8 Romantic Staycation Ideas for Valentine’s Day in Chicago—Hotels, Restaurants and Dinner at Home

This Valentine’s Day, stay close to home for an intimate night with the one you love most. Chicagoland hotels are creating packages for lovebirds that are both sexy and safe, so you can have fun and focus on your sweetheart for a romantic staycation.

The Publishing House Bed & Breakfast

Photo courtesy of The Publishing House

Room service gets upgraded Valentine’s Day weekend at The Publishing House, thanks to a partnership with Chef Sarah Grueneberg and Monteverde. Lovebirds can enjoy a three-course family-style dinner with wine pairings in their rooms, including lobster and burrata bruschetta and potato-filled zlikrofi dumplings with truffles. Each of the 11 rooms at The Publishing House are one-of-a-kind, designed and decorated in honor of the literary character or author for which it is named. All the books, from Upton Sinclair’s The Jungle to Ana Castillo’s Peel My Love Like an Onion, take place in Chicago, making it possible to immerse yourself in the city from the comfort of your room. There’s a piano and fireplace in the common area for guests, along with cozy window seats at the end of the hall to curl up and read. Even if you’re totally stuffed from pasta the previous night, do get out of bed in time for breakfast (easier said than done with the stellar blackout curtains) because innkeeper Kimberly Lowery is a fantastic baker and cook, whipping up delicious frittatas, Aussie pastries, burrata scrambles and homemade granola with yogurt and fresh fruit.

Kimpton Gray Hotel

Photo courtesy of Kimpton Gray Hotel

The Kimpton Gray Hotel wants to help you de-stress with 20% off a spa or suite guestroom for Valentine’s Day — perfect to savor with your partner, or on your own. The package includes a calming MTI soaking tub, bath bombs and two bottled concierge cocktails to take the edge off while giving back to charity. A portion of cocktail proceeds go to Support Staff, a community of Chicago hospitality professionals working alongside mental health professionals and community organizers to break down stigmas surrounding mental health and advocate for employees’ mental and emotional well-being. This fun new cocktail series was pioneered by Bobby Gonzalez, the director of concierge services.

If you don’t quite feel comfortable leaving home yet, tease a future romantic getaway with the Gray @ Home package, including two Frette herringbone shawl collar robes, concierge cocktails and Atelier Bloom bath salts delivered to your doorstep along with the promise of 25% off a future stay.

Langham Chicago

Photo courtesy of Langham Chicago

Chicago’s most luxurious hotel has created a couple of over-the-top Valentine’s Day packages for lovebirds. Guests can rent the 12th floor Langham Club with panoramic city views to exchange vows with their partner for life, celebrate a wedding anniversary or for a bespoke dinner for two. The $3,500 package includes accommodations in a one-bedroom suite, champagne toast and after-dinner cocktails too.

The Cooking With Love package includes a private cooking class for two with the Langham’s executive chef, Damion Henry. Learn to prepare a four-course curated menu with wine pairings along with an overnight stay in a one-bedroom suite and breakfast for two through the private kitchen for $1,790.

Swift Alps Yurt Dinner

Photo courtesy of Swift & Sons | Kehoe Designs

Through the end of February, Swift & Sons is partnering with American Express and Resy to bring an Alpine yurt dining experience to the West Loop. The yurt village consists of 10 tents that seat up to six people, each with a unique theme decorated by Kehoe Designs. We love the decadent Gatsby tent and chic party vibes of the Future tent. The six-course prix-fixe menu ($85) is full of hearty Alpine fare by chefs Chris Pandel and Leigh Omilinsky, from the tartiflette en croûte filled with melted Reblochon cheese and leeks, to buttery celery root agnolotti and a ribeye and bone marrow main course. Begin the night with a glass of biodynamic grower champagne from Vincent Couche, or opt for Alpine wine pairings. Portions are generous and this is one of the best value — and most comfortable — outdoor dining experiences in the city. 

Nobu Chicago

Photo courtesy of Nobu Chicago

Between February 11-15, guests at the West Loop’s sexiest hotel can book a Love Nobu package to savor a long weekend full of luxurious touches like lavender bath salts from Chicago’s Scratch Goods skincare line and a confectionary bento box of housemade chocolates accompanied by a half bottle of champagne. A special Valentine’s Day dinner menu will also be offered by Nobu Restaurant (takeout/ delivery if indoor dining restrictions are still in place) featuring signature dishes like black cod miso, yellowtail jalapeño sashimi and prime tenderloin teriyaki will be available on the rooftop and for in-room dining. 

Deer Path Inn

Photo courtesy of Deer Path Inn

Couples staying at Deer Path Inn in Lake Forest can enjoy the hotel’s famous afternoon tea in the privacy of their suite, with English-inspired treats, finger sandwiches and petit fours accompanied by an assortment of more than 50 teas hand-selected by Master of Tea Malcolm Ferris-Lay. For a boozier affair, book a private wine or whiskey tasting in the wine cellar, or a personal cocktail making class with the inn’s chief spirits officer. Lovers can choose an intimate evening tucked away at The English Room and indulge in an exclusive Valentine’s Day dinner or dine in-suite and conclude the night with French wine and a bathtub (spacious enough for two) that fills from the ceiling in the Cornwall and Buckingham suites.

Gourmet Dinner at Home

Photo courtesy of Truffle Shuffle

Seduce your partner with a decadent fine dining meal at home with ingredients and instruction from Truffle Shuffle. Founded by three chefs who met working together at The French Laundry, the truffle company makes fresh white and black truffles more accessible to home cooks, along with a host of other small batch truffle products and cook along experiences. There are on demand video classes to make black truffle risotto or truffle mac and cheese at home — we can’t think of more luxurious comfort foods in the depth of a Chicago winter. And just for Valentine’s Day, there’s a live virtual fresh pasta class with black truffles, and the option to purchase a surprise dessert. A special guest will serenade you with love songs as you prepare your meal while sipping Krug Champagne cocktails.

Stay Sweet At Home

Photo courtesy of West Town Bakery

If you’re more comfortable staying at home, there are still plenty of ways to spice up your Valentine’s Day. Chicago’s own Vosges Chocolate frequently uses spices like curry, paprika and cayenne to flavor adventurous truffles inspired by founder Katrina Markoff’s global travels. For Valentine’s Day, she’s releasing Egyptian-inspired chocolate alchemy collections fit for a goddess with love potion Krug Grande Cuvee Champagne truffles, vegan raspberry blossom truffles and an eternal love collection.

West Town Bakery is also shipping their cult-favorite cakeballs nationwide, including new flavors like coconut toffee, Mexican hot chocolate, rum raisin and Snickers. The bite-sized balls are just the right size for sharing with your sweetheart, made of crumbled cake mixed with frosting or icing, then rolled in nuts, sprinkles, candy or drizzled with chocolate. A limited-edition Valentine’s Day flavor features strawberry cake and freeze-dried strawberries mixed with pink frosting, coated with a milk chocolate shell studded with pink peppercorns.

Stick With Me Sweets has some of the most beautiful chocolate bonbons you’ll find, in equally beautiful packaging, with unique flavors like guava passion fruit, speculoos s’mores and bourbon maple pecan. The delicate, glossy shells hide sophisticated layers of flavor within – chocolatier Susanna Yoon is a master.

Another fun chocolate to try? The Big Orgasm adaptogen-infused chocolate bar from Eat Gold Organics featuring organic, plant-based ingredients including libido-boosting cayenne, wild strawberries and maca powder.


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Amber Gibson spends 340 nights a year in hotels searching for the latest and greatest in the travel industry. Her writing and photographs have appeared in print, online, and on the radio for outlets including Four Seasons Magazine, NPR, Saveur, Departures, Rhapsody, Hemispheres, American Way, Private Air, Wine Folly, Plate, Chicago Magazine, Tasting Table, and Serious Eats. She graduated as valedictorian from Northwestern University’s Medill School of Journalism and received a fellowship to attend the 2017 Wine Writers Symposium at Meadowood Napa Valley. Champagne, dark chocolate, and gelato are her biggest weaknesses. She also admires and supports CAASE in Chicago. Follow her adventures on Instagram and Twitter.