How You Can Celebrate Valentine’s Day at Home in Chicago

Windy City Cosmo Valentine's Day Gifts and Dates in Chicago

February in Chicago – the time for hibernation and romance!

Since it’s been extra snowy and cold (hello 0 degrees), and of course COVID is still very much a thing, I wanted to put together things you can do at home or little things you can get that special someone in your life.

Honestly, dating and being in a relationship during COVID can be very difficult, especially in the winter when no one wants to go outside. But, I love romance and you can still show someone you care by making it a special weekend at home – as hard to believe as that is.

If you haven’t already, follow me at Windy City Cosmo on Instagram. I’ve created a guide for Valentine’s Day in Chicago and also cool date spot ideas in Wicker Park.

These are just some ideas to support local businesses and also make someone feel special. Some OJ and kisses on Sunday with a cute note by the shower isn’t a bad idea either.

1. Say it with Charcutiere

Netflix and Chill is definitely a thing. But you can add a little pizzazz (and also help out local businesses and artisans) with a handmade Charcutiere Board.

Grazing Table Chicago is offering a $90 Valentine’s Day Board~
Perfect for couples trying to indulge or a small group of Gals getting together 👯‍♀️

🧀 Brie, Merlot Bellavitano, and Point Reyes Blue
🍖 La Quercia Prosciutto, Calabrese Spicy Salumi
🍒 Fig Jam, Sour Cherries in Cherry Syrup, and Honeycomb
🍇 Red Grapes, Strawberries, Blackberries, Figs, Pomegranate
🥜 Pistachios, Chocolate Covered Almonds
🍫 Sea Salt Chocolate Covered Caramels
🥖 Crackers

Limited Availability. Bouquet Additional Charge starting at $30. Fresh Baguettes available for $3 each

2. Fondue and You

“The nation’s most romantic restaurant,” via USA Today, Geja’s has fondue and cocktails to-go! They also have chocolate fondue kits to-go because sometimes chocolate is better than cheese.

This Valentine’s Weekend they have special at-home Fondue Experiences which you can learn more about here.

2. Virtual Wine Tasting Kit

Chicago based VIN312 Winery teamed up with two other local businesses, The WineGrasp and Lucila’s Alfajores, to create a fun wine tasting event for celebrating Valentine’s Day at home this year.

These three local businesses have created a Valentine’s Day Tasting Gift Box, which includes: five 2oz VIN312 wine samples, two Alfajores By Lucila (a caramel like goodness sandwiched between 2 butter cookies then dipped in dark chocolate or white chocolate), a set of WineGrasps (gadgets that hold your glass of wine for you), a virtual tasting with the winemaker on Webex, tasting notes, a free tasting coupon for future winery visit and 20 percent off new wine club memberships.

Valentines Day box 2021

You can order The Valentine’s Day Tasting Gift Box cor pick up locally at VIN312 Winery located at 4710 N Ravenswood Ave. in Chicago. Orders can be placed and picked up until Sunday, Feb. 14th by 6 p.m. Curbside service available or visitors can come inside the winery. Face masks are required. 

For more information, visit:

3. When You Want to Feel Like You’re Away

There’s something about a view and hotel sheets. A staycation is nice, but for Valentines’ Day, you can really level up with a staycation at The Viceroy – which even has a proposal package that includes a diamond ring! You can be basic and go for the rose petals and champagne package – I think that’s the most romantic, actually.

4. Sunday Brunch at Home

I feel like brunch makes sense because Valentine’s Day is on a Sunday. So, I wanted to include Beatrix’s At Home Brunch option. You can also do the dinner option and they also provide flowers, which is a nice touch on Valentine’s Day.

You can also semi-cook breakfast in bed with these cinnamon rolls from West Town Bakery or these speciality croissants.

If you really want to impress – you can take the virtual breakfast in bed at Chopping Block. You can feel like Selena Gomez and join a chef who will teach you and your love how to whip up something special.

Goddess and The Grocer is turning your home into a hotel with room service breakfast in bed. Get all the Valentine’s Day Room Service details here.

5. Send a Sweet Message

I love a little something sweet and now you have options. Local bakery, Love, Sugar and Grace have a few options for you to get this weekend. I met the owner, Grace Lee, at the opening of women’s co-working space, and she catered the cookies. I love to support female entrepreneurs and especially ones that have helped other women-owned businesses.

She has six options to choose from including a Valentine’s Day box (which is gluten-free) with roses on top and sweets on the bottom, a cookie letter scramble and a sugar cookie making kit. Check them all out here.

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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