for a guestroom or suite, thoughtful touches include complimentary Wi-Fi, an iPod docking station, and a Keurig® coffee-maker. Hoyt’s American Tavern serves reinvented comfort food classics, while in-room spa services and valet parking are available for a fee. 

The Kimpton brand is known for stylish, upmarket luxury, and its recently-opened Chicago Gray hotel — located in the former New York Life Insurance building in the Financial District — is no exception. Located in the heart of the city’s downtown, guests are less than a 15-minute walk to top Loop, business, and lakeside destinations like Millennium Park, Navy Pier, Union Station, and the Willis Tower.

Sleek, sophisticated design in trendy shades of gray, blue, and brass marry in-room creature comforts and Downtown Loop views.  Although Kimpton’s amenities always go above and beyond, they do so in wonderful ways at this property: free yoga mats in each room, exercise bikes that hail from the Peloton studio in New York, loaner cruiser bikes, and free coffee and tea in the mornings. At night, take in the views from Boleo, the hotel’s rooftop bar complete with retractable roof.

For the best of both Lake Michigan and Chicago skyline views, the city’s Four Seasons delivers. Choose from lake-view rooms that look out on water so close, you’d be forgiven for thinking you weren’t in Chicago after all. City-view rooms, on the other hand, look out toward the iconic Midwestern skyline, which is beautifully illuminated at night. Of course, the Four Seasons delivers more than just views: You’ll get the hotel chain’s legendary service and standards of luxury. There’s a 50-foot indoor pool, and around 900 shops beginning on the floor directly below the hotel — and if you have kids, they’ll even go so far as to gift a free movie and popcorn once each stay. Plus, the location is great: You’ll be in the center of the city’s famed Gold Coast neighborhood downtown, right on the Magnificent Mile. 

Situated at the center of hipster enclave Wicker Park, Urban Holiday Lofts is the hostel of choice for style-conscious backpackers. Choose a gender-specific shared dorm or a classy private room (with or without an ensuite bathroom). All rooms have heating and air-conditioning. There’s a complimentary breakfast and a communal kitchen, as well as an on-site gourmet market. The highlight, however, is the Urban Sky Lounge — where you can watch movies, play pool, or jam arcade games. Make the most of free amenities, including Wi-Fi, luggage storage, and parking.