#1
Navy Pier, Downtown, the Loop & West LoopSun, Nov 1, 2026 · 1:00pmFree
Día de los Muertos at Navy Pier
Downtown, the Loop & West Loop
Día de los Muertos at Navy Pier at Navy Pier.
FreeOne Day Only
Outdoors in West Loop, Chicago Halloween Weekend 2026
4 picks
The 4 best outdoor picks in West Loop, Chicago over Halloween Weekend (Oct 30 – Nov 1)
- Día de los Muertos at Navy Pier — Sun, Nov 1 1:00pm · Free · Downtown
- Hot Chocolate Run Chicago — Sun, Nov 1 race times on official site · Downtown
- The Winter's Tale — Sat, Nov 7 7:00pm · Downtown
- City Cruises Chicago Seadog Haunted River Tour — Fri, Oct 30 3:00pm · $37 – $60 · Downtown
Navy Pier, Downtown, the Loop & West Loop#1Sun, Nov 1, 2026 · 1:00pm · One Day Only
Navy Pier, Downtown, the Loop & West Loop#2
Grant Park, Downtown, the Loop & West LoopSun, Nov 1, 2026 · race times on official site
Hot Chocolate Run Chicago
Downtown, the Loop & West Loop
Chicago's chocolate-themed race returns to Grant Park with 5K, 10K, 15K and two-mile routes.
One Weekend Only
#2Sun, Nov 1, 2026 · race times on official site · One Weekend Only
Grant Park, Downtown, the Loop & West LoopHot Chocolate Run Chicago
Chicago's chocolate-themed race returns to Grant Park with 5K, 10K, 15K and two-mile routes.
Add to calendar#3
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West LoopSat, Nov 7, 2026 · 7:00pm
The Winter's Tale
Downtown, the Loop & West Loop
The Winter's Tale at Chicago Shakespeare Theater.
Limited Run
#3Sat, Nov 7, 2026 · 7:00pm · Limited Run
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West Loop#4
City Cruises Chicago – Navy Pier, Downtown, the Loop & West LoopFri, Oct 30, 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.
Limited Run
#4Fri, Oct 30, 2026 · 3:00pm · Limited Run
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.
Add to calendarAbout this list
Stumblday's hand-checked ranking of the best outdoors in West Loop, Chicago, Downtown, the Loop & West Loop over Halloween weekend 2026 (Oct 30 – Nov 1): 4 picks.
