Lunch/Cocktails at Cindy's Rooftop Bar (Loop) - There's no better view than Cindy's Rooftop Bar overlooking Millennium and Grant Parks. Located in the storied Chicago Athletic Association hotel, this semi-hidden gem will feel like a retreat within the city. The views at sunset are stunning but the best time to get a seat is between lunch and dinner.
Nearby Routes: CTA Buses #3, 4, 26, 143, 147, 151, J14; CTA Brown, Green, Orange, Pink and Purple Line Trains
Thalia Hall (Pilsen) - Thalia Hall, an iconic Chicago music venue and historic landmark, is a must-see. Built in 1892, the stone building has the feel of an old Bohemian theater inside. Known for its excellent acoustics, intimate atmosphere, and for bringing in some of the best comics and musicians coming through Chicago like Dave Chapelle, Joss Stone, Jenny Slate, Courtney Barnett & Kurt Vile.
Nearby Routes: CTA Bus #18 16th/Cicero; CTA Bus #60 - Blue Island; CTA Pink Line Train, Metra BNSF Line
Concert under the stars at Ravinia (Ravinia Park) - Pack your picnic basket and bring your wine because there's no better way to end a summer day in Chicagoland than taking in a concert under the stars at Ravina. It's a romantic, relaxing, and refreshing end to a great day in Chicago with your favorite person.
Nearby Routes: Metra UP-North Line; Pace Bus #213