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

635 reviews 4.9/5 stars

My favorite place to buy wine

I was so happy to learn about this company from a fun that worked there. The wines are AWESOME and I love getting my box each month. Getting the discount online for more wine is great, can you can't beat shipping. Everyone who works here is also awesome. From the people in store to those who have given virtual help when I need assistance selecting wines. The prices are similar to in store but you can't be the quality. So happy I can get vineyard quality wines all the time now delivered right to my home. Thanks Winestyr!!

Love the craft wineries!

My favorite part about Winestyr is the fact that you get access to small batch wineries and interesting wines that you can't find at the local grocery store. I highly recommend to anyone looking to mature their palette!

Great experience and wonderful wines

We had a great experience learning about different wineries and unexpected grapes. We’ve enjoyed all of our wines from winestyr

Love Winestyr!

It's so simple, and the wine is superb. Every single bottle, no matter what the price, has been delicious! Highly recommend joining the wine club!


Very smooth. Good after taste. 3 stars