bars · Chicago
The best nights in Chicago start at these addresses — award-winning cocktail rooms, beloved locals' haunts and views worth ordering a second round for. All rated 4.5 stars or higher.
West Loop · $$
Grant Achatz applies Alinea-level technique to cocktails—drinks arrive in porthole infusers or under ice shells you crack open yourself. Seating is table service only, with optional tasting flights.
Insider tip: Reserve on Tock a few weeks ahead; standby walk-ins sometimes clear after 9pm on weeknights.
Wicker Park · $$
The speakeasy that launched Chicago's craft cocktail scene in 2007, hidden behind an unmarked, ever-repainted mural facade. It won the James Beard Award for Outstanding Bar Program in 2015.
Insider tip: Look for the single yellow lightbulb over the door and go before 7pm to skip the weekend line.
Uptown · $
Al Capone's favorite jazz club, pouring since 1907 with the original curved booths still in place. Live jazz plays seven nights a week, plus the long-running Sunday Uptown Poetry Slam.
Insider tip: It's cash only—bring bills and arrive before the first set to claim a booth.
The Loop · $$
A glasshouse rooftop atop the Chicago Athletic Association with a terrace hanging directly over Millennium Park and the lake. Punch bowls and seasonal cocktails come with the best Bean-adjacent view in town.
Insider tip: Walk-ins queue at the hotel's Michigan Avenue elevators—arrive before 5pm or book ahead for sunset.
Logan Square · $
A tiny, banana-leaf-wallpapered tiki bar from Paul McGee that has taken top honors at Tales of the Cocktail. Expect more than 100 rums and flaming shared bowls.
Insider tip: Seats are first-come and fill by 8pm on weekends; the daiquiri is the benchmark order.
River North · $$
A subterranean tiki temple reached down a skull-lined stairwell off an alley behind Clark Street. Its rum-heavy mugs and the flaming Treasure Chest for six made it a leader of the tiki revival.
Insider tip: Enter via the alley off Hubbard Street and book ahead Thursday through Saturday.
April–June & September–October
US Dollar (USD)
English
How this list is made: we only feature places rated 4.5 stars or higher with 1,000+ reviews from real travelers. Ratings and review counts are approximate and move over time — always check current numbers before booking. Photos are sourced from Wikimedia Commons under free licenses (credits in each gallery).
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Good to know
Three to four days covers the Loop's architecture and museums, a ballgame or blues club, and a neighborhood day in Wicker Park or Pilsen. Add a summer day for the lakefront beaches and an architecture river cruise.