Posted 19 hours ago in Trending, Things to Do, Valentine's Day, Fun events
6 MIN READ – It’s a day for love, and there's few places like being in the Loop to keep your romance alive. Celebrate love with intimate and enjoyable experiences downtown.
valentines day events
on the market: be my valentine
Feb. 8, 2026, 3:00 PM - 7:00 PM
Chicago Athletic Association - 12 S. Michigan
Fall in love with community at On The Market: Be My Valentine—a lively, community-forward market spotlighting local makers, creative expression, and meaningful connection. Join over 30 Chicago-based artists and vendors in Stagg Court for an afternoon filled with shopping, crafting, and heart-forward fun.
Explore the market from 3–7pm, or grab a ticket to one of their featured experiences:
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Matchmaking with The Yente Pages | 3–5pm
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Scorpion Heart Pinning Workshop with RIP Repurposed | 5–7pm
Guests can also stop by the Valentine’s-inspired photo booth and gather at a community craft table hosted by The Artistic Alphabet Mafia to decorate bookmarks for Liberation Library, supporting youth in Illinois prisons.
*Tickets cost $5 per/person
crush: floral workshop, valentine's edition
Feb. 12, 2026, 6:00 PM - 7:30 PM
Chicago Athletic Association - 12 S. Michigan
Whether planning a romantic outing or a moment of self-care, this hands-on floral experience offers the perfect reason to stop and bloom. After a brief demo and design tips, guests will choose from two curated bouquet recipes and select from fresh blooms and greenery to create a handheld arrangement—no floral experience required.
Each guest will enjoy a complimentary pastry from local baker and home chef Niki, along with non-alcoholic refreshments and a 20% off drink voucher for the Game Room. Guests leave with flowers in hand, a sweet treat enjoyed, and a Valentine’s memory to take home.
*Tickets cost $70 per/person
speed friending
Feb. 13, 2026, 6:30 PM - 9:00 PM
International Museum of Surgical Sciences - 1524 N. Lake Shore Drive
A fun, platonic Valentine’s activity centered on learning, conversation, and making new connections.
*Tickets are $23.18 per/person
raised, an urban rooftop bar
Feb. 14, 2026, 7:00 PM - 10:00 PM
Raised, An Urban Rooftop Bar - 1 W. Wacker Drive
For the Gal-entines (and couples) looking for a fun disco night out.
Whether you’re coming hand-in-hand or rolling deep with your girls, Raised is the ultimate Valentine’s Day plan! Step into a disco-lit love fest for Love on the Rocks, a high-energy night of dancing, drinks, and feel-good vibes. Your ticket includes a welcome champagne Jell-O shot, draft beer and wine, sparkling pours, themed cocktails, a live DJ spinning all night, and a selfie-worthy photo booth to capture the memories. From flirty date night moments to the perfect Galentine’s celebration, this is Valentine’s Day- Raised, remixed, and ready to party.
*Tickets are $103 per/person.
rapt in plastic: Blind Love
Feb. 14, 2026, 7:00 PM - 9:00 PM
International Museum of Surgical Sciences - 1524 N. Lake Shore Drive
Rapt in Plastic will perform Twin Peaks classics, bringing a dreamy, Lynchian twist to Valentine’s Day night in the Museum.
*Tickets are $28.52 per/person
skate night at the track
Fe.13, 2026 3:00 PM - 9:00 PM & Feb 14. 2026 3:00 PM - 9:00 PM
Chicago Athletic Association - 12 S. Michigan
Get ready for playful, themed vibes and a soundtrack to match. Bring your friends—or your date—and lean into the nostalgia this Valentine’s Day weekend.
Ticket includes: a 2-hour skate session, skate rental, and a welcome drink.
pie in the sky
Love is in the air, and Skydeck Chicago will be offering an intimate dinner package couples don’t want to miss this Valentine's Day. Skydeck is adding a romantic twist to their Pie in the Sky dinner series; starting February 1st, guests have the option to indulge in a special heart shaped Giordano’s pizza over breathtaking views of Chicago.
Throughout February on select nights, guests are invited to dine high above the city, either with a late-night experience on the 103rd floor or an early evening dinner on the 99th floor:
- 103rd floor dining: Thursdays & Fridays at 9:30 PM
99th floor dining: Fridays & Saturdays at 6:00 PM - Valentine’s Weekend Special (February 12–15)
- 103rd floor dining: 9:30 PM
- 99th floor dining: 6:00 PM
So, this year, skip the overcrowded restaurants downtown and soak up the romance of the city from above.
*Please note that reservations must be made at least 3 business days in advance. To make a reservation, please call (312) 875-9447.
valentines day specials
couples retreat package
Available to book for the month of February 2026 ONLY
Palmer House - 17 E. Monroe
This Valentine's Day, whisk your special someone away for a night of pure romance and relaxation. The Couples Retreat Package includes an overnight stay for two plus 30% off all spa services -- because nothing says love like a little pampering together.
The Couples Retreat Package includes:
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- Accommodations for one overnight stay for two people
- 30% off all spa services during stay with advance reservation by Spa Concierge
- Two glasses of champagne at Lockwood Restaurant & Bar
- Two heart-shaped brownies from Lockwood Restaurant & Bar
- Access to indoor pool, dry heat sauna, fitness facility
the self care suite package
You deserve a little luxury, and the Self-Care Suite Package is all about you. Enjoy an overnight stay in style, plus The Empire All-Inclusive Spa Package for one—because pampering is non-negotiable. Wrap yourself in a plush spa robe, savor a decadent heart-shaped brownie from Lockwood, and sip on a rich Peanut Butter Cup Martini that tastes like pure love.
But why stop there? As a guest, you’ll have full access to the indoor pool, dry heat sauna, and fitness facility—because self-care comes in many forms. This Valentine’s Day, skip the clichés and celebrate the most important person: you.
Details: The Self-Care Suite Package includes:
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- Accommodations for one overnight stay at Palmer House
- The Empire All Inclusive Spa Package for one person. This spa day service includes a 50 minute RELAX Massage, 50-minute Signature Facial, and a 50-minute Signature Body Wrap and is inclusive of all service fees and gratuities. Hotel Destination Fees may not be applied.
- One Plush Spa Robe to take home from Spa at Palmer House
- One heart-shaped brownie from Lockwood Restaurant & Bar
- One Peanut Butter Cup Martini from Lockwood Restaurant & Bar
Access to indoor pool, dry heat sauna, fitness facility
v-day specials at the lockwood restaurant and bar
Open Daily, 5 PM - 10 PM, Bar Open Daily, 5 PM - 11 PM
Lockwood Restaurant and Bar, Located inside Palmer House Hotel Lobby
Featuring swoon worthy bites and sips, such as Bertha's Heart Brownie, the Chocolate Martini, Peanut Butter Cup Martini, and Ruinart Rosé, Veuve Clicquot champagne and more.
View full menu here.
truffles and prosecco
Need a place to stay for V-day?
This Valentine’s Day, Renaissance Downtown Chicago invites you to create unforgettable memories with someone special. Enjoy decadent truffles from Amy’s Candy Bar, a bottle of Prosecco to toast your love, and the added luxury of late checkout for a relaxed, romantic morning. Let us help you celebrate in the heart of the city with a getaway that’s all about you and your love story.
Why It’s a Perfect Romantic Destination: The hotel offers a prime location right on the city’s river- perfect for couples wanting to explore Chicago OR stay in and enjoy the romance. The hotel’s rooftop bar- Raised, also allows guests the chance to celebrate with the most romantic views in town- all without leaving the hotel!
