The Best Bars in Near North Side & Loop

1. VinePair Food & Beverage Program of the Year · The Next Wave Awards
2. The Pinnacle Guide 1 Pin
3. The 50 #27 · North America's 50 Best Bars

You find this tiki bar by following strangers down a narrow alley off Clark Street, which is either a great sign or a terrible one depending on your instincts. A staircase descends under a wall of skulls into a big, dim basement decked out in modern tiki grandeur. The drinks are serious and the room knows it. Difford's Guide gives it five stars, and the wait on weekends is its own kind of endorsement.

1. Difford's Guide 5 stars · Difford's Guide
2. The Infatuation The Best Cocktail Bars In Chicago
3. The 50 The 50 Discovery

1. Esquire Martini · The Best Martinis in America

The Art Deco bones of this Gold Coast lobby bar date back to the Jazz Age, and the cocktail program leans into that: Cuban classics and Caribbean-inflected originals served under ornate ceilings that most bars would kill for. Sparrow calls itself a neighborhood bar, which is technically true, though the neighbors here wear better shoes than most. A named honoree at the Spirited Awards, it draws people in from well outside the Gold Coast.

1. The Infatuation The Best Cocktail Bars In Chicago
2. The 50 The 50 Discovery
3. Spirited Awards 2024 · Regional Honoree · Best U.S. Cocktail Bar – U.S. Central

1. Spirited Awards 2025 · Regional Top 10 Honoree · Best U.S. Hotel Bar – U.S. Central
2. Spirited Awards 2024 · Regional Honoree · Best U.S. Hotel Bar – U.S. Central
3. Spirited Awards 2023 · Regional Honoree · Best U.S. Hotel Bar – U.S. Central

1. The 50 The 50 Discovery
2. Spirited Awards 2026 · Regional Top 10 Honoree · Best U.S. Cocktail Bar – U.S. Central
3. Spirited Awards 2023 · Regional Honoree · Best U.S. Bar Team – U.S. Central

Cindy's is a rooftop cocktail bar on top of the Chicago Athletic Association, with a terrace looking over Millennium Park and Lake Michigan. It's a hotel bar, so expect dressed-up visitors, bachelorette sashes, and relatives in town, plus plates meant for three or four people to share. Regional Top 10 for hotel bars at the Spirited Awards, which is one more reason the terrace fills up first.

1. The Infatuation The 14 Best Restaurants In The Loop
2. Spirited Awards 2025 · Regional Top 10 Honoree · Best U.S. Hotel Bar – U.S. Central

1. Spirited Awards 2026 · Regional Top 10 Honoree · Best New U.S. Cocktail Bar – U.S. Central

1. AAA Four Diamonds
2. The Banchets Winner · Best Design
3. The Banchets Nominee · Sommelier of the Year · Kat Hawkins

1. Food & Wine The Top 10 Hotel Bars in the US

The cocktail menu runs 32 pages and opens with a table of contents, which tells you everything about how seriously this hotel bar takes its work. Originals are sorted by style; classics are filed by decade. The room holds up in daylight just as well as it does after dark, which isn't something most hotel bars can say without lying. Bring someone who likes to read before they order.

1. Difford's Guide 4.5 stars · Difford's Guide

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

Zarella is a River North tavern-style pizzeria run by the Boka group, which means the thin, cornmeal-dusted pies come with a cocktail menu and a downstairs speakeasy lounge. Two well-known Chicago chefs developed the crusts, and the toppings include mortadella and all-beef pepperoni, so expect River North prices for what is, technically, bar pizza. Eater has named it among the city's best tavern-style pizza spots.

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants
2. Eater The Best Restaurants in River North

1. Difford's Guide 4 stars · Difford's Guide

1. Difford's Guide 4 stars · Difford's Guide

A self-described "continental tavern" that reads more like an oversized gastropub once you're inside, Hubbard Inn is a big, convivial bar in River North with a serious beer program: around twenty draught handles and nearly as many cans and bottles, skewing craft. If you came for Miller Lite, it's on the menu too, quietly listed at the bottom of the beer page, which is a very polite way to handle the situation.

1. Difford's Guide 4 stars · Difford's Guide

You ride a repurposed service elevator to reach this speakeasy-inspired rooftop cocktail bar perched atop the Rafaello Hotel. Dim lighting, dark wood, bronze fixtures, and mushroom-toned walls set a moody, upscale tone, and a resident DJ keeps the energy pointed firmly toward party. The crowd skews young and loud, so if you're after a quiet drink and a view, the elevator goes both ways.

1. Difford's Guide 3.5 stars · Difford's Guide