Chicago cocktail fans will soon be able to sip award-winning drinks 46 floors above Michigan Avenue without a plane ticket to New York. Sip & Guzzle, the Greenwich Village bar recently crowned the best in North America, opens a five-month residency at Four Seasons Hotel Chicago's Mile High Cocktail Club starting October 15, running through March 14.
The residency lands at a notable moment for the bar. In April 2026, Sip & Guzzle was named No. 1 on the 2026 North America's 50 Best Bars list during an awards ceremony in Vancouver, a jump from its No. 5 debut ranking the year before, according to Time Out Worldwide. Sip & Guzzle placed No. 14 globally on the World's 50 Best Bars 2026 list, unveiled in Milan.
Sip & Guzzle first opened at 29 Cornelia Street in Manhattan's Greenwich Village in January 2024, founded by Tokyo-based bartender Shingo Gokan of The SG Club and veteran New York bartender Steve Schneider of Employees Only, per the seed report. The pair had previously worked together on The Odd Couple in Shanghai before launching the dual concept in Manhattan, according to The Spirits Business. Justin Weitz serves as the bar's operating partner, per the seed report.
A Tale of Two Bars, Transplanted to the Sky
The Manhattan original is built as a bi-level space with two distinct identities: an upstairs saloon called Guzzle, modeled after 1860s New York drinking halls and serving highballs and casual pours, and a subterranean speakeasy called Sip, inspired by the 1860 Japanese ship Kanrin Maru, according to Secret NYC. That split personality carries over conceptually in Chicago, where the bar blends Tokyo izakaya culture with classic New York hospitality, with Sip leaning on technique-driven mixology and Guzzle built around reimagined classic drinks, per the seed report.
The Chicago pop-up will pour both sides of that philosophy inside the Mile High Cocktail Club, a converted luxury hotel suite on the 46th floor of Four Seasons Hotel Chicago that operates as the city's highest speakeasy, seating just 30 guests, according to the Four Seasons Press Room. The suite offers panoramic views over Lake Michigan and the Magnificent Mile, and the seed report notes the residency will also showcase views of the Chicago skyline.
Following in Handshake Speakeasy's Footsteps
Sip & Guzzle isn't the first world-ranked bar to take over this particular suite. Before its arrival, Four Seasons Hotel Chicago hosted Mexico City's Handshake Speakeasy — ranked the World's No. 1 Bar in 2024 — for pop-up residencies at the Mile High Cocktail Club across 2024 and 2025, the hotel's press room notes. The hand-off reflects a deliberate strategy by the hotel to keep rotating globally recognized bar programs through its sky-high suite.
Chicago's own cocktail scene has plenty to be proud of, too. Four Chicago bars landed spots on the 2026 North America's 50 Best Bars list released in April, led by West Loop dining bar Kumiko at No. 11 — which also won the Michter's Art of Hospitality Award — alongside Best Intentions at No. 16, Gus' Sip & Dip at No. 27, and Bisous at No. 30, per Time Out's local coverage.
What's Being Poured, and What It Costs
The Chicago pop-up runs Thursday through Sunday from 5pm to 10pm, with tastings priced at $85 per person for two curated drinks from a rotating menu, according to the seed report. Executive chef Isaac Leidenfrost crafted a bar-bites menu specifically for the residency. Drinks on offer reportedly include the Drunk Grandma's Apple Pie, the Dirty Mango, the Tomato Tree, the Mint 75, and a Rum & Cola.
The residency also arrives alongside a broader overhaul of the hotel's food and beverage program. Four Seasons Hotel Chicago announced on October 7 a fall 2026 culinary refresh that includes an updated Chicago-inspired menu at Adorn Restaurant and the debut of Tasse, a new seventh-floor morning coffee lounge, according to the Four Seasons Press Room. The changes are part of a broader autumn dining revamp under General Manager Stephen Wancha, the hotel said.
A Bar on the Move
Chicago is just the latest stop for a team that has been testing its hospitality model well beyond Greenwich Village. In late August, Sip & Guzzle ran a short-term pop-up on the rooftop of The Vanderbilt hotel in Newport, Rhode Island, bringing its Manhattan cocktail program to the New England coast, according to What's Up Newp.
Back home, the bar's leadership is also expanding on its own turf. Weitz is planning a new restaurant, per the Village Reader. Gramercy Tavern has also hosted a bar-takeover series.
