A Logan Square café for brunch or a seasonal dinner. The current restaurant schedule separates afternoon service from dinner and keeps Tuesdays closed.
Belgian beer and a meal in Andersonville. Everyone entering must be 21 or older, so this is an adults’ outing rather than a family stop.
A jazz room in Uptown where the performance is the reason to go. Read the set and admission details before arriving; the room’s late-night programs vary by day.
A live band is part of the room. Choose the current set and seating for the evening you want.
Japanese drinks and small plates in the West Loop. Bar service and the weekend daytime café are separate visits; choose the room and menu when booking.
Chicago Over 50
Over 50 Chicago
A good meal, a favorite band or a neighborhood bar. Find an evening that feels like yours.
21 spots
Soccer, pub food and a neighborhood table on Ashland Avenue. The posted sports calendar is the useful starting point when an early match is the whole reason to go.
Vegan Asian-inspired dishes in a small Edgewater dining room. Chicago is walk-in only; the Glenview and Oak Park branches have different booking arrangements and menus.
A multi-course dinner in Lincoln Park where the meal is the evening’s main event. Choose the actual room and reservation; the current 2026 selection lists Two MICHELIN Stars.
Central Texas-inspired smoked meats and a drink in a warehouse-style West Loop room. The entrance is down the brick alley; choose the tray from the current menu.
Vegan comfort food, a full bar and a beer garden on North Avenue. The whole menu is not vegan: choose the marked dishes. The published weekly menu includes Sunday tacos with a beer and tequila shot.
Belgian beer and a meal in Andersonville. Everyone entering must be 21 or older, so this is an adults’ outing rather than a family stop.
Plant-based comfort food and brunch on Montrose Avenue. Wraps, burgers and loaded plates give a mixed group plenty to choose from without making a separate meal of the vegan order.
Filipino food with two very different visits: daytime bakery and counter service, or a reserved evening tasting menu. The 2026 Two MICHELIN Stars belong to the dinner restaurant.
Japanese drinks and small plates in the West Loop. Bar service and the weekend daytime café are separate visits; choose the room and menu when booking.
Rib tips and hot links connect this Chatham counter to Chicago’s own barbecue story. Takeout is the point here; this is the 75th Street restaurant.
A Logan Square café for brunch or a seasonal dinner. The current restaurant schedule separates afternoon service from dinner and keeps Tuesdays closed.
A reserved tasting dinner on Walnut Street in the West Loop. The current 2026 selection lists Two MICHELIN Stars; choose the restaurant’s own booking for the full evening.
A wood-smoked barbecue meal in Beverly. Meat is sliced to order, and the restaurant asks groups to order together so the meal moves through the line together.
Smoked meats beside Wrigley Field, with published Bears and Cowboys watch parties. This is the Wrigleyville restaurant; the former Wicker Park branch is closed.
Brisket, ribs and sides make this Pulaski Road smokehouse the meal. This is the original restaurant, separate from the former Smoque Steak business.
Plant-based soul food on 75th Street, with a deli counter and a sit-down meal. This is the Chicago restaurant formerly known as Original Soul Vegetarian.
Carhop service and a hot dog meal at the original Milwaukee Avenue drive-in. This is the Chicago location under the rooftop hot dogs, separate from Wheeling.
A meat-free diner meal with vegan shakes and a seitan Reuben. The menu marks vegan choices; this is the continuing Halsted Street location, separate from the closed Logan Square branch.
An international-sports pub in North Center with its own match schedule. Early opening depends on the fixture; use the current calendar rather than assuming every morning is the same.
A Memphis-style barbecue meal with a band in Pilsen. The former Honky Tonk BBQ now uses The Tonk name; the current restaurant address is on Racine Avenue.
A live band is part of the room. Choose the current set and seating for the evening you want.
A Streeterville pub with published game viewing. This is the Fairbanks Court location; suburban branches have their own calendars and should not be mixed into a Chicago visit.
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