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
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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

743 reviews 4.9/5 stars

Support small batched wineries

Winestyr has such a fun business model. Winestyr is the opposite of a boring, undifferentiated wine club. They focus on the story behind each winery and wine.


For someone who buys a lot of wine regularly, wine takes me to directly to hard to find wineries and secures pricing well below market value! I could not be happier.

2015 Sonoma Coast Pinot Noir

This was the first wine we tried from our Winestyr shipment and it was great! Very easy drinking!

Lincoln Park Tasting Room

Great experience at the LP tasting room! The staff was extremely knowledgeable about the wineries they were featuring and able to give insight as to the story behind each one, which was a really nice touch! Great quality wines that you don’t find at the grocery/liquor stores!

Winestyr is Awesome!

We found our experience at Winestyr to be a wonderful wine adventure! The staff is so knowledgeable and accommodating. They explained in as much detail as we wanted the various wines, regions, and grapes as well as the wine-makers they feature. We never felt pressured to make a purchase, but we did join a club. Our wine was delivered in the two different locations we requested; was a prompt delivery and the bottles were in perfect condition.