Last updated: May 4, 2026 at 12:32 AM
Best Happy Hours, Deals & Events in San Jose, CA — Monday, May 4, 2026
Tonight in San Jose, find fantastic happy hour deals across the city! Head to Downtown San Jose for $7 Jameson at O’Flaherty’s Pub or $4 pints at The Old Wagon Saloon & Grill. In Willow Glen, Blue Water Seafood & Crab Bar offers $2 off draft beers and $3 oysters, ensuring a vibrant start to your week.
🍺 Happy Hours in San Jose, CA Tonight & This Week
Downtown San Jose / San Pedro Square
Five Points
Address: 169 W Santa Clara St, San Jose, CA 95113
Happy Hour: Mon–Fri 4–7 PM
Deals: $12 select cocktails (like the mezcal-based Daybreaker or tequila reposado Paloma), $17.25 wings or coconut shrimp.
Vibe: A popular craft cocktail bar with a warm, dimly lit, and vintage-inspired atmosphere, drawing from 19th-century New York.
Why go: Step back in time with unique craft cocktails and delicious bites in a lively setting, perfect for an after-work unwind this Spring.
O’Flaherty’s Irish Pub
Address: 25 N San Pedro St, San Jose, CA 95110
Happy Hour: Mon–Fri 4–7 PM; Late Night HH Thu 9 PM–last call
Deals: $7 beer, $7 Jameson, $7 well spirits, plus discounted bites.
Vibe: An authentic Irish pub in historic San Pedro Square, known for its hospitality, 38+ beers on tap, and traditional comfort food.
Why go: Experience genuine Irish warmth and enjoy affordable drinks and classic pub fare, especially welcoming on a Monday night.
The Continental Bar
Address: 349 S 1st St, San Jose, CA 95113
Happy Hour: Daily 3–7 PM
Deals: Great food and drink specials.
Vibe: An upscale local bar in the Historic SOFA district with a unique atmosphere, comfortable seating, and a patio, often featuring DJs and live music.
Why go: Enjoy craft cocktails and specialty beers in a chic downtown setting, perfect for a sophisticated yet relaxed start to the week.
The Pressroom
Address: 196 N 3rd St, San Jose, CA 95112
Happy Hour: Daily 3–5 PM
Deals: 50% off all cocktails, martinis, and wine by the glass; $7 draft beers; $12–$16 snacks like fried artichoke and guajillo short rib sliders.
Vibe: A buzzy spot located in the historic 1884 Lyndon Building, offering a pretty and vibrant atmosphere.
Why go: Indulge in high-quality drinks and elevated snacks at half price, ideal for a refined happy hour experience in Downtown.
Dr. Funk
Address: 29 N 2nd St, San Jose, CA 95113
Happy Hour: Daily until 7 PM (excluding SAP Center event nights)
Deals: $12 hand-crafted drinks (try the Mai Tai or Puka Punch), $9 curry or nacho fries.
Vibe: A lively and spirited bar offering unique hand-crafted tiki-inspired cocktails.
Why go: Kick off your evening with exotic drinks and flavorful fries in a fun atmosphere before the downtown crowd picks up.
Meso Modern Mediterranean
Address: 306 S 1st St, San Jose, CA 95113
Happy Hour: Mon–Fri 3–6 PM
Deals: Snacks under $10 (falafel bites, kufta meatballs, crostini), $8 glasses of wine, $10 Fresa Margarita.
Vibe: A modern Mediterranean restaurant offering flavorful dishes and a stylish ambiance.
Why go: Perfect for light bites and refreshing drinks after work, with a menu that’s both exotic and approachable.
Olla Cocina
Address: 173 W Santa Clara St, San Jose, CA 95113
Happy Hour: Daily 3–6 PM
Deals: Half-price wine and cocktail carafes, half-price beer pitchers, $5 tacos, $10 ceviche tostada, plus free chips & salsa.
Vibe: A vibrant Mexican eatery offering a lively atmosphere and delicious, shareable plates.
Why go: Ideal for groups looking to share carafes and enjoy tasty Mexican street food at great prices in a bustling downtown spot.
District Bar
Address: 60 S Market St, San Jose, CA 95113
Happy Hour: Daily 5–6 PM
Deals: Two-for-one oysters on the half-shell, $7 rotating draft pilsners or IPAs, $9 cocktails and bites like crispy spiced chicken wings.
Vibe: A chic bar with a focus on craft drinks and refined small plates, offering a sophisticated happy hour experience.
Why go: Elevate your Monday happy hour with exquisite oyster deals and carefully crafted cocktails in a trendy downtown setting.
San Pedro Social
Address: 101 E San Fernando St, San Jose, CA 95113
Happy Hour: Mon–Fri 3–6 PM
Deals: Discounts on drinks, $15 slice + pint combo, $7 fried ravioli, $10 spicy chicken sliders.
Vibe: A casual and lively spot near San Pedro Square Market, known for craft cocktails, beer, and a loft-like setting.
Why go: Enjoy robust food and drink specials after work, with substantial deals on pizza and comfort food in a vibrant downtown locale.
The Old Wagon Saloon & Grill
Address: 73 N San Pedro St, San Jose, CA 95110
Happy Hour: Daily 3–7 PM
Deals: $6 select appetizers, $4 pints, $5 well drinks.
Vibe: A classic saloon and grill in San Pedro Square, offering a friendly and relaxed atmosphere for drinks and American comfort food.
Why go: Grab some of the cheapest pints in town and hearty appetizers to kick off your evening in a laid-back environment.
Santana Row
LB Steak
Address: 334 Santana Row #1000, San Jose, CA 95128
Happy Hour: Sun–Fri 3–5 PM (Bar & Patio Only)
Deals: $6 rotating beer selection, $10 wine (sparkling, white, rosé, red), $1.5 raw oysters on the half-shell, $6 Fritto Misto, $8 shrimp cocktail.
Vibe: An upscale steakhouse with a sophisticated bar and patio area, perfect for people-watching on Santana Row.
Why go: Indulge in luxury for less with discounted oysters and fine wines in the chic ambiance of Santana Row.
Willow Glen
The Table
Address: 1110 Willow St, San Jose, CA 95125
Happy Hour: Mon–Tues 4–5:30 PM
Deals: Various snacks ranging from $6–$18, and a $22 “One-Hitter Quitter” combo including a signature burger with a daily selected beer and a shot.
Vibe: A popular American eatery with a rustic-chic ambiance, focusing on farm-to-table cuisine and craft drinks.
Why go: Enjoy upscale American dishes and unique drink pairings, perfect for a gourmet happy hour experience in Willow Glen.
Blue Water Seafood & Crab Bar
Address: 860 Willow St, San Jose, CA 95125
Happy Hour: Mon–Sun 3–6 PM & 10 PM–Midnight
Deals: $2 off draft beers and 19-25oz cans, $5 shots, $9 glasses of house wine, $11 signature drinks. Food specials include $3 oysters, $4.49 French fries, $5.99 cheeseburger slider hot dog, and more.
Vibe: A lively seafood bar known for its fresh offerings and extensive drink menu.
Why go: Dive into fresh seafood deals and a wide selection of discounted drinks, perfect for a relaxed evening in Willow Glen.
West San Jose
Yard House
Address: 925 Blossom Hill Rd, San Jose, CA 95123
Happy Hour: Mon–Fri 3–6 PM; Sun–Wed 10 PM–close
Deals: 50% off select appetizers and pizzas, $2 off beer, wine, spirits, and cocktails.
Vibe: A spacious and popular sports bar with an enormous selection of draft beers and a lively atmosphere.
Why go: With a vast beer selection and half-price food, it’s an excellent choice for casual gatherings and catching a game after work.
| Venue | Days | Hours | Best Deal | Neighbourhood |
|---|---|---|---|---|
| Five Points | Mon–Fri | 4–7 PM | $12 select cocktails | Downtown San Jose |
| O’Flaherty’s Irish Pub | Mon–Fri | 4–7 PM | $7 beer, Jameson, well spirits | Downtown San Jose |
| The Continental Bar | Daily | 3–7 PM | Great food and drink specials | Downtown San Jose |
| The Pressroom | Daily | 3–5 PM | 50% off cocktails, wine, $7 drafts | Downtown San Jose |
| Dr. Funk | Daily | Until 7 PM | $12 hand-crafted drinks | Downtown San Jose |
| Meso Modern Mediterranean | Mon–Fri | 3–6 PM | Snacks under $10, $8 wine | Downtown San Jose |
| Olla Cocina | Daily | 3–6 PM | Half-price carafes/pitchers, $5 tacos | Downtown San Jose |
| District Bar | Daily | 5–6 PM | Two-for-one oysters, $7 drafts | Downtown San Jose |
| San Pedro Social | Mon–Fri | 3–6 PM | $15 slice + pint combo | Downtown San Jose |
| The Old Wagon Saloon & Grill | Daily | 3–7 PM | $4 pints, $5 well drinks | Downtown San Jose |
| LB Steak | Sun–Fri | 3–5 PM | $1.5 raw oysters, $6 rotating beer | Santana Row |
| The Table | Mon–Tues | 4–5:30 PM | $22 burger + beer + shot combo | Willow Glen |
| Blue Water Seafood & Crab Bar | Mon–Sun | 3–6 PM & 10 PM–Midnight | $2 off drafts, $3 oysters | Willow Glen |
| Yard House | Mon–Fri | 3–6 PM | 50% off select appetizers/pizzas | West San Jose |
🎁 Best Deals & Offers in San Jose, CA This Week
🍽️ Dining Deals
While many excellent dining deals are part of happy hour specials (see above for venues like The Table and Olla Cocina), specific prix-fixe meals or BOGO offers outside of these times for this week were not prominently found.
🍸 Drink Specials
Five Points — Cocktail & Wine Specials
Address: 169 W Santa Clara St, San Jose, CA 95113
Deal: $9 select cocktails, drafts, and mocktails, plus 20% off all starters and wine until 9 PM.
Availability: Thursday–Saturday 6:30–9 PM. ⏰ This week only (Thursday, May 7th is included)
Vibe: A chic cocktail bar with an old-school New York charm, perfect for a sophisticated night out.
Why go: Enjoy premium cocktails and wines at a significant discount, making it an ideal spot for a mid-week or weekend gathering.
🎭 Entertainment Offers
O’Flaherty’s Irish Pub — Trivia Night
Address: 25 N San Pedro St, San Jose, CA 95110
Deal: Engage in a fun night of trivia.
Availability: Every Wednesday 8–10 PM. ⏰ This week only (Wednesday, May 6th is included)
Vibe: A lively and authentic Irish pub atmosphere, perfect for a casual and competitive night with friends.
Why go: Test your knowledge and enjoy a classic pub experience with friends over discounted drinks and bites.
MINIBOSS — Free Arcade Games
Address: 52 E Santa Clara St, San Jose, CA 95113
Deal: All arcade games are free to play.
Availability: Thursdays (during happy hour, Tue-Sun 5–7 PM). ⏰ This week only (Thursday, May 7th is included)
Vibe: A vibrant arcade bar combining classic games with a relaxed, social atmosphere.
Why go: Relive your childhood or challenge friends to classic arcade games without spending a dime on tokens this Thursday.
📱 Loyalty & App Deals
No specific loyalty programs or app-exclusive deals for San Jose venues were found in current searches for this week.
🎉 Events & Parties in San Jose, CA — May 2026
📅 Tonight & Tomorrow
Karaoke Night at O’Flaherty’s Irish Pub
Date & Time: Monday, May 4, 2026 & Tuesday, May 5, 2026, 9 PM–close
Venue: O’Flaherty’s Irish Pub, 25 N San Pedro St, San Jose, CA 95110
Tickets: Free
Don’t miss: Sing your heart out or enjoy the performances in a friendly and energetic Irish pub setting.
Live Irish Seisiún at O’Flaherty’s Irish Pub
Date & Time: Tuesday, May 5, 2026, 6:30 PM
Venue: O’Flaherty’s Irish Pub, 25 N San Pedro St, San Jose, CA 95110
Tickets: Free
Don’t miss: Experience the lively spirit of traditional Irish music, San Jose’s only up-tempo live music in the Irish tradition.
📆 This Weekend
The Bay ❤️’s R & B
Date & Time: Saturday, May 9, 2026, 1:30 PM–8:30 PM
Venue: Plaza De Cesar Chavez, 194 S Market St, San Jose, CA
Tickets: Check website for ticket price
Don’t miss: Groove to smooth R&B tunes spun by hot DJs in a lively outdoor setting, perfect for dancing and good vibes.
🗓️ Coming Up This Month
Cielo Rooftop Wine Bar Seasonal Opening Soirée
Date & Time: Wednesday, May 14, 2026, 5:30 PM–8:30 PM
Venue: Hotel Valencia Santana Row, 355 Santana Row, San Jose, CA 95128
Tickets: Tickets required
Don’t miss: Celebrate the seasonal opening of this intimate rooftop wine bar with stunning views of the Santa Cruz Mountains.
San Jose Memorial Day Weekend Bar Crawl 2026
Date & Time: Saturday, May 23, 2026, starts 4 PM
Venue: Starting point: The Old Wagon Saloon & Grill, 73 N San Pedro St, San Jose, CA 95110
Tickets: Tickets required
Don’t miss: Kick off Memorial Day Weekend and the start of summer by exploring San Jose’s top bars with exclusive drink specials.
🆓 Free Events
Karaoke Night at O’Flaherty’s Irish Pub
Date & Time: Every Sunday & Monday, 9 PM–close (including May 4th & 5th)
Venue: O’Flaherty’s Irish Pub, 25 N San Pedro St, San Jose, CA 95110
Tickets: Free
Don’t miss: A chance to showcase your vocal talents or enjoy the free entertainment in a classic pub environment.
Live Irish Seisiún at O’Flaherty’s Irish Pub
Date & Time: Every Tuesday, 6:30 PM (including May 5th)
Venue: O’Flaherty’s Irish Pub, 25 N San Pedro St, San Jose, CA 95110
Tickets: Free
Don’t miss: Immerse yourself in the authentic sounds of live Irish traditional music without a cover charge.
| Event | Date | Venue | Ticket Price |
|---|---|---|---|
| Karaoke Night | Mon, May 4 & Tue, May 5 | O’Flaherty’s Irish Pub | Free |
| Live Irish Seisiún | Tue, May 5 | O’Flaherty’s Irish Pub | Free |
| The Bay ❤️’s R & B | Sat, May 9 | Plaza De Cesar Chavez | Check website |
| Cielo Rooftop Wine Bar Seasonal Opening Soirée | Wed, May 14 | Hotel Valencia Santana Row | Tickets required |
| San Jose Memorial Day Weekend Bar Crawl | Sat, May 23 | The Old Wagon Saloon & Grill (starting) | Tickets required |
❓ Frequently Asked Questions — San Jose, CA Happy Hours & Nightlife
Q: What time does happy hour start in San Jose?
Happy hour times in San Jose commonly begin between 3 PM and 4 PM. For example, Yard House starts its happy hour at 3 PM from Monday to Friday, and The Continental Bar offers daily happy hour starting at 3 PM.
Q: Which San Jose bars have the cheapest drinks?
For some of the cheapest drinks, check out The Old Wagon Saloon & Grill in Downtown San Jose, offering $4 pints and $5 well drinks during their daily happy hour. O’Flaherty’s Irish Pub is another great option with $7 beers, Jameson, and well spirits during their weekday happy hour.
Q: What are the best neighbourhoods for nightlife in San Jose?
Downtown San Jose, including the SOFA District and San Pedro Square, is a vibrant hub for nightlife, home to popular cocktail bars like Five Points and O’Flaherty’s Irish Pub. Santana Row also offers a sophisticated evening experience with venues like LB Steak and Cielo Rooftop Wine Bar.
Q: Are there free events in San Jose this month?
Yes, O’Flaherty’s Irish Pub hosts free Karaoke Nights every Sunday and Monday, and a Live Irish Seisiún every Tuesday. Additionally, MINIBOSS offers free arcade games every Thursday.
Q: What are the best rooftop bars in San Jose?
Cielo Rooftop Wine Bar at Hotel Valencia Santana Row offers stunning views of the Santa Cruz Mountains and an intimate seasonal wine bar experience. The Loft Bar & Bistro in Downtown San Jose also features a beautiful rooftop garden patio, open for public enjoyment on Thursday, Friday, and Saturday nights.
