The 100 Best Places to Drink and Do in Chicago

Julia Momosé's Japanese-inspired dining bar on West Lake holds a James Beard Award for Outstanding Bar and the Spirited Awards title for World's Best Bar, which tells you something before you've even sat down. Staff in sharp black uniforms somehow manage to feel genuinely warm rather than stiff, and the tasting menu now matches the cocktail program's precision, leaning into Japanese flavors and technique. Come for the drinks, stay through dinner, and plan to linger longer than you intended.

1. The Pinnacle Guide 3 Pins
2. Spirited Awards 2025 · Winner · World’s Best Bar
3. James Beard Awards 2025 · Winner · Outstanding Bar

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

1. The 50 #16 · North America's 50 Best Bars
2. Spirited Awards 2025 · Top 4 Finalist · Best U.S. Bar Team
3. Spirited Awards 2025 · Top 4 Finalist · Best U.S. Cocktail Bar

1. Bon Appétit America's Best New Bars
2. The 50 #76 · North America's 50 Best Bars
3. Esquire The Best Bars in America

Velvet booths, globe lights, and wallpaper that belongs in a Left Bank salon set the mood at this Fulton Market cocktail bar, one of the few standalone drinking spots on a street that is otherwise all restaurants. The Paris-in-the-sixties premise runs through everything: French wines, classic martinis, caviar with chips. Named to North America's 50 Best Bars and a James Beard semifinalist, Bisous earns its kisses.

1. The 50 #30 · North America's 50 Best Bars
2. Esquire The Best Bars in America
3. The Banchets Winner · Bar of the Year

1. Forbes Travel Guide Forbes Five Star

1. The 50 #65 · North America's 50 Best Bars
2. Esquire The Best Bars in America
3. The Infatuation The Best Cocktail Bars In Chicago

1. The 50 #80 · North America's 50 Best Bars
2. Esquire Martini Service · The Best Martinis in America
3. Esquire Market Price Martini · The Best Martinis in America

1. Forbes Travel Guide Forbes Four Star

1. Forbes Travel Guide Forbes Four Star

1. Forbes Travel Guide Forbes Four Star

1. Forbes Travel Guide Forbes Four Star

A mosaic-tiled lap pool and changing rooms lined with white stone set the Greek-inspired tone at this hotel spa on the fourth floor of the Waldorf Astoria. Massages and facials are the bread and butter, but the signature two-hour treatment layers a coffee-and-lemon scrub, a clay wrap, and a full-body massage into something that reads less like a spa menu and more like a Roman senator's afternoon. Forbes Four Star.

1. Forbes Travel Guide Forbes Four Star

Two buildings knocked into one give Scofflaw two distinct personalities: an industrial front room with the bar counter, and a Victorian-ish back room with wingback armchairs that somehow doesn't feel ironic. It's a gin-focused cocktail bar in Logan Square that also leans dive, with craft beer and pub grub to prove it. Expect a line on weekends; they don't take reservations, and forty minutes is a reasonable opening bid.

1. Difford's Guide 4.5 stars · Difford's Guide
2. Wildsam The 50 Most Essential Bars in America
3. The Infatuation The Best Cocktail Bars In Chicago

A pre-Prohibition corner tavern in Bridgeport where the chef behind it grew up, came back, and quietly made the Chicago dog the most labored thing on any bar menu in the city, built on housemade duck-fat sausage. The rotisserie duck arrives on a chopping block, the Italian beef uses prime rib shavings, and the whole room reads like fine-dining instincts filtered through a neighborhood tavern that never forgot what it was supposed to be.

1. The Banchets Nominee · Chef of the Year · Kevin Hickey
2. James Beard Awards 2024 · Semifinalist · Outstanding Restaurant
3. Eater Chicago’s Best Brunch Restaurants

The menu at this Bucktown coffee and cocktail bar is split in two: morning drinks for one crowd, evening drinks for another, with cold brew threading through both halves. The food runs from pizza bagels to caviar, which tells you something about the room's sense of humor. A James Beard semifinalist for Best New Bar in 2025, Truce has figured out that the best argument for staying all day is not having to change venues.

1. Eater Best New Bar
2. James Beard Awards 2025 · Semifinalist · Best New Bar
3. The 50 The 50 Discovery

The Txuletón, a Basque-style ribeye from mature dairy cows, grilled over open charcoal with salt, heat, and not much else, is the organizing principle of this Basque-inspired chophouse in River North. The kitchen takes its cues from the asador tradition, applying that discipline to seriously sourced beef, carefully aged. Spanish reds anchor the wine list. Esquire named it among the best new restaurants in America, and it lands at number 15 on the World's Best Steak Restaurants list.

1. World's 101 Best #15 · World's Best Steak Restaurants
2. Esquire Dirty Dirty · The Best Martinis in America
3. Esquire The Spanglish · The Best Martinis in America

1. Punch The Who’s Who of Beer Cool

1. The Infatuation The Best Cocktail Bars In Chicago
2. Eater Chicago’s Best Speakeasies and Secret Bars
3. Spirited Awards 2024 · Regional Honoree · Best U.S. Hotel Bar – U.S. Central

1. Esquire Dukes Hotel Martini · The Best Martinis in America

The checkered tile floors and art-lined stone walls make it look like a Parisian bistro that wandered into the West Loop and decided to stay. Creepies is a neighborhood French restaurant from the team behind Elske next door, with a concise menu that leans classic and slides Midwestern where it can. The vesper martini landed on Esquire's list of the best in the country, which is not nothing for a place called Creepies.

1. Esquire Vesper · The Best Martinis in America
2. The New York Times 2026 · The Restaurant List
3. Michelin Guide Selected Restaurant

1. Esquire The Best Bars in America

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. Wildsam The 50 Most Essential Bars in America

1. Esquire The Martini You Drink Before You Fly · The Best Martinis in America

1. Huckberry The 50 Best Dive Bars in America

1. Huckberry The 50 Best Dive Bars in America

1. Esquire The Best Bars in America

1. Esquire Martini · The Best Martinis in America

1. Esquire The Best Bars in America

1. The 50 One to Watch Award
2. Spirited Awards 2026 · Regional Top 10 Honoree · Best U.S. Cocktail Bar – U.S. Central
3. Spirited Awards 2025 · Regional Top 10 Honoree · Best U.S. Bar Team – U.S. Central

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. The Infatuation The Best Cocktail Bars In Chicago
2. Eater Chicago’s Best Speakeasies and Secret Bars

1. The Infatuation The Best Cocktail Bars In Chicago
2. Eater Chicago’s Best Speakeasies and Secret Bars

Taxidermy on the walls, an Art Deco bar, and big comfy booths: Sportsman's Club is a neighborhood tavern that looks like it's been on Western Ave forever but drinks like something that arrived much more recently. The rotating menu leans spirit-forward and serious, even if the vibe emphatically does not. It's the kind of place that made this particular Chicago formula feel worth copying.

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

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

1. The Banchets Nominee · Bar of the Year

The Beef & Liberty Bar is the second-floor cocktail room of a London steakhouse that took over a restored River North building, all barrel-vaulted ceilings and jewel-toned booths. It's known for sub-zero martinis served cold enough to count as a personality trait, plus a happy hour with Reuben nuggets. Expect dressed-up regulars and a bar program that landed a Top 10 Nominee spot for U.S. Bartender of the Year.

1. Spirited Awards 2026 · Top 10 Nominee · U.S. Bartender of the Year · Daddy Long Legs
2. Eater Chicago’s Best Steakhouses
3. Eater The Best Restaurants in River North

1. The 50 The 50 Discovery
2. Spirited Awards 2024 · Regional Honoree · Best U.S. Cocktail Bar – U.S. Central
3. Spirited Awards 2026 · Regional Top 10 Honoree · Best U.S. Bar Team – U.S. Central

Exposed brick, custom tile floors, and floor-to-ceiling wine storage fill what was once a 19th-century print shop, now a Michelin-starred fine dining room in the West Loop. Chef Andrew Zimmerman folds Southeast Asian, Korean, and Mediterranean instincts into American cooking without making it a thesis. Wine Enthusiast put the cellar in its Restaurant Hall of Fame, and the room's warm enough that you'd never know you were being impressed.

1. AAA Four Diamonds
2. Michelin Guide 1 Star
3. Difford's Guide 4.5 stars · Difford's Guide

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

1. The 50 The 50 Discovery

1. Spirited Awards 2026 · Regional Top 10 Honoree · Best New U.S. Cocktail Bar – 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 2025 · Regional Top 10 Honoree · Best New U.S. Cocktail Bar – U.S. Central

1. The 50 The 50 Discovery

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

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

1. Spirited Awards 2026 · Regional Top 10 Honoree · Best U.S. Restaurant 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. James Beard Awards 2026 · Semifinalist · Outstanding Bar

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

Pasta and vegetables carry most of the weight here, at this bright, sun-flooded Italian restaurant in Logan Square that holds a Michelin Bib Gourmand. The house-made pappardelle and rigatoni keep regulars coming back, but the onion dip with house-made ruffles has become a thing people talk about. A bakery tucked in the back means the pastry situation at the end of a meal is genuinely hard to navigate. The bar program turns heads too, a James Beard semifinalist for hospitality.

1. AAA Three Diamonds
2. Punch Best New Bartenders · Becca Petersen
3. Michelin Guide Bib Gourmand

1. Difford's Guide 5 stars · Difford's Guide

1. Spirited Awards 2024 · Regional Honoree · Best New U.S. Cocktail Bar – U.S. Central

The back bar holds what might be the most bewildering collection of vintage Italian Fernet you'll encounter outside of Milan. Billy Sunday is a polished amaro and cocktail bar in Logan Square, narrow and dark-wooded, with green walls and vintage lamps that suggest a gentlemen's club that loosened up considerably. The bar stools fill early with people who know their bitter spirits, and the classically built cocktails give them good reason to stay.

1. Difford's Guide 4.5 stars · Difford's Guide
2. The Infatuation The Best Cocktail Bars In Chicago
3. The 50 The 50 Discovery

1. The Infatuation The Best Cocktail Bars In Chicago

1. The Infatuation The Best Cocktail Bars In Chicago

1. James Beard Awards 2022 · Nominee · Outstanding Bar Program
2. The Infatuation The Best Cocktail Bars In Chicago
3. The 50 The 50 Discovery

Tucked into a historic greystone next door to Moreno's Liquors, a southside family institution, Osito's Tap is a neighborhood cocktail bar where the drinks lean hard into Latin American classics, agave spirits, and Micheladas done right. The connection to the liquor store isn't just sentimental; the spirits selection reflects it. Low-key enough that you might walk past it, specific enough that regulars don't want you to find it.

1. The Infatuation The Best Cocktail Bars In Chicago
2. The 50 The 50 Discovery

Parachute HiFi is a Korean listening bar from the Parachute team, built for people who'd rather hear a record than their own thoughts. Vinyl spins while the menu runs street-food mashups, like a burger drowned in Comté fondue and tteokbokki in a pad Thai situation, alongside cocktails. It's casual and dressy-ish in the way a good record collection is, and it takes reservations but still keeps room for walk-ins.

1. James Beard Awards 2022 · Nominee · Outstanding Restaurant
2. The Infatuation The Best Cocktail Bars In Chicago
3. Eater Chicago’s Best Korean Restaurants

1. Midwest Living 2023 · Best of the Midwest
2. Difford's Guide 3.5 stars · Difford's Guide
3. The Infatuation The Best Cocktail Bars In Chicago

1. The Infatuation The Best Cocktail Bars In Chicago

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

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

The ground floor runs dark wood and dim light, with a long bar and clandestine booths; upstairs it's velvet couches and armchairs, like someone's very well-stocked living room. This Lincoln Avenue cocktail bar leans into an old-time saloon feel without making it a costume, pulling sixty-plus classics-leaning drinks organized by spirit and style. The Harry Johnson-style etchings on the menu are either charming or insufferable, depending on your mood.

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

Bungalow is the Logan Square brewpub where the beer runs on wild yeast and the wine is made with as little intervention as the law allows. Tavern-style thin-crust pizza shows up on Tuesdays, cut in squares, but the toppings come from regional farms and the sauces wander off script. Order a pepperoni pie here and you'll feel like you've missed the point. The Beard folks named the beverage program a semifinalist in 2024.

1. The Banchets Nominee · Best Neighborhood Restaurant
2. Bon Appétit America's Best New Restaurants
3. James Beard Awards 2024 · Semifinalist · Outstanding Wine and Other Beverages Program

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants

1. Eater Chicago’s Best Speakeasies and Secret Bars

Dimmi Dimmi is a corner Italian spot in Lincoln Park that took over a three-decade neighborhood fixture and somehow kept the regulars from rioting. The tavern-style pizzas have crackly edges and come cut in squares, and the handmade pastas hold their own beside them. It's a sit-down dinner, so book ahead, or try your luck at a weekday lunch, which is when the people who know things tend to walk in.

1. Eater Lincoln Park’s Best Restaurants
2. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants
3. Eater Chicago’s Best Italian Restaurants

1. Eater Chicago’s Best Speakeasies and Secret Bars

Flo & Santos is a South Loop pub that can't pick a lane, so it picked three: tavern-style thin-crust pizza, Polish comfort food, and a beer garden with daily specials. Order the pie with kielbasa and sauerkraut and a pierogi sampler on the side, and your cardiologist will lose track of the subplots. Casual, reasonably priced, and equally happy to see you in a work shirt or a ballgame jersey.

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

This Edgewater pizza shop does deep-dish on a sourdough crust that borrows from a Greek bread called lagana, then turns around and makes cracker-thin tavern pies from the same dough. There's barely any seating and the oven is small, so most people order online and take it home, where an uncut pizza stays crunchy. Eater has put it on its lists for deep-dish, thin-crust, and best pizza overall.

1. Eater Chicago’s Best Pizza
2. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants
3. Eater Chicago’s Best Deep-Dish Pizza

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants

1. Eater Chicago’s Best Speakeasies and Secret Bars

This Pilsen pizza-and-coffee spot wears its owners' Filipino and Mexican roots on the crust, most memorably with longganisa and giardiniera together on a tavern-style pie. The menu includes pan pies and slices, plus coffee drinks from the people behind Side Practice, so you can have breakfast and dinner in one visit. It tends to sell out, which is the polite way of saying go early and bring a plan B.

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants
2. Eater Chicago’s Best Pizza

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants
2. Eater Chicago’s Best Pizza

1. Eater Chicago’s Best Pizza
2. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants

Pizz'amici is a tavern-style pizza shop in West Town, where the thin, cracker-crisp crust gets charred on the bottom and cut into squares. It's a nostalgic room with a pepperoni Negroni on the menu, plus tall focaccia and sausage and peppers for the old-school completists. Tables go quickly, so plan ahead or order carryout, which is easier than winning the lottery and only slightly less crowded.

1. The Infatuation #10 · The Top-Rated New Restaurants
2. Esquire The Best New Restaurants in America
3. Eater The 38 Best Restaurants in Chicago

Pizza Matta is a small Logan Square pizzeria from the team behind Giant and Chef's Special, which tells you the people running it have opinions about pie. You build your own 16-inch pizza from red, white, or green sauce, then pile on things like mortadella or caramelized pineapple, no judgment. Seating is limited, so order online and take the whole project home. Eater has it on its list of Chicago's tavern-style thin-crust spots.

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants

1. Eater Chicago’s Best Speakeasies and Secret Bars

Professor Pizza is a casual West Town pizzeria run by a competitive pizza maker, which means the pies come with a résumé. The tavern-style thin crust cuts to cracker-snap, and the deluxe pepperoni gets hot honey and whipped ricotta, as if the sausage needed a little more going on. The Grand Avenue spot adds two more pie styles, and the pizzas turn up backstage at comedy clubs around town. Eater includes it among Chicago's best tavern-style thin-crust spots.

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants

The bar is in the basement, which is the point. The Drifter is a tiny subterranean cocktail lounge tucked beneath the Green Door Tavern, a speakeasy in the old sense of the word, not just the aesthetic. Low ceilings, dim light, and the general feeling that you've wandered somewhere you weren't supposed to find. The kind of place where a well-made drink tastes better simply because you had to descend a staircase to get it.

1. Difford's Guide 4 stars · Difford's Guide
2. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

Villa Nova is a no-frills, family-run pizzeria in suburban Stickney, the kind of place where the pie arrives square-cut, the way thin-crust tavern pizza is supposed to. The sausage is fennel-forward and left in chunky, meatball-ish clumps, which is a bold choice for a topping and a good one. It's been around forever, so expect regulars who haven't looked at the menu in years. Eater included it among Chicago's best tavern-style thin-crust spots.

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants

1. Time Out #9 · The 25 best restaurants in Chicago
2. Eater Chicago’s Best Pizza
3. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants

1. Eater Chicago’s Best Speakeasies and Secret Bars

WG Pizzas is a Lakeview tavern-style pizzeria, a spin-off of an old suburban Highwood joint that has been feeding Lake County for ages. The crust is cut thin but keeps a few proud bubbles at the edges, so it lands chewier than the cracker-crisp stuff, closer to what South Side spots turn out. Order online, grab a BLT pie, and mind the monthly chef takeovers, which are a good excuse to pretend you planned ahead.

1. Eater Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants

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

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