Chicago, Eat, Entertaining, River North, South Loop, Top 10

Top 10 Hidden Gem Chicago Valentine’s Date Ideas 2018

Here we are, a week away from that silly, but kind of cute, sometimes over-the-top, okay, sometimes ridiculous, made up holiday that we either love or don’t love in any given year. Maybe the only thing to love about it is remembering those cute Valentine’s treats we used to give out in grade school to our favorite friends or the whole class, or picking up the on-sale candy the day after. But, let’s embrace V-day for just a minute, as a day or night to meet up with a friend, date, spouse, or family to enjoy each other’s company and hopefully a sweet treat. After all, it’s a good excuse to dine out with a unique menu, grab a speciality cocktail, or splurge on dessert, because, well, there’s no shortage of it on the Day of Love.

If you’re in the camp that just realized what date Valentine’s Day falls on this year (hint – it’s the same every year – February 14th), here are some outside the box ideas for places to go for that special someone or to appreciate your favorite people. The Top 10 hidden gem ideas are:

  1. L.A. Burdick Handmade Chocolates (River North) – This is not only the coziest of dessert spots, the East Coast-based chocolatier opened up it’s Chicago location last year with a picturesque storefront showcasing chocolates being handcrafted by the window for passers-by who can’t resist on State Street between Ohio and Ontario. Having been to their New Hampshire location years ago, I tracked it’s progress and stopped by on opening day, just in time to meet master chocolatier, Michael and snag a sample. This stop also resulted in a warm invitation for the friends and family grand opening event with samples aplenty. Why does this top the list? Well, for one, their hot chocolate is not your ordinary cup of hot cocoa. Stop by for a rich and comforting cup and you’ll likely become a converted fan instantly. Also, their mice, elephant, and penguin chocolates are just the cutest, and it’s easy to pick a small bonbon from the case, or a sampler gift pack to taste test their many unique, authentic, and pure ingredients. No reservations needed.



Head chocolatier, Michael, shows off L.A. Burdick chocolate mice on opening day in Chicago.

2. Commons Club Upside Down Tea Party (Saturday & Sundays – 2-5pm) (The Virgin Hotel – The Loop) – It’s pretty unexpected to experience a funky, spiked tea party accompanied by sweet treats, especially on a cozy winter weekend. The scenery at The Virgin Hotel creates a feeling of skipping decades and “the pond” and entering the world of Austin Powers. Bright colors, extravagant details, and unique textures, not to mention inventive tea cocktails and treats make this a memorable experience. Grab your pals, or surprise a date and make sure to call for a reservation.




3. Cozy Dinner or Brunch at Nana (Bridgeport) – This restaurant just feels like you walked into your Nana’s home (if Nana was hip) – twinkle lights, eye-catching artwork, and tasty American and Latin-inspired cuisine just hits the spot and the location is unexpected, especially for frequent downtown goers. Favorites include the matcha or chai tea latte (brunch time), empanadas (any time), fish and steak entrees, and caramel flan.




4. Warm up with Authentic Mexican in Pilsen (Pilsen) – You know what they say about spicy food kicking up the feelings of love. My now husband woo’d me on our first Valentine’s Day together by going outside the downtown bubble, and picking a new (at the time) authentic Mexican restaurant in Pilsen that knocked my socks off: Canton Regio. They don’t even have a website – that’s how this family-owned business rolls. It was no frills, and we felt like we had walked into a large family dinner with generations-old recipes and chicken swirling on rotisseries, complete with a live musician too. Get there early or try to call ahead and you’ll have more luck on a week night Valentine’s Day than a Saturday night, where people may be lining up against the staircase eagerly awaiting it’s lasting flavors. Another favorite is 5 Rabanitos – another neighborhood joint known for it’s honey garlic chicken, but you can’t go wrong with anything on their menu.

5. Cook at home with ready-made pizza dough, toppings, wine, and a bunch of fresh flowers at Trader Joe’sIt’s never been easier to make pizza at home with your favorite ingredients and refrigerated dough that simply needs to be rolled out and baked. It’s also a no-reservations-needed, no wait, and cost-effective, but interactive way to make your dinner and enjoy it together with a night in. Try a bottle of Espiral Vinho Verde (a slightly effervescent white wine) for about $5/bottle or TJ’s Petit Reserve Pinot Noir for about $6/bottle.

6. Grab Coffee and a Hearty Breakfast at Beatrix Before Work. (Gold Coast, Streeterville, West Loop) – We usually hear about Valentine’s Day dinner dates, but a breakfast date – especially before work on a weekday Valentine’s Day – is a sweet way to start the day. Hit the juice or coffee bar at one of the Beatrix locations and grab a quick pastry or make a reservation for breakfast and ask to sit by the window to see your honey by natural light before the real day starts.

7. Split an Ice Cream Sundae or Banana Split at Margie’s Candies. (Bucktown or Montrose) – This candy making and ice cream scooping shop has been serving sweet treats for over 90 years and while we scream for ice cream, it screams classic Chicago. There’s nothing more romantic (okay, maybe splitting spaghetti string like in Lady and the Tramp) than splitting a banana split.

8. ‘Hooking Up with Second City’ Comedy Show.  (Old Town) – There’s nothing like celebrating relationships or striving for one like laughing about dating and love. Check out this show at The Second City for a light and fun Valentine’s activity. (And affordable too!) Grab dinner at a nearby Old Town restaurant like Topo Giggio for a bite before the show.

9. Enjoy a Valentine’s Inspired Cocktail at True Food Kitchen and Other Cute Spots. (River North) – Cheers to love, lust, or just a nice cocktail around town, at places like True Food Kitchen, where you’ll find a tasty and healthy meal, bright ambiance, and Valentine’s Day themed cocktails. Other cocktail spot Rebeccammendations that are cozy, off the beaten path, and with a nice vibe include: Sparrow (rum bar), the bar at Quartino for a casual drink and delicious small plates, and Lone Wolf, or catch a martini and some lively tunes at Red Headed Piano Bar.


10. Go Euro with Cheese and Wine at Bar Pastoral. (Lakeview) Partake in the special Valentine’s Day dinner menu or order an app and some vino at the bar. This quaint wine and cheese bar (with a full menu) is approachable and inviting and their staff is always ready with an explanation or recommendation for new cheese-o’s or wine-o’s.


There you go – easy ways to celebrate with those you love that won’t break the bank and will leave you with a lasting flavor, laugh, or memory from this year’s Day of Love in Chicago! What are your go-to’s?

2 thoughts on “Top 10 Hidden Gem Chicago Valentine’s Date Ideas 2018”

  • Tony | Simple Awesome Cooking February 8, 2018 at 4:41 pm

    Great suggestion about Margies on Montrose, that’s a favorite of ours as well.

  • TheRebecca February 8, 2018 at 5:15 pm

    Thanks, Tony! It’s always fun to go back to the classics for a playful evening!

Leave a Reply

Your email address will not be published. Required fields are marked *