5 Romantic Date Night Ideas During the Holidays

The holiday season has such a romantic quality to it. You don’t even really need to put in too much effort. Maybe it’s the movies that make you feel warm and nostalgic, or the cold weather that makes you want to cuddle. Or maybe it’s just the thought of getting together with your loved ones and eating, drinking, and laughing. Whatever it is, no one can deny that the feeling comes out naturally. So here is a list of 5 romantic date night ideas so you can build on the romantic vibe that’s already in the air this time of year

Dine in Macy’s Walnut Room next to the Great Tree

The Great Tree in the Walnut Room at Macy's on State St

Macy’s Walnut Room is one of the most beloved landmarks in Chicago. It’s decorated in an elegant style with a 17-foot marble fountain, Circassian Walnut paneling, and Austrian chandeliers. When you’re there, you feel like royalty. It’s located in a department store, but it also has a very intimate feel. You can duck inside and take a break from the hustle and bustle of shopping or seeing a show and relax with a glass of wine. The Walnut Room is a romantic place any time of the year, but it gets taken up a level during the holidays. It’s renowned for the holiday decorations and the Great Tree. The Great Tree hangs from the ceiling and is decorated with over 1,200 ornaments and 15,000 lights. It’s an awe-inspiring sight that is sure to add that little extra something to your night out.

After enjoying a meal in the Walnut room you can stop outside and indulge in some holiday shopping in River North. You can also add a night cap to the evening with a visit to Starbucks Reserve Roastery. It’s the largest Starbucks in the world and located on Michigan Ave. They offer drinks you can’t find at any other Starbucks, which is a nice change of pace. Don’t show up just to get a standard Americano or a Flat White. The way they do it here is bigger and better, and some of their drinks even have a Chicago flair. Go ahead and order a Malort cocktail, I bet you’ll enjoy it.


Lightscape at the Chicago Botanic Garden

The Cathedral of Light at LightScape

LightScape at the Chicago Botanic Garden is a magical event. Over one million lights are set up in numerous displays. You and that special someone can get a little bit closer in the cold weather while you walk the one mile path through the grounds. There are Singing Trees, a Japanese Zen garden, and the Cathedral of Light. It’s one of those places where you don’t need a lot of words to connect, it happens on a deeper level. You can just look at the person you’re with and feel it. The atmosphere is a little different and there’s something about it that just brings you closer. The music, the lights, the holidays, maybe it’s one or maybe a combination of everything, it’s tough to say. One thing is for sure though, it’s the type of place where you make memories.

After you leave LightScape is a perfect time to enjoy a drink, but you can’t go just anywhere. Some dive bar will kill the mood after the magic. Instead, stop by Frosty’s Christmas Pop Up Bar and grab a seat with the one you love. You’d be hard pressed to find a place that is more festive that Frosty’s; it’s packed from wall-to-wall with holiday decorations. Singing Santa shows every hour on the hour, life-size toy soldiers, and two dance floors are guaranteed to keep you in the best of spirits.


Ice Skating at McCormick Tribune Ice Rink in Millennium Park

Ice Skating under Cloud Gate in Millennium Park

This is the type of date that makes it into movies, or Christmas commercials. Laughing, and falling all over the ice, the special couple grabs each other and holds on tight. They look into each other’s eyes, and slowly lean in for a magical kiss. Don’t you want that to be part of your story?! Exactly! Now’s your chance to get down to the ice rink and build some lasting memories.

After building up an appetite ice skating and setting the mood, it’s time to take it to the next level. Bring out your inner James Bond and go to one of Chicago’s ‘secret’ bars. Places like this probably still have so much appeal because it reminds us of Chicago’s past. Alcohol and this town have a history that goes all the way back to prohibition. But these days, it just makes for some really cool places. Booze Box, located in the basement of Sushi Dokku, is the perfect place. It’s dark, sexy, and just the right amount of exotic. They serve Japanese style street food that is both casual, and sophisticated. Booze Box isn’t your average bar, they have Eastern-inspired drinks that are different than what you get everywhere else. If you’re really feeling adventurous…don’t leave without indulging in the sake flights.Entrance: Head to the alley just south of Sushi Dokku and look for the door that has a small Booze Box sticker near the handle.


The Nutcracker performed by Joffrey Ballet

The Nutcracker Ballet

The Nutcracker is a timeless, classic tale. Set in the late 19th century, during the holiday season, it’s a story of romance and adventure. The version performed by the Joffrey Ballet has some unique Chicago flair. It’s set within the World’s Columbian Exposition of 1893, and instead of the story centering around a wealthy family, they are working-class immigrants. However, the storyline remains the same, one that is as old as time itself. It has become a holiday custom as much as baking cookies or decorating the Christmas tree. It serves as the perfect backdrop for a night out. Take the one you love and allow yourself to be whisked away.

Chicago is a city for food lovers and having a bite to eat after a show is a tradition. Bombobar is the perfect place to stop for some dessert and hot chocolate. Most of the items on the menu will amaze you. The food is beautiful. They’re not just chefs, they’re artists.


Horse Drawn Carriage Ride

Horse Carriage riding through River North

There’s few things that scream romance like taking a ride in a horse drawn carriage. You can go through River North, down by the lake front, or one of many other places. Either way, it should prove to be an experience that takes you to a different time. The clacking of the horse hooves as the backdrop of the city slowly passes by. Everything seems to slow down a beat and become a little more relaxed.

End the evening with dinner at Boka restaurant. Boka has to be one of the most romantic restaurants in the city. A relaxed, casual atmosphere with a candlelit garden patio. It has retained a Michelin one star rating for many years, and the service is excellent.