United States Illinois Chicago Chicago Guide Things To Do Essentials Restaurants Nightlife Where to Stay Neighborhoods Events All Chicago Chicago's Most Romantic Hotels Written by Susan Breslow Sardone Facebook Twitter Linkedin Susan Breslow Sardone is a travel journalist who specializes in honeymoons and romantic getaways, and who originated New York Magazine's highly successful "City Weddings and Honeymoons" sections. Tripsavvy's Editorial Guidelines Susan Breslow Sardone Updated 06/26/19 Share Pin Email Our editors independently research, test, and recommend the best products; you can learn more about our review process here. We may receive commissions on purchases made from our chosen links. Couples planning a honeymoon don't normally consider Chicago, yet its most romantic hotels are ideal perches to rest and regroup after a Midwestern wedding and before you jet off to a more exotic destination. Along with those celebrating a birthday, anniversary, or in need of some city fun, it's worth a visit thanks to world-class shopping (Magnificent Mile!), museums (Art Institute!), and other Chicago must-sees. Waldorf Astoria Chicago Courtesy of Waldorf Astoria Chicago Buy on Tripadvisor.com Luxury Hotels 4.3 Couples who appreciate excellent service, chic accommodations and outstanding comfort will find that the Waldorf Astoria Chicago delivers on all three. Although it's one of the city's most expensive hotels, it also won't nickel-and-dime you. The no-tipping policy is a reprieve from having to dip into your pocket every time you deal with a staffer. And there's even a house car to drive you to your choice of location within two miles of the property. Isn't It Romantic: Complimentary slippers provided in sizes for him and her along with spa-like robes. The Peninsula Hotel Chicago The Peninsula Chicago offers an elegant address in the city’s chic shopping district. The Peninsula Chicago. Buy on Tripadvisor.com The palatial Peninsula can't help but make you feel important. The sumptuousness of the setting puts it among the city's most expensive hotels, but if you intend to go in style, this is the place. Every year since it opened, the Peninsula Chicago has received a Forbes Travel Guide Five-Star rating. Z Bar isn't the city's only rooftop terrace, but it is the most comfortable. Isn't It Romantic: VIP “Keys to the City” perks include a priority pass, Art Institute guidebook, and private shopping session at Saks Fifth Avenue. And if the weather outside is dreadful, treat yourselves to Afternoon Tea, a gourmet repast. Four Seasons Chicago View of Lake Michigan. Four Seasons Buy on Tripadvisor.com Luxury Hotels 4.6 The ageless Four Seasons Chicago evokes European elegance with its marble floors, crystal chandeliers, and magnificent floral bouquets in public spaces. Isn't It Romantic: High-rise views that make you feel on top of the world and an in-room visit from the Martini Man with his traveling cart to concoct your favorite cocktail. The Blackstone Courtesy of The Blackstone Buy on Tripadvisor.com This 23-story beaux-Arts Chicago landmark, which opened in 1910, has a unique provenance: It routinely hosted Al Capone. Today's more law-abiding visitors appreciate that it's a short walk to the Art Institute and is home to one of the city's most distinctive eateries, a Barcelona-inspired tapas joint, Mercat a la Planxa. Isn't It Romantic: The king-size bed is made for comfort and its multiple down and foam pillows provide ample ammunition for a zesty pillow fight. And the marble bathroom features a shower big enough for two. Virgin Hotels Chicago Couples massage in the spa. Virgin Hotels. Buy on Tripadvisor.com Romantic Hotels 4.4 Inside a restored 1920s Art Deco landmark, the world's first Virgin Hotel has the vibe of a private club. Free daily cocktails are served during the 6-7 pm social hour. Bring your pooch; two rooms on each floor are pet-welcoming. Isn't It Romantic: Patent-pending lounging beds in rooms and minibar featuring a Lovers' Intimacy Kit. Londonhouse Chicago, Curio Collection by Hilton Roof terrace at Londonhouse Chicago. Londonhouse Chicago. Buy on Tripadvisor.com Best positioned for city viewing at the corner of North Michigan Avenue and Wacker Drive, the historic, landmark Londonhouse Chicago features a sociable roof terrace on the 22nd floor. Views take in the Chicago River, Magnificent Mile, and towering examples of the city's famed architecture. Isn't It Romantic: Cocktails on the terrace at night, when the city glitters below. Park Hyatt Chicago We love a room with a nook. Park Hyatt Buy on Tripadvisor.com Romance 4.2 Spacious rooms and suites with captivating views in a cool, comfortable setting are certain to seduce lovers. The Park Hyatt Chicago features great sound systems, spa-like bathrooms, and 24-hour room service. You may never want to leave. Isn't It Romantic: Oversize bathtubs and a nook big enough for two by the window. Sofitel Chicago Water Tower Hotel Sofitel Chicago Buy on Tripadvisor.com What's unique about Sofitel hotels around the world is the French chic the company applies to design and hospitality. This property rises 32 stories, offering views of Lake Michigan and the city. Isn't It Romantic: Sofitel's lush feathertop bed and duvet, 24-hour room service, and the French spirit of ooh-la-la. The Gwen Rooftop aerie. Gwen. Buy on Tripadvisor.com Right above the Magnificent Mile, this Starwood property is a fine location to repair after a shopping spree. The rooftop terrace features an expansive cocktail menu so you can try new tastes as you toast your love and look over the city. Isn't It Romantic: In-room spa services can put you in the mood without having to leave and lose the mood. The Talbott Hotel Traditional furnishings in a modern hotel. JDV Hotels Buy on Tripadvisor.com Two blocks from the Magnificent Mile, The Talbott combines traditional décor with contemporary amenities (some rooms have Apple minis). Frette bed linens and a lobby lounge that features a working fireplace makes it particularly cozy. Isn't It Romantic: Upon arrival, the two of you will be offered a complimentary glass of wine or beer at 20 East. Was this page helpful? Thanks for letting us know! Share Pin Email Tell us why! Submit Continue to 5 of 10 below. Continue to 9 of 10 below.