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

621 reviews 4.9/5 stars

Couldn’t be happier with this wine club

Every bottle I’ve recieved has been great so far. I am not a big white wine drinker but I’ve even loved the bottles of white I’ve been sent in my quarterly shipments.

An extremely enjoyable experience

I'll be honest at first, I was a little skeptical about a wine club, but then I found Winestyr. I went in for a consultation and Lauren was very knowledgeable. The space was great and I have ordered many bottles after becoming a member. Their small batch wine is affordable and always delicious!

Great Wine and Fun Tasting Room

I discovered Winestyr a few months ago and absolutely love it! The tasting room in the West Loop has such a great atmosphere, and Erin is a wonderful host every time I show up with friends. Also, as someone who lives in the city without a car, I absolutely love that I get free shipping on wine. I hate hauling heavy bottles of wine to my apartment, so now I can just get delicious wine from Winestyr without any of the hassle. Highly recommend joining the club! Cheers!!

Love it

Winestyr is awesome. The wines are really good at a really reasonable price. I've liked everything I've received.

Tasting Excellence

I brought a non-member friend for a tasting and she had such a wonderful time she signed up before we were even done sipping. Lauren does an amazing job making you feel welcome. Love being part of this club.