Sommelier Showdown: Chicago
Sommelier Showdown comes to Chicago. Celebrate the art of food & wine pairing, through the lens of some of the industries finest wine professionals.
THE EVENT: Two leading Sommeliers compete to pair the perfect wine with each course at a decadent 4-course dinner. You vote to pick the winner, who proceeds to the final showdown.
WHERE: S.K.Y. Restaurant, 2300 N Lincoln Park W, Chicago, Illinois
THE DINNER: Reception with amuse bouche, 4-course dinner, and 9 beautiful wines.
WHEN: Round 1 – October 21, Round 2 – November 18, The Final Showdown – December 9, 2026
$250 per person plus tax and gratuity
THE SHOWDOWN
The sommelier’s mission is to pair the perfect wine with each of the 4 courses designed by S.K.Y.’s Chef Stephen Gillanders. Your mission is to be the judge. Using your smartphone you will vote for whichever wine you felt paired best with the dish. The votes will be tallied, culminating in a winner. The winning Sommelier from each of the first two dinners will proceed to the showdown on December 9, 2026, where the final winner will be crowned.
THE DINNER
At 6 pm we begin with a reception of bubbly and amuse bouche. The 4-course dinner will begin at 6.30 p.m. with introductions to each Sommelier and the Chef. S.K.Y. is one of the finest restaurants in Chicago. Come and meet other food and wine lovers at this exceptional celebration of food and wine. There is a different menu at each of the dinners.
YOU VOTE
A smart device/tablet will circulate the room, providing you with the opportunity to discretely cast your vote for each of you favourite pairings. Votes are tallied electronically and the results revealed after each course, culminating in a winner.
Chicago Dates
Chicago
November 18, 2026
$250 per person plus taxes and gratuities
ABOUT SOMMELIER SHOWDOWN
The Venue
S.K.Y.
Welcome to SKY — Chicago’s elevated destination for contemporary fine dining. Blending classic culinary technique with a modern, seasonal sensibility, SKY showcases locally sourced ingredients, a carefully curated wine list, and polished, attentive service in a sleek, sky‑high setting.
The Food
The night begins with a pre-dinner reception, with sparkling wine and amuse bouche. A 4-course dinner is then served showcasing the Chef’s talents. We cannot accommodate allergies because everyone needs to taste the exact same food and wine for the votes to be fair.
The Wine
You will enjoy 9 different wines during the evening. There are two different wines served blind with each course, wine A and B. You pick and vote for your favourite. The wines are revealed after each course and the Sommelier who picked the winning wine explains their choice.
The Format
At 6 pm we begin with a reception of bubbly and amuse bouche. At 6.30 pm you will be seated and the MC will introduce the event and the two competing Sommeliers. With each course two wines are served blind. Simply pick the wine that paired best with the dish and vote. Then all will be revealed!
The Finale
At the final event on December 9th 2026 the winners of the first two events will compete for the crown in the grand finale of the Sommelier Showdown Chicago.
TERMS AND CONDITIONS
All sales are final and non-refundable but you can transfer your booking to someone else for free. Just give us the new names for our reservation list. We cannot accommodate allergies as everyone needs to taste the exact same food and wine for the votes to be fair.
Chicago
November 18, 2026
$250 per person plus taxes and gratuities
