What to Drink With Dinner at City Winery Chicago
City Winery Chicago pours more than a dozen wines straight from the tap — which means every glass arrives fresh, consistent, and ready to work with whatever you're ordering. The mains menu covers a lot of ground, from composed salads to a 14-oz strip. This guide covers all of it.
Whether you're building a night around a show or settling in for a longer dinner, here's how to match what's on the tap list with what's coming out of the kitchen.
Salads
Kale Salad — Curly Kale, Savoy Cabbage, Fresh Herbs, Spicy Sunflower Seed Vinaigrette, Parmesan
Sauvignon Blanc — Windrem Vineyard, Lake County, CA '25
The Sauv Blanc's bright grapefruit, lime zest, and Meyer lemon are built for a vinaigrette with heat in it. The zippy acidity cuts through the Parmesan and keeps the whole plate tasting fresh. If you're adding a grilled chicken skewer, stay with the Sauv Blanc.
Caesar Salad — Little Gem, Chopped Kale, Reggiano, Herbed Breadcrumbs
Pinot Blanc — Old Mission Peninsula, MI '25
The Caesar needs something with enough structure to stand up to anchovy and Reggiano, but light enough not to compete with the dish. The Pinot Blanc — tart orchard fruit, zesty lime peel, long citrus finish — does exactly that. Precise and refreshing without being thin.
Or: Adding a grilled steak skewer shifts the pairing toward the Sonoma County Pinot Noir, where the ripe cherry and refined tannins meet the beef without overwhelming the greens.
Watermelon & Feta Salad — Arugula, Feta, Red Onion, Mint, Jalapeño Lime Dressing
Rosé of Chambourcin — Shawnee Hills, IL '24
This is the only Illinois wine on the tap list, and it earns its place here. Ripe strawberries, lemon, juicy melon, and a dry, mouthwatering finish — the Chambourcin rosé mirrors the fruit in the watermelon and has the acidity to handle the jalapeño lime dressing. The mint in the salad brings out something floral in the wine that you won't expect. Worth ordering.
Greek Farmers Salad — Barrel Aged Feta, Cucumbers, Tomatoes, Red Onion, Kalamata, Greek Oregano, Red Wine Vinegar, Olive Oil
Rosé of Chambourcin — Shawnee Hills, IL '24
Red wine vinegar plus kalamata olive is exactly the kind of acidic, briny combination that needs a wine with freshness and fruit behind it. The Chambourcin delivers both. If you're sharing this salad at the table as a starter, a half carafe goes a long way.
Burgers and Sandwiches
All served with French fries or mixed greens. Truffle fries available as an upgrade.
CW Burger — 8 oz Patty, Lettuce, Tomato, Onion, Pickle, American Cheese, Secret Sauce, Brioche Bun
Cabernet Sauvignon — Eli's Ridge Vineyard, Lake County, CA '24
Juicy cranberry and ripe red cherry up front, then a velvety, savory, earthy finish that lands perfectly against the secret sauce and American cheese.
Prosciutto & Pesto Smash Burger — Crispy Prosciutto, Basil Aioli, Peppadew Relish, Mozzarella, Brioche Bun
Cabernet Franc — Alder Springs Vineyard, Mendocino County, CA '22
Bright raspberry, roasted red pepper, black pepper, licorice, leather. The Cab Franc has enough acidity to cut through the basil aioli and enough structure to meet the prosciutto's salt. The Peppadew relish brings a sweet heat that the fruit in this wine handles well. A Cab Franc doing exactly what Cab Franc is supposed to do.
Truffle Smash Burger — Madeira Mushroom, Fontina, Truffle Aioli, Brioche Bun
Grenache — Alder Springs Vineyard, Mendocino, CA '22
Most people won't think to order this one with a burger. They should. The Grenache carries chocolate, dried fruit, bay leaf, and wild mushroom — which is essentially a flavor map of what the Madeira mushroom and truffle aioli are doing on the plate. It's a complex wine that rewards attention, and this burger gives it something real to work with.
Grilled Chicken Caprese — Grilled Chicken, Tomato Jam, Basil Aioli, Fresh Mozzarella, Dressed Spring Mix, Brioche Bun
Roussanne Reserve — Alder Springs Vineyard, Mendocino County, CA '25
Fresh apricot, butter croissant, baking spice, buttercream, caramel. The Roussanne is opulent without being heavy, and that balance makes it a natural partner for the fresh mozzarella and tomato jam here. The basil aioli pulls out the stone fruit in the wine. Full-bodied whites paired with grilled chicken often disappoint. This one doesn't.
Chicken Tinga Tacos — Braised Chicken, Avocado Crema, Baja Slaw, Queso Fresco, Cilantro, Corn Tortilla
Rosé of Chambourcin — Shawnee Hills, IL '24
The rosé's ripe strawberry and lemon brightness has exactly the refreshing acidity you want against braised chicken, avocado crema, and baja slaw. The corn tortilla keeps everything grounded. This is also the most food-friendly pour on the list at its price point. The Illinois provenance is a quiet bonus — a local wine with a dish that travels well.
Short Rib Grilled Cheese — Braised Short Rib, Havarti Dill, Crispy Onions, Creamy Horseradish, Rustic Bread
Syrah — Alder Springs Vineyard, Lake County, CA '23
Cedar, mesquite, fig, black pepper, bay leaf — the Syrah's structure is built for braised short rib, and the smokiness in the wine does something useful against the Havarti dill. The creamy horseradish is the detail that makes this pairing work rather than just coexist. A wine with backbone was the right call.
Buffalo Crispy Chicken Sandwich — Buffalo Blanc Sauce, Lettuce, Tomato, Onion, Pickle, Blue Cheese Dressing, Brioche Bun
Sauvignon Blanc — Windrem Vineyard, Lake County, CA '25
The acidity in the Sauv Blanc cuts right through buffalo sauce and blue cheese dressing, and its grapefruit and lime zest finish resets the palate between bites. A red wine next to buffalo heat tends to fight. This doesn't.
Or: The Pinot Blanc from Old Mission Peninsula — tart orchard fruit, zesty lime peel, long citrus finish — is a slightly softer move that works just as well.
Large Plates
Braised Short Rib — Braised Beef, Parsnip Puree, Gremolata, Crispy Parsnip
Syrah — Alder Springs Vineyard, Lake County, CA '23
The same pairing logic that works on the Short Rib Grilled Cheese applies here at full scale. The Syrah's cedar and mesquite aromatics play against the braised beef, and the gremolata — lemon zest, parsley, garlic — cuts through the richness in a way that the wine's acidity supports. The parsnip puree calls for something with body. The Syrah has it.
Or: The Cabernet Sauvignon from Eli's Ridge — velvety body, savory earthy finish — is the more classic move and equally at home with braised beef.
Spicy Rigatoni alla Vodka — Spicy Vodka Cream Sauce, Rigatoni, Extra Virgin Olive Oil
West Loop Red — American Wine '24
Fresh raspberry preserves, dark chocolate, ripe plum, black pepper. The West Loop Red is approachable enough to work with a cream sauce and has just enough spice in the finish to keep pace with the heat in the vodka sauce. It's also the most Chicago-specific wine on the list by name, which feels right for a dish this unfussy and satisfying.
Or: The Zinfandel from Bacigalupi Vineyard — jammy black raspberry, baking spice, sweet tobacco — is a bolder move that amplifies the spice rather than balancing it. Depends what you're after.
Seared Salmon — Pan Seared Salmon, Sweet Corn Puree, Grilled Broccolini, Fennel & Radish Salad
Chardonnay — Scopus Vineyard, Sonoma Mountain, CA '24
Rich tropical aromas of coconut and pineapple, full-bodied with bright acidity and a creamy texture. The Chardonnay's weight matches the salmon, its acidity cuts through the sweet corn puree, and the tropical notes echo the fennel and radish without competing with them. The tasting notes on this wine even suggest grilled seafood directly — which is about as clear a signal as a wine sends.
Or: The Roussanne Reserve — apricot, baking spice, buttercream — brings a more aromatic angle that's especially good against the fennel in the salad.
Lobster Ravioli — Lobster Mascarpone Ravioli, Lump Crab Meat, Crispy Brussels Sprouts, Peppadew Relish, Lobster Cream
Roussanne Reserve — Alder Springs Vineyard, Mendocino County, CA '25
This is the most luxurious dish on the mains menu, and the Roussanne Reserve is the tap list's most opulent white. Fresh apricot, butter croissant, caramel, buttercream — a wine that's already leaning into richness meets a lobster cream sauce without flinching. The Peppadew relish and crispy Brussels sprouts provide enough contrast to keep the plate from tipping into excess. Let the wine do the same work.
14 oz New York Strip — Garlic Mashed Potatoes, Baby Carrots, Au Poivre
Cabernet Sauvignon — Eli's Ridge Vineyard, Lake County, CA '24 / Reserve Wine List
For a cut this size, the reserve wine list is worth asking about. If you're staying on tap, the Cabernet Sauvignon — velvety body, ripe red cherry, savory earthy finish — holds up well against an au poivre preparation, where the peppercorn crust calls for a wine with enough fruit to soften the heat. The Syrah is also worth considering here: the black pepper and mesquite aromatics essentially mirror what's happening on the plate.
One More Note
The Riesling — Old Mission Peninsula, Michigan, off-dry with apple, peach, and a touch of spice — didn't anchor a primary pairing on this menu, but it's an easy pour for the table if the group is split or if someone wants something light and slightly sweet before the night gets going. It also handles spice well, so keep it in mind if you're ordering the Chicken Tinga Tacos and want something other than rosé.