A date plan
Date · Prospect Heights · Fun & Playful
Start with cocktails and fun at a top-rated bar, move to an intimate dinner in the neighborhood's foodie heart, and finish with late-night ice cream—the perfect recipe for a flirty, unforgettable evening.
Prospect Heights · $$ · Cocktail bar · Bar
This intimate cocktail bar is where Prospect Heights' cool factor peaks. Expert mixologists craft complex drinks in a cozy, candlelit space that practically begs you to lean across the bar and chat. The vibe is sophisticated but never stuffy—perfect for setting a playful, romantic tone.
~5 min walk (0.2 mi). After cocktails, head south on Fulton St—the neighborhood gets quieter and more intimate as you move toward Vanderbilt Ave. You'll pass Prospect Heights' charming brownstones and feel the shift from bar energy to dinner energy.
Prospect Heights · $$$ · Italian restaurant
Seasonal Italian done right—think handmade pasta, wood-fired vegetables, and a wine list that actually makes sense. The dining room has that effortless warmth where romance happens naturally, and the kitchen's playfulness shows in every dish (hello, unexpected flavor combinations). Definitely snag a reservation.
~2 min walk (0.1 mi). Post-dinner, Ample Hills is just a few blocks away on Vanderbilt. Walk it off, enjoy the cooler evening air, and let your conversation naturally wind down over ice cream. The avenue is lovely at night.
Prospect Heights · $$ · Ice cream shop · Dessert restaurant
It's iconic for a reason—Ample Hills slings some of the city's best ice cream with flavor names that'll make you smile. Grab a cone (or share a sundae for maximum cuteness points) and stroll Vanderbilt Ave under the lights. The perfect low-key finish to a night that hit all the right notes.