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.

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

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

651 reviews 4.9/5 stars

Wine Tasting and Overall Experience

We were recently invited by friends to attend a personal tasting at Winestyr, and were so impressed by our experience that we decided to become members ourselves! The staff was warm, friendly, and knowledgeable and made the experience that much better. So far we have received one shipment and were very pleased with the selection! I would highly recommend Winestyr to anyone who is looking for a wine club membership!

Absolutely fantastic service!

The wine selection from Winestyr is second to none in the subscription world! I look forward to my box every month, the selection is always great and I love that it is "small" vineyards that I can not get personally here in Chicago. Already looking forward to my next box!

Great wine, great customer service

My husband and I were very pleased with our first wine shipment, especially with the Dichotomy Pinot Noir. It drank like a $70 bottle, but we only paid a little more than $20 for each bottle. We cannot wait to see what is in the next shipment. Furthermore, I am very happy with the quick customer service. There was a little mix up with our first shipment, but it was resolved within a few hours.

I love every bottle!

I joined winestyr because I love wine, but I'm not super knowledgeable about it. It's great to have wines chosen for me, and I've loved every bottle I've received. I feel like I'm getting really high quality wines for reasonable prices, and I'm learning about wineries that I wouldn't have otherwise known about.

Great experience, better wine.

I went on a Winestyr tasting after getting my first three bottles and it was fantastic. Learning about new wines that I've never even heard of before and fell in love with was incredible. After the tasting, I love reading the background information on the wine, vineyard, and history of the wines I receive in the mail. Great idea overall!