Chicago

Mart Anthony's punches above its weight class for a neighborhood Italian — the Terre Nere on the list alone earns goodwill, and half-price bottles on Wednesday makes it a legitimate weekly move. Send a friend, order the agnolotti, and ask about what's open.

Siena Tavern's wine list is a serious Italian-forward program dressed up in a lively River North atmosphere — the WS Award of Excellence is well-earned. Markups keep it from being a steal, but if you navigate toward the Italian heavy-hitters, you'll drink well.

Shaw's Crab House earns its Wine Spectator credential — the list is thoughtfully seafood-focused, the sommelier is a real asset, and the depth at 400+ bottles means you won't feel cornered into bad choices. Markups lean steep, which is the tax you pay for a River North institution, but the bones of this wine program are solid enough to send a friend here without hesitation.

Prime & Provisions earns its Wine Spectator credential — the list is well-curated, the staff knows their stuff, and the setting delivers on the steakhouse promise. Just come in knowing you're paying Loop prices for Loop prestige, and budget accordingly.

Perilla is a genuinely fun concept with a wine list that mostly keeps up — three sommeliers, serious producers, and a Burgundy-California spine that plays well with bold Korean flavors. The markup is real and the list plays it safe beyond the French-Cali lane, but if you engage the staff and lean into the pairings, this is one of the more interesting steakhouse wine experiences in Chicago.

Osteria Langhe isn't trying to be everything to everyone on the wine front, and that restraint is exactly what makes it worth the trip. If you have any curiosity about Piedmont's wine culture, this is the most approachable classroom in Chicago.

NoMI Kitchen is a trophy wine list inside a trophy hotel, and it earns its Wild Card badge by combining a serious California-France cellar with a French-Japanese menu that actually gives you somewhere interesting to take those bottles. Come with a budget and a specific wine in mind — the list rewards the prepared diner more than the casual one.

Miru is a Wild Card because nobody expects their omakase-adjacent Japanese dinner spot to be hiding Domaine Dujac and Ridge Monte Bello — but here we are. The markups are real and the by-the-glass program won't change your life, but for a special night with the lake as your backdrop, there's enough here to drink very, very well.

Lyra earns its Wine Spectator nod by doing something genuinely rare in Chicago: building a wine list that takes Greek producers seriously and prices them fairly. If you've been sleeping on Greek wine, this is the restaurant that will change that.

Hugo's is a reliable wine destination for Gold Coast dining — not thrilling, but never embarrassing, and the staff knows what they're doing. Send a friend here for a big seafood night knowing the list will hold up; just steer them away from the obvious trophy bottles.

Gibsons is a reliable destination for big-bottle California and French wine in a room that was made for exactly that kind of drinking. The pricing is steep across the board, but Monday's half-price wine night turns this into a genuinely compelling night out — show up then, order the ribeye, and spend the difference on a second bottle.

Gene & Georgetti isn't trying to be a wine destination, but the Italian cellar is deep enough and serious enough that you won't feel shortchanged. Stick to the Barolo, Brunello, or Amarone, avoid the obvious California markup traps, and you'll drink well in one of Chicago's great rooms.

Geja's is a date-night institution in Chicago for good reason, and the wine list — while California-safe and a touch steep — is earnest enough to earn its Wine Spectator credential. Come on a Wednesday, order the Jordan, and let the classical guitar do the rest.

Galit is doing something almost no one else in Chicago is doing with a wine list, and they've got a Wine Spectator Award of Excellence since 2023 to show it's not accidental. If you care at all about Israeli or Lebanese wine, this is your excuse to make a reservation.

Frontera Grill and Topolobampo are the rare Mexican restaurants where ordering wine is actually the right call — the Mexico section alone makes it a destination for the curious drinker. Come for Bayless's food, stay for a Baja California bottle you won't find anywhere else in the city.

Fioretta earns its Wine Spectator credential — sommelier Katia Savinkova has built an Italian-driven list that genuinely belongs in a room this theatrical. The markups lean steep, but when the Conterno Barolo is on the table and the lights are low, you're probably not doing the math anyway.

Coco Pazzo is a dependable play for Tuscan wines in a setting that earns them — just go in knowing you're paying for curation and atmosphere, not discovery. If you want Italy's classics delivered with confidence, this list delivers.

Brasero isn't a wine destination, but it's a damn good wine restaurant — focused, fairly priced, and built around a list that actually matches what's coming out of the kitchen. If you're eating wood-fired Latin food in Chicago, this is where you want a bottle of Argentine Malbec in your hand.

If Spanish wine is your thing — or you've been meaning to make it your thing — Asador Bastian is the best argument in Chicago for why it should be. The markups aren't gentle, but the list is curated with real conviction and a sommelier who can actually guide you through it.

Andros Taverna isn't trying to be a wine destination — it's a neighborhood taverna that happens to have built the best Greek wine list in Chicago. If you eat here and order a beer, that's on you.

Brass Tack has the bones of a genuinely great wine program — a Best of Award of Excellence since 2019 backed by producers like Chave, Leflaive, and Kistler doesn't lie. The pricing runs steep in spots, but if you're eating on Walton Street, you already knew the neighborhood.

The Village is the real deal for Italian wine in Chicago — deep list, serious producers, and a Wednesday half-price program that makes the steep markups survivable. Send your wine-curious friends here and tell them to order Nebbiolo.

Swift & Sons is the full steakhouse wine experience done right — deep cellar, strong California and Italian bones, and glassware that respects what's in it. Markups run predictably high for the format, but if you pick smart, you'll drink very well in one of Chicago's best dining rooms.

Kinzie Chophouse is doing exactly what a Wine Spectator Best of Award of Excellence steakhouse should do — deep California and French list, serious glassware, and a by-the-glass program that doesn't embarrass the room. Markups run steep as expected in this zip code, but the bones of this wine program are genuinely strong; send your Cab-loving friends here without hesitation.

Gibsons Italia is the real deal — a deeply stocked, expertly staffed wine program in one of Chicago's best dining rooms. Markups run steep at the top end, but if you know where to look (and the sommeliers will help), this is a list worth getting lost in.

El Che's wine program does exactly what it needs to: support a meat-forward menu without getting in the way. The markups are steakhouse-standard (read: steep), and you won't find any surprises, but if you're here for Argentinean beef and want Argentinean wine to match, it delivers.

Mon Ami Gabi delivers on ambiance and French bistro classics, but the wine program feels like an afterthought with tourist-trap pricing. Order a cocktail or bring your own if they allow corkage—this list isn't worth the premium.

Joe's delivers exactly what it promises: a serious steakhouse wine program with proper service, varietal-specific glassware, and a list that won't surprise you but won't disappoint either. The markups sting and the selections play it safe, but if you're here for stone crab and a mature Napa Cab, you're in good hands.

Le Colonial delivers a solid, French-focused wine program that complements the cuisine without taking risks. It's reliable for a date night or business dinner, but markups are steep enough that you'll want to stick to glass pours or explore their lower-tier bottles.

This is the wine list you wish every Italian restaurant in America had. Serious depth, fair pricing on the bottles that matter, and a sommelier team that actually cares.