Can you believe we’re talking about Valentine’s Day already?
I know this “holiday” can be 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!
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 in the city, so I wanted to refresh this post with date ideas, favorite restaurants, cocktail spots, and more!
Whether you’re looking to hit a comedy show with your best girlfriends, plan a romantic dinner with your significant other, or looking for a more out of the box experience, 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 for the restaurants and bars below, so you can star away until your heart is content!)
Valentine’s Day Events + Fun Date Ideas in Chicago:
Valentine’s Day in Chicago Activities and Events:
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 Bingo during everyone’s favorite reality TV dating show — The Bachelor! Enjoy sparkling rosé, red, and white wine, time with your friends and some reality TV!
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. 17-27, Chicago Theatre Week features value-priced tickets to more than 100 performances across the city. It’s perfect timing to give the gift of a new comedy, musical, or drama for Valentine’s Day to enjoy a follow-up date in the near future!
The Newport Theater in Lakeview is transforming into an intimate speakeasy this year for Valentine’s Day, featuring circus-inspired cabaret performers from around the world.
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 it 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!
Catch a show at Second City:
You can never go wrong with a comedy show! Check out Second City’s upcoming shows for a hilarious date night.
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. 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!
Keep the ice and add some competition (and laughter!) with some Valentine’s curling at the Gwen! $30 gets you a cocktail and 45 minutes of curling time surrounded by a stunning view of Chicago from the rooftop of the Gwen Hotel on Michigan Avenue. The outdoor curling rink is open-air, with fire pits and string lights providing warmth and atmosphere.
Sip rooftop cocktails
Get in the festive spirit with some bubbly overlooking the skyline! Here are some all-season rooftops that are decked out for winter temps (cuddle up together fireside in an igloo!):
- I|O Godfrey: The year-round rooftop bar atop The Godfrey Hotel has a festive space featuring their popular heated igloos.
- Whiskey Business ski chalet: A lesser-known Wicker Park spot, despite what the name suggests, actually NOT a total frat scene, and you can rent out an adorable mini ski-chalet for cozy, socially-distanced fun!
- ABA’s rooftop: One of my #1 spots I recommend for visitors, ABA has it all–fresh California-inspired Mediterranean cuisine, gorgeous west-loop skyline views and a rooftop patio that feels like summer all year long!
There are tons of options for cooking classes in Chicago! A quick google search will lead you to plenty of them, but I shared some over in this post that were recommended by readers!
We’ve only done this once but LOVEDDDD our experience here. It’s not terribly expensive and it was as fun as it was relaxing! I would highly recommend doing it with a significant other or with girlfriends!
Chicago Valentine’s Day Restaurants–Best Dinner Spots:
This is really just the tip of the iceberg, but here are some of our personal favorites. If you’re looking for really good food with romantic, but unstuffy atmosphere, these all fit the bill!
One of our favorite restaurants! 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! Their wine list is also phenomenal, I would highly recommend leaving your wine pairings up to the staff!
A long-time Neal and Jess favorite. They moved locations a few years ago, so now it’s much more trendy, swanky, and beautiful. A fantastic spot for a date in the Gold Coast. Start with a Lychee Martini and don’t miss the fried rice, crispy rolls, and pho. Also love the spareribs!
If you love steak and super dark and shadowy, swanky vibes, you absolutely cannot beat Bavette’s. (Although they have a LOT more than steak). If you can snag a reso, stop your search–this is the place you want to be!
One of the most romantic restaurants in Chicago, and a GG reader favorite! It’s BYOB Argentinian. SO good and very budget-friendly. (The portions are HUGE!) Their sister restaurant, Folklore, located in Wicker Park, is a great spot, too!
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!
Another swanky steak spot with an old Hollywood vibe. If you want steakhouse fare without the traditional vibe (much easier to get into than Bavettes, but still very good) this is it!
I lived across the street from this Lincoln Park staple 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.
Sometimes, you just want a classic steakhouse experience, you know? In particular, we love the lounge area of Eddie V’s. 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!
Not your average Italian–Osteria Langhe is a small, romantic, but homey spot in Logan Square that serves up upscale Northern Italian dishes. It is NOT to be missed. Leave your wine pairings up to your server–they also make a fantastic martini.
From the moment you walk in, you’ll be transported to your favorite Parisian bistro. It’s a tiny, bustling restaurant serving up classic French fare.
One of my favorite “new to me” spots I’ve been in a long, long time. The menu is Eastern European focused with fresh, intentional, and fun dishes–the cocktails inventive and creative, and the service absolutely outstanding. Everyone here has a passion for what they do and it’s really fun to watch. The bar is by far the best seat in the house.
Chicago Valentine’s Day Drinks–Best places to go for cocktails:
The Brasserie at the Waldorf: (Formerly Margaux)
This is one of our favorite places in the Gold Coast to grab a nightcap or a pre-dinner drink. It’s almost never crowded, and we always snag spots at the small bar. 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! ????
It might sound cheesy, but even after living here for so many years, I still get butterflies from the view of the city from the 95th floor. A great spot for visitors. I wouldn’t eat here, but going for a glass of champagne is always fun!
The best view in Wicker Park! 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.
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’re looking for a low-pressure, laid-back vibe with really awesome cocktails, try Pub Royale. They make their own tonics that they put on draft, so their G&T’s are phenomenal, and the cocktails are always really interesting! Plus, they have some really delicious Indian small-plates. If I were going on say, a third date that happened to be on Valentine’s Day, this is the spot I’d pick. (But also, great for anyone that wants something cozy, different, and unfussy!)
We love Queen Mary, it’s one of our favorite neighborhood spots. It’s a beautiful old-school “English pub” vibe specializing in craft cocktails. They always have a delicious daily batched punch, and some bar nibbles (like caviar and kettle chips) to keep you from going hungry. (Folklore is right across the street, making the two a great dinner/drinks pair!)
If you’re looking for a spot near the South Loop, I LOVE the vibe of Cherry Circle Room in the Chicago Athletic Association. The bar is absolutely stunning (I’ve never eaten here though, so can’t comment on the food). Would make the perfect post-museum drink after a date at the Art Institute!
Whether you’re planning a Valentine’s date or just looking for a great night out, I hope this list is helpful! ❤️
If you live in Chicago or are planning a trip here, also check out 16 Chicago Winter Date-Night Ideas and 25 things to do in Chicago during Winter
P.S. If you’re in the Valentine’s Day spirit, you’ll want to read this post on how we met.