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 f206a165ac976a0aeb77f29c72891bb506a4be9cff9d0738da415c208579e93c
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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 8500289cb3a9d2e7cbc7ec0f26777935581b83439c99899a3b3138d4fe3bd010
Expert Wine Consultants
Location 55aece24a0116eb000e435d7d5a5058a1a8bccc702ca2c96abae2be64758416c
Conveniently Located
Small lot wines 541743b8c87c29ed6960b08a6129fb526b91250548910c19238513b51f295a5b
Small Lot Wines and Craft Beer
Catered 5cb95574c65cbebb0c60ddb3770777c7af1e9f8bed17ef450411dc13faf84cb7
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

474 reviews 4.9/5 stars

Best Wine Experience!

Although I've only been a Winestyr member for a few weeks, so far I can't say enough good things! Each of the wines I've tried has exceeded expectations, and I'm already planning on buying several to send as gifts. I love that you have the option to customize your orders, and the flexibility to change them at any time (if you're going out of town, for example). Not to mention, the lounge in the West Loop is AMAZING. The staff are extremely accommodating & friendly at all times, and truly want you and your guests to have the best experience possible. I've already referred several friends, and everyone is obsessed. I highly recommend you check out Winestyr if you are interested in exploring various wines - you won't regret it.


I joined about 6 weeks ago and it has been an incredible experience. The Chicago lounge is full of extremely helpful and cheerful staff along with some great wines. The first box I received was shipped quickly and carefully. Can't wait for the next one!

Amazing Winery and Wines

I was introduced to Winestyr by a friend and have fallen in love. Their space is warm and the perfect place for wine tastings. The wines that I have received through the wine club and have also purchased have all been amazing. This has become my go-to place for ordering wine as their choices are excellent.

Customer service and tasting

I contacted Winestyr when I realized they had a space nearby and offered some unique wines. The experience at the tasting room was great from the welcome to the follow up after. The personal responses regarding wines available and shipping were very helpful. I am looking forward to the next shipment and tastings.

Quality wines

We loved our tasting experience with Erin at Winestyr! Erin and Scott were knowledgable and approachable. Great evening in the tasting room. Can't wait to taste our first selections from their wine club.