2026 Old Town Valentine's Month Guide
Check out these amazing offerings from some of your favorite Old Town businesses for this Valentine’s! Whether you’re looking to celebrate with a special someone, get into the dating scene, have “galentines” with your besties, or partake in some self-care; Old Town has what you’re looking for this month.
Little Learners Academy
Valentine’s Parents’ Night Out at Little Learners Academy offers children a special holiday evening in a familiar, nurturing environment. While parents enjoy a night out, children will participate in dinner, Valentine-themed games and bingo, hands-on crafts, and cookie decorating, all led by trusted teachers.
Friday, February 14 | 5:00–7:30 PM
Dinner included
$90 per child
Ages 3–6, must be fully potty trained
Sign up HERE
Natural Thai Bodywork
Book your couple’s massage now by calling or texting 773-693-5367 or book online HERE
Chiropractic Chicago
Whether your looking for a couple’s experience or a way to treat yourself this Valentine’s day – Chiropractic Chicago is here for you!
Call or text 312-255-9500 to book your visit.
The Fudge Pot
Ivy Dating // Burton Place Bar
Ivy Dating is a new dating app on a mission to bring back real life connections in hopes of helping people grow attractions in the wild–not behind a screen. To bring this mission to life, Ivy partners with venues across the city to host curated events that drive engaged, intentional singles to local spaces to meet one another. Alongside connecting with people at events, Ivy users can also check-in practically anywhere to meet other singles in real time. To experience Ivy Dating for yourself, come out to one of the Valentine’s Day events!
Download the app HERE
RSVP to the February 12th event at Burton Place Bar HERE!
Slant of Light Books
Stop by Slant of Light Books this valentine’s day to get your romance novel fix for 20% off! Or bring your date in and broaden your literary horizons by picking out books for eachother!
Cocoa + Co.
Orso’s
Valentine’s Day is in the air
Celebrate love this Valentine’s Day (and all of Valentine’s season) in a cozy, romantic restaurant nestled in the heart of Old Town.
Whether it’s a first date, a forever kind of love, or just you and your girls, let Orso’s set the mood for an unforgettable evening. 
Reservations recommended
Book on OpenTable or call Orso’s directly at 312-787-6604
Marge’s Still
Thursday 2/12 – Saturday 2/14
12 oz New York strip with mashed potatoes, green beans, and a brandy peppercorn sauce $35.00
Two 6 oz homemade meatballs with rosemary polenta topped with marinara and a dollop of ricotta cheese $25.00
6pc fried shrimp appetizer with homemade garlic aioli $18.00
The Vig
MoonStar Kitchen & Bar
Make any date night or get together special with shareable bites, cocktails, and a cozy, romantic atmosphere.
Corcoran’s
Celebrate Valentine’s Day at Corcoran’s and finish the night with a cozy Irish Coffee for the perfect nightcap.
