Valentine’s Day in Lakeview East isn’t just one night of overpriced roses and prix fixe menus. It’s a whole vibe. Whether you’re planning a romantic date, a bold brunch with friends, or something a little more “let’s go out and see what happens,” the neighborhood has options that actually feel fun. From cozy dinners to over-the-top performances and everything in between, here’s where to go, what to do, and how to celebrate love (or at least a really good night out) this Valentine’s Day in Lakeview East.

Paint, Sip, Hooray! At Clover Lincoln Park | Feb 10

Clover Lincoln Park is hosting a paint party the Tuesday before Valentine’s Day! For $35 you’ll receive expert art direction, paint supplies, two drinks, snacks, and all the laughs. The fun starts at 7 pm! Reservations required. Register in-house or email events@cloverlincolnpark.com.

Tango, Chocolate & Champagne Night at Fred Astaire Dance Studio Lakeview | Feb 13

If your ideal Valentine’s date involves a little movement, a little romance, and a lot of fun, Fred Astaire Dance Studio Lakeview has you covered. On Friday, February 13 at 7 PM, couples are invited to slip into the rhythm of tango while enjoying decadent chocolates and a champagne toast. It’s equal parts classy and playful, whether you’re seasoned dancers or just there to laugh your way through the steps together. Tickets are $75 per couple, and spots are limited, so this is one date night you’ll want to lock in early.

Tapas & Salsa: Valentine’s Dinner & Dancing at Get in the Kitchen! | Feb 15

Dinner and dancing? Say less. On Sunday, February 15 from 1–4 PM, Get in the Kitchen! is throwing a Valentine’s Day experience that’s part cooking class, part salsa lesson, and part controlled chaos in the best way. You’ll make tapas together, learn Latin dance moves, eat what you cooked, and probably laugh your way through all of it. It’s interactive, high-energy, and perfect for couples who’d rather move, cook, and flirt than sit quietly at a table all night.

Sip & Dance: Valentine’s Night Edition at BottlesUp! | Feb 12

If your Valentine’s plans include wine and a little movement, this one’s a win. On Wednesday, February 12 from 7–8:30 PM, Sip & Dance: Valentine’s Night Edition brings Waltz, Tango, and Rumba to BottlesUp! alongside curated wine tastings designed to set the mood. Come with a partner, a best friend, or solo and let the music and wine do the heavy lifting. It’s flirty, fun, and just structured enough to feel special without feeling stiff.

Galentine’s Party at Felix | Feb 12

Felix is throwing an amazing Galentine’s party! Each ticket includes your choice of one cocktail or mocktail, a build-your-own bouquet, a guided self-love letter experienc, and Peach & Lily glass-skin glow moments. Additional à la carte services will be available for purchase from amazing local women-owned businesses, including psychic readings by Psychic of Wrigleyville, a waist bead experience, facial waxing and massage services from house of esthetics Chicago, live caricature portraits, and intuitive massage services. Get tickets before it’s too late!

Raks Inferno: A Valentine’s Speakeasy at The Newport Theater | Feb 13

If your Valentine’s plans lean bold, intimate, and a little dangerous (in a hot way), this is the one. On Thursday, February 13 at 7 PM, Raks Inferno transforms The Newport Theater into a burlesque circus speakeasy packed with cirque-style cabaret and fearless performances by artists who headline festivals around the world. Think seductive, high-skill, up-close performances that feel equal parts glamorous and thrilling. It’s sexy, theatrical, and absolutely not your average Valentine’s night, perfect for couples who want something unforgettable.

Valentine’s Origami Fold & Sip at Konbini & Kanpai Wrigleyville | Feb 11

Get crafty and festive with this Valentine’s Origami Fold & Sip on Wednesday, February 11 from 6–8 PM — a chill, creative twist on Valentine’s fun. Hosted by the Japanese Culture Center at Konbini & Kanpai Wrigleyville, you’ll learn traditional Japanese origami while you sip your favorite drink and hang with friends, dates, or fly solo. It’s low-pressure, highly Instagrammable, and the perfect way to do something together (or just make cool paper hearts). Tickets are super affordable and include all the materials you need, so bring your curiosity and leave with some handmade love.

Galentine’s Cocktail Making Class at Neva Hangry | Feb 15

Galentine’s Day Cocktail Class is officially taking over Chicago, featuring a heavy-hitting lineup and growing buzz as one of the most anticipated Galentine’s experiences of the season. Curated by Potions by P and hosted by Tati, with sounds by Kid Breeze and appetizers by Neva Hangry Wrigleyville, the event takes place at Neva Hangry Wrigleyville on February 15 from 4 to 6 PM. The $85 experience includes three signature cocktails, good music, karaoke, and a perfect excuse to get dressed up and enjoy an afternoon out with friends. This is a 21+ event, and a physical ID is required.

Cesar’s Killer Margaritas Galentine’s Fiesta | Feb 15

On Sunday, February 15th, Cesar’s invites to you join for their Galentine’s Day Fiesta, from 1:00pm – 5:00pm. Celebrate friendship in style with vase decorating, DIY flower bouquet, food and margaritas. So whether you’re planning a cozy gathering or a lively party, it’s the perfect occasion to honor your closest friends. Tickets, which are $45, can be purchased here – Galentine’s Fiesta – Cesar’s Chicago.

All throughout February, sip on the tasty Strawberries & Cream Margarita, or enjoy the “Heartbreaker” Margarita Flight, featuring three lovely flavors: cherry, strawberries & cream, and raspberry.

Nori Sushi Lakeview’s Three Course Dinner

If your love language is incredible sushi and a beautifully curated dining experience, Nori Sushi Lakeview is pulling out all the stops this Valentine’s Day. They’re offering a three-course Valentine’s Day dinner for $50 per person, featuring a premium, creative menu that highlights both tradition and innovation. The star of the evening is the Edomae Nigiri Omakase, a chef-curated selection that honors the origins of Nigiri Zushi from Japan’s Edo era, served as a beautiful five-piece moriawase alongside a crunchy spicy tuna maki. Want to go a little extra? Guests can add on the Wagyu Beef Nigiri Experience for $25, showcasing luxe wagyu beef prepared by Chef Win and finished with his house-brewed soy sauce. It’s intimate, elevated, and perfect for a date night that feels special without feeling stuffy.

Lovespell: Pole Dancing & Burlesque Show at The Newport Theater |

Whether you’re celebrating with a lover, a bestie, or flying solo, Lovespell is all about honoring every version of love. This multi-date Valentine’s show blends pole dancing and burlesque into an expressive, high-energy performance that explores romance, lust, heartbreak, healing, and everything in between. If you’ve felt it, someone on stage is dancing it. Come for the artistry, stay for the emotion, and don’t forget to bring some singles to show the performers a little love.

Taylor Swift Lovers Brunch at Lark | 3441 N Halsted St

If your Valentine’s plans lean more glam, flirty, and a little unhinged (in a good way), Lark’s Taylor Swift Lovers Brunch is calling your name. Happening Saturday and Sunday, February 14–15 from 11 AM–3 PM, this brunch brings big Eras energy with show-stopping performances by Pixel, Cupid Julez (Saturday), and Cupid Jr Love (Sunday). Expect bold looks, high-energy performances, and five bottomless drink options including Nutrl canned cocktails. Come for the brunch, stay for the drama, and leave with stories.

Heat of the Moment: Soul, R&B & Disco Night at Gman Tavern | 3740 N Clark St

If your Valentine’s Day plans are less candlelit dinner and more dance-it-out energy, Heat of the Moment at Gman Tavern is the move. Presented by 400 Conejos and Gran Centenario, this Soul, R&B, and Disco Night takes over Saturday, February 14 with a DJ set spinning from 8 PM to midnight. It’s free, 21+, and all about good music, good drinks, and letting the night unfold naturally. Perfect for couples, friends, or anyone who believes Valentine’s Day should come with a great soundtrack.

Cupid’s Castaway Karaoke at Trader Todd’s | 3210 N Sheffield Ave

Valentine’s Day goes delightfully off-key at Trader Todd’s with Cupid’s Castaway Karaoke, happening from 5 PM on February 14 through 2 AM. Expect love songs, rum drinks, and brave souls grabbing the mic under bamboo and torchlight. This is not about hitting the high notes, it’s about committing to the moment, meeting strangers mid-chorus, and maybe ending the night in an unexpected duet. Come unattached, come curious, come ready to sing your heart out, preferably with a cocktail in hand.

Anti-Valentine’s Day Party at Old Crow Smokehouse | 3506 N Clark St

Valentine’s Day feeling a little too Hallmark for your taste? Old Crow is flipping the script with an Anti-Valentine’s Day Party on Friday, February 14 from 9 PM–1 AM. Tickets include a drink, a shot, and live country music, aka everything you actually want on a Friday night in Wrigley. Come single, taken, or emotionally unavailable, this is a judgment-free zone built for dancing, drinking, and ignoring the pressure of the holiday entirely. Consider this your permission slip to party it up instead.

Valentine’s Drag Show at Shakers on Clark | 3162 N Clark St

Stop by Shakers on Clark on Valentines evening for a free drag show! From 8 to 10 pm, join queens Sofia Saffire, Monique Green, and Ruby Saffire! Afterword, do some karaoke, from 10:30 pm to 2:30 am.

Anti-Valentine’s Day at Trace Chicago | 3714 N Clark St

Want to not celebrate Valentine’s Day? Bring a photo of your ex to shred, or to use as dart practice for a chance to win a prize! All happening at Trace in Wrigleyville.

Valentine’s Afternoon Tea at Bittersweet | 1114 W Belmont

Join Top Chef Katsuji Tanabe at Bittersweet for an enchanting Valentine’s Day tea! Featuring distinctive, fine tea blends from the masters at Rare Tea Cellar and a three-tiered, traditional tea tray overflowing with savory bites and sandwiches by Top Chef Katsuji Tanabe, Bittersweet’s classic scones served with preserves and whipped cream, and a sweet selection of tarts and bites for dessert.

All reservations include unlimited mimosas to accompany your tea and bites. Seatings are available at 1:30 pm and 3:30 pm and the full tea seating is 90 minutes. $98 per person. Includes gratuity. They are politely declining any dietary restrictions or substitutions as our tea service has a set menu.

Sushi Box | Grab and Go | 2811 N Broadway

Enjoying Valentine’s Day at home? Grab sushi from our neighborhood sushi takeout restaurant – Sushibox! Use code “Valentine” for 10% off your order!

Dinner for Two at Lark | 3441 N Halsted St

If your Valentine’s vibe is romantic dinner without taking itself too seriously, Lark has you covered. From February 13–15, they’re serving up a Dinner for Two for $69.95, featuring a three-course meal plus select cocktails for each of you. It’s cozy, fun, and very Lark, the kind of place where you can dress up a little, laugh a lot, and linger over drinks. Bonus points for the no-pressure, neighborhood energy that makes this feel more like a great date night than a stuffy Valentine’s obligation.

Craft Beer & Caviar at Pilot Project Brewery | 3473 N Clark St

This Valentine’s Day, indulge in an unexpected pairing where craft beer meets caviar. Pilot Project Brewing and Caviar Dream are teaming up for an educational tasting experience designed for couples, friends, and anyone who loves great food and drink. Guests will enjoy a curated flight of premium caviar paired with small bites from our kitchen, each matched with one of Pilot Project’s innovative craft beers. From bright and briny to rich and indulgent, every pairing is designed to highlight how beer and caviar can go together in surprising and delicious ways.

El Mariachi Tequila Bar & Grill | 3906 N Broadway

El Mariachi is hosting a special dinner for two, available from February 13-15. For $89.99 per couple, you can enjoy an elevated Mexican three course meal.

Menu: For starters, choose between Dragon Fruit Rose Petal Infused Aguachile, OR Pomegranate & Queso Panela Guacamole. The entrée is Parrillada del Amor, and for desser, a Red Velvet Choco Flan!

Bittersweet Pastry and Café | 1114 W Belmont

Bittersweet has an entire Valentine’s Day collection! From heart-shaped sugar cookies to chocolate-dipped strawberries to a macaron gift box! Check out the full collection here, and place your order for pickup.

Chicago Sugar Daddy | 3243 N Broadway

The Sugar Daddy’s are here to make your Valentine’s Day delicious! With over 20 cake and cupcake flavors, and a team of cake decorating professionals, you can make your Valentine’s wildest dreams come true. Order online and view the full menu here!

Crave Cookies | 2951 N Broadway

Are cookies the way to your better half’s heart? Crave Cookies has huge gourmet cookies with rotating flavors each week. Surprise your date with a variety box! Order here

Dat Donut | 947 W Wellington Ave

At Dat Donut, they’re serving more than just donuts—they’re sharing a Chicago staple. From their iconic oversized classics to warm, freshly made pastries, every visit delivers a taste of something special. Wake up your valentine with some fresh baked deliciousness!

Jeni’s Ice Creams | 3657 N Clark St

Real ice cream heads eat ice cream year-round. Jeni’s sells pints of their famous flavors, stop in and grab a few to go for your Valentine!

Jennivee’s Bakery & Café | 2925 N Halsted

Jennivee’s is ready to spoil your valentine! Order a delicious whole cake, or get an array of decadent cupcakes. Keep in mind, all pre-orders must be placed by 8 pm three days prior to the pickup date! Place your order here

Klein’s Bakery and Café | 426 E Diversey

Klein’s is selling an adorable “Sweet Love Cake” for the holiday! This soft vanilla buttercream is topped with red hearts, making it perfect for the occasion. Klein’s also has their usual collection of cookies, macarons, cake shooters, and more! Browse all of Klein’s offerings, here.

Windy City Sweets | 3308 N Broadway

The Chicago candy store chocolate bar has over 1200 specialty sweet treats you simply won’t find in many places including fudge, s’mores, truffles, gummy candy, caramel nut patties, and chocolate-covered fruit! Create a tin of goods to sweep your Valentine off their feet! They also have some of the best chocolate-covered strawberries in the city! Place your order online here

The Colette Collection | 2858 N Clark

At The Colette Collection, pink and girly is always in style. Come browse the affordable boutique for all your accessory and clothing needs (and wants)!

Goldplaited the Boutique | 3119 N Broadway

Want to show off some heart-shaped style not just for Valentine’s Day, but all year round? Goldplaited The Boutique has an amazing selection of trendy clothes and accessories to keep you feeling cute and stylish no matter the season. Plus, they’ve got the perfect pieces to elevate your next date night look!

CRAM Fashion | 3331 N Broadway

For the modern man who appreciates sleek, stylish pieces, CRAM Fashion offers a carefully curated mix of American and European designs. From tailored shirts and jackets to unique accessories, this boutique provides everything needed to elevate his wardrobe. Whether for formal occasions or casual outings, CRAM’s collection ensures he’ll look sharp and feel confident. Shop for your big night out, or grab something as a gift he will LOVE!

Goldie’s | 3744 N Broadway

Goldie’s is a family-owned flower shop located on Broadway Street! Make your Valentine’s Day golden with something classic like a bouquet of red roses, or do something more exotic for your better half. The staff is so friendly and makes the most beautiful bouquets, stop in or order online!

Plant Stand Collective | 3247 N Broadway

Not everyone is a fan of flowers—some prefer a gift that grows with them! If your Valentine has a green thumb, Plant Stand Collective is the perfect place to find a gift that will thrive for years to come. With a wide variety of plants, expert care instructions, and an array of stylish pots to choose from, it’s a plant lover’s paradise. Plus, they offer 15% off their featured Plant of the Week every week, making it even easier to find the perfect addition to their collection!

Luna Flowers | 3226 N Sheffield

They specialize in events, but you can pop in the shop anytime and pick up an “express” bundle. They even sell specialty candles, which makes the perfect sidekick for a bouquet!

Wicked Plants | 3240 N Clark

Get your sweetheart something wicked cool at wicked plants! From funky planters to unique plants, Wicked Plants has something for everyone with a green thumb.