Love the One You're With: Chicago's Most Romantic Hotels

In addition to the obvious, a romantic hotel getaway offers a stack of benefits like lowering stress, rekindling intimacy and it's just plain fun to discover new digs together. 

Not only does the Windy City boast tony properties like the Four Seasons, Ritz-Carlton, Waldorf-Astoria, JW Marriott, Radisson Blu Aqua with it's undulating architecture and The Langham's European hospitality right on the riverfront in an historic Mies van der Rohe building (the last designed by the exalted architect), but there is new boutique lodging popping up everywhere from Wicker Park to the Gold Coast.

With spa services, world renowned restaurants and even rotating art collections by local, national and international artists, you barely have to leave the building. Each of our selections is surely a place for rest, romance and rejuvenation but many also aim to entertain and captivate.

Consider the copious options to celebrate romance any time of the year in one or more of Chicago's fabulous hotels. 

— If you book a hotel by clicking one of our booking links, 10Best may earn a small commission. Our picks and opinions are independent from any business incentives.


Named the #1 Hotel in Chicago for two consecutive year by Condé Nast Traveler's 30th annual Reader's Choice Awards, Virgin Hotels Chicago offers a number of intriguing amenities fit for a romantic stay. Each of the casual "chambers" includes a custom designed hybrid bed with an ergonomic headboard and footboard that allows for a range of positions for, well, you know. There's a set of sliding privacy doors separating the sleeping area from the dressing area and spacious showers (big enough for two) with rainfall showerheads are a plus. Each chamber's minibar offers an intimacy kit which includes condoms, lubricant and a feather tickler. Commons Club is the second floor restaurant/bar offering sharable "Nosh Towers" and Miss Ricky's, the hotel's All-American diner, is fun for brunch. Upstairs is the intimate live entertainment venue with free nightly shows to insure complete indoor fun.

Recommended for Romantic Hotels because: The playful property is located in the old Dearborn Bank Building close to attractions like Millennium Park, the Art Institute and the Chicago Theater.

Read more about Virgin Hotels Chicago →

Located between Streeterville and the Loop, Swissotel Chicago is a sleek 4-diamond all glass hotel that offers spectacular wrap-around views from the Chicago River and Navy Pier to Millennium Park and the Wrigley Building. Steps away from the Magnificent Mile, it's close to everything but still tucked away. Available year round, Swissotel Chicago's Date Night package will make it easy to celebrate an anniversary, birthday, or an "I love you" occasion with your special guy or gal. The package includes signature chocolate dipped strawberries in your room, a champagne toast for two in Amuse (the lobby eatery); complimentary breakfast at The Palm; and 2pm late check out. Enjoy a sumptuous dinner at The Palm, just an elevator ride away from your room, serving Italian specialties, steaks, seafood and lobster.

Recommended for Romantic Hotels because: The views are phenomenal and you can walk to some of the best shopping, dining and activities in the city.

Read more about Swissotel - Chicago →

The prestigious AAA Five Diamond award-winning Waldorf Astoria Chicago offers elegance otherwise available only in Paris. An urban sanctuary tucked into the Gold Coast neighborhood, the luxury hotel offers apartment-style rooms, an award-winning spa retreat and two Michael Mina Signature Restaurants serving seasonal and artisanal French cuisine. Guest rooms and suites are spacious boasting private terraces and ornate fireplaces, keen accessories for a perfect romantic stay. Exit the large marble bathrooms with separate shower and soaking tubs and don your soft, comfy robes. The hotel is located near Oak Street which is lined with designer shopping, including jewelry stores where you can begin browsing engagement rings.

Recommended for Romantic Hotels because: The on-site dining options receive kudos for quality of food and ambiance

Read more about Waldorf Astoria Chicago →


With just 11 private and beautifully appointed rooms inspired by Chicago literary references, the B & B elevates the traditional bed and breakfast experience by offering stylish interiors, impeccable service and a freshly cooked breakfast each morning. Housed in a 110-year-old building, Publishing House'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. Husband and wife owners prepare breakfast for their guests each morning and for romantic getaways, ask for Champagne to be waiting in the room on arrival (from the intimate subterranean Press Room wine bar). The Everleigh room has a vintage claw foot tub and steam room for extra romance.

Read more about Publishing House B&B →

Thompson Chicago
Photo courtesy of Courtesy of Thompson Chicago

One of the sensory characteristics of a romantic rendezvous is sound - as in, not so much and Thompson Chicago may be one of the city's most hushed hotels tucked away on East Bellevue just off of Rush St. The neighborhood can't be beat for upscale shopping, cafes, people watching and a stroll to the lake. The lobby feels like a tasteful living room filled with books and cheeky art. Rooms feature masculine lines and color yet feminine flashes of texture and sparkle. Book one of the bi-level suites: four have outdoor terraces with lake views. Soaking tubs and showers big enough for two are a plus and the on-site Italian restaurant, Nico Osteria, is a winning example of refined Italian dining. An engagement package includes a private helicopter tour, complimentary Lexus car service, Champagne toast and a photo of the moment you become new fiancés.

Recommended for Romantic Hotels because: Everything about Thompson Chicago is effortlessly smart and stylish plus the seafood driven Nico Osteria is one of the city's best.

Read more about Thompson Chicago →

The Peninsula is one of Chicago's toniest hotels and its understated elegance is ideal for a romantic rendezvous. Expect top-rate gracious service, and if you're hoping for a room with a view, ask for corner suite. Event staff will help you plan special surprises for your paramour from candlelight, rose petals on the bed, or perhaps a strategically placed gift? Whatever you like. Spa treatments are heavenly at the outstanding luxury spa. The rooms are traditionally furnished with marble bathrooms that include a soaking tub and steam-free inset television and lodging amenities are controlled via iPad. Dine in The Lobby (which also offers afternoon tea service); Shanghai Terrace for Asian cuisine; or Pierrot Gourmet's European cuisine, A fitness center schedules dozens of complimentary classes each week and a heated 25-meter pool overlooks the city's skyline.

Recommended for Romantic Hotels because: On-site activities include music in the lobby nightly and ice skating on the hotel's private rooftop rink.

Read more about The Peninsula Chicago →

LondonHouse Chicago, Curio Collection by Hilton
Photo courtesy of LondonHouse Chicago

LondonHouse Chicago boasts some of the most impressive views of the Chicago River and the city's sweeping architecture from rooms and especially its 22nd floor rooftop terrace. Foodie couples should look into a luxe, customizable dinner in LH Cupola, the intimate, private space at the apex of the hotel offering 360-degree views of the city. Work with the culinary team at LH Rooftop to craft a menu of reimagined American cuisine up to 18 courses. After all, Prince Harry did propose to Meagan Markle over roast chicken. Staff can help with popping the question, too. The hotel's "elevated engagement package" allows a couple to steep in LH Cupola's original beaux-arts design, ornamental details and intimate space for memorable moments before and after s/he says "Yes, yes, a thousand times yes!" Look into booking a Vista Suite featuring floor-to-ceiling windows for dreamy views, separate living area and a luxe King bed.

Recommended for Romantic Hotels because: LomdonHouse Chicago resides in an historic building across from the Riverwalk with vintage details inspired by the Jazz Age.

Read more about LondonHouse Chicago, Curio Collection by Hilton →

Chicago Athletic Association
Photo courtesy of Photo courtesy of Chicago Athletic Association

Once an elite private men's club circe 1891, this property was restored and converted into a wood, stained glass and architecturally beautiful boutique hotel. Cindy's, the hotel's rooftop bar, is a stylish, romantic spot for a happy hour drink or two accompanied by a fantastic view of Millennium Park, Buckingham Fountain and the lakefront. Enjoy the multiple fireplaces and marble staircase in the lobby and when it's time for friendly competition, head to The Game room for bocce ball, pool tables and table shuffle board. Holy Cow Suites (a nod to dear old Harry Caray) offer cozy fireplaces, separate seating areas, oversized bathrooms and most offers views of Millennium Park, The Bean, Michigan Ave. or Lake Michigan. Walk to theater, symphony, park or the lakefront.

Recommended for Romantic Hotels because: The Loop is challenging the Gold Coast with one of the most architecturally and historically beautiful properties in Chicago.

Read more about Chicago Athletic Association →


The Hard Rock Hotel Chicago transformed into the St. Jane in summer 2018 taking its name as homage to activist Jane Addams. Which sounds serious but the edifice, the landmark 1929 Art Deco Carbide and Carbon building on Michigan Ave., is anything but. The 38-story hotel includes a main building plus The Tower at St. Jane, a boutique luxury section above St. Jane. Book it for your romantic encounter to have access to a 24th-floor lounge, The Nobel. Your dedicated concierge staff is ready to take care of any needs. Free Rein, a New American brasserie led by Michelin-starred chef Aaron Lirette, does not disappoint. Tower rooms feature black walls and velvet furniture in jewel tones lending a sexy ambience and sweeping views of the Chicago skyline, river and Lake Michigan are inspiring. You're in the middle of some of the city's top attractions, dining and shopping, too.

Read more about St. Jane →

A luxurious bath does a body good and indulging in a soak in one of The Langham's granite tubs, which are in front of large picture windows, is simply unforgettable. The Langham may be the best luxury hotel in Chicago exuding British elegance and modern sophistication tucked into an historic Mies van der Rohe building, the last designed by the renowned architect. Sidled up to the downtown riverfront, the building designed in the 1970s is sophisticated inside and out. The hotel's interior features appealing art and sculpture and rooms are done in neutral colors with tasteful furniture., Floor-to-ceiling windows welcome the jaw dropping skyline and views of water traffic meandering down the Chicago River. Chuan Spa recently earned cheers at the American Spa awards so consider a couples treatment. The "River Romance" package includes great extras like spa credit, bubbly, valet parking and Travelle features wonderful seasonal American cuisine.

Recommended for Romantic Hotels because: Feel free to take a pampering deep soaking bath in a bathroom offering a voluptuous view of the city.

Read more about The Langham, Chicago →


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