3 editor picks in Chicago.
3 rooftop bars in Chicago our editors have drunk at, sorted by score. All Chicago nightlife.
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.
TipWeekends 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.
TipOpen 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.
TipOpen daily from 17:00, weekends until 01:00. Sunset window books fast; weeknights walk in easy and the inside lounge stays open in winter.
Water activity · 1.5 hours
Climb aboard a 90 passenger historic riverboat & sip cocktails while cruising the Chicago River! Relax and learn about the history & architecture of the city via live ...
2 hours
Unleash your creativity with a fun paint and sip experience in Chicago. Enjoy a relaxed atmosphere with music, drinks, and plenty of laughs as you create your own masterpiece.
Guided tour · 2 hours
Discover Chicago's Ukrainian Village on a Mid-Century Cocktail Bar tour. Visit three hidden bars, enjoy craft cocktails & beers for you to purchase, and maybe experien...