700 Italian Bottles Inside a Tuscan Fever Dream
Streeterville · Chicago · Italian · Visit Website ↗
Updated April 2026
Reviewed March 8, 2026
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
West Toledo / Reynolds Corner · Toledo · Italian
There's one reason to come here for wine: Thursday. Half-price bottles on a standing weekly basis is a genuinely good deal, especially on the Santa Margherita. Any other night, the markups are steep and the list doesn't justify them.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Seasonal Rotation
Acceptable
West Toledo/Monroe Street · Toledo · Italian
Carrabba's Toledo isn't a destination for wine — but it's not an embarrassment either. The Ruffino Chianti Classico alone earns its keep, and if you stick to the Italian side of the list, you'll drink reasonably well without drama.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
La Jolla · Chula Vista · Italian
Marisi is a reliable Italian wine list with genuine ambition hiding behind a steep markup structure — the producers are right, the regions are right, but you'll pay for the privilege. Go for the Produttori Barbaresco and the Pre-Phylloxera Barbera, and you'll leave satisfied.
Solid Range
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.