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Valentine’s Day is here, and it’s time to break free from the ordinary. Skip the tired flowers and predictable dinners. Chicago offers excitement, adventure, and romance in every corner. Whether you’re celebrating love, friendship, or simply the joy of a great night out, this city has something for you. Seize the moment. Make this Valentine’s Day one to remember.
Eat Out
Chicago BLACK Restaurant Week (Feb. 9-23, 2025)
Support Black-owned restaurants while indulging in some of the city’s best cuisine. Don’t miss these standout dining experiences and pick out a restaurant to support from this list of CBRW eateries:
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- Feb. 14, 10 a.m. – 3 p.m.
- 3137 W Logan Blvd.
- Bottomless mimosas. Fantastic food. No excuses.
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- Feb. 14, 7-9 p.m.
- 1040 Sterling Ave, Flossmoor
- Smooth tunes. Great company. Perfect night.
Bronzeville Winery Valentine’s Day Dinner
- Feb. 14, Seatings at 5:30 p.m. & 8:00 p.m.
- Three-course meal + sparkling wine. Elevate your night.
Do Stuff
Chicago Auto Show (Feb. 8-17)
- Open daily at 10 a.m.
- McCormick Place, 2301 S King Dr.
- The latest cars, bold designs, pure adrenaline.
R&B Valentine’s Day Lovefest featuring Jeffrey Osborne & Will Downing
- Feb. 14, 8 p.m.
- Auditorium Theatre, 50 E Congress Pkwy
- Legendary voices. Unforgettable night.
Valentine’s Day Smooth Jazz Friday
- Feb. 14, 6 – 9 p.m.
- 616 E 71st St, Chicago
- Smooth sounds. Relaxed vibes. Perfect date night.
Project a Black Planet: The Art and Culture of Panafrica at the Art Institute of Chicago
- Dec. 15, 2024 – Mar. 30, 2025
- A journey through Pan-African culture, history, and power.
Valentine’s Day Pizza Cooking Class at Pizzeria Due
- Feb. 14, 9:30 – 11:30 p.m.
- A delicious date night win.
Lovers and Friends Paint and Sip
- Feb. 14, 7-9 p.m.
- Pose Cultural Art Gallery, 2136 W Chicago Ave
- BYOB. Creativity. A night to remember.
A Night of Love & Luxury: Couples Facial & Candle Making
- Feb. 14, 6-7 p.m. and 9-10 p.m.
- Civinte Candle Bar, 807 S Oak Park Ave, Oak Park
- Romantic. Relaxing. A sensory experience.
Pop The Balloon Valentine’s R&B Night
- Feb. 14, 8 p.m.
- Dynasty Room
- For singles and couples. Live R&B. Food. Drinks. A vibe.
Ain’t No Love in the Club – R&B, Trap & Twerk Valentine’s Affair
- Feb. 14-15, 10 p.m.-2 a.m.
- Bar 22, 2244 S Michigan Ave
- No romance required. Just good music and good energy.
Valentine’s Day Bachata Semi-Private Class
- Feb. 15, 9:15 – 10 p.m.
- Ballroom Dance Chicago
- Romance in motion. Learn the steps. Feel the rhythm.
Chicago doesn’t do boring. Whether you want an elegant dinner, live music, a cultural deep dive or a wild night out, this city delivers. Don’t wait. Make your reservations. Lock in your plans. Own the weekend.