Best Date Night Restaurants in Old Town
13 hand-picked restaurants, critic-reviewed and ranked
Last Updated: February 2026
Our Top Pick
Alinea
Two-Michelin-star modernist temple where dinner plays out like theater.
Essential Picks
#1
Alinea
9.1
Alinea is a Michelin-starred modernist dining room where Grant Achatz’s multi-course tasting menu turns dinner into an immersive, theatrical experience. Since 2005 it’s been Chicago’s most famous special-occasion restaurant, drawing couples for intricate courses like hot potato–cold potato and a choreographed, tableside dessert finale.
Must-Try Dishes:
Hot Potato–Cold Potato, Black Truffle, Parmesan, Black Truffle Explosion Ravioli, Tabletop Dessert Finale
What Makes it Special: Two-Michelin-star modernist temple where dinner plays out like theater.
Notable Picks
#2
Boka
8.8
Opened in 2003, Boka is a Michelin-starred, candlelit dining room where Chef Lee Wolen’s seasonal American cooking and a polished service team anchor one of Lincoln Park’s most reliable date-night experiences. Couples come for the combination of refined plates, deep wine list, and a room that feels celebratory without being stiff.
Must-Try Dishes:
Whole Roasted Dry Aged Duck, Dry Aged Beef Tartare, Duck Leg Ravioli
What Makes it Special: Michelin-starred neighborhood stalwart pairing seasonal tasting-style plates with warm polish.
#3
SHŌ
8.6
SHŌ is a modern Old Town omakase where chef Mari Katsumura runs a tightly edited 10-course menu that moves from sashimi to playful composed dishes and DIY hand rolls. The counter-only format, music-forward room, and focus on seasonal Japanese technique with global twists make it one of the most ambitious sushi experiences in 60610.
Must-Try Dishes:
Corn cream croquette with jalapeño and yuzu, Sukiyaki-inspired wagyu hand roll, Tonkotsu ramen with Iberico ham
What Makes it Special: Music-driven omakase that blends serious technique with interactive, DIY hand rolls.
#4
Gavroche
8.4
A compact Old Town dining room built around modern French cooking that leans playful without losing technique. It’s best when you order the menu’s bistro-to-chef’s-counter hybrids—salads and seafood that read classic, but land with sharper plating and richer sauces.
Must-Try Dishes:
Lyonnaise salad, Hamachi niçoise, Foie gras duo
What Makes it Special: Modern French cooking in a small Old Town room that feels chef-driven.
8.3
Chicago’s original sushi bar, Kamehachi has anchored Old Town since 1967 with a sprawling menu of maki, nigiri, hot appetizers, and combo platters. It’s less about avant-garde omakase and more about reliable rolls, bento-style meals, and a neighborhood crowd that spans families, regulars, and pre-Second City dinners.
Must-Try Dishes:
Crouching Tuna Hidden Crab roll, Spicy Tuna Deluxe roll, Kamehachi Combo
What Makes it Special: Long-running Old Town institution where generations of Chicagoans had their first sushi.
8.2
Topo Gigio is an Old Town standby where a sprawling menu of classic pastas and red-sauce plates is backed by a busy dining room and brick-walled patio. It’s the move for group dinners and lively dates that prioritize big portions and familiar flavors over hushed conversation.
Must-Try Dishes:
Fusilli alla Topo Gigio, Conchiglie alla Sarda, Tortellini alla Panna
What Makes it Special: High-energy Old Town classic with a deep pasta menu and busy patio.
8.2
A compact Old Town room with a buzzy soundtrack and a Peru-meets-Nikkei menu that’s strongest in bright, citrus-forward lanes. Build your meal around one ceviche, one hot wok or skewer dish, and one rich rice plate to keep the pacing clean.
Must-Try Dishes:
Ceviche, Lomo saltado, Smoked duck breast rice
What Makes it Special: Peruvian-Japanese flavors in a small, high-energy room.
8.2
An Old Town Neapolitan-leaning spot where the pizzas read more chef-driven than basic, with a menu that invites a couple of shared plates alongside your pie. The best experience comes from ordering one signature pizza and one starter, then letting the table pace itself.
Must-Try Dishes:
Margherita, Tartufata, Pistachio Pesto
What Makes it Special: Neapolitan-leaning pizzas with a more chef-driven topping play than average.
Gussie's Handmade Italian focuses on fresh pastas, seasonal sauces, and cocktails in a modern Old Town space just off North and Wells. It fills a niche between neighborhood trattoria and special-occasion spot, with enough polish for dates but a menu flexible enough for casual plates at the bar.
Must-Try Dishes:
Rigatoni Pomodoro, Brown Butter Honey Ravioli, Linguine al Limone with Shrimp
What Makes it Special: Handmade pasta and seasonal seafood plates served with a cocktail-focused bar program.
#10
Nepal House
8
The Old Town outpost of Nepal House brings a sit-down menu of Nepali momos, curries, and familiar North Indian staples to Division Street. It works as a reliable option when a proper table, full plates, and a mix of vegetarian and meat dishes are the priority.
Must-Try Dishes:
Chicken Momo, Chicken Tikka Masala, Garlic Naan
What Makes it Special: Nepali momos share the menu with classic Indian curries in a full-service setting.
Worthy Picks
#11
Orso's
7.9
Orso's Italian Restaurant has served Old Town for decades with a long menu of pastas, chicken dishes, and pizzas in a classic dining room and grapevine-covered patio. Regulars lean on familiar standards and relaxed, slightly nostalgic energy more than chef-driven reinvention.
Must-Try Dishes:
Lasagna Bolognese, Chicken Parmesan, Salmon Vesuvio
What Makes it Special: Long-running Old Town stalwart with a leafy patio and crowd-pleasing classics.
#12
The Glunz Tavern
7.8
An Old Town tavern with serious history and a smaller, more intimate feel than the neighborhood’s bigger sports bars. It’s best as a snacks-and-drinks destination where the comfort menu supports the main event: lingering over beer, wine, and conversation.
Must-Try Dishes:
Potato pancakes, Schnitzel sandwich, Chicken fritters
What Makes it Special: Historic Old Town tavern energy with a focused food-and-drink program.
7.7
Hom Mali Thai Sushi is a newer Old Town spot pairing classic Thai curries and noodles with a compact sushi menu in a polished, relaxed dining room. Locals use it as a weeknight standby when a table of pad thai, curry, and a few maki rolls sounds better than committing to a full omakase.
Must-Try Dishes:
Pad Thai, Green curry with vegetables, Spicy tuna roll
What Makes it Special: Thai dishes and approachable sushi share one room, making it easy for mixed cravings at one table.