You’ve seen the photos. Sunlight streaming through massive windows, lush greenery hanging from the ceiling, and glasses of Cabernet that look like they cost more than your first car. It’s easy to dismiss Oakville Grill and Cellar as just another "pretty" restaurant in Fulton Market. Honestly, Chicago has plenty of those. But there’s something different happening at the corner of Lake and Elizabeth. It’s not just a restaurant; it’s a very specific, very intentional love letter to Northern California, tucked away in the middle of a Midwestern industrial-chic neighborhood.
What is Oakville Grill and Cellar, Anyway?
People get confused. Is it a steakhouse? Is it a wine bar? Is it a brunch spot? Basically, it's all of those things, but filtered through a Napa Valley lens. This isn't the dark, moody, leather-booth vibe of a traditional Chicago chop house. Instead, the team at Lettuce Entertain You Enterprises—specifically Executive Chef Max Robbins—decided to lean into the airy, ingredient-focused ethos of Oakville, California.
The space is massive. We're talking 175 seats inside and a sprawling terrace that makes you forget you’re three blocks from a Google office. It feels like a vineyard estate. If you’ve ever spent a weekend driving down Highway 29 in Napa, you’ll recognize the textures: light woods, stone accents, and that specific shade of "California green" that feels expensive but approachable.
The wine list is the real star, though. It’s curated by Richard Hanauer, and it doesn't just feature California wines; it obsesses over them. They have one of the largest selections of 750ml and 1.5L bottles from the Oakville AVA (American Viticultural Area) in the entire country. That’s a bold claim for a place in Illinois, but they back it up with labels from Bond, Harlan Estate, and Silver Oak.
The Menu: It’s Not Just About the Wine
You might expect the food to be secondary to the cellar. It isn't. Chef Robbins, who previously put in serious time at Land and Sea and Bluegrass, treats the ingredients with a sort of reverence that is common in California but sometimes lost in the heavy-sauce culture of the Midwest.
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Take the Coal-Roasted Golden Beets.
Most places just throw beets on a plate with some goat cheese. Here, they're paired with pistachios and a citrus-honey vinaigrette that actually cuts through the earthiness. It’s simple. It’s bright. It’s exactly what you’d want to eat while sitting outside on a 75-degree day.
Then there’s the Rotisserie Chicken. It sounds boring, right? Every restaurant has a chicken dish for the person who doesn’t know what to order. But this one is brined, herb-rubbed, and slow-cooked until the skin is shatter-crisp. It’s served with a pan drippings jus that you’ll want to drink with a spoon. Honestly, it’s one of the best iterations of the bird in the city.
What to Order If You're Actually Hungry
- The Proper Burger: Two patties, American cheese, and a "secret sauce" that tastes suspiciously like a high-end In-N-Out.
- Steak Frites: They use a 10oz prime hanger steak. It’s tender, well-marbled, and topped with a herb butter that melts into the fries.
- Fresh Pasta: The menus rotate, but the Agnolotti with seasonal vegetables is usually a winner.
The Cellar Door Experience
One thing most people miss is "The Cellar Door." It’s a separate tasting room within the restaurant. If you’re a wine geek, this is your hallowed ground. They host monthly rotating tastings that focus on specific Napa producers. It’s meant to mimic the experience of visiting a tasting room in the valley without the $400 flight from O'Hare.
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You can walk in, try a flight of world-class Cabernets, and actually talk to someone who knows the soil types of the Vaca Mountains versus the Mayacamas. It's nerdy. It's niche. And it's incredibly well-done.
The prices? Yeah, they aren't cheap. You’re in Fulton Market. You’re drinking wine that was hand-carried from some of the most expensive real estate on earth. But the value is there if you appreciate the curation. You can find a $15 glass of Sauvignon Blanc, or you can drop four figures on a rare vintage. The choice is yours.
The Vibe Shift: Brunch vs. Dinner
Brunch at Oakville Grill and Cellar is a different beast entirely. It’s loud, it’s vibrant, and the "Lemon Poppyseed Pancakes" are legendary. They are thick, fluffy, and covered in a lemon curd that is tart enough to wake you up but sweet enough to feel like dessert.
Dinner is more refined. The lighting dims, the candles come out, and the volume drops just enough to have a real conversation. It’s a great date spot, mostly because the service is polished without being stiff. The servers actually know the menu. If you ask about the difference between a Rutherford Cab and an Oakville Cab, they won't stare at you blankly. They'll give you a three-minute masterclass.
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Real Talk: The Challenges
Is it perfect? Nothing is. On a Friday night, the noise level can get a bit "Chicago loud," which clashes with the zen-like California decor. And if you aren't a fan of West Coast wine, you might feel a bit limited by the list. They stay strictly in their lane. No French Bordeaux. No Italian Barolos. It’s California or bust.
Also, getting a reservation on the terrace during the summer is basically a combat sport. You need to book weeks in advance if you want those prime sunset vibes.
Practical Steps for Your Visit
- Book the Terrace Early: If the weather is even remotely nice, the outdoor seating fills up first. Use OpenTable or call the host directly three weeks out.
- Ask for the "Off-List" Pours: Sometimes the sommelier has a few bottles open for the Cellar Door that aren't on the main glass list. It never hurts to ask what’s being sampled that day.
- Don't Skip the Bread: The sourdough is served with a cultured butter that is dangerously good. Just order it.
- Explore the Neighborhood: Since you're already in Fulton Market, use Oakville as your "anchor" and hit up the nearby art galleries or grab a drink at one of the rooftops like The Hoxton or Soho House afterward.
- Check the Events Calendar: They frequently host "Meet the Winemaker" dinners. These are high-ticket items but offer unparalleled access to the people behind the labels.
Oakville Grill and Cellar succeeds because it doesn't try to be everything to everyone. It knows it’s a California embassy in a city of deep-dish and Italian beef. By leaning into that identity with high-quality ingredients and a world-class wine program, it has carved out a space that feels both luxurious and surprisingly relaxed. Whether you’re there for a quick burger at the bar or a three-hour tasting menu, the focus remains the same: good wine, fresh food, and a total lack of pretension.