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

October 21, 2026


$250 per person plus taxes and gratuities

Buy Tickets

About the sommeliers

Chicago

November 18, 2026


$250 per person plus taxes and gratuities

Buy Tickets

About the sommeliers

Chicago

December 9, 2026


$250 per person plus taxes and gratuities

Buy Tickets

About the sommeliers

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.

 

MEET YOUR sommeliers

Our Sommelier Showdowns feature some of the top sommeliers in Chicago. The sommeliers will be announced this summer.

Jelena Prodan

CHICAGO

JELENA PRODAN


Beverage and Service Director

MEET JELENA

Born and raised in Belgrade, Serbia, Jelena Prodan developed an early passion for wine, food, and hospitality through travel across Europe. At 24, she moved to Chicago and built her career across back- and front-of-house roles.

Since 2021, she has served as Beverage and Service Director at S.K.Y. Restaurant, curating a global wine program that highlights classic and emerging regions, small producers, and thoughtful pairings. She has also played a central role in the development of S.K.Y., Apolonia, and Valhalla.

Prodan is the creator of Le Mistral, a Southern European-inspired wine and cocktail bar centered on distinctive wines, boutique spirits, inventive cocktails, and culturally driven hospitality. Her programs include “All Champagne” and “Anything but Wine,” alongside more than 20 wines by the glass.

In 2025, she received the Jean Banchet Award for Sommelier of the Year. She continues to deepen her expertise through travel, harvest work, and relationships with producers.

Nathan Ducker

CHICAGO

NATHAN DUCKER


General Manager and Sommelier

MEET NATHAN

Nathan Ducker is the beverage director and general manager at Feld restaurant in the Ukrainian village. Prior to opening Feld, he worked in wine programs including the José Andrés Group, The Allison resort in the Willamette Valley, and Alinea. The 20+ course menu and pairings change daily at Feld, making constant evolution and creative agility essential.

While this means the job is never “done,” Nathan has always preferred constant engagement with the process. He considers himself an “expert follower” in the kitchen-led dance of food & beverage pairing, drawing from classic producers and new global trailblazers. He is an Advanced Sommelier through CMS-A.

Khalil Skinner

CHICAGO

KAHLIL SKINNER


Certified Sommelier

MEET KAHLIL

Kahlil Skinner has worked in restaurants for a decade and has focused on wine for the past five years. He began his career in San Diego at wine‑driven fine‑dining restaurants before committing fully to wine in 2021, completing both his Introductory and Certified Sommelier certifications with the Court of Master Sommeliers in 2022. 

He then moved to Napa Valley to join PRESS in St. Helena, where he spent three years working under Master Sommelier Vincent Morrow. Kahlil is currently pursuing his Advanced Sommelier certification while working as a sommelier for Lettuce Entertain You at RPM Seafood, RPM Steak and RPM Italian.

Kathleen Hawkins

CHICAGO

KATHLEEN HAWKINS


Wine Director and Sommelier

MEET KATHLEEN

Kathleen “Kat” Hawkins is the Wine Director and Sommelier at The St. Regis Chicago, where she oversees the acclaimed wine programs at Miru and Tre Dita. A respected leader in Chicago’s dining scene, she previously served as Wine Director at RPM Steak, managing one of the city’s most celebrated cellars with more than 1,300 rare and sought-after wines. Since moving to Chicago in 2018, Hawkins has become a prominent voice in the hospitality community, combining exceptional beverage leadership with a passion for mentorship and education.

A Detroit native, Hawkins earned a degree in Communications from Wayne State University before pursuing a career in wine. She is a Certified Sommelier through the Court of Master Sommeliers and a Certified Specialist of Wine and Spirits through the Society of Wine Educators. Named one of Wine & Spirits magazine’s “Best New Sommeliers” in 2019, she also serves on the board of Second City Sommeliers, advancing wine education and professional development throughout Chicago.

Chicago

October 21, 2026


$250 per person plus taxes and gratuities

Buy Tickets

About the sommeliers

Chicago

November 18, 2026


$250 per person plus taxes and gratuities

Buy Tickets

About the sommeliers

Chicago

December 9, 2026


$250 per person plus taxes and gratuities

Buy Tickets

About the sommeliers

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