Crowd-Pleasers and Monday Night Deals
Chicago · Chicago · Wine Bar · Visit Website ↗
Updated April 2026
Reviewed by the RagingWine Tasting Desk · March 8, 2026
RagingWine reviewed Montage Wine Bar’s wine list and gave it The Reliable — RagingWine’s Vibe-Check rating. How RagingWine reviews wine lists →
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Wingman Metrics
A 120+ bottle list that reads like a greatest hits compilation from wine country gift shops. The by-the-glass pours at $19-$23 hit that sweet spot between grocery store markup and wine bar gouge, and Monday half-price bottles means this place knows its audience.
The list plays it safe with recognizable names across California, Australia, Italy, Argentina, France, Spain, and Germany — think Napa stalwarts like Black Stallion, crowd-pleasing Aussie brands like Mollydooker, and solid Argentine workhorses like Catena. There's nothing rare or challenging here, no natural wine rabbit holes or esoteric appellations. What you get is a wine bar built for people who want to recognize labels and not feel intimidated. The 120+ bottle count offers breadth without depth — lots of countries represented, but mostly commercial producers you'd find at Binny's.
Eight glass pours span from Tiamo Prosecco to Orin Swift 'Machete', covering the bases from sparkling Italian to big California red. The $19-$23 range is honest pricing for a wine bar — not a steal, but not highway robbery. Rotation seems minimal based on the sources, so expect the same lineup week to week.
Catena Malbec Mendoza 2022 — $22
Only a 22% markup over retail ($18) is practically charitable for a wine bar, and Catena delivers consistent quality
Novellum Languedoc-Roussillon
Southern France gets overshadowed by California here, but Languedoc offers serious value and more complexity than the typical Napa Cab
Orin Swift 'Machete'
Orin Swift's celebrity pricing doesn't translate to value — you're paying for the label, not what's in the bottle
Mollydooker 'Too Left Feet' South Australia 2022 + Charcuterie board
This fruit-forward, jammy Aussie red needs rich, fatty meats to balance its sweetness — classic wine bar pairing
Monday — 1/2 priced bottles of wine every Monday. Some wines marked (*) not available for 1/2 price offer.
The Bottom Line
Montage Wine Bar isn't going to blow your mind, but it'll treat your wallet fairly and get you buzzed on recognizable labels. Monday half-price bottles make it a solid neighborhood hang.
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
Mountain Road corridor · Stowe · Wine Bar
Dedalus Stowe is a legit wild card — a destination wine bar hiding in plain sight on a ski mountain road. If you care about what's in your glass, detour here before or after the slopes.
Deep & Eclectic
Fair
Varietal Specific
Knowledgeable & Friendly
Set & Forget
Proper
Downtown / South Main Street · Canandaigua · Wine Bar
Acquilano isn't trying to be a destination wine bar — it's a Finger Lakes producer pouring its own work in a casual Main Street setting, and it does that with charm and absurdly fair prices. If you're in Canandaigua and you skip this, you've made a mistake.
Small but Thoughtful
Steal
Basic Stemmed
Willing but Green
Set & Forget
Proper
Downtown Paso Robles · Paso Robles · Wine Bar
Indigené is a focused, fairly priced boutique tasting room doing honest work with Central Coast fruit — it's not trying to be a full wine bar, and that clarity is actually the point. If you want to understand what a small Paso Robles producer can pull off without the tourist-trap markup, this is worth an afternoon.
Small but Thoughtful
Steal
Basic Stemmed
Knowledgeable & Friendly
Set & Forget
Proper
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