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

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860 reviews 4.9/5 stars

Happy Customer

I’m young, on a modest budget, and trying to learn more about wine - Winestyr has been the perfect avenue. The club was a gift to my girlfriend, and we’ve enjoyed the variety in the routine shipments as well below-retail prices on some of our favorites. As a bonus, the shipping is free and lightning fast, and customer service has been great! I look forward to bringing friends to the tasting room.

Great concept, great execution!

I like wine but I don't enjoy shopping for wine. I am in a few CA wine clubs which I like a lot but I also like to try new stuff. Winestyr does the hard part of finding interesting new wines for me. Their descriptions provide better information than most wine store personnel so I am buying with a little more confidence. Their price points are reasonable and that is meant as a compliment. Their selection is outstanding and their order processing is superb. I've been through three cases shipped to three different locations in the last couple months with no problems...and the wine was great, too!

So far we’re quite happy

We have never had any luck with wine clubs which weren’t direct. This wine is great for the price and the prompt service is top notch. Highly recommend. Thank you

Love Winestyr and their quick delivery

Winestyr has become my go to wine website/shipper. I switched from because they take a couple of weeks for their shipment to arrive - winestyr does so in matter of days. Not as big a selection as, but sometimes too big is overwhelming and Winestyr curates and recommends for me. As I said, love Winestyr - try them.

Lovely tasting room and delicious wine

My husband and I had a great time trying wines in the tasting room and look forward to our wine delivery!