Date Night: Bringing Sexy Back Through the Five Senses

Date Night: The Gwen

When you have family and/or work obligations, getting time away, alone with your partner, is like eyeballing a four-leaf clover. When you do finally have a coveted free night penned in your calendar, you know that you need to make the most of it. From special dinner menus to romantic packages at a Chicago hotel, here’s how to stoke up the flames in your relationship and keep the fire red-hot.


We live in one of the most beautiful cities in the world. Fittingly, a date with a killer view of our cityscape hits the mark. The Gwen has a lovely (recently renovated) rooftop where you can hold hands, clink glasses and nosh on sharable bites while lounging on a comfy love seat during the warmer months. Located on the historic McGraw-Hill building, Upstairs at The Gwen offers packages that include reserved seating, food and beverage credits, and a complimentary room upgrade should you stay the night. During chillier months, visit Circa Restaurant and Lounge to enjoy belly-warming drinks in a luxurious space with a variety of cozy, snuggle-worthy seating options.

Sexy Date Night Out: The Gwen
Upstairs At The Gwen.

Isn’t it amazing when a long-forgotten Chicago art deco building, like the one located at the bustling six-corner intersection of Milwaukee, North and Damen avenues, gets a new lease on life? The Flatiron-like skyscraper, once called Northwest Tower, has been renovated and renamed The Robey. The décor, interior and hallways are a sight to see. Reminiscent of Marvel superhero Jessica Jones’ New York City detective agency, The Robey is super cool. So cool in fact that you and your loved one can sip cocktails on the roof; indulge in amazing, twinkling, unobstructed skyline views; and pop in the heated rooftop grotto for a private rom-com moment.

Sexy Date Night Out: The Robey
The Robey rooftop.

And, what about a date that incorporates a view of the stars? Visit Adler Planetarium for an adult-only Adler After Dark event held once a month from 6-10 p.m. You’ll have lots of fun with free rein of the museum, access to unlimited sky shows, live entertainment and a stellar view of our city after hours (the Doane Observatory is awesome and available, weather permitting).


Why not kick the traditional dinner-and-a-movie date up a notch and check out local theater, giving your ears something to be happy about? From big productions through Broadway in Chicago to smaller ones presented by Drury Lane, First Folio, Lake Forest Theatre, Marriott Theatre, Royal George Theatre, Stage 773 or The Chicago Theatre, there is something for every interest or curiosity.

For a few fun date-night suggestions, check these productions out:

  • “Tony n’ Tina’s Wedding” has returned to the stage, but this time the interactive and energetic musical will be held in a real church — Resurrection Church — followed by a reception at Chicago Theater Works. (Tickets are available through April 2017.)
  • Apollo Theater Chicago is home to the laugh-out-loud production of “Thrones! The Musical Parody”, which pays homage to “Game of Thrones.” If your spouse has never seen the show, this might get him or her on board. (Tickets are available through February 2017.)
  • Founded in 1975, The Marriott Theatre is known by many as the leading venue for launching Broadway’s shows. In 2017, you can see these exciting live performances: “Mamma Mia,” “She Loves Me,” “The Bridges of Madison County,” “Honeymoon in Vegas” and “Newsies.”
  • Stage 773 is home to several productions — comedy, musicals, dance and theatre as well as a few festivals. Notably, “Cupid Has a Heart On,” Chicago’s longest running musical sketch-comedy show, is an adults-only must-see. This show is sure to spark conversation, and loads of giggling, between you and your date long after the curtain closes.

Add on to your overnight staycation at The Waldorf Astoria Chicago with the Love, Luxe & Fire package, which includes Veuve Clicquot and dessert, one complimentary movie to watch in your room or suite and 20 percent off a Bespoke spa treatment. Now, how’s that for a date?


The Peninsula Chicago has many options to choose from in the way of tasty food — Cantonese and Shanghainese at Shanghai Terrace, European food and wine at Pierrot Gourmet and bar bites at The Bar — but if you’re looking for stellar floor-to-ceiling views and delectable Contemporary American cuisine (or incredible High Tea), look no further than The Lobby. You might even consider visiting just for the sweet dinner desserts — Ligurian Lemon Cake, Madeleines, Strawberry & Elderflower Soup — and port wines.

Allium, located at the Four Seasons Hotel Chicago, serves up Midwestern Contemporary Cuisine prepared by Executive Chef Sean Murray. Murray was previously the Executive Sous Chef at Four Seasons Hotel Vancouver and we’re lucky to have him in our city. At Allium, under Murray’s care, you’ll taste the finest and freshest seasonal ingredients prepared thoughtfully.

Sexy Date Night Out: Allium


Put your nose and cooking or baking skills to the test and attend a couples cooking class at Sur La Table, with locations in Chicago, Naperville, Northbrook and Skokie. Hands-on instruction available, beginning in January, includes: Date Night: Winter Dinner in France; Date Night: Passport to Tuscany; Date Night: Italian Romance; and Valentine’s Day Macarons. You’ll learn a new technique while sharing the experience with someone you love.


Sitting at the corner of North Michigan Avenue or Wacker Drive is LondonHouse Chicago, named as a nod to the original name still etched in the building’s façade: London Guarantee & Accident Building circa 1923. LondonHouse Chicago, which opened its doors in May 2016, is already known for being Chicago’s only tri-level rooftop — the views are unmatched and indelible — however, their spa is noteworthy as well. Couples can indulge in a relaxing massage treatment together, side-by-side, and the therapist is more than willing to make the experience bespoke.

Perhaps a Week-Long Date Night?

And, if you happen to have a week to get away with your significant other, consider a luxury, all-inclusive couples retreat with SwellCo-ed, which has locations across the globe: Indonesia, El Salvador, Hawaii, Sri Lanka and more. Have an adventure and invest in your relationship.

Sexy Date Night Out


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