700 Italian Bottles Inside a Tuscan Fever Dream
Streeterville · Chicago · Italian · Visit Website ↗
Updated April 2026
Reviewed by the RagingWine Tasting Desk · March 8, 2026
RagingWine reviewed Tre Dita’s wine list and gave it The Rager — RagingWine’s Vibe-Check rating. How RagingWine reviews wine lists →
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Wingman Metrics
You open a wine list the size of a small phone book and realize you're holding 700+ Italian wines. The sommelier arrives at your table like they've been waiting for you their whole life. This is a serious wine destination wrapped in Tuscan luxury.
The list is an Italian pilgrimage that goes impossibly deep on Tuscany — Super Tuscans, Brunello, Chianti Classico for days — but doesn't ignore the rest of the boot. You'll find northern Piedmont heavyweights, volcanic Etna reds, and a grappa collection that could fuel a small village. The real flex? More than 30 types of Vin Santo, which is either committed curation or beautiful madness. Either way, we're here for it.
The glass program runs 18-25 pours at $15-$30, which feels measured for a list this ambitious. It's a solid intro to the regions they champion, though the selection skews safe rather than adventurous. Expect familiar Tuscan names and crowd-pleasing varietals — nothing that'll scare off expense account diners.
Unable to specify without verified wine names from research data — N/A
The deep Tuscan selection suggests strong value plays exist in Chianti Classico and lesser-known Brunello producers, but markup data shows aggressive pricing overall
One of the 30+ Vin Santo selections
Most people skip dessert wine entirely, but this collection is clearly a labor of love. Ask the somm for their favorite — you're at the only place in Chicago with this kind of depth
Pol Roger NV Brut Champagne
$200 for a $60 retail bottle is a 233% markup. That math doesn't work, even with the lake views
A classic Brunello di Montalcino from their deep Tuscan selection + Bistecca alla Fiorentina
You're at a Tuscan temple. Order the 40oz Florentine steak with a properly aged Brunello and pretend you're in the hills of Montalcino instead of a St. Regis tower
The Bottom Line
The markups sting, but the depth and expertise are undeniable. If you're serious about Italian wine and don't mind paying St. Regis prices, this is Chicago's Italian wine mothership.
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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