Last-Minute Valentine’s Day Ideas: It’s Not Too Late to Plan the Perfect Romantic Day in Chicago

Last-Minute Valentine’s Day Ideas: It’s Not Too Late to Plan the Perfect Romantic Day in Chicago

Have you made plans for Valentine’s Day yet? Don’t worry, we’ve got you covered. Here’s a foolproof guide to the most romantic things to do, see, taste, and indulge in around Chicago with your significant other this Feb. 14.

For a Romantic Meal… 


Valentine's Day Ideas: Yūgen
Yūgen Crab Rice (Photo by Anthony Tahlier.)

Chicago’s first contemporary Japanese fine-dining restaurant, Yūgen is a rarified breed — the kind of restaurant where the rest of the world melts away and the only things that matter are your dining companion and the exquisite food on your plate. The 13-course tasting menu evokes an avant garde kaiseki approach. Begin with a medley of sakizuke one-bite canapés, followed by miso soup, chawanmushi with foie gras ganache, seasonal sashimi, and shabu shabu wagyu. The austere dining room will be familiar to foodies who dined at this location when it was home to Grace. One year after Grace’s abrupt closure, a young trio of women run the show. Executive chef Mari Katsumara leads the kitchen, working alongside general manager Morgan Olszewski and beverage director Olivia Noren. It’s still early days, but this ambitious new restaurant is off to a dazzling start. 652 W. Randolph St., Chicago, 312-265-1008

The Darling

Valentine's Day Ideas: The Darling
The Darling (Photo by Kyle Flubacker.)

You’re welcomed with a rose from the flower shop before being whisked away behind the facade into Chicago’s English-manor style speakeasy for dinner and a show. The Darling is unlike any other restaurant or bar in Chicago, offering a different experience every night with immersive, captivating performances from burlesque and drag to magic tricks and live music. You never know what to expect. For Valentine’s Day, special drinks include a raspberry Caipirhina-style cocktail and the “Dark Heart” black Manhattan with chocolate bitters and rhubarb. Plus, you’ll depart with a gift of hand-rolled chocolate truffles. 905 W. Randolph St., Chicago, 312-285-2609

For the Perfect Staycation Escape…

The Four Seasons Chicago

Valentine's Day Ideas: The Four Seasons Chicago
The Four Seasons Chicago (Photo by Christian Horan.)

After renovating all rooms and junior suites last year, The Four Seasons Chicago is debuting two new packages for Valentine’s Day. Smitten sweethearts (who maybe just won the lottery, or whose company had a successful IPO) can book the $25,000 Element 79 package, named after gold, atomic number 79. Stay in the presidential suite occupying an entire corner of the hotel’s 46th floor and receive a gold and pavé diamond cuff by John Hardy. You’ll never have to leave your suite, enjoying an in-suite couple’s massage and five-course dinner with wine pairings. The Moonstruck on Michigan package is more moderate but just as enchanting, including an overnight stay in a lake-view or city-view room, bottle of Champagne, food and beverage credit, custom massages, and a sweet turndown surprise by pastry chef Scott Gerken. 120 E. Delaware Place, Chicago, 312-280-8000 

Ambassador Chicago

Rates start at just $209 for the J’adore package at Ambassador Chicago. Your stay includes a bottle of prosecco and a prix fixe dinner at Booth One. Your meal concludes with a decadent baked Alaska for two —­ chocolate cake, passion fruit sorbet, and Swiss meringue flambéed tableside is a fiery finale. Upgrade to a suite for an extra $50. 1301 N. State Parkway, Chicago, 312-787-3700 

For an Indulgent Spa Day…

Kohler Waters Spa — Burr Ridge

Valentine's Day Ideas: Kohler Waters Spa Burr Ridge
Kohler Waters Spa — Burr Ridge Pool (Photo courtesy of Kohler Co.)

You don’t need to go all the way to Wisconsin to indulge in five-star hydrotherapy. Kohler Waters Spa — Burr Ridge is the sister property to the acclaimed spa at The American Club with many of the same amenities. It’s undoubtedly the top day spa in the Chicagoland area, with signature treatments like the lavender rain shower and Kohler waters wrap featuring dry-brush exfoliation and a detoxifying wrap with Chinese herbs. New treatments for winter include a cupping massage and medical-grade HydraFacial with healing LED light therapy. Arrive an hour early to enjoy the self-guided Circle of Tranquility, a co-ed water journey through sauna, steam, and a cascading waterfall. 775 Village Center Drive, Burr Ridge, 630-323-7674

For an Experience to Remember (and Commemorate)…

Chicago Helicopter Experience

Valentine's Day Ideas: Chicago Helicopter Experience
Photo courtesy of Chicago Helicopter Experience.

See the city you know and love from new heights with Chicago Helicopter Experience. The new fleet of helicopters can fit groups of up to six and it makes for an unforgettable date-night surprise. You’ll cruise over Chicago’s Museum Campus, heading north over Buckingham Fountain, Grant Park, Willis Tower, and the Wrigley Building. Daytime tours are better for identifying landmarks, but night tours are more glamorous and romantic. Consider chartering a private chopper to pop the question. 2420 S. Halsted St., Chicago, 312-967-8687


Flytographer is best known for vacation photos, with a network of talented freelance photographers in hundreds of cities available to capture the memories of your time together with loved ones. There are seven great photographers to choose from in Chicago if you want to book a romantic photoshoot at one of your favorite places around the city. Thirty-minute shoots start at $250 and you’ll receive a link to an online gallery of edited images within five business days. The website and app make communicating with your photographer a breeze.

For a Memorable Gift…

Ethereal Confections

Valentine's Day Ideas: Ethereal Confections
Ethereal Confections Truffles (Photo by Tasha Schalk Redwall Photography.)

They say chocolate is an aphrodisiac, and there’s no better place to get local, artisan chocolate than Ethereal Confections. The Woodstock chocolate shop is the only bean-to-bar confectionary in the state. For Valentine’s Day, you can’t go wrong with the smooth red raspberry and vanilla meltaway bar or the 66 percent dark chocolate bar strewn with strawberry, rose petals, and pink peppercorn. All their chocolate is vegan and gluten-free, and while the cafe is worth a visit for in-store-only desserts and drinking chocolate, you can also find their truffles and bars at Cocoa + Co in Old Town and Writers Theatre in Glencoe. 113 S. Benton St., Woodstock, 815-687-0320

Artists Frame Service

Valentine's Day Ideas: Artists Frame Service
Photo courtesy of Artists Frame Service.

Rather than just updating your Facebook profile photo or posting your favorite couples pic on Instagram, make a more permanent, artful tribute to that image by getting it framed by the friendly professionals at Artists Frame Service. The largest framing store in the country, from the same team behind home décor favorite Jayson Home, recently opened a new River North showroom to celebrate their 40th anniversary. They’re keeping the dying art of framing alive, sourcing frames from all over the world and promising a one-week turnaround for framing (procrastinators rejoice!) thanks to their fully stocked and staffed warehouse on Chicago’s West Side. 1867 N. Clybourn Ave., Chicago, 773-248-2800; 443 N. Wells St., Chicago, 312-755-2800

For a Weekend Getaway…

Lake Geneva, Wisconsin

Escape with your valentine for a long weekend in Lake Geneva. Walk along the Shore Path or take a carriage ride with Dan Patch Stables (sleigh rides are available weather and snow-conditions permitting). Book a relaxing couples massage at Clear Waters Salon Spa, Mia Faccia, or Well Spa + Salon at Grand Geneva Resort. Snuggle up with a cocktail in a private igloo at The Ridge Hotel. Toast each other at Geneva Lake Brewing Company or Staller Estate Winery in nearby Delavan, Wisconsin. Or, enjoy a show at Tristan Crist Magic Theatre. Start planning your trip today.


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.