The 12 most romantic hotels in Chicago for 2025

Checking into The Guesthouse Hotel feels less like a hotel stay, and more like moving into your own stylish Chicago apartment. Located in Uptown, just north of Andersonville, this boutique spot has a warm, residential vibe that makes it a unique alternative to all the big downtown towers.

Made up entirely of fully self-sufficient suites, each with a full kitchen, this home-from-home has all the mod-cons you could ever need. If home cooking is your thing, look no further; you can grab ingredients from the local market, rustle up a romantic dinner, then enjoy a bottle of wine with your beloved on a private balcony. And with roomy living spaces, comfortable furnishings and thoughtful details throughout, it’s easy to settle in and treat this place like home. 

Venture outside your quarters and you’ll find shared spaces with a similarly snug vibe. The club room and library feature sleek sofas, printed artwork and shelves bursting with books and artisanal local produce. There’s also two roof decks with contrasting views, a fitness centre and even in-room wellness treatments if you’re feeling ultra-indulgent. Downstairs, the lobby is worlds away from all the noise usually plaguing city hotel foyers—and at the 24/7 reception, the service is impeccable. There’s also a small shop with thoughtful gifts and a pantry stocked with snacks and drinks, for when you need something quick. 

The staff are warm and on hand to share their neighborhood favorites, too, allowing you to experience Andersonville like a local. With its mix of stylish home comforts and easygoing independence, The Guesthouse feels like one of Chicago’s best-kept secrets.

Time Out tip: Walk a few blocks to Hopleaf, Andersonville’s legendary Belgian beer bar. Famous for its mussels and frites and vast beer list, it is a neighborhood institution that makes for a lively night out. 

Address: The Guesthouse Hotel, 4872 N Clark St, Chicago, IL 60640, US
Price per night: Two beds / two bathrooms suites starting from $550 per night peak season (May–Sep); $275 off-peak (Jan–Mar).
Closest transport: Ravenswood (10 min walk) and Argyle (15 min walk) Metra stops.

Tucked into the upper floors of a historic downtown building, The LaSalle Chicago combines old school grandeur with all the polish of a brand new hotel. Opened in 2022 in the city’s Financial District, it feels stylish and suave, with top-notch service and a central location that makes it an excellent choice for a romantic getaway. 

Step inside and you’ll notice its unique blend of history and modern design. The soaring honey colored columns at the entrance nod to the building’s past as the Continental and Commercial National Bank, while chic interiors and stylish décor keep things firmly in the present. There’s a clean cut, Art Deco charm to the hotel’s 232 rooms and suites, which feature midnight blue and slate grey tones, soft rugs laid across oak floors, and bougie marble bathrooms that feel suitably luxurious. Plus, you can expect blackout curtains, plush bedding and spacious walk-in showers, adding a sense of comfy cool to your romantic weekend. It’s a polished, intimate environment, and they’ve thought of every detail.  

Though small in size, The LaSalle packs a lot in; you can book a table at the glitzy steakhouse restaurant, Grill on 21, or drop into the hotel’s elegant bar to catch some live jazz. On weekends, make use of the complimentary chauffeur service, which’ll whisk you and your beau around the city (within a two mile radius). It’s exactly this kind of personal touch that makes a stay here feel special. Nothing feels like too much hassle for the hotel’s friendly staff, who always go the extra mile (or two) to ensure your every need is met—all you have to do is enjoy. 

Time Out tip: The Willis Tower is just a five minute walk away. Head up to the Skydeck and step onto The Ledge, a glass box on the 103rd floor, for dazzling skyline views.

Address: 208 LaSalle Street, Chicago, Illinois, 60604
Price: Superior King rooms start from $313 per night.
Closest transport: Quincy is the closest ‘L’ train stop, a two-minute walk away; for the Blue line, Monroe station is just over five minutes away.

Themed hotels often feel a little too cheesy, but Hotel EMC2 in Streeterville manages to pull it off with flair. Named after Albert Einstein’s famous equation (E = mc2) and greeting guests with a Leonardo Da Vinci quote on the lobby wall, this hotel is far from subtle in its intent to present itself as ‘the intersection of art and science’—but that’s exactly why it works. With colorful art all over, a distinctly boutique feel, and a pair of cute robot attendants to cater to your every need, EMC2 has more personality than most of the neighboring hotels combined. 

The art-meets-science concept is fully realized throughout, with swirly amoeba-like hallway carpets and digital frames flashing sketches and paintings. Rooms are compact but thoughtfully designed, pairing ebony herringbone floors with mercury glass accents and caramel leather headboards that lend a sophisticated social club vibe. The undeniable focal point, however, is the gorgeous glass-walled shower planted squarely in the center of each room. For couples, it’s a sexy, playful touch. But, if you’re weirded out by being on display while you lather up, don’t worry—there’s also a curtain that slides around the shower stall for privacy—it’s one for the exhibitionists and the modest-minded. 

Also well-worth a visit is The Albert, the hotel’s first-floor restaurant. Remaining firmly on theme, the dining room is lined with towering shelves filled with books, surrealist art and all kinds of curios, giving it an art museum-meets-nutty professor vibe. Despite being named after famously-German Einstein, the cuisine here is Italian-inspired, but expect beautifully balanced, palate-tickling flavors and artfully plated dishes, plus splurge-worthy cocktails., It’s a solid spot for date night or an anniversary dinner.

And then, of course, there’s Cleo and Leo. While the service from EMC2’s human employees isn’t lacking in any way, no stay is complete without a visit from these loveable robot attendants, who add a touch of futuristic whimsy to an already imaginative stay. Fancy cozying up under a surrealist painting while room service robots attend to your every need? Then this delightfully quirky hotel is the one for you.

Time Out tip: For a more retro kind of romance, take the 20-minute walk to Navy Pier, where you can catch a show, ride the Ferris wheel or stroll along the lakefront promenade.

Address: 228 E. Ontario St., Chicago, IL 60611
Price per night: Starting from $249
Closest transport: 1.5-block walk to Michigan Avenue buses; 10-minute walk to Grand station (Red Line train); 1-hour taxi ride to O’Hare airport and 45-minute drive from Midway Airport

Nestled in the heart of Chicago’s Gold Coast neighborhood, the Viceroy is sleek and sexy. This blue-hued glass tower, sat atop the building’s original 1920s brickwork, houses 180 rooms spread across 18 floors, providing a gorgeous backdrop for a downtown staycation. Think chic gold accents, plush furnishings and floor-to-ceiling windows offering city views and (if you’re lucky) glimpses of Lake Michigan.

The interiors have a rich and moody feel, with emerald and navy tones layered against brass details and velvet textures. Bathrooms feel spa-grade, each featuring walk-in rainfall showers and luxe toiletries. And, if you’re looking to splash out, why not splurge on a suite? These come with deep soaking tubs, separate living areas and breathtaking corner views—perfect for impressing that special someone.

For date night dining, consider Somerset, the hotel’s crown jewel. This ground-floor restaurant pairs Mediterranean flavors with retro-glam interiors and an open-air patio in the summer. Stylish yet relaxed, it’s the kind of spot that sets the tone for a night to remember. Then, as the evening progresses, you’ll want to head upstairs to the rooftop cocktail lounge and pool. A rare find in Chicago, this oasis boasts crisp pool waters and stunning skyline views, making it all too easy to linger here into the early hours. Come for the cocktails, stay for the sunrise.

If that’s not tempting enough, what really sets Viceroy apart is the service. Attentive staff greet you with warmth, happily point you toward their favorite local haunts, and keep everything running with a polish that never feels stiff. It’s a hotel that manages to balance stylish sophistication with a genuinely warm welcome, meaning you’ll want to visit again and again.

Time Out tip: Book a city-view room to make the most of those floor-to-ceiling windows. Stay mid-week if you can—the rates are friendlier and you won’t have to jostle for space by the rooftop pool.

Address: 1118 N State St, Chicago, IL 60610
Price: Starting from $375 per room, per night
Closest transport: Clark/Division Red Line, five-minute walk

One of the best romantic hotels in Chicago for couples with a creative side, this London import is decked out in handsome furniture, locally sourced art and clever design touches. The 182 guest rooms range from snug to roomy and are equipped with floor-to-ceiling windows and slick modern bathrooms. Add in a complimentary bagged breakfast that’s delivered to your door each morning, and you’ll want to stay in bed for as long as possible.

But it’s what happens outside the rooms that really makes The Hoxton stand out. In-house restaurants Cira and Cabra are excellent options for date night. At Cira, you’ll find Mediterranean-inspired plates in a stylish all-day setting, while upstairs at Cabra, Top Chef winner Stephanie Izard delivers bold Peruvian flavors amongst rooftop views and a lively vibe. Both are wildly popular with locals as well as hotel guests, so booking ahead is essential if you want to secure a table.

And there’s no better spot for a cozy nightcap than Lazy Bird, situated downstairs, which is one of the best basement bars in Chicago. Low-lit and atmospheric, with a polished cocktail list and live music on select nights, it’s the kind of bar that makes staying in feel every bit as exciting as heading out. The Hoxton is one of the city’s most versatile, stylish choices for a romantic escape.

Time Out tip: Step outside and you’re at the entrance to Fulton Market, Chicago’s hottest dining district. From cult burgers at Au Cheval to Michelin Bib Gourmand fave Girl & the Goat, this strip is packed with all sorts of flavors. Whatever cuisine you fancy, you’ll probably find it here. 

Address: 200 N Green St, Chicago, IL 60607
Price: Starting from around $279 per night
Closest transport: Morgan L stop (Green and Pink lines), just outside the hotel

With views of the Chicago River and Lake Michigan, a top-notch restaurant, a massive ballroom and 316 spacious rooms and suites, it’s not surprising that The Langham is often recognized as one of the best hotels in the country. Need to be enticed even further? Fine, we’ll indulge you. This five-star hotel offers all the high-end comforts you’d want for a romantic staycation or getaway. 

The generously sized rooms boast massive windows looking out on enviable city views, plus a myriad of thoughtful touches designed to make you feel properly at ease. There’s hardwood floors, punctuated by built-in rugs, which give the space a sleek, high-end feel throughout, and an in-room living area, hidden mini bar, and heaps of storage, all combining to create an unmistakably, ultra-luxe, home-away-from-home vibe.

Most impressive, though, is the array of wellness options on offer. The Langham truly elevates the standard hotel experience with a varied tome of treatments all designed to help you find your zen. The five star Chuan Spa offers facials, foot therapies and massages, meaning you’ll definitely leave lighter in spirit (and wallet). And don’t neglect the 67-foot swimming pool and soothing hydrotherapy hot tub. If R+R is your thing, this is the stay for you. 

Dining-wise, the hotel’s restaurant Travelle serves up delicious dinners with views of the river, while The Pavilion lounge adds a touch of class to proceedings with daily afternoon tea. Here you’ll find Wedgwood china, delicate pastries, finger sandwiches and optional Champagne upgrades. Charming, right?

Time Out tip: The hotel sits right by the Magnificent Mile, Chicago’s most famous shopping strip. Stretching along Michigan Avenue, it’s packed with luxury boutiques and department stores. Ideal for some retail therapy. 

Address: 330 North Wabash Avenue, Chicago, IL 60611.
Price per night: From $500, depending on dates and accommodations.
Closest transport: Millennium Station is a five minute walk. 

Striking the right balance between the glamour of 1930s Chicago and all the modern comforts you could possibly need, The Gwen feels tailor-made for a romantic city break. The Art Deco-inspired interiors add a dash of old Hollywood drama to the affair, while an undeniable modern polish keeping everything stylish and welcoming. It’s retro meets contemporary—and it’s seriously chic.

Guest rooms are spacious and serene, designed for downtime after a day in the city. Think king-sized beds, sumptuously soft bedding and gleaming bathrooms with both tubs and walk-in showers—the sort of details that are designed to impress. Oversized windows draw in natural light, while calming tones keep the atmosphere cocoon-like and restful. 

While those super-soft linens might tempt you to stay tucked in, upstairs at The Gwen, the hotel’s terrace bar, makes leaving your room more than worth it. In summer it’s all cocktails and skyline views, while cooler months bring fire tables and cozy seating that turn the rooftop into a gorgeously atmospheric date spot. It’s the kind of place where a quick drink easily drags out into an entire evening. 

Location is another win: the hotel sits right on Michigan Avenue, with the Riverwalk and endless shopping and dining options just steps away. All in all, The Gwen wraps classic Chicago charm and modern comfort into one very enticing package.

Time Out tip: For a more lively experience, check out the Gwen’s tipsy tea parties, which feature live DJs and cocktails along with towers of snacks. Those in search of a quick drink can grab a split from a Moët & Chandon vending machine in the lobby.

Address: 521 N Rush St, Chicago, IL 60611
Price per night: From around $194 to $494, depending on dates and room type
Closest transport: Grand L stop (Red Line), five-minute walk

Celeb-adored boutique hotel chain Nobu makes its Chicago debut with an 11-story, 115-room tower in the West Loop. For the unfamiliar, this neighborhood is jam-packed with great restaurants and bars, making this a smart spot for foodies in search of date night dining. 

As for the accommodation, rooms range from a 360 square foot deluxe room to the 1,900 square foot two bedroom Nobu Villa. Interior design elements across all rooms mixes Japanese minimalism with Chicago cool: low platform beds, blonde wood, and massive windows that pour in soft light at sunrise and dusk. Upgraded features include soaking tubs, steam showers, room service and yoga mats, but guests can also explore the property’s fitness center and indoor tranquility pool. Downstairs, a subterranean spa includes a 40 foot pool and separate saunas; there aren’t treatment rooms, but it’s a calm spot to slow the pace before you head back into Fulton Market.

Of course, one of the hotel’s main draws is the in-house restaurant by the same name, a sushi haven helmed by master chef Nobu Matsuhisa. It’s a destination in its own right. People book a table here even if they aren’t staying at the hotel, so if Nobu dinner is the plan, reserve well in advance, especially at weekends. Afterwards, ride the lift to the ever-so-sophisticated rooftop bar, where you can enjoy saké, Japanese whisky, or just take in the skyline views. Happy hour is every day from 3 pm to 6 pm, where a DJ spins mellow house and the whole place braces itself for the night ahead.

Time Out tip: Nobu is famous for a reason. Eat there.

Address: 155 N Peoria St, Chicago, IL 60607
Price per night: From around US $375–$425 (depending on dates and room type)
Closest transport: Morgan L stop (Green and Pink Lines, 4-minute walk) or Clinton L stop (Green and Pink Lines, 10-minute walk)

To say the Chicago Athletic Association is beautiful is putting it mildly. Set in a restored 1890s Venetian Gothic building right on Michigan Avenue, this landmark property combines historic grandeur with a playful sense of fun. For couples, it offers a one-of-a-kind base in the heart of Chicago, full of character and romance.

The 240 boutique rooms are designed as throwbacks to the club quarters of the building’s past, with wood panelling, vintage sporting flourishes and leather accents that nod to its athletic heritage. While the style is rooted in history, the comforts are thoroughly modern: soft bedding, glistening bathrooms and thoughtful amenities that make it easy to relax together after a day in the city.

Food and drink are a huge part of the experience here. Cindy’s, the rooftop restaurant and bar, is celebrated for its panoramic views of Millennium Park and Lake Michigan. Whether you’re stopping in for brunch, a sundowner cocktail or a full dinner, you will not regret visiting. Downstairs, the hotel keeps things low key and casual—with a Shake Shack tucked into the lobby, perfect for a no-frills bite or late-night burger run.

Then there’s the Game Room. It’s a sprawling lounge with its own alley entrance, where you can challenge each other at bocce, shuffleboard or billiards, with a side order of congratulatory (or commiseratory) cocktails. It’s a lively, social and unique space, located in the building’s original billiards room, and we’d definitely recommend paying it a visit if you’re 

Blending historic style with modern comfort, grand architecture and playful touches, the Chicago Athletic Association is a distinctive romantic escape in an unbeatable central location. It’s aesthetic, historic, and buzzy—what more could you want?

Time Out tip: Chicago’s cultural heavyweights are right on the doorstep. For a taste of the high-brow, head to The Art Institute or go and see the Chicago Symphony Orchestra. 

Address: 12 S Michigan Ave, Chicago, IL 60603
Price per night: Double rooms from $265, year-round (breakfast extra)
Closest transport: Adams/Wabash L stop (three-minute walk)

Just a hop, skip and a jump from downtown cultural jewels like the Art Institute of Chicago and Millennium Park, the Fairmont is ideal for a romantic getaway. Its location alone makes it a great choice for couples who want to spend the day roaming the city together before retreating to somewhere indulgent—back at the hotel, champagne and chocolates await in the couple’s suite.

From standards to suites, all 686 rooms offer ample space and an organic, modern feel, but if you sign up for the Gold floor, you’ll also gain access to a private lounge with its own check-in—a little perk that makes the stay feel extra exclusive. The aforementioned couple’s suite, meanwhile, takes things further, thanks to its infinity-edge tub with soothing jets. Oversized bathrooms, fluffy robes and separate dressing areas all contribute to the hotel’s sense of retreat, with plenty of space to spread out and properly unwind.

Another one for the wellness lovers, the Fairmont offers your standard couples’ massage treatments, as well as a full-service spa menu that stretches far beyond the usual fare. Facials, scrubs and specialty therapies are on offer here, which’ll leave you feeling properly pampered. And if you’d rather relax over a drink, the lobby’s cocktail and small-plates lounge provides a vibey setting for late night tipple. 

Whether you’re after a romantic base for exploring downtown or simply want to spend time wrapped up in each other’s company, the Fairmont blends location, comfort and luxury in a way that few big hotels manage. Go on, treat yourself. 

Time Out tip: Take a short stroll to Millennium Park after dark to see ‘Cloud Gate’ (better known as The Bean). This infamous shiny steel sculpture reflects the skyline and city lights beautifully at night, and without the daytime crowds posing for selfies, it becomes a surprisingly intimate spot for two.

Address: 200 N Columbus Dr, Chicago, IL 60601
Price per night: From around $299, depending on dates and room type
Closest transport: State/Lake L stop (Brown, Green, Orange, Pink and Purple lines) or Lake L stop (Red Line). Several bus routes also stop nearby, including the 4, 20 and 60.

Feel like splurging on your next couple’s trip? Why not go all out at this Gold Coast hotel, where the guest rooms average 890 square feet? With rooms this large, you’ll have more space than many city apartments, but it’s not just size that makes them special. It’s all about the finer things in life here, so expect marble bathrooms with soaking tubs, vanities with inset LCD televisions, and beds covered with 460-thread count sheets. Perfect for lounging together on a chilly Chicago night.

The romance continues in the details: newly refreshed décor with a palette of creams and golds, Nespresso machines for lazy mornings, nightly turndown service, and staff that are as friendly and attentive as you could ever find. It’s this incredible service that seriously sets the Waldorf apart; step inside, and you’ll receive a welcome like nowhere else in the city. Every single detail is seamlessly handled, often before you’ve even realized you needed it—a rare kind of hospitality that makes the whole experience feel effortless.

If money’s no object, book a suite and you’ll find oversized marble bathrooms, walk-in closets and the kind of dreamy fireplaces usually reserved for stuffy period dramas. The spa deserves a mention, too. Alongside treatments like massages and facials, it features a saline lap pool, whirlpool and sauna. A word of warning, though: this is closed off to regular guests, with spa facilities only available to those who’ve purchased treatments. Another reason to splash the cash.

Unsurprisingly, dining is also a classy affair. Brass Tack serves as the main restaurant, Bernard’s is the bougie on-site cocktail bar, and in summer the courtyard becomes a destination in itself, offering champagne tastings. For those looking for a taste of opulence, the Waldorf is truly one of Chicago’s most indulgent romantic stays.

Time Out tip: Take your date night sky-high at 360 Chicago, the John Hancock Center’s observation deck just a short walk away. Sip a cocktail as you gaze out over the glittering skyline—it’s one of the city’s most dazzling views.

Address: 11 E Walton St, Chicago, IL 60611
Price per night: From around $575, depending on dates and room type
Closest transport: Chicago L stop (Red Line), six-minute walk

If your elaborate plans for a dreamy European vacation aren’t looking likely to happen this year, a taste of Tuscany in the middle of Lincoln Park will at least make up for it. Sort of. Tucked behind a classic Chicago greystone, this little villa feels made for two, with Italian-style flourishes and a cozy, lived-in warmth that bigger hotels can’t match.

The luxury Lincoln Park B&B offers eight rooms at varying price points, with enticing amenities varying from room to room, including a fireplace, an in-room wet bar, a private terrace, and a home theater with quality surround sound. Pick the set-up that suits your mood, then settle in for some proper downtime.

No matter which room you call your own, all guests have access to the full gourmet kitchen for breakfasts or late-night paninis, an intimate private grotto, and a sun deck with a hot tub. Molto bene! With only a handful of guests staying at a time, even the communal spaces feel cosy and romantic, meaning you can share a soak in the hot tub with minimal interruption. Maybe save the full blown nudity for your private quarters, though.

It’s the location that really seals the deal. The villa is situated right in the heart of Lincoln Park, with Armitage and Halsted’s boutiques, cafés and wine bars a short wander away, so it’s easy to set out on an unhurried, romantic day without wandering too far.

Time Out tip: Book dinner at Alinea, Chicago’s world-famous fine dining restaurant, which is only a short cab ride away. It’s a splurge, sure, but if you’re staying in a Tuscan-style villa in the city, why not?

Address: 2230 N Halsted St, Chicago, IL 60614
Price per night: From around US $149–$599, depending on room type and season
Closest transport: Fullerton L stop (Red, Brown and Purple Lines), about a 7-minute walk; or Armitage L stop (Brown and Purple Lines), about a 10-minute walk