Valentine’s Day in Lakeview East 2025

Roses are red, violets are blue—this Valentine’s Day, we want to celebrate with you! Love is in the air in Lakeview East, and so are countless ways to make the day unforgettable. From romantic dining reservations and thoughtful gifts to unique experiences that will sweep your special someone off their feet, our neighborhood has it all. Discover everything happening this Valentine’s Day in Lakeview East!

Bittersweet Pastry and Café: 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: 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: 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

Jennivee’s Bakery & Café: 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: 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: 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

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 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 just opened in Lakeview East in 2023, however they’ve been a Chicago business for years! 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!

Foursided: If you’re looking for a niche, adorable, or hilarious Valentine’s Day card, spend some time browsing the wonderful collection at Foursided! While you’re there, you’ll notice the entire store is dedicated to the holiday of love, with books for your boo, pink and red decor, pillows, and so much more. Treat your Valentine with something sentimental, as they also do custom framing! Bring some memorabilia to get professionally framed, whether it’s a photo, concert tickets, or anything sentimental you’ve kept.

BottlesUp!: Give the gift your Valentine NEEDS… a bottle of wine! BottlesUp has a fantastic team of winos on board, that can get the perfect bottle for your special someone. They also sell unique hand-crafted gifts, like planters, candles, chocolate bars, coffee beans, and more! You can even give the gift of attending a wine class with your Valentine. BottlesUp hosts multiple classes and tastings a month!

The NOW Massage: Fall in love with the NOW! Receive a $20 promotional card with every $100 gift card purchase, from now until February 14th.

Richard Dayhoff Trunks: Heat things up this Valentine’s Day, with the new RICHARD DAYHOFF Supersoft Trunk
In Black, Sizes S, M, L, XL, for $48! Like all RICHARD DAYHOFF offerings, his new Supersoft Trunk shows his finesse for clothing that is exceptionally sculptural, with sharply defined outlines and contours. And as always, it is sustainably fabricated. The Supersoft Trunk comes in a sleek black drawer-pull box, designed to express both architectural sturdiness, and minimalist elegance.

Wrigleyville Sports: Is your Valentine a sports fanatic? Visit Wrigleyville Sports (right across the street from Wrigley Field) for ALL the sports clothing, accessories, and memorabilia that you can imagine.

Goldplaited the Boutique: 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!

The Colette Collection: 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)!

CRAM Fashion: 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!

Fly in Fundamental: Feel like spoiling your Valentine? Fly is Fundamental is a new luxury streetwear store in Wrigleyville, carrying brands like Diesel, Save the Duck, Ugg, Family First, and more! Get something to really wow your Valentine.

Early Valentine’s Day Champagne Tasting on February 13:

Looking for a fun and unique Valentine’s plans? Join Bamboo Club for an exclusive Champagne Tasting. Your ticket unlocks an exclusive experience, featuring 8 curated champagne tastings paired with an assortment of charcuterie, sweets & desserts – a sensory journey for your taste buds. Tickets Include: 8 Champagne Tastings and an Assortment of Charcuterie, Sweets & Desserts! Get tickets here

Tango & Chocolate: A Sweet St. Valentine’s Celebration at Fred Astaire Dance Studio

Celebrate Valentine’s weekend with an evening of passion, dance, and indulgence. Join Fred Astaire Dance Studio Lakeview for tango lessions February 15th at 5PM & 6:30PM for an unforgettable Tango & Chocolate event. Immerse yourself in the rhythm of tango while savoring decadent chocolates and champagne. Whether you’re a seasoned dancer or stepping onto the floor for the first time, this is the perfect way to enhance your Valentine’s celebration.

Limited spots available—RSVP by February 12 by phone at (773) 882-0099 or via email at chicagolakeview@fredastaire.com, or you can always snag tickets online here.

Tapas & Salsa Dancing Lessons: On Sunday, February 16th, Get In the Kitchen is hosting Tapas Making and Salsa Dancing Lessons! Celebrate Valentine’s Day like never before! Mix and mingle, and have fun while cooking a meal you won’t soon forget! Join for a night of food, salsa dancing, socializing, and fun!

Menu that you’ll be making!
Homemade Red Pepper Garlic Bread accompanied by Chimichurri Salsa and Garlic Shrimp
Crispy Albondigas & Asiago Dumplings with a Bravas Goat Cheese Sauce
Mixed Salad with a Paprika Red Pepper Vinaigrette Dressing
Homemade Cardamom Cinnamon Ice Cream for Dessert Register here!

Anti-Valentine’s Day Party: Don’t care for Valentine’s Day? Old Crow Smokehouse is throwing a Anti- Valentine’s Day Party on February 14th! Tickets include a welcome drink before 10pm, a welcome shot before 11pm, LIVE country music & more! Get tickets here.

Celebrate Love at El Nuevo Mexicano – 40 Years of Flavor!: El Nuevo Mexicano is serving up something extra special this Valentine’s Day! From February 12-15, enjoy a special Valentine’s menu featuring their signature authentic Mexican dishes in a warm and inviting atmosphere. Whether you’re dining inside or on their all-season patio, you’ll find the perfect setting for a romantic evening. Celebrating 40 years in Lakeview East, El Nuevo Mexicano is a neighborhood gem offering happy hour specials, weekend brunch, and private dining options. Reserve your table today and make this Valentine’s Day one to remember!

Salsa with your Sweetie: Grab your Valentine and join Dance on Broadway for an unforgettable evening of fun, laughter, and dancing at the much-anticipated Salsa with Your Sweetie event! Happening on Saturday, February 8th. In this beginner-friendly class, you and your partner will:

Learn the fundamentals of Salsa, including lead and follow partner work.
Master basic spin drills and proper framework.
Practice a short combination to build confidence for social dance settings.
No experience needed—just bring your partner!
After the class, enjoy a glass of champagne as you unwind and celebrate your new dance moves! Register here

Anti-Valentine’s Day Comedy Special: Uncommon Ground is hosting an Anti Valentine’s Day Comedy Special on February 12th starting at 7 pm! Tickets are only $15 and is perfect for singles, skeptics, and couples who prefer jokes over mushy moments. Get tickets here

Valentine’s Day Trivia: Lark hosts trivia every Wednesday night but on February 12th, it is Valentine’s Day edition! From 7 to 9 pm, win prizes and enjoy specials like $10 Double Cheeseburgers, and 50% off mules!

Tango & Chocolate: This Valentine’s Day, join Fred Astaire Dance Studio Lakeview for a night of passion, dance, and fun. Feel the rhythm of the Tango while indulging in decadent chocolates and sipping on refreshing champagne. The event takes place on Saturday, February 15th, with sessions at 5 p.m. and 6:30 p.m. at 2825 N Halsted St, Chicago. Grab your partner and dance the night away, but don’t wait too long—spots are limited. RSVP by February 12th by calling +1 (773) 882-0099 or emailing chicagolakeview@fredastaire.com.

Friendship Bracelet Making: Lola and Bowie invite you to come browse the shop and make your own friendship bracelets. Make one bracelet for $10, or two for $15. Get a free friendship bracelet with any $30 purchase! The bracelet making is from 5 to 7 pm and is BYOB. No reservation necessary, just stop in the shop at 3335 N Broadway.

Galentine’s Day Wine Glass Paint & Sip: Celebrate friendship and fabulous fun this Galentine’s Day with a Galentine’s Wine Glass Paint & Sip! Grab your besties, pour some bubbly, and unleash your creativity – it’s the perfect girls’ night out! Pricing includes a thin stemmed wine glass for you to paint and take home. They’ve got all the supplies covered: paint, glitter, glitz, brushes, and aprons. And of course, you’ll sip on a complimentary glass of champagne to keep the good vibes flowing. Reserve your spot here

A Night for the Gals at Yak-zies: Celebrate the love of friendship at A Night for the Gals on February 13th at 7 PM! This Galentine’s Day event is the perfect excuse to grab your besties for an evening of bouquet-arranging, bubbly drinks, and delicious bites. Enjoy sips from Hardly Water, snacks from Yak-Zies, and fresh florals from With Love, Chicago—all in a fun, festive atmosphere. Tickets are $40, and spots are limited! Send a DM to reserve your place.

Galentine’s Dance Class: On Friday, February 7th, join the Dance on Broadway community for the annual Galentines Jazz class—the perfect way to celebrate friendship and fun! Whether you’re a seasoned dancer or a beginner, this Beginner/Intermediate Jazz class is sure to get you moving and grooving with your gals and pals.

What’s Included:
Class from 6:00-7:00 PM: Learn some fun Jazz moves with your friends in a supportive, energetic environment.
Wine Tasting at Bottles Up: After class, unwind with a delightful wine-tasting experience with your Galentines and the Dance on Broadway community! Register here

PJs & Prosecco Galentine’s Day Party: Grab your besties, throw on your PJs, and join Bamboo Club for PJs & Prosecco – the ultimate Galentine’s celebration! Enjoy 2000’s RomCom Trivia at 7 PM, Girl Dinner, heart-shaped pizzas, charcuterie boards, fun games, and drink specials. Celebrate friendship, laughter, and all things Galentine’s! Taking place on Thursday, February 13th.

Specials:
Heart-Shaped Pizzas & Charcuterie Boards
$7 Patron Margaritas
$5 Glasses of Rosé
$25 Buckets of High Noons
$40 Girl Dinner: Caesar Salad, French Fries, and Martini (Choice of Espresso, Lemon Drop, or Lychee Martini)
+ 2000’s RomCom Trivia at 7 PM
+ Play ‘Never Have I Ever’ Game

Register here for the PJs & Prosecco Party!

Galentine’s Party at Cuddle Bunny: On February 12th, Cuddle Bunny is hosting a Galentine’s Special Tight-Knit group! At this Galentine’s event, you’ll spend an 1.5 hours relaxing and knitting/crocheting/needle pointing/crafting with the sweetest group of free roaming bunnies. To celebrate Galentine’s day, they will also be providing materials to create bunny-themed jewelry and/ or wine charms! Get tickets here

Charcuterie Styling Workshop: Grab your pals and head to Alma at Hotel Zachary for Galentine’s Charcuterie Styling Workshop, where you will craft your heart-shaped charcuterie box! Taking place on Thursday, February 13th from 6 to 9 pm. Your ticket includes:
The hour-long workshop
Premium meats, cheeses, and charming decorations
A heart-shaped box, and a complimentary glass of wine

Have Roses at the Table When You Arrive at The Lanzaga: Impress your Valentine by having roses at the table when you arrive for dinner! The Lanzaga is offering this for Valentine’s Day only. Reserve your table (and roses) by calling 773-200-3303

Gourmet Specials at Mordecai: Enjoy Valentine’s Day cocktails and a la carte menu specials at Mordecai in Wrigleyville. The Cupidity is made using 5-year rum, pistachio, Meletti amaro, honey, lemon, and egg white, and the spirit-free Heart-Shaped Negroni offers a zero-proof take on the classic cocktail with strawberry syrup, n/a amaro lucano, noroi aperitivo, and noroi l’espirit de London. Chef Djibril Webb has created specials, including Seafood Fettuccine, Dry-Aged Porterhouse, and Chocolate Lava Cake. Valentine’s Day specials at Mordecai will be available from Friday, February 14th until Sunday, February 16th. Make reservations here

Lark: Lark is having a Dinner for Two special from February 11-17th! This special includes a three-course meal with select cocktails for $69.95!

Dryhop Brewers: Chef Eric Halvorsen created a custom three-course Valentine’s Day prix fixe menu available only on Valentine’s Day! Diners can choose what they would like from each course, for only $57 a person. Click here to reserve your spot!

Drew’s on Halsted: Drew’s has a huge Valentine’s Special Menu available from February 14-16. Treat your special someone to a night out of gourmet food at one of Lakeview’s most popular restaurants. View the special menu and make reservations, here!

El Nuevo Mexicano: Say “I Love You” by treating your Valentine to one of the best Mexican restaurants in the city! Enjoy a special four-course dinner for only $50 from Feb. 12-15. Great time to celebrate with ALL your loved ones! Click here for reservations, or to order carry out.

Cesars Killer Margaritas: Love is in the air, and Cesar’s Killer Margaritas, in Lakeview, is setting the mood with their Valentine’s specials available all February long! Make a toast with their Chocolate Raspberry Margarita, blending creamy Abuelita chocolate with fresh raspberry sauce, or try out the Mazapan Margarita, a dreamy mix of peanut-based Mexican candy, rich chocolate, and Cesars’ signature margarita blend. Looking for something sweet and refreshing? The Strawberries & Cream Margarita is a luscious mix of strawberries and sweet condensed milk – like love in a glass! Pair your cocktails with a meal made for sharing, like Mar y Tierra, featuring Cesars signature carne asada, butterflied shrimp, and roasted veggies, or spice things up with Camarones a la Diabla, Butterflied shrimp seared in a smoky chile de arbol reduction and topped with avocado. End on a sweet note with the Tres Leches Cake, soaked in a rum-laced three-milk medley and topped with whipped cream and wafer hearts. Whether it’s date night or simply a reason to treat yourself, Cesar’s February specials are here all month long—so don’t wait to fall in love with these flavors!

Check out the brand new 2025 Lakeview East Dining Guide to find the perfect spot for you and your plus one!