15 Best Cocktail Bars in Chicago

Here's the thing about a bar that calls itself "Sip & Dip": it has to deliver on both, and Gus' actually does. This River North spot from beverage director Kevin Beary (Three Dots and a Dash) and chef Bob Broskey (RPM, Intro) takes its name from Gus' Good Food, which held this address from 1906 to 1966 — so there's a neighborhood-tavern soul under all the Michelin pedigree. The play here is dipped sandwiches and reimagined classics. The Smoked Ham Dip ($23) is a brown-sugar-glazed pork roast on pan de cristal with mustard jus for dunking, and the Wagyu Steak Frites piles thin-sliced rare top round on toast with horseradish cream. The Rangoon Dip deconstructs a crab rangoon into something craveable. Thirty cocktails, all $12 — the Breakfast Martini comes with Earl Grey-infused gin and a honey-buttered toast point, which is exactly the kind of cheeky move I'm here for. It's racked up serious hardware: No. 27 on North America's 50 Best Bars, a 2026 Jean Banchet for Best New Bar. Walk-ins only, first come first served. Worth the wait.

Aba is a Lettuce Entertain You production perched on a Fulton Market rooftop in the West Loop, and the room appears to be doing considerable work before a single plate arrives. By reputation, the space runs on bleached wood, hanging greenery, and a terrace that draws crowds the moment Chicago allows it — an effect that, by multiple accounts, reads less like a Midwestern restaurant and more like a long lunch somewhere coastal. The Mediterranean framework is deliberately plural: Lebanese, Israeli, Greek, and Turkish threads are woven together without pretending to belong to any single tradition, which gives the kitchen a generous mandate and the menu an appealing sprawl.

Because no verified dish list exists for this review, what can be said with confidence is that the concept centers on the logic of mezze — a format that rewards tables willing to order broadly and let small plates do the social work. Lettuce Entertain You properties typically invest in consistent execution and trained front-of-house rhythm, and Aba's reputation suggests this one holds to that standard. Diners consistently describe the room as flexible: appropriate for a date on the terrace, a group dinner where the ordering structure relieves conversational pressure, and a cocktail-forward evening at the bar. The rooftop, specifically, is reported to be the main event in warmer months, shifting the entire atmosphere toward something unhurried.

Practical reality: reservations are essential for prime evening slots, and the rooftop books out weeks ahead through summer. Walk-in bar seating exists and is reportedly worth pursuing if you've missed the window. Budget sits at a moderate price point for the neighborhood, which makes ordering across several plates financially reasonable. Come with at least one other person — this is a menu that expands in proportion to the size of the table.

Seventeen floors up in Fulton Market, The Oakville Grill & Cellar makes its case for California-by-way-of-Chicago: an all-California wine list, 750-plus bottles deep, with Wine Director Richard Hanauer steering toward the lesser-known Santa Barbara County and Santa Ynez pockets rather than the obvious Napa cabs. The room is romantic and Napa-inspired, and there's a six-seat Cellar Door tasting nook for rotating producer flights — book it if you're a wine person who likes to corner a sommelier.

Executive Chef Tim Havidic (Eden, Gilt Bar) keeps the food deliberately uncomplicated. Start with the grilled avocado, slicked with California olive oil and togarashi, and the deviled eggs with pepperoncini aioli. The Costa Mesa salad — roasted corn, avocado, queso fresco, lime vinaigrette — travels well at a group table. Mains lean oak-grilled: wagyu steaks and petrale sole.

A word on the bill: this is fine-dining pricing in casual clothing. Dinner entrees run $19–49 (the So-Cal Steak Frites is $49), and fries-plus-pizza-plus-two-drinks tops $100. Come for the wine, stay for the view.

James Beard winner and Iron Chef Stephanie Izard designed Duck Duck Goat as a love letter to Chinese-American cooking — not a single regional tradition but the whole dreamy, neon-lit mythology of an everytown Chinatown. The West Loop room reportedly leans into that fantasy with a warmth that feels genuinely inhabited rather than engineered for content, and at price level two, it punches well above what you might expect from a chef with this many trophies on the shelf. The concept is deliberate: Izard is not chasing authenticity to one province but rather the full, sprawling emotional register of the genre.

The menu is built for sharing, and diners consistently point to the same anchors. The Crab Rangoon is known for its charred pineapple and sweet-and-sour sauce — Izard's way of taking a retro-classic and giving it a reason to exist in 2024. The Jiaozi Beef Short Rib & Bone Marrow Potstickers are widely regarded as the table-unifier, a rich filling in a reportedly crispy-bottomed wrapper that the kitchen has refined into a signature. From there, the Dan Dan Slap Noodles center on the numbing, sesame-forward heat the dish is known for — exactly the register this city calls for in colder months — while the Taiwanese Beef Noodle Soup is described by regulars as a long-braised, deeply built bowl, the kind that signals patience in the kitchen.

This is a strong group restaurant: the format rewards a larger table working through the menu collaboratively rather than ordering in isolation. Weekends book up, so reservations are worth securing in advance. Lead with the potstickers and noodles while the table is still decisive — the menu rewards momentum.