Okay, so admittedly, I definitely intended to get my Valentine’s Day posts up earlier––it snuck up on me!! You too!? Luckily, these reccos are great for ANY time of the year, but especially on Valentine’s Day–but if you need inspiration for Valentine’s weekened, this is a great place to start. 😉
I know Valentine’s Day is always a love/hate type of thing, but honestly, any excuse to go out, dress up and spend quality time together is a win in our book!
And I always get lots of questions around this time of year asking for restaurant recommendations and ideas for things to do to celebrate the holiday, so I wanted to refresh this post with our big list of favorites–whether you’re hanging with your best girlfriends or with your significant other, I promise you’ll find a lot of Valentine’s Day Chicago inspiration in this list!
(I also linked to all these Google Maps locations so you can star away until your heart is content!)
Valentine’s Day Events + Fun Date Ideas:
Valentine’s Day in Chicago:
This sounds so fun and unique! Every Friday in February at the Chris Farley Cabaret, you can check out comedians create a never-before-seen soap opera, featuring drama, spice and tequila shots- ha!) This would be a great idea for a date or girls’ night, and tickets are less than $20 – so fun!
Eataly is one of my FAVORITE places in the city, and they have really fun classes year round! (Classes are sold out on the 14th, but there are other classes you can still sign up for to celebrate early or a little late!) Pasta making includes wine pairings and a multi-course meal, or there’s a Gelato class, an Eating Tour of Italy, a Mozzarella making class, and more! Would be such a fun activity for a date or with girlfriends!
On Valentine’s Day, the Chicago Athletic Association is hosting two parties in one night! Get your karaoke on in their Swing Suite lounge, hosted by People’s choice Karaoke Champion Elise Barrington, and/or visit the Game Room upstairs for their Annual No Scrubs Dance Party. These would be really fun to do with a group!
Reader Elizabeth recommends checking out Bottle & Bottega painting classes (they have a few on Valentine’s Day!) “It’s something you’re both working on, can figure out together or laugh about together. My husband surprised me with this for Valentine’s Day last year and it was so much fun!” Similarly, Reader Cat recommended Penguin Foot Pottery! “It was so hysterical because we were SO terrible at it, it made it more fun because we struggled together! But we did come out of it with 2 bowls each for our home!”
This would be a fun (and festive!) activity to swing by on Valentine’s Day! The garden features more than 10,000 blooms, and they have Orchids After Hours on Valentine’s Day — where you can enjoy drinks and light bites!
From Feb. 13-23, Chicago Theatre Week features value-priced tickets to more than 100 performances across the city. It’s perfect timing to check out a new comedy, musical or drama around Valentine’s Day!
Valentines Day Chicago Date Ideas:
Dinner, drinks, and music at Thalia Hall:
Spa Day at the Four Seasons or Waldorf Astoria:
Highly recommend both of these for a spa day! We did a staycation at the Waldorf for our anniversary and I can’t imagine a more amazing experience anywhere else! Highly recommend if you’re wanting a splurge!
Our friend Jax suggested this fun idea: pick a fun new-to-you neighborhood and do cocktails at one spot, apps at another, entree at another, and post-dinner drinks at another! It’s a fun way to explore and try a bunch of different things!
Walk along the Lake Michigan Lakefront Trail:
I mean, that is if it’s not below zero. There are few things more beautiful than the icy, peaceful lakefront in the winter! (If you can feel your face!) Start at North Avenue Beach and walk South. Grab a drink at The Drake Hotel’s historic old-school bar, Coq d’Or afterward to warm up!
One of my personal favorite activities for a cold day. I’m not sure what it is, but there’s something about an art museum that’s just really romantic. End with a glass of wine at Terzo Piano, which overlooks the park! Plus, you can explore downtown Chicago before or after!
If you can brave the cold, Maggie Daley park’s skating “ribbon” is such a fun spot for ice skating downtown! You get great views of the skyline, too!
There are tons of options for cooking classes in Chicago! I shared a bunch over in this post!
We’ve only done this once but LOVEDDDD our experience here. It’s not terribly expensive (at least compared to a couple’s massage) and it was as fun as it was relaxing! I would highly recommend doing with a significant other or with girlfriends!
Chicago Valentine’s Day Restaurants–Best Dinner Spots:
Our #1 favorite Chicago restaurant. (Okay, it’s probably tied with Nando, but you can’t compare the two.) Another place we love to sit at the bar–the bartenders are always amazing and are so knowledgable! The service is always incredible–if you go back more than once, they’ll remember you. The steak is unreal–and I’m not usually a big meat person. It’s definitely not a stuffy “steakhouse” vibe, more like a cozy, casual bistro, but they are very well-known for their meat.
Make sure to start with their seasonal market salad–a bunch of freshly shaved root veggies with the most amazing dressing–or the crudité–which is basically the most incredible veggies and dip you’ve ever tasted. Split the ribeye for your entree (it’s huge) and get a bunch of sides. The best meal you’ll have in a long, long time. Tell Jessica (she will likely greet you when you walk in!) we sent you! She’s wonderful!
Another one of my favorite restaurants, though we don’t get here often. The seasonal, farm-to-table fare is incredible as is the staff. It’s a small, cozy space, and I’ve never met anyone who has been disappointed with their meal here!
One of the most romantic restaurants in Chicago in my opinion! It’s BYOB Argentinian. SO good and very budget-friendly. (The portions are HUGE!) They don’t take resos, so be prepared to wait! Luckily, they have a back waiting room where you can pop open your wine!
One of our favorite neighborhood spots. Club Lucky is an old-school diner that serves up home-cooked Italian American dishes. We love sitting at the bar and it’s worth the wait to snag a spot, but if you’d like a table, they have cozy booths in the front, and a huge dining room in the back. It gets BUSY!
(Formerly Nando Trattoria–but same staff!) Another amazing neighborhood spot of ours, if you want a tiny, quaint, romantic Italian restaurant with traditional dishes, this is your place! We adore the staff here (tell Lucca and Umberto we say hi!), they always make you feel welcome, and have the best recommendations!
A super swanky supper club with an old Hollywood vibe. Definitely go for the steak here too–they serve it with a bunch of different seasoning salts, and it’s one of the coolest experiences. If you want something out of the ordinary in terms of your dining experience, this is it! You feel like a movie star!
I lived across the street for years (look across the street above the bar–see the middle apartment unit? That was my window. Haha!) and it’s always been one of my favorites. They recently revamped it and it’s absolutely beautiful inside. They also make the best sidecars! You can’t go wrong with the steak frites!
If you like old school Italian, you can’t get more classic than Rosebud in Little Italy! (They have other locations in the city too!)
Sometimes, you just want a classic steakhouse experience, you know? We love Eddie V’s lounge! Their booths are super cozy and the service is wonderful. Neal loves their oysters and the steak is really great (this sounds weird, but I hate when a lot of steakhouses char it on the outside–they don’t do that here!) Make sure you order the bananas Foster for dessert! It’s a great way to end a day of shopping on Michigan Ave!
If you want something different and dark romantic restaurants aren’t your thing, we LOVE Little Goat. It’s upscale, trendy Chinese and the food is insanely good. They have a fun, lively atmosphere too!
Chicago Valentine’s Day Drinks–Best places to go for cocktails:
The Waldorf’s new french-inspired bar is drop-dead gorgeous, ultra-romantic, and our favorite place in the Gold Coast to grab a nightcap. Split some frites, too! If you’re hungry, their duck wings l’orange are so good. (And I don’t even like duck!) I promise I’m not just biased because we got engaged in the circle drive! 🤣
I love this place for cocktails, they’re supposed to have really good food too but we’ve never eaten here!
It might sound cheesy, but even after living here for 8 years, I still get butterflies from the view of the city from the 95th floor.
One of my favorite, favorite places in the city. The Robey’s Up Room offers a truly unique skyline view and one of the only ones you can get from the West Side! Their cocktails are always great, too.
Another Wicker Park staple that has been around forever, Violet Hour is an experience. It’s known for pouring the most creative cocktails in the city, and it’s dark, quiet, romantic, and no phones allowed!
Gilt Bar downstairs lounge:
Gilt Bar is good for dinner, but way better for drinks and live music in their downstairs lounge! Their live Jazz bands always kill it, and the intimate vibe is perfect for a Valentine’s Day date.
If you want downtown romance with a buzzing atmosphere and a great city view, DrumBar can’t be beaten!
Want great cocktails and romantic ambiance without all the fuss? Scofflaw in Logan Square will be your new go-to! It’s part cocktail bar, part dive bar, with a fireplace and lots of little nooks to cozy up in.
If you want more lively action than romantic vibes, you’ll love the atmosphere of this cocktail lounge in Humboldt Park. You’ll feel like you’ve stepped into the 1930s, with awesome live music and great old-school cocktails. It is busy, and make sure to bring cash (they don’t take cards) and get there early for any chance at scoring a table! (And make sure you bring a warm coat, there is often a line outside, but I promise it’s worth the wait!)
What are your favorite ways to celebrate Valentine’s Day in Chicago?
I would love to know your ideas! Leave them in the comments below. You guys always have the best ideas!
If you live in Chicago or are planning a trip here, also check out 16 Chicago Winter Date Night Ideas, 20 things to do in Chicago during Winter & a list of the best Chicago coffee shops.
P.S. If you’re in the Valentine’s Day spirit, you’ll want to read this post on how we met.