Located in the landmark McGraw-Hill building on the Mag Mile, The Gwen was renovated in 2017 to understated, elegant perfection. King bedrooms are equipped with soaking tubs and steam showers and hotel amenities are numerous: Peloton Bikes in the 24-hour fitness center; complimentary clothing pressings for two items per room daily; Epicurean Experience for all guests at 2pm daily; free-to-use bikes, helmets, and locks for short trips around the city; and the hotel just added a Moet Chandon vending machine in the lobby, Tipsy Tea Party experience weekends; and La Mer in-suite spa services (when booked in advance). Indulge in vibrant Mediterranean fare at Kostali or small plates and cocktails Upstairs at The Gwen, a rooftop terrace that buzzes year round: there’s Aperitivo Hour weekdays and enclosed access to the Shops at Northbridge. For something really special, look into The Gwen Glamping Experience – a multi-bedroom suite and glamping tent in the open air.

Eclectic, hip art exhibitions within the hotel tickle the neurons while an exceptional on-site restaurant, Lure Fishbar, has all the right stuff for romance: cocktails, Champagne, caviar service, oysters and sushi, steak and lobster, and a parade of beautifully presented desserts. When you book the 21c Suite, complete with a deep soaking tub, sparkly night views of the city and open concept living/dining area – you may not want to leave the property, but an easy walk in the fresh air takes you to some of Chicago’s most popular attractions. Consider an in-room couples massage with CBD oils or percussive therapy and check the calendar for frequent special events. For example, February brings a conversation with a relationship expert and speed dating, among others.

A night at Sofitel Chicago will have you whispering “Je t’aime à la folie” in no time flat. Located steps from the Magnificent Mile and Lake Michigan, the hotel draws inspiration from local culture and celebrates the French art of joi de vivre for a special romantic getaway. Consider booking the ongoing “Magnifique Romance Package” offering luxe comfort in elegant accommodation, a bottle of champagne on ice delivered during your stay, a romantic welcome amenity, and a complimentary full American breakfast for two from CDA takeaway, so you can enjoy breakfast in bed. Sofitel Chicago offers an ongoing wine dinner series, too.

LondonHouse Chicago easily has some of the most impressive views of the Chicago River and the city’s lovely architecture from rooms and especially its 22nd-floor rooftop terrace. Couples should look into a luxe, customizable experience in LH Cupola, the intimate, private space at the apex of the hotel offering 360-degree views of the city. The historic Cupola, the property’s highest point dating back to 1923, is a secluded space to pop the question. The basic proposal package includes a full hour private access of the Cupola; rose petals; bottle of Dom Perignon (Brut); and a photographer (full hour coverage). If s/he says “Yes, yes, a thousand times yes!” consider the Juliette Ballroom with floor-to-ceiling windows and riverfront views for an extravagant wedding or a more intimate yet perfectly glamorous celebration in the
Whistler Ballroom.

Virgin Hotels Chicago offers intriguing amenities 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 with rainfall shower heads. Each chamber’s minibar offers an intimacy kit and talk to the team about custom amenities for couples from chocolate-covered strawberries to Champagne and roses. The minibars are stocked at reasonable prices and you can book an in-room couples massage through a third-party partner. One of the most romantic areas of the hotel is Cerise Rooftop, a lively venue with a fireplace, cocktails, a compact but delish menu of appetizers, veg and sandwiches and sweet views of the city. Miss Ricky’s, the hotel’s diner, is fun for brunch indoors and al fresco.

The prestigious AAA Five Diamond award-winning Waldorf Astoria Chicago offers elegance akin to that available in Paris. An urban sanctuary tucked into the Gold Coast neighborhood, the luxury hotel offers apartment-style rooms, an award-winning spa retreat (with the addition of a new couples’ treatment space), dining at the new Brass Tack, and a fabulous Sunday brunch featuring the signature bottomless Rosé complemented by live musical performances from the Champagne All Stars. Guest rooms and suites are spacious boasting private terraces and ornate fireplaces. Couples can be among the first to experience the hotel’s newest premier suites, the Presidential Suite and Astoria Suite, both evoking the charm of a Parisian pied-à-terre. The hotel is located near Oak Street which is lined with designer shopping, including jewelry stores where you can begin browsing engagement rings.

A longtime favorite among discerning travelers, the Park Hyatt unveiled a breathtaking $60 million redesign of guest rooms and public spaces in 2022. Its restaurant, NoMI, is one of the best in Chicago and in warmer weather snag a table at NoMI Garden for Water Tower and lake views in addition to excellent sushi and modern American cuisine rooted in French technique. The vibrant new art program lifts spirits at every turn and oversized soaking tubs enhance in-room relaxation. Although you’re on busy Michigan Ave., triple-pane glass windows ensure a hushed overnight experience. Spa treatments feature cutting-edge products and ancient techniques and there’s a couples’ treatment room for side-by-side “aahs.” Ask about the the exclusive “Romance Package”, a personally curated experience for couples looking for a memorable retreat: softly glowing tea candles in your room, Champagne, house-made sweets, fresh flowers, and a bubble bath kit are some of the options.

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 in some suites, is simply unforgettable. The Langham is one of the best hotels in Chicago exuding British elegance and modern sophistication tucked into a 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 earns awards on the regular so consider a couple’s treatment and be sure to book any of Club rooms or suites to get access to the unequalled Langham Club.

The Four Seasons’ Chicago upholds the chain’s reputation for luxury and service and staff makes your visit effortless so you can concentrate on your love connection. The limestone and glass building is home to spacious, understatedly elegant guest rooms, suites and multi-bedroom apartment units plus stunning views of the skyline and Lake Michigan. The Spa has a Roman-style indoor pool, steam rooms, whirlpool and fitness center. Live in the Lounge features performances on select nights by local artists playing jazz, blues and house, among others. Airy, Michelin-endorsed Adorn Bar & Restaurant lists sensuous items like Blue crab bisque, oysters, Kingfish crudo, miso-glazed sablefish and a caveman-sized beef short rib. The Mile High Cocktail Club is a “secret” cocktail destination that begins as a vivid 1960’s Pan Am waiting room, on through a classic London phone booth into the classy Cocktail Club serving globally-inspired drinks and dreamy views of the city at night. Ask about exclusive excursions and interactive chef-driven dining experiences.

The Peninsula is one of Chicago’s most luxurious hotels and its understated elegance is ideal for a romantic rendezvous. Expect gracious service, and if you’re hoping for a room with a view, ask for a corner suite. Event staff will help you plan special surprises for your paramour from candlelight, rose petals on the bed, or a hidden ring delivered by the culinary team. The Sky Rink has become a favorite place for proposals (how about a message in lights shining on the center of the rink like “Will You Marry Me?”) Couples’ spa treatments are heavenly at the outstanding luxury spa. Dine in The Lobby (which features edible aphrodisiacs around Valentine’s Day) or Shanghai Terrace for superb Asian cuisine. The hotel has great house seats to every Broadway in Chicago production for theater aficionados. Stop by the Krigler Boutique (one of just a few outside of France) to treat your paramour to a wonderful fragrance gift.