The 12 Best Spots for Wine Tasting in Chicago

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When you think of Chicago, “wine country” doesn’t exactly come to mind. After all, with so many brutal winters to get though, it takes a strong grape to survive this neck of the woods. But while we may not be blessed with vineyards galore, à la Napa, California, or even the variety of soils seen in Walla Walla, Washington, we’re here to assure you that you can still have a good fabulous vino experience in the Toddling Town. In fact, we found 12 wine tasting Chicago experiences that even the biggest connoisseurs of the beverage will delight in. See which ones made the cut—and why they’re so special—below.

Socially Distant Napa Wine Tasting Experiences

wine tasting chicago rpm
Lindsay Eberly

1. Rpm Seafood

We’ve got one word of advice when it comes to RPM Seafood’s newly launched Sommelier Experience: Go. Yes, it’s on the pricier side at $225 a guest (there’s room for up to four), but we can honestly say that we think it’s worth every penny. Not only will you get to savor limited wine selections as chosen by the restaurant’s wine director, Richard Hanauer, but each one comes with a perfectly paired (and sized) dish to accompany it courtesy of chef Bob Broskey, who marries unexpected textures and flavors into his menu with verve (think a crunchy potato chip atop a melt-in-your-mouth piece of tuna). The seating is semi-private, making you feel like a VIP, and you’ll have plenty of face time with your sommelier, so you can ask as many questions as you want about the glasses you’re being presented with (each one in its own appropriate vessel, naturally). The best part? The menu changes nighty. While we enjoyed pearl oysters with a citrusy flair, the absolute best Georges Bank scallops we’ve ever had in our life, New Caledonian blue prawn risotto and Maryland black bass, tonight’s offerings include prestige oysters, bigeye tuna with wasabi vinaigrette and Australia Murray cod, for instance, so you’re not likely to have the same experience twice. Not into seafood? Try RPM Italian’s version instead, which has a heavier focus on homemade pastas.

Tuesday through Saturday, 6 p.m. to 8:30 p.m.; $225, 317 N. Clark St., Chicago IL 60654;

wine tasting chicago fromagerie
The Fromagerie & Tasting Room

2. The Fromagerie And Tasting Room

Put quite simply, The Fromagerie and Tasting Room is a wine-lover’s dream. This gem of a wine and cheese shop and sampling space in the heart of Andersonville has all the usual trappings, from the rotating meats and cheeses, conservas and jams to the charmingly rustic décor. Its standout feature, however, are the insanely educational wine tastings it offers diners every Wednesday, Thursday and Saturday night. Whether you prefer to tune in virtually on Wednesdays or join the intimate group that gathers in-person on Thursday evenings, you’ll be treated to a class-style learning session about a region of your sommelier’s choice (currently, France and South America, respectively). Complete with a full-on slideshow packed with information about everything from the supplier and the tasting notes to the meal pairings, you’ll take in a ton of information—even if you’re already well-versed in the art of vino. That’s partly because the team members here go out of their way to challenge themselves, presenting lesser-known wine terroirs that aren’t typically touched upon. Upon our visit, for example, the focus was on Uruguay—a region with just one known producer currently shipping to the Windy City. You’ll also benefit from the knowledge of your fellow class-takers, who may pick up on a subtle note of leather in a glass where you had only detected spiciness. And, if all that’s not enough to whet your whistle, there’s always the one-off tasting sessions that happen every Saturday.

Wednesdays, 6. p.m., Thursdays, 6 p.m. and Saturdays, 3 p.m., From $35, 5555 N. Clark St., Chicago IL 60640;

wine tastings chicago city winery
Nicole Briese

3. City Winery

You can’t mention wine tasting in Chicago without mentioning City Winery in the same breath. With two locations to speak of (one at the Riverwalk and one on Randolph Street), the facility has been serving up its own blends in Chitown since 2012, so there’s plenty to try—and to see. We visited the sprawling space on Randolph and were blown away by the vast, open dining rooms (yes, plural), which are aptly decorated with wine bottles and barrels galore, and even more impressed by what lay behind the scenes: namely, the industrial-sized coolers, fermentation vessels and barrels where all the wine-making magic happens. Thanks to the private tastings being offered here, you can take it all in with the help of a vastly knowledgeable guide, who will talk you through the finer parts of wine-making or, should you prefer to get a little more hands-on, you can learn how to produce it yourself with the winery’s blending option. Either way, the interactive element that you’ll get from joining a group tour or the ongoing Q and A and discussion you’ll have with your guide is sure to make for a perfect girls’ day out. And when you’re done? You can take in a little entertainment, since the venue hosts everything from comedians and TV personalities (The Bachelorette’s Katilyn Bristowe recently swung by) to music acts galore. Eat your heart out, Sonoma.

Fridays, 4 p.m., Saturdays and Sundays, 12 p.m., 2 p.m. and 4 p.m., $50, 1200 W. Randolph St.;

wine tasting in chicago cooper s hawk

4. Cooper’s Hawk Wintery & Restaurant Esquire Chicago

We get it: Things can get a little…hairy when you’re “tasting” multiple adult beverages on an empty stomach. If you’re looking for a place where you can get your nosh on as well as your sipping, Cooper’s Hawk is your best bet. The meals are not only delicious, but hearty, and top notch for the value—we recommend the restaurant’s version of a surf and turf, which comes with perfectly sized portions and mouthwatering finishes of the classic dish (pistachio-crusted grouper, anyone?). The tasting room is set up in a Napa style, and each sipping session gives you carte blanche to try out seven to eight different glasses with an attendant as your guide. (Pro tip: Sign up for the winery’s membership club to get a free monthly tasting for two.) As for the wines themselves, which feature grapes transported to the winery straight from vineyards in California, Washington and Oregon, they’re a big step up from many you’d find on the grocery store shelves. Whites, like the Cooper’s Hawk sauvignon blanc, present as light and effervescent, while reds, like the Lux cabernet sauvignon, are smooth without a hint of bitterness. While the Oak Street location won’t reopen until March 21, you can still get your fix in the meantime: Plenty of the company’s 47 other locations are ready for dining now (we’re partial to the nearby and equally charming Oak Park venue, which has the most charming gift shop known to man).

No reservations required, From $15, 58 E. Oak St., Chicago IL 60611;

wine tasting chicago ever

5. Ever

It’s no secret that Chicago is a foodie town, so it stands to reason that some of its top (we’re talking two Michelin star top) restaurants would have some amazing wine offerings, to boot. Case in point? Ever. The Fulton Market eatery has once-a-month blind tastings led by wine director and co-owner Michael Muser, during which guests will explore flavors from both the New and Old Worlds. Despite the restaurant’s many accolades, however, there’s nothing pretentious about the way Muser guides the small groups that join him each week through each varietal, with a rotating roster that could take you around the world or delve deep into one particular wine territory in equal measure. You’ll want to book your spot early, however, as these events tend to sell out, and quick.

Saturdays, March 12, April 2 and May 14, 10:30 a.m., $150, 1340 W. Fulton St., Chicago IL 60607;

wine tastings chicago wc winery
WC Winery

6. Wc Winery & 25 Boccé

If you’re a fan of reds, you won’t want to pass up a tasting at WC Winery with the facilities’ own winemaker, Jeff Doornbos. Hosted in a private room with space for up to 10 guests, each private tasting includes a flight of no less than four rouge blends (cab, sangiovese, barbera and syrah), plus a blended 10-year-old port. Add in a few barrel-aged masterpieces and a sparkling riesling, and you’ve got the starting lineup of your very own wine Super Bowl. Good thing there’s plenty of hors d’oeuvres included to go around!

Fridays, 7:00 p.m. to 9:00 p.m., $40, 4045 N. Rockwell St., Chicago, IL 60618; wc-winery-com

wine tastings chicago aba

7. Aba

On Wednesdays, you’ll want to sidle up to a spot at the bar at Aba (or the dining room, if you can snag a table), where sommelier Alex Augustine will undoubtedly be hosting “wine Wednesdays.” With pours from rare bottles that will pique the interest of even seasoned winos, each weekly event has an agenda (next week, for instance, guests can enjoy a red blend called Birichino Scylla that hails from the west coast), and you don’t even have to make a reservation to get in on the action (though we’d highly recommend it).

Wednesdays, 302 N. Green St., Chicago IL 60607;

8. Wild Blossom Meadery And Winery

If you’ve had your fill of chardonnay, pinots and even rosé, why not try something new? Wild Blossom Meadery and Winery offers daily tastings of mead on the city’s south side. What is mead, you ask? It’s a dry to sweet alcohol that’s made by fermenting honey with yeast that the winery says dates back roughly 8,000 years or so (nbd). For $20, you can choose to try it as a flight of four, on the patio, by a firepit with s’mores (um, yes?) or in an educational session. For $125 per couple, you can even make your own for a brewing class. Prefer the classics? Opt for the winemakers’ class for $149 per couple instead.

From $20, 9030 S. Hermitage Avenue, Chicago, IL 60620,

9. Winestyles

While many tastings end at four glasses, WineStyles’ weekly events offer up to six samples for the bargain price of $10. Here, regions from around the world are discovered (at least in the culinary sense), allowing you to take a tasty journey across the globe. This week’s destination is Paso Robles, California, with selections being poured from the area’s own Vino Robles Winery.

Thursdays, 6:00 p.m. to 8:00 p.m., From $10, 6182 Northwest Hwy., Chicago, IL 60631;

10. Le Sud

Relatively new to the tasting scene is French Mediterranean neighborhood haunt Le Sud. Each month, wine aficionados gather at the Roscoe Village hot spot to dive into different flavors that span the continents. Selections include reds, whites and bubbles, with hors d’oeuvres pairings from chef Michael Woodhill to accompany their exotic flavors. The cool thing about this one? You’ll leave with a whole lot more than the experience—your ticket price includes three complementary bottles of wine, tasting notes and pairing recs.

Thursday, March 3, 7:00 p.m. to 8:00 p.m., $69, 2301 W. Roscoe St., Chicago, IL 60618;

11. Picnic Wine & Provisions

You don’t have to spend a ton of cash to have a fun wine tasting experience. For $5 (yes, you read that right), you can hit up this Rogers Park destination to share a glass with other members of the community at a table, on the patio, or, in the summer months, on a blanket, picnic style. In fact, that’s kind of the point: Owner Liz Ahearn does what she can to “[bring] people together to share ideas and get to know their neighbors over wine, food and art.” The menu is sustainably sourced, the company is jovial and the wine is all available to take home by the bottle, with the $5 fee being waived for those who make a purchase.

Thursdays, 5 p.m. to 7 p.m., $5, 7301 N. Sheridan Rd., Chicago IL, 60626;

12. Vin312 Winery

Many restaurants got creative in the face of COVID-19, and Ravenswood’s Vin312 Winery is certainly no exception. While it’s now welcoming customers back in for in-person tastings, we can definitely see the continued appeal of the virtual tasting kit winemaker Warner DeJulio has cooked up, which is essentially the perfect date night in a box. Once you purchase it, you’ll receive a link to schedule a walkthrough of the five 2-ounce bottles found inside from DeJulio himself at your convenience (just be sure to book at least a week out to ensure they’re delivered by your desired date). The box also contains tasting notes, a coupon for a future visit and 20 percent off a winery membership. Need more? Upgrade to the full bottle tasting for $149.

From $35,

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