Winestyr Chicago | Wine Consultations in Chicago's West Loop

Winestyr Chicago

Visit our appointment-only lounge to learn more about
our wine club options in one of the coolest settings
in the city of Chicago.
Request an Appointment

How It Works


Schedule a private consultation for you or your small group. Your wine consultant will greet you upon arrival.


Relax and unwind over wine and hors d'oeuvres while your wine consultant presents our portfolio of products and wine clubs.


Join the wine club that suits your needs and have your first order sent directly to your home or office.

The Winestyr Chicago Lounge is accessible by appointment only. Appointments are available by request, and must be made at least one hour in advance.


Lounge amenities 1
Lounge amenities 2
Lounge amenities 3

Located in Chicago's West Loop, just steps from notable restaurants Avec, Grace, and Blackbird, our Chicago Lounge is accessible by appointment only. These private appointments serve as an opportunity for us to show and tell what makes our wine club service the best in the country for discovering and accessing the best small-production, hard-to-find wines that you won't find anywhere else.

648 W Randolph
Chicago, IL 60661
(707) 791-0216
We're a short walk from The Loop, Union Station, Ogilvie Transportation Center, and just off the 90/94 Expressway.
Appointments Available:
And by Special Request


Expert wine consultants
Expert Wine Consultants
Conveniently Located
Small lot wines
Small Lot Wines and Craft Beer
Professionally Catered Hors d'oeuvres

Winestyr is a highly curated online wine marketplace that streamlines the discovery and purchase of hard-to-find wines from over 100 of America's best small wine producers. We are the only wine service that never retails wine and never makes our own wine. When you purchase through Winestyr, you truly are supporting the wineries we serve.

Join us in our Chicago Lounge

Request an Appointment

Not in Chicago? We offer wine consultations over the phone and video chat.

Wine Club Reviews

"Great wines you can't find in stores. Easy to use, nice interface."
- John, San Francisco

"I love it...the personal touch...the reasonable prices...the quality of the wine...all of it."
- Leslie, Chicago

"My first order was executed seamlessly and i love the first 3 bottles I have opened."
- Chris, New York City

We'll Host Your Special Event

Inquire by emailing

821 reviews 4.9/5 stars

Great wine and awesome perks!

I received my first Winestyr order and loved the selection of wines! They were unique and delicious. My husband, family and friends all agreed! I also love how I can schedule free wine tastings with complimentary appetizers at the locations near my house. I have a tasting scheduled with a group of my girlfriends and they cannot wait to try all of the wines! I'm super excited about this membership and can't wait to get the next shipment :)

Great Winestyr experience so far!

The wine selection has been wonderful - we found a bottle at the Winestyr location in Chicago and have really enjoyed the case we ordered. The bottles come very quickly and the customer service is great. Looking forward to going to the Winestyr location in Boston when it opens!

Love it

Great wines so far. Beautiful Pinot, unique Sauvignon blancs. Excellent service too

First wine club shipment

My shipment was timely and the variety of wine was incredible. I thoroughly enjoyed receiving the booklet which explained each wine and its flavor profile and origin!

Amazing seleciton

We were very impressed with the presentation & selection of wine sent to us. Our favorite was the pinot noir.