Celebrate Sweetest Day with Your Sweetie
Romantic ways to spend Saturday, October 17
Sweetest Day is a great excuse to show your love and appreciation to your partner. Whether you’re planning in advance or just remembered this Hallmark holiday, we’ve got your back. Here’s an itinerary to help make Saturday, October 17, a day to remember for you and your sweetie.
Let’s dive into the sweetest ideas for celebrating! You might also like our date night guide.
Warm Cookie Sundae + Day at the MCA
After spending an afternoon taking in the exhibits at the Museum of Contemporary Art, share a Warm Cookie Sundae at The Cookie Bar by Summer House, an indulgent dessert that’s its own little masterpiece.
Learn more about The Cookie Bar by Summer House.
Bagel Pop-Up + Bike Ride
Show them they’re you’re everything with an Everything Bagel by Chicago’s favorite hand-rolled, artisan sourdough bagels, Decker’s Sourdough Bagels, popping up at Wildfire – Chicago on Saturday, October 17 starting at 9:00 AM. Hop on your bike (a tandem if you’ve got one!) and head to River North for fresh baked bagels, whipped cream cheese, coffee, house-made pastries and more. Plus, for the first time this weekend, Decker’s is rolling out gluten-free Plain and Everything bagels—yum! (A couple that schmears together…)
Learn more about Decker’s Sourdough Bagels.
Chicago Riverwalk Stroll + Heart-Shaped Pizza
Go for a late morning or early afternoon stroll around the River Walk and then stop by Pizzeria Portofino and surprise your special person with a heart-shaped pizza. On Sweetest Day, you can have any pizza shaped into a heart for $5, plus tax (gratuity not included).
Make a Sweetest Day reservation at Pizzeria Portofino.
A Glam Night Out
Impress your sweetheart with a cocktail from the cold room or perfectly executed martini made tableside from a trolley at Kitty’s Cosmpolitan Club. They deserve the best and the team at Kitty’s delivers just that and more, every time.
Make a Sweetest Day reservation at Kitty’s Cosmopolitan Club.
Wine Tasting
Whisk your sweetest away to California’s Wine Country without leaving Chicago! The Cellar Door at the Oakville Grill & Cellar emulates the rustic feel of Napa Valley’s exquisite vineyards, and this October they are featuring pours from Tablas Creek Vineyard. For $65 per person, plus tax (gratuity not included), enjoy this wine-tasting experience. You can add a chef-curated cheese & salumi pairing for an additional cost. Or, check out The Oakville’s new brunch menu and add on the Cellar Door Tableside Experience for $36 per person, plus tax.
Make a Sweetest Day reservation for The Cellar Door tasting experience.
Curated Dinner for Two
For those looking for a unique tasting menu experience, opt for the RPM Sommelier Tasting Experience. Hosted by RPM Seafood, you’ll enjoy a guided tasting of expertly paired wine and food menus. The best part? No bottle is off-limits. You might be sipping vintage Champagne, Grand Cru Burgundies, and more. Plus, the executive chefs create menus that change daily to match the expertly chosen wines.
Book the Sommelier Experience for Sweetest Day at RPM Seafood.
18-Course Omakase Experience
For the foodie in your life, consider The Omakase Room at Sushi-san. You’ll enjoy a one-of-a-kind 18-course menu from Master Chef Kaze Chan, starting at $250 per person (plus tax). Add the beverage pairing of your choice (sake, wine, non-alcoholic) and you’re in for a culinary journey.
Make a Sweetest Day reservation at The Omakase Room.
Start A New Tradition
As you may have heard, oysters are for lovers, and the couple that slurps together, stays together. So, start a new tradition with a sip and slurp at Shaw’s Oyster Bar! With a half-dozen varieties of East and West Coast oysters available daily, it’s a surefire to make every Sweetest Day shuckin’ delicious.
Make a Sweetest Day reservation at Shaw’s Crab House – Chicago.
Make a Sweetest Day reservation at Shaw’s Crab House– Schaumburg.
Late Night Romance + Rum Flights
For your cocktail lover, head to The Bamboo Room at Three Dots and a Dash for a guided rum tasting. After taking your taste buds on a tropical tour around the world, get nostalgic over the award-winning cocktail bar’s inventive menu, featuring whimsical creations like the Jamaican Ten-Speed and Clairvoyant Missionary.
Make a Sweetest Day reservation at The Bamboo Room.
Dessert with a View
Put a sweet finish on your Sweetest Day dinner at Miru with mouthwatering desserts like the Coconut-Mango Mousse, Chocolate Silk Tart with Matcha Ice Cream, and signature Black Sesame Mochi, made with charcoal-vanilla ice cream, black sesame praline, and mochi sponge cake. It’s dessert heaven, complete with stunning and romantic views of Chicago.
Make a Sweetest Day reservation at Miru.
Vegas Getaway
For a truly unforgettable and unexpected Sweetest Day, consider a surprise trip to the dazzling lights of Las Vegas. Whether you’re looking for world-class entertainment, gourmet dining at Eiffel Tower Restaurant, or a club night, Vegas has it all. Plan your escape and indulge in the excitement of Sin City with your sweetheart. View the Lettuce Vegas Vacation guide for more ideas.
Make a Sweetest Day reservation at Eiffel Tower Restaurant.
Sweets for Your Sweetie
If your sweetheart is a pastry lover, take them on a coffee date to Beatrix! With locations near the Chicago River, some of the city’s best museums, and your fave shopping destinations (including in the ‘burbs at Beatrix at Oakbrook Center), grab favorites such as the Honey Butter Cinnamon Roll, Chocolate Chunk Cookie or gluten-free Dark Chocolate Brownie plus a Vanilla Oat Draft Latte to-go and take a leisurely lovers’ stroll.
Make a Sweetest Day reservation at the Beatrix location nearest you.
Brunch + Gift Shopping
Make your Sweetest Day in Orlando extra magical with brunch at Summer House on the Lake at Disney Springs® West Side! The gorgeous indoor-outdoor restaurant has menu of hearty coastal California-inspired brunch dishes like the Vegan Breakfast Burrito, Mexican Hash Browns, Pancake Tacos and more. On your way out, stop at The Cookie Bar for a sweet treat and a glass of Summer House Rosé to-go for a day of outdoor shopping!
Make a Sweetest Day reservation at Summer House on the Lake Disney Springs® West Side.
Cozy Night In
Sometimes, the most romantic moments happen at home. Plan a cozy night in with your loved one. Light some candles, order in or cook a special meal together (click here to explore our many recipes!), and enjoy a movie marathon or some binge-worthy TV and takeout.
(Does your partner like a good candle? Aba, Pizzeria Portofino and RPM Restaurants all offer signature scented candles for purchase.)
You can also order carryout or delivery from our restaurants, which is easier than ever through the LettuceEats® app.
Sweetest Day from Afar
Even if your sweetie is miles away, you can still make Sweetest Day special. Send a surprise delivery, like a heartfelt letter and a basket with their favorite treats, to let them know you’re thinking of them. Here are some of our favorite treats available for nationwide shipping. Plus you can include a Lettuce Gift Card so they can visit their favorite restaurant! Distance may separate you, but love knows no bounds.
