#1
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West LoopFri, Oct 23, 2026 · 7:00pm
The Winter's Tale
Downtown, the Loop & West Loop
The Winter's Tale at Chicago Shakespeare Theater.
One Weekend Only
Outdoors in West Loop, Chicago the Weekend of Oct 23–25, 2026
Hand-picked every week — checked against organizers’ own pages.
Stumblday's hand-checked ranking of the best outdoors in West Loop, Chicago, Downtown, the Loop & West Loop the weekend of Oct 23–25, 2026: 2 picks.
2 picks · checked Oct 6
2 picks
The 2 picks
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West Loop#1Fri, Oct 23, 2026 · 7:00pm · One Weekend Only
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West Loop#2
City Cruises Chicago – Navy Pier, Downtown, the Loop & West LoopFri, Oct 23, 2026 · 3:00pm$37 – $60
City Cruises Chicago Seadog Haunted River Tour
Downtown, the Loop & West Loop
City Cruises Chicago Seadog Haunted River Tour at City Cruises Chicago – Navy Pier.
One Weekend Only
#2Fri, Oct 23, 2026 · 3:00pm · One Weekend Only
City Cruises Chicago – Navy Pier, Downtown, the Loop & West LoopCity Cruises Chicago Seadog Haunted River Tour
City Cruises Chicago Seadog Haunted River Tour at City Cruises Chicago – Navy Pier.
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