The Best Romantic Hotels in Chicago

Start your romantic getaway right with a couples massage at the Peninsula Chicago
Start your romantic getaway right with a couples massage at the Peninsula Chicago | © Image Professionals GmbH / Alamy Stock Photo
Photo of Sarah Gillespie
11 November 2020

Romantic getaways in Chicago are all about mid-century glamour, experimental cocktails, and high concepts. Enjoy a boat ride down the Chicago River, shop along the Magnificent Mile, or snag a seat in a cozy speakeasy. Ranging from science-themed digs to a hotel in a museum, you’ll be sure to impress your date with a stay at any one of these romantic hotels.

Viceroy Chicago

A retro bedroom in the Viceroy Chicago with turquoise curtains and cityscape views seen through floor-to-ceiling windows
Courtesy of Viceroy Chicago / Expedia

Pop the question or perhaps renew your love among the jewel-hewn interiors of the Viceroy. The sapphire-accented lobby sparkles with understated 1920s glamour, but it’s the rooms that truly shine. Tear yourself away from the window and bask in the retro-chic of blue velvet curtains, metal-patterned wallpaper, and curvy light fixtures. After dark, indulge in fine American dining at Somerset or poolside cocktails at Devereaux as the city twinkles below.

theWit Chicago - a DoubleTree by Hilton Hotel

A brown-and-cream one-bed guest room with a pop of red in the art and a yellow chaise lounge at theWit Hotel
Courtesy of theWit Hotel / Expedia

The acid green lightning bolt slicing down the front of this romantic hotel in Chicago encapsulates its youthful vibe. Young – or young-at-heart – couples will appreciate these nightclub-inspired digs, where cadmium-yellow sofas add zing and alarm clocks can be programmed with the voices of Al Capone or Barack Obama. The screen-bedecked bar, ROOF, serves Instagrammable cocktails under bright lights.

Eurostars Magnificent Mile

A sleek corner guest room with wrap-around windows, cherry-toned hardwood floors, a double bed, a comfy leather armchair, a tall free standing mirror, a writing desk and TV at Eurostars Magnificent Mile
Courtesy of Eurostars Magnificent Mile / Expedia

Unfussy mid-century chic and dark-wood paneling are the cornerstones of this sleek hotel among the buzzy bars and clubs of River North. Relax in the orchid-filled spa, which specializes in treatments for couples. The highlight is the Duet package – a three-hour, side-by-side treatment of body scrubs, aromatherapy massages, and pedicures topped by a glass of sparkling wine. Don’t leave this romantic hotel in Chicago without sharing a seafood platter at the Portsmith restaurant.

Hotel EMC2, Autograph Collection

A stylish, city-view king room with a walk-in shower with a glass door and a privacy curtain at Hotel EMC2
Courtesy of Hotel EMC2 /

The science theme prevails at Hotel EMC2, a fun concept hotel in Streeterville inspired by Einstein. Room numbers are magnified, the glass-paneled bathrooms, otherwise known as WetLabs, are laced with copper tubing – and if you forget your toothbrush, one will be delivered to you via robot. Don’t miss the experimental cocktails with inventive names such as the Penicillin at the on-site restaurant, the Albert.

Thompson Chicago

A lounge area with a sleek dark gray couch and a modern armchair in a suite with a private balcony at the Thompson Chicago
Courtesy of Thompson Chicago / Expedia

Antler chandeliers, leather ottomans, and wall art by contemporary artists give this Gold Coast hotel an edgy, industrial vibe. Sophisticated city slickers sip an old fashioned in the Salone Nico lounge, and Nico Osteria offers home-made pasta with tender seafood. There’s no pool or spa, but the excellent fitness center provides complimentary refreshments.

21c Museum Hotel Chicago

A 21c Museum Hotel Chicago one-bed guest room with a purple polka dot carpet, white linens and striped curtains
Courtesy of 21c Museum Hotel Chicago / Expedia

Redefining the notion of “room with a view,” this outpost of art collector Steve Wilson’s hotel-in-a-museum concept features 10,000sqft (930sqm) of space dedicated solely to 21st-century art. Exhibitions change seasonally but guarantee thought-provoking works covering religious beliefs, identity, and political polarization. The location is excellent; you’ll find the hotel in the heart of River North – the center of the interior design studios and independent galleries in Chicago.

The Robey

Boutique Hotel
A compact, art-deco-inspired guestroom at the Robey with a double bed, dark-wood floor and two black-frame windows
Courtesy of The Robey /

High concept on a low budget is made possible at the Robey, where whitewashed brick and exposed concrete attract a crowd of trendy, latte-sipping hipsters. Couples should head straight to the Cabana Club rooftop pool and bar for 180-degree views of the Chicago skyline. It’s a little far from downtown – but with the independent boutiques and cafes of the surrounding Wicker Park area, the neighborhood is worth a visit in itself.

The Peninsula Chicago

A white guest room with pops of blue, a double bed, a smart ipad room system and a couch at the Peninsula Chicago
Courtesy of The Peninsula Chicago / Expedia
There could be no more fitting a location for this award-winning five-star hotel than the Magnificent Mile, rubbing shoulders with Ralph Lauren and Saks Fifth Avenue. Visiting celebrities love the Peninsula for the deluxe indoor pool and old-school service, where bellhops wear white gloves. Follow tender filet mignon at the Lobby with an evening of skating on the illuminated rooftop rink.

For more options, discover where to book your stay in Chicago. If relaxation is what you’re after, read our guide on the top spa and wellness hotels in Chicago, and book now on Culture Trip.

Since you are here, we would like to share our vision for the future of travel – and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Epic Trips, Mini Trips and Sailing Trips. Our Trips are suitable for both solo travellers and friends who want to explore the world together.

Epic Trips are deeply immersive 8 to 16 days itineraries, that combine authentic local experiences, exciting activities and enough down time to really relax and soak it all in. Our Mini Trips are small and mighty - they squeeze all the excitement and authenticity of our longer Epic Trips into a manageable 3-5 day window. Our Sailing Trips invite you to spend a week experiencing the best of the sea and land in the Caribbean and the Mediterranean.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm – and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.

Cookies Policy

We and our partners use cookies to better understand your needs, improve performance and provide you with personalised content and advertisements. To allow us to provide a better and more tailored experience please click "OK"