A date plan
Date · Prospect Heights · Romantic
A slow, indulgent evening in the heart of Prospect Heights — starting with Prohibition-era cocktails, moving into rustic Italian by candlelight, and landing somewhere wine-forward and intimate for a nightcap dessert.
Prospect Heights · $$ · Cocktail bar
Weather Up is the kind of bar that makes you feel like you have a secret. Tucked along Vanderbilt Ave, this Prohibition-style den does craft cocktails with serious intention — think perfectly balanced Old Fashioneds and bar snacks that are way too good for how casually they're presented. Slide into a seat at the dark wood bar and let the bartender set the tone for the night.
~5 min walk (0.2 mi). From Weather Up, head south on Vanderbilt Ave toward Fulton St — it's a lively stretch on most nights, so take your time and window shop. The neighborhood has a good energy after dark.
Prospect Heights · $$ · Italian restaurant · Bar
Belli Ristorante is candlelit in the best possible way — not performatively romantic, just genuinely warm and a little moody. The homemade pastas are the move here, rich and restrained in the way only Italian food done right can be. It's the kind of place where you order one more glass of wine because neither of you wants the night to end.
~5 min walk (0.3 mi). Belli is over on Fulton St, which puts you a few blocks west of the Vanderbilt Ave corridor — worth noting you're drifting slightly from the epicenter of Prospect Heights, but it still counts as the neighborhood. After dinner, make your way back up toward Vanderbilt for dessert at The Vaux Social.
Prospect Heights · $$$ · Wine bar · American restaurant
The Vaux Social is the perfect place to linger — a wine bar with an American sensibility and just the right amount of low lighting to make everything feel like it's going well. Pull up a couple of seats, order a glass of something interesting, and let dessert be the excuse to stay out a little longer. It's a nightcap wrapped in good taste.