Right near where Brent lived in Wicker Park, Mott St. became a favorite of ours for their Burger (voted #1 in Chicago by Thrillst)! It's available everywhere during brunch and from 6-7PM. After 7, it's only available at the bar so be sure to grab a spot!
Located in the heart of "Restaurant Row" in Chicago's West Loop neighborhood, Bar Siena is a favorite date night spot of ours. If you have room for dessert, be sure to stop by Bombobar - a walk-up window connected around the corner on Green Street. Closer to the Ambassador Hotel, their sister restaurant Siena Tavern is another great option in River North.