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Zachary's Chicago Pizza
Master Critic Reviews (3 Lists)
Zachary's Chicago Pizza
8.8
Employee-owned since 1983, this East Bay institution brings authentic Chicago-style stuffed pizzas to downtown Pleasanton with over 225 best pizza awards. Their signature spinach and mushroom stuffed pizza features layers of cheese and toppings between two crusts, plus they offer excellent thin-crust options.
Must-Try Dishes:
Spinach & Mushroom Stuffed, Zachary Special, Mediterranean Pizza
Scores:
Value: 7.8
Service: 8.3
Consistency: 9
Food Quality: 9.2
Atmosphere: 8.5
Cultural Relevance: 9.3
What makes it special: Authentic Chicago-style stuffed pizzas with California twist
Who should go: Deep-dish lovers and groups celebrating
When to visit: Happy hour weekdays 3-5:30pm for deals
What to order: Stuffed spinach mushroom, craft cocktails, Caesar salad
Insider tip: Call 45 minutes ahead - stuffed pizzas take time to bake
Logistics & Planning
Parking: Street parking on Main St fills up evenings/weekends, public garage 2 blocks away free first 2 hours
Dress code: Casual to smart casual - anything from jeans to business attire fits in
Noise level: Lively buzz but conversation-friendly, patio quieter than inside
Weekend wait: 30-45 min without reservation, 60+ during peak summer
Weekday lunch: Usually seated immediately, 10-15 min during lunch rush
Dietary Options
Vegetarian options: Yes - extensive options including signature spinach & mushroom stuffed
Vegan options: Yes - vegan cheese available for thin crust only, not stuffed pizzas
Gluten-free options: Yes - 10" gluten-free crust available, prepared separately
Good to Know
Is this good for a first date? Perfect - upscale casual vibe, full bar for cocktails, and the patio offers intimate seating. Sharing a stuffed pizza is a fun icebreaker.
Can I get a table without a reservation? Weeknights usually yes with 20-30 min wait. Weekend dinners are tough - reserve or try the bar seating.
Is it kid-friendly? Yes - kids love watching the stuffed pizzas arrive, high chairs available, and staff are accommodating. Best before 7pm when it gets louder.
Best For
Better for: Authentic Chicago deep-dish experience with craft cocktails and patio ambiance - no other local spot matches their stuffed pizza expertise
Skip if: You're in a rush (45+ min cook time) or want cheap eats - try New York Pizza for quick slices instead
Zachary's Chicago Pizza
7.9
Known for deep-dish, but the weekday happy hour adds a sleeper wing deal that’s perfect with a pint. Small-bites pricing makes it easy to stack wings with a slice or salad.
Must-Try Dishes:
Buffalo Wings (HH small-bites), Zachary’s Meatballs, Stuffed Spinach & Mushroom Slice
Scores:
Value: 8.4
Service: 7.9
Consistency: 8.3
Food Quality: 8.2
Atmosphere: 7.6
Cultural Relevance: 8.1
What makes it special: Weekday HH features discounted wings alongside drink specials.
Who should go: Wing fans who also want pizza
When to visit: Weekdays 3–5:30pm for HH pricing
What to order: Buffalo wings, meatballs, house cocktail
Insider tip: Sit at the bar for faster HH service and easy refills.
Logistics & Planning
Parking: Free 2-hour street parking on Main and adjacent side streets; small downtown lot behind the building fills by 6pm.
Dress code: Casual—jeans, tees, and sneakers fit right in; after-work bargoers may skew business casual.
Noise level: Moderate to lively; bar area buzzes during happy hour, but booths allow normal conversation.
Weekend wait: 30–45 minutes typical wait; call-ahead recommended for groups.
Weekday lunch: Usually no wait before noon; quick seating at bar or patio.
Dietary Options
Vegetarian options: Yes—deep-dish veggie pies, salads, and garlic bread are solid picks.
Vegan options: Limited—can customize thin crust with no cheese and extra veggies.
Gluten-free options: Yes—thin crust gluten-free option available; separate bake surface used.
Good to Know
Is this good for a first date? Yes, if you’re after a relaxed, casual start—share wings and deep-dish while watching the game or chatting at the bar.
Can I get a table without a reservation? Most days yes—walk-ins are fine before 6pm, especially on weekdays. Peak weekends can mean a short wait.
Is it kid-friendly? Yes—high chairs, crayons, and a pizza-focused menu make it easy for families; avoid bar area during peak happy hour.
Best For
Better for: Ideal when you want hearty wings and pizza in one spot with dependable happy-hour pricing and downtown energy.
Skip if: You’re seeking a quiet dinner, upscale cocktails, or health-forward plates—go to Sabio on Main or Lokanta instead.
Zachary's Chicago Pizza
8.6
Employee-owned Bay Area staple known for Chicago-style stuffed pies and a crisp thin crust. Families come for shareable pizzas, reliable pacing, and kid-friendly service right on Main Street.
Must-Try Dishes:
Stuffed Spinach & Mushroom, Zachary's Special (sausage, onions, mushrooms, green pepper), Thin-Crust Pepperoni (weekday lunch slice)
Scores:
Value: 8
Service: 8.2
Consistency: 9.1
Food Quality: 9
Atmosphere: 7.9
Cultural Relevance: 8.8
What makes it special: Bay Area–famous stuffed pies from a 100% employee-owned pizzeria.
Who should go: Families who like shareable deep-dish
When to visit: Early dinner 5–6pm to avoid waits
What to order: Stuffed Spinach & Mushroom, Zachary’s Special, Caesar
Insider tip: Half-baked stuffed pies travel well for at-home finishing.
Logistics & Planning
Parking: Free two-hour street parking along Main Street and nearby side streets; public lots within a one-block walk near the Firehouse Arts Center.
Dress code: Casual and family-friendly—jeans, tees, and weekend wear are the norm.
Noise level: Moderate to lively during dinner; can easily hold a family conversation but expect buzz from full tables.
Weekend wait: 30–50 minutes without a reservation during peak 6–8pm hours.
Weekday lunch: Usually immediate seating or under 10-minute wait.
Dietary Options
Vegetarian options: Yes – several signature stuffed and thin-crust pizzas are fully vegetarian, like Spinach & Mushroom or Super Veggie.
Vegan options: Limited – vegan cheese available on request, but toppings list is modest.
Gluten-free options: Yes – gluten-free thin crust offered, though shared ovens mean possible cross-contact.
Good to Know
Is this good for a first date? It’s better for a relaxed, casual date than a formal one—shared deep-dish pizza and beer make it fun and low-pressure.
Can I get a table without a reservation? Yes, they don’t require reservations. Walk-ins are common, but go before 6pm on weekends to avoid long waits.
Is it kid-friendly? Very—staff are used to families, offer booster seats, crayons, and small plates for sharing deep-dish slices. Best for ages 3+ given portion sizes.
Best For
Better for: Chicago-style stuffed pies and crisp thin crust that feel handmade and hearty—few others in the East Bay match its authenticity.
Skip if: You want quick individual slices or New York–style thin pizza; this is a sit-down, share-a-pie experience.