Italy's Greatest Hits, Chicago Style
River North · Chicago · Italian · Visit Website ↗
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 →
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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.
West Loop · Chicago · Californian
The Oakville Grill earns its Wine Spectator credential and the sommelier duo makes this list accessible, not intimidating. Wednesday half-price wine night alone is reason enough to get a reservation — just let go of the idea that anything other than California is on the agenda.
Plays It Safe
Steep
Varietal Specific
Knowledgeable & Friendly
Active Program
Proper
Lincoln Park · Chicago · American
John's is a neighborhood spot that punches well above its casual format — two sommeliers, a thoughtful France-and-California list, fair prices, and half-price bottles every Monday. Send your friends here, especially on a Monday.
Small but Thoughtful
Fair
Basic Stemmed
Knowledgeable & Friendly
Active Program
Proper
River North · Chicago · American, Seafood
Terrace 16 earns its Wine Spectator badge and delivers a respectable, California-and-France-focused list in one of Chicago's most dramatic dining rooms. Just don't expect to be surprised — the wine is as reliable as the skyline view, and nearly as expensive.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
River North · Chicago · French, Indian
Indienne is the Wild Card in the truest sense — a fusion kitchen with a genuinely considered wine program that earns its Wine Spectator nod. Yes, send a friend here for wine, but make sure they skip the Napa Cab and lead with Riesling.
Small but Thoughtful
Fair
Basic Stemmed
Knowledgeable & Friendly
Set & Forget
Proper
West Loop · Chicago · Steak house
BLVD Steakhouse doesn't reinvent the steakhouse wine list, but it executes the formula competently — solid producers, proper storage, and enough range to keep a table of Cab loyalists happy all night. Just go in with your eyes open on the markups and skip the trophy-bottle trap.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Proper
Magnificent Mile · Chicago · American
Adorn is a reliable, well-staffed wine program in a high-overhead setting — you're paying for the view and the address, but the list itself is legitimate. Send a friend here who wants solid French and California bottles without doing homework first.
Solid Range
Steep
Basic Stemmed
Knowledgeable & Friendly
Set & Forget
Proper
· Atlanta · Italian
Bici's wine list won't knock you sideways, but it's honest, Italian-focused, and fairly priced — a reliable partner to the food. We'd send a friend here and tell them to skip the Sauvignon Blanc and go straight for the Greco.
Small but Thoughtful
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
East Parkway / Elks Plaza · Gatlinburg · Italian
The Best Italian's wine list does exactly what it needs to do: keep casual diners happy, not drain wallets, and get out of the way of the garlic knots. We wouldn't drive to Gatlinburg for the wine, but if you're already there and want something decent with dinner, you'll be fine.
Crowd Pleasers
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Vail Village · Vail · Italian
La Nonna brings a legitimately serious Italian cellar to a town where most restaurants are content to coast on their ski-town captive audience — and that deserves real credit. The markups are steep across the board, but the bones of the list are strong enough that the right bottle makes the whole evening.
Solid Range
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
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