✦ Dinner with Friends · Old Town

Best Dinner with Friends Restaurants in Old Town

5 ranked dinner with friends restaurants in Old Town, Chicago — with ratings, must-try dishes and live availability.

5 picks

These are the 5 best Old Town restaurants for a group dinner, ranked. Topo Gigio is the pick if you want the surest thing — 4.8 stars across 2,764 reviews. Most of this list stays under $40 a head. If you only order one thing, make it the conchiglie alla sarda at Topo Gigio. None of these take online reservations — they are walk-in or phone-only, so go early.

Old Town covers a lot of ground for its size — Italian, Breakfast and Pizza are all well represented across the 5 spots we track here, and the neighborhood averages 4.4 stars.

Topo Gigio Watch

Topo Gigio

Italian  ·  Old Town  ·  $$

★★★★½ 4.8

Italian in Old Town — 4.8 across 2,764 diner reviews

Must-try: Conchiglie Alla Sarda, Eggplant Parm

📍 1516 N Wells St, Chicago, IL 60610

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Cal's Corner Watch

Cal's Corner

Breakfast  ·  Old Town  ·  $$

★★★★½ 4.7

Breakfast in Old Town — 4.7 across 386 diner reviews

Must-try: Breakfast

📍 UNKNOWN

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Professor Pizza Watch

Professor Pizza

Pizza  ·  Old Town  ·  $

★★★★½ 4.6

Pizza in Old Town — 4.6 across 3,585 diner reviews

Must-try: NY-Style Pizza, White Pizza with Hot Honey

📍 1610 N Wells St, Chicago, IL 60614

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Kayao Watch

Kayao

Peruvian Nikkei  ·  Old Town  ·  $$

★★★★☆ 4.0

Peruvian Nikkei in Old Town — 4 across 1,557 diner reviews

Must-try: Yellowfin Tuna Tartare, Grilled Octopus, Chaufa

📍 1252 N Wells St, Chicago, IL 60610

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Twin Anchors Restaurant & Tavern Watch

Twin Anchors Restaurant & Tavern

BBQ ribs  ·  Old Town  ·  $$

★★★½☆ 3.9

BBQ ribs in Old Town — 3.9 across 3,626 diner reviews

Must-try: Ribs, BBQ Sauce

📍 1655 N Sedgwick St, Chicago, IL 60614

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Frequently Asked Questions

What is the best dinner with friends restaurant in Old Town?

Topo Gigio — 4.8 stars across 2,764 reviews, the highest on this list. Italian in Old Town — 4.8 across 2,764 diner reviews.

Do these restaurants take reservations?

None of the 5 on this page take online bookings — they are walk-in or phone-only. Going early, or on a weeknight, is the reliable move.

What should I order?

The conchiglie alla sarda at Topo Gigio, the breakfast at Cal's Corner and the ny-style pizza at Professor Pizza. Those are the dishes regulars point to first.

How were these picked?

Ratings and review volume decide the order, but the list itself is drawn from restaurants people actually post about — 5 of the 5 here have a TikTok attached to their card. Every entry is checked as open before it ships.

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