The Hideout in Chicago is the Wabansia Avenue clapboard cottage in the Elston industrial corridor, hosting Americana, experimental and the Robbie Fulks Monday residency.
Tip: Tuesday through Thursday close at midnight, Friday and Saturday at 01:00. The room holds about 100 and the bands play through the bar conversation.
Address: 1354 W Wabansia Ave, Chicago, IL 60642
The Up Room crowns the 13th floor of The Robey, Wicker Park's tallest building, with a wraparound terrace facing the Loop skyline and the six-corners street.
Tip: Open daily from 17:00, weekends until 01:00. Sunset window books fast; weeknights walk in easy and the inside lounge stays open in winter.
Thalia Hall in Pilsen, built 1892 and modeled on the Prague State Opera House, runs touring indie, hip-hop and electronic shows in an 800-capacity balcony room.
Tip: Doors usually 19:00 with show at 20:00. The balcony bench seating fills first; Dusek's restaurant and Punch House bar share the building entrance.
Buddy Guy's Legends in Chicago is the South Wabash blues room the man himself opened in 1989 and where he still plays a residency every January.
Tip: Closed Monday and Tuesday. Wednesday and Thursday close at midnight; weekends run to 01:30. Cover usually $20, kitchen serves Louisiana barbecue.
Cindy's rooftop in Chicago sits on the 13th floor of the Chicago Athletic Association with all-season terrace seating that frames Millennium Park and Lake Michigan.
Tip: Weekends fill from 21:00; reserve via OpenTable or arrive at 16:00 for the sunset window. The terrace stays heated and open year-round.
LH Rooftop in Chicago crowns LondonHouse on the corner of Wacker and Michigan with three tiers of terrace facing the river and the Trump Tower clock face.
Tip: Open every day until midnight, food last call 22:00. The top tier is the photo spot; weekend brunch from 11:00 is the easy walk-in window.
The Up Room crowns the 13th floor of The Robey, Wicker Park's tallest building, with a wraparound terrace facing the Loop skyline and the six-corners street.
Tip: Open daily from 17:00, weekends until 01:00. Sunset window books fast; weeknights walk in easy and the inside lounge stays open in winter.
The Aviary in Chicago opened 2011 as Grant Achatz's Alinea Group cocktail lab, applying fine-dining technique to a five-course tasting of cocktails paired with small plates.
Tip: Tock reservations only, no walk-ins. The seasonal 5-course tasting is $145; sit at the bar to watch the kitchen build the drinks.