The Gillman Group Valentine's Day Gift Guide 2026

They say love goes through the stomach and we tend to agree. Food is basically the ultimate Valentine’s Day gift - it’s thoughtful, delicious, and guaranteed to make someone smile. Whether you’re shopping for your bestie, your partner, your spouse, your kids - or loving yourself - there’s a tasty sweet for everyone. Here's some gift-worthy foods from local shops to make your Valentine’s Day shopping extra sweet. 

 

Vosgues Haut-Chocolat, Logan Square

Assorted chocolates in a heart-shaped box surrounded by colorful butterflies.

Treat someone special (or yourself!) to The Aurelia Ensemble, a radiant 26-piece chocolate celebration that’s all about bold, joyful bites and buttery, wing-inspired flavors that feel like love taking flight.

 

Beautiful Rind, Bucktown

Charcuterie gift box with cured meats, cheeses, blueberries, pickles, honeycomb, and fig spread.

Pick up a custom board for a romantic evening that feels effortless and elevated. Whether you’re planning an intimate date night at home or surprising someone special, a personalized spread like this makes the night feel deliciously thoughtful from the first bite to the last.

 

Le Midi, Wicker Park

Three wine bottles on a wooden bar counter, including bottles labeled GROSS and ESPORÃO.

The Bundle of Love is a curated trio of wines that’s perfect for surprising someone special or elevating a cozy Valentine’s at-home celebration. Whether you’re gifting it or uncorking it together, it’s an effortless way to make any evening feel a little more romantic and memorable.

 

Art Effect, Lincoln Park

A pink cocktail beside a heart-topped glass decanter and two lemons.

The Glass Decanter w/ Heart Stopper pairs perfectly with the previously mentioned Bundle of Love wine trio from Le Midi Wine. The combination turns uncorking and sharing the bottles into a thoughtful, elevated experience that feels just right for sipping together or gifting to someone you care about.

 

Hotel Chocolat, Lincoln Park

Hotel Chocolat heart-shaped gift box with a white ribbon and assorted chocolates

Straight from the Heart is a beautifully curated collection of rich, artisan chocolates that turns sweets into an art form. It’s the kind of gift that feels both thoughtful and indulgent, perfect for surprising someone special or making your own Valentine’s Day a little more luxurious.

 

Judy Maxwell Home, Old Town

Boxed chocolate man in heart-patterned underwear, surrounded by foil-wrapped chocolate hearts.

The Perfect Man Decorated Milk Chocolate is a deliciously smooth and rich milk chocolate “man” that’s a humorous and irresistible Valentine’s treat. 

 

Old Town Oil, Old Town

Two bottles of Old Town Oil beside a white gift box on a wooden counter.

Signature EVOO & Old Town Oil Reserve Balsamic is a perfect gift for the food lover who appreciates the little details. The olive oil paired with a beautifully aged balsamic elevates everything from simple salads to candlelit homemade dinners. It’s thoughtful, versatile, and the kind of pantry upgrade that keeps giving long after Valentine’s Day.

 

Amy's Candy Bar, Lincoln Square

Valentine’s Day gift box filled with chocolates, pink candies, and red ribbon.

The Valentine's Gift Box Assortment is a delightful mix of handcrafted chocolates and sweet treats that feels like indulgence wrapped up with a bow. Whether you’re surprising your Valentine or treating yourself, it’s an easy way to make someone’s day a little sweeter and more memorable.

 

The Chopping Block, Lincoln Square

A couple makes fresh pasta together, stretching dough over a pasta machine.

Take a cooking class to turn a regular evening into a lively kitchen adventure where you chop, sauté, and laugh your way through hands-on lessons with expert chefs, then get to enjoy the delicious meal you helped create. It’s the kind of experience that makes learning to cook feel like a celebration rather than a chore.

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