Italy's Greatest Hits, Chicago Style
River North · Chicago · Italian · Visit Website ↗
Updated September 2026
Reviewed by the RagingWine Tasting Desk · April 13, 2026
RagingWine reviewed Siena Tavern’s wine list and gave it The Reliable — RagingWine’s Vibe-Check rating. How RagingWine reviews wine lists →
Wingman Metrics
The wine list at Siena Tavern feels like it was built by someone who genuinely loves Italian wine and wanted to show off — in a good way. Italy leads the charge, California backs it up, and there's enough depth here to satisfy both the Barolo devotee and the person who just wants a solid glass of Cab with their short rib. Wine Spectator has recognized this list since 2018, and it's easy to see why.
The Italian spine is serious: Sassicaia and Super Tuscans anchor the high end, Gaja and Ceretto represent Barolo with authority, and Biondi-Santi and Banfi give you legitimate Brunello di Montalcino options that most River North spots wouldn't bother stocking. Amarone della Valpolicella rounds out the northeastern flank. California gets a respectable supporting role — Caymus and Jordan hold it down for guests who won't venture outside familiar territory. Where the list shows its limits is in the middle — there's a gap between entry-level and the trophy bottles that could use more interesting producers to bridge it.
With 20-30 options by the glass, this is one of the stronger BTG programs in River North — you're not stuck choosing between house red and house white. Glasses run $12-$20, which is fair for the neighborhood and the quality level. We'd love to see more rotation to keep things interesting, but what's here covers Italian varietals and California staples without embarrassing itself.
Jordan Cabernet Sauvignon — $60
Jordan consistently punches above its retail price point, and in a restaurant where bottles can sprint toward triple digits fast, it's a reasonable landing spot for California Cab fans who want quality without the Caymus premium.
Ceretto Barolo
Most tables at Siena Tavern are ordering pizza and pasta with something safe. Meanwhile, Ceretto's Barolo is sitting there — structured, earthy, genuinely great — waiting for someone to give it a shot with the braised short rib. It's the move.
Caymus Cabernet Sauvignon
Caymus is everywhere, and at restaurant markup it's rarely a value play. You're paying a premium for a brand name that retail has already overexposed. The Jordan next to it almost always makes more sense.
Biondi-Santi Brunello di Montalcino + Braised Short Rib
Biondi-Santi's Brunello brings Sangiovese tannin and bright acidity that cuts right through the richness of braised short rib — this is the pairing the list was built for. It's a splurge, but it earns it.
The Bottom Line
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.
Logan Square · Chicago · Italian
Come to Osteria Langhe for a focused trip through Piedmontese wine. Thursday’s advertised half-price selection is worth asking about, and Wednesday offers a wine pairing alongside the four-course menu. The linked wine list is dated December 2025, so confirm today’s bottles and prices before choosing.
Small but Thoughtful
Fair
Basic Stemmed
Willing but Green
Active Program
Proper
Lincoln Park · Chicago · American Casual
Summer House is not a wine destination, but it's a reliable place to drink well enough without getting gouged on the low end — just steer clear of the big-name bottles where the markup climbs. Send your friend here if they want something easy and good; don't send them here if they're chasing something serious.
Solid Range
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
· Chicago · Italian
il Carciofo is doing something genuinely rare: building a wine list that treats Italian regional variety as the main event, not the footnote. If you're tired of the same Pinot Grigio and Chianti Classico circuit, this is exactly where you should be eating dinner.
Deep & Eclectic
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Chicago · Chicago · Steakhouse
STK Chicago is here to sell you a night out, and the wine list is just part of the set dressing. If you care about what's in your glass, eat here for the steak and order water.
Crowd Pleasers
Steep
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
· Chicago · French Brasserie
La Grande Boucherie Chicago is a reliable wine destination for anyone who wants a French-focused list executed with genuine effort and the occasional smart value. The markups aren't shy, but the BTG program and specials take some of the sting out — go in with a plan and you'll drink well.
Solid Range
Steep
Basic Stemmed
Willing but Green
Active Program
Acceptable
· Chicago · Steakhouse
This is not the wine list you expect to find at The Palm, and that's exactly why it earns attention. Six bottles, zero filler, genuinely fair pricing — if someone's tending this list, they deserve a raise.
Small but Thoughtful
Fair
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
· Healdsburg · Italian
Ciao Bruto is running one of the smallest and most coherent wine lists in wine country, which is either audacious or brilliant — probably both. If you want a 200-label deep-dive, go somewhere else. If you want eight smart picks at prices that won't make you wince, this is the move in Healdsburg.
Small but Thoughtful
Steal
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
Geyserville · Healdsburg · Italian
Diavola earns its Wild Card badge because it's a wood-fired pizza joint that punches well above its weight on wine — sommelier on staff, regional focus, and a setting that practically demands you order a second glass. We can't give you the bottle-by-bottle breakdown until we get eyes on a current list, but the bones here are good enough to say: don't just order a beer and move on.
Small but Thoughtful
Fair
Basic Stemmed
Knowledgeable & Friendly
Set & Forget
Proper
· Healdsburg · Italian
Ca'Bianca is a genuinely lovely place to eat, and if the food lives up to its reputation for house-made pasta and classic Italian technique, a bottle of something from the list is absolutely worth ordering. We just can't tell you exactly which bottle to order yet — the wine program's specifics aren't publicly documented well enough for us to make a confident call. When in doubt, ask your server what's local and what they're excited about, and go from there.
Plays It Safe
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
One wine list review, one adventure pick, one quick tip, and a personal note. Every week. Under 500 words.
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