30+ Ways to Celebrate Valentines Day, Chicago Style

Anddd we’re still on the V-Day train over here!

If you missed yesterday’s post, make sure to check out my Valentine’s Day/Galentine’s Day Gift Guide! On to day #2 of Valentine’s Day! (Don’t worry this is likely going to be the end of the V-Day posts this year 😂)

So. I know I’ve said this before, but we love Valentine’s Day. Any excuse to go out and spend quality time together is a win in our book. This year, we’ll actually be spending it in Dallas! Neal has a work trip out there and since we have the Southwest companion pass, I decided to tag along–I’m also really looking forward to some warm sunshine for a change!

I always get lot’s of questions around this time of year asking for restaurant recommendations and ideas for things to do to celebrate the holiday, so I’ve put together a giant list of my favorites–whether you’re celebrating Galentine’s 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 😉 Or, let’s be honest, this is a really good list for any other day besides Valentine’s Day too 😜 (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: 

Valentines Day Chicago Events:

Steppanwolfe’s “You’re Being Ridiculous” show: The famous theatre offers up a comedic storytelling show called “You’re Being Ridiculous” with the central theme of love throughout the month of February. Each night there is a different rotation of comedians telling their real-life stories. Be sure to grab a drink beforehand at their adorable cozy and swanky bar called Front Bar!

Hooking Up with Second City: Chicago’s Famous comedy company is putting on a show at Up Comedy Club called “Hooking Up with Second City“–centered around funny dating humor.

“Naked at the Art Museum” Scavenger Hunt: This would be a HILARIOUS thing to do with your girlfriends–tour group, Watson Adventures offers a very, um, different sort of art tour of Chicago’s Art Institute, focusing on nude art 😂 The website says, “You’ll scrutinize bathing beauties, peeping Toms, sultry sirens, a muscleman who’ll ruin his birthday suit while wrestling a lion, a woman enjoying a golden shower from Zeus, cads and cuckolds, provocative Picassos, dangerous natives, a mystic who has gone too far with the Slim-Fast, and much more!”

Valentines Day Chicago Date Ideas:

Dinner, drinks, and music at Thalia Hall: Thalia Hall in Pilsen is basically like “building crawl”–it has so many cool bars in it! Do dinner at Duseks, and drinks at The Tack Room, Punch House, and catch a concert at Thalia Hall!

Spa Day at the Four Seasons: The Four Seasons is the most luxurious, fun spa experience! The couples massage is such a treat, and surprisingly, not as expensive as you’d imagine!

Neighborhood crawl: 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 old-school bar, Coq d’Or afterwords to warm back up!

Chicago Art Institute: 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!

Maggie Dailey Ice Skating Ribbon: If you can brave the cold, Maggie Dailey is such a fun spot for ice skating downtown! You get great views of the skyline, too!

BYOB Pottery or Painting Class: BYOB art classes are super fun no matter who you’re with–a group of girls or your significant other!

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!”

Similarly, reader Elizabeth recommended Bottle & Bottega painting classes. “It’s something you’re both working on, can figure out together or laugh about together. My husband surprised me with this for Valentines Day last year and it was so much fun!”

Cooking classes: There are tons of options for cooking classes in Chicago! I shared a bunch over in this post!

Chicago Valentine’s Day Restaurants–Best Dinner Spots: 

Tango Sur: One of the most romantic restaurants! BYOB Argentinian. SO good and very budget-friendly. They don’t take resos, so be prepared to wait! Luckily, they have a back waiting room where you can pop open your wine!

Club Lucky: Our go-to Italian spot. It’s an old-school diner that serves up home cooked Italian dishes. We love sitting at the bar, but if you’d like a table, they have cozy booths in the front and in the back!

Boufhaus: Probably our #1 favorite restaurant right now. 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. Make sure to start with their seasonal salad–it’s a bunch of freshly shaved root veggies with the most amazing dressing. Split the ribeye (it’s huge) and get a bunch of sides. Best meal you’ll have in a long, long time.

BLVD: 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 dinner experience, this is it! You feel like a movie star!

Le Colonial: A French-Colonial Vietnamese restaurant, and another one of the most romantic spots in the city. Make sure to request a table upstairs–sitting on the patio is our favorite (it’s enclosed during the winter! If you’re chilly, they give you blankets!) For resos, ask for Michael, the Maitre D upstairs–he is absolutely wonderful–tell him Neal and Jess say hi 🙂 Make sure to get the Pho, and ask your server’s reccos on everything else. They never steer you wrong!

Gemini Bistro: 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 or shortrib ravioli. Go to Barrelhouse Flat after–it’s just a short Uber up the road!

The Rosebud: If you like old school Italian, you can’t get more classic than Rosebud in Little Italy!

Allium at the Four Seasons: One of my favorite Valentine’s Day dates was here and we’ve loved visiting ever since! It’s the restaurant in the Four Seasons–super swanky, old-school, and ultra cozy. The perfect place to be on a cold night. It’s great just for drinks, too!

Eddie V’s Lounge: 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!

Chicago Valentine’s Day Drinks–Best places to go for cocktails: 

Margeaux Brasserie: 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! 😉

The Barrelhouse Flat: Neal and I went here when we first started dating and it’s still one of my most favorite nights ever. They have the coolest cocktails with combinations you’d never think to try, and the setting could not be cooler. Make sure to get some of their fancy popcorn to snack on!

The Signature Room: 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.

The Up Room at Hotel Robey: 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.

Violet Hour: 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.

RM Champagne Salon: If you ask someone what the most romantic restaurant in Chicago is, they will likely say RM Champagne! It’s truly beautiful, quaint, candles everywhere–and what’s more fun than a champagne bar!? Plus, it’s in West Loop, which is a perfect location for bar hopping!

DrumBar: If you want romance with a buzzing atmosphere and a great city view, DrumBar can’t be beat!

Scofflaw: Want great cocktails and romantic ambience 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 lot’s of little nooks to cozy up in.

The California Clipper: 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 1930’s, with  awesome live music and great old-school cocktails. It is busy, so 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 Valentines 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 20 things to do in Chicago during Winter & a list of the best Chicago coffee shops.

P.S. If you’re in the Valentines Day spirit, you’ll want to read this post on how we met. 

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