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
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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

713 reviews 4.9/5 stars

Attential to detail is amazing!

Ordered my Winestyr box after seeing it on Instagram. I was blown away by the attention to detail in their packaging! Really lovely! The first wine we've tasted (Dichotomy Pinot Noir) was absolutely delicious! Will definitely order again!

4/5 Friends Joined the Club on the Spot!

I recently took a group of 5 friends to the tasting room, and by the time we got to the 3rd wine, 4 had decided to join! It speaks volumes to your awesome service and the great ambiance and service….and of course the great wine.

Great service! Fun exploring new wines

Winestyr ships so quickly and has a great selection of wines from smaller wineries. It has been so fun trying out new wines! It’s a great way for us to build our collection of unique wines and find out about wineries we otherwise would not.

Love Winestyr

Absolutely loving being a member! I’ve been sent great wine and it’s a surprise every time. I love that there are events in my area as well! Looking forward to being a member for life!

Great Experience

I had a great time at Winestyr, the host was knowledgeable about the wine being poured and shared personal info about the wine maker as well. The bites they had were equally delicious and paired very nice with the wine tasted. I became a member after my first visit!