Stumblday's hand-checked ranking of the best things to do in Downtown, the Loop & West Loop the weekend of Oct 2–4, 2026: 18 picks, refreshed weekly.
18 picks · checked Sep 10
CIBC Theatre, 18 West Monroe, Downtown, the Loop & West Loop(vincent desjardins) from Paris, France · CC BY 2.0 · Wikimedia CommonsOperation Mincemeat turns a bizarre Second World War deception plot into a musical comedy at the CIBC Theatre.
CIBC Theatre, 18 West Monroe, Downtown, the Loop & West Loop(vincent desjardins) from Paris, France · CC BY 2.0 · Wikimedia CommonsOperation Mincemeat turns a bizarre Second World War deception plot into a musical comedy at the CIBC Theatre.
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsMäkelä leads the orchestra through Mahler's Ninth at Orchestra Hall.
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsMäkelä leads the orchestra through Mahler's Ninth at Orchestra Hall.
The Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopUpstateherd · CC BY-SA 4.0 · Wikimedia CommonsBill Burr, host of the Monday Morning Podcast and creator of specials including Paper Tiger, takes his stand-up to the Chicago Theatre.
The Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopUpstateherd · CC BY-SA 4.0 · Wikimedia CommonsBill Burr, host of the Monday Morning Podcast and creator of specials including Paper Tiger, takes his stand-up to the Chicago Theatre.
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopDuke Ellington’s music carries Twelfth Night’s disguises and romantic mix-ups into 1930s Harlem in Play On!
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopDuke Ellington’s music carries Twelfth Night’s disguises and romantic mix-ups into 1930s Harlem in Play On!
Columbia College Chicago Dance Center, Downtown, the Loop & West LoopBeyond My Ken · CC BY-SA 4.0 · Wikimedia CommonsCerqua Rivera hosts a Latinx/e contemporary movement festival at the Dance Center for $35.
Columbia College Chicago Dance Center, Downtown, the Loop & West LoopBeyond My Ken · CC BY-SA 4.0 · Wikimedia CommonsCerqua Rivera hosts a Latinx/e contemporary movement festival at the Dance Center for $35.
Harris Theater for Music and Dance, Loop, Downtown, the Loop & West LoopYan Da (flicker user darajan) · CC BY 2.0 · Wikimedia CommonsSpend a day with ideas and live performances at Harris Theater as TEDxChicago explores collective action and belonging.
Harris Theater for Music and Dance, Loop, Downtown, the Loop & West LoopYan Da (flicker user darajan) · CC BY 2.0 · Wikimedia CommonsSpend a day with ideas and live performances at Harris Theater as TEDxChicago explores collective action and belonging.
Huntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West LoopZol87 · CC BY-SA 2.0 · Wikimedia CommonsMt. Joy marks ten years with an October concert at the Huntington Bank Pavilion on Northerly Island.
Huntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West LoopZol87 · CC BY-SA 2.0 · Wikimedia CommonsMt. Joy marks ten years with an October concert at the Huntington Bank Pavilion on Northerly Island.
Soldier Field, Downtown, the Loop & West LoopPhoto by Joon Han Contact: onejoon@hotmail.com · CC BY-SA 3.0 · Wikimedia CommonsThe Bears face the Jets at Soldier Field at noon.
Soldier Field, Downtown, the Loop & West LoopPhoto by Joon Han Contact: onejoon@hotmail.com · CC BY-SA 3.0 · Wikimedia CommonsThe Bears face the Jets at Soldier Field at noon.
The Auditorium, 50 E Ida B. Wells Drive, Downtown, the Loop & West LoopWarren LeMay · CC BY-SA 2.0 · Wikimedia CommonsThe Chicks play Taking the Long Way in full for its 20th anniversary, then close with catalog favorites at the Auditorium.
The Auditorium, 50 E Ida B. Wells Drive, Downtown, the Loop & West LoopWarren LeMay · CC BY-SA 2.0 · Wikimedia CommonsThe Chicks play Taking the Long Way in full for its 20th anniversary, then close with catalog favorites at the Auditorium.
Goodman Albert Theatre, Downtown, the Loop & West LoopThe Goodman premieres a 7 Fingers acrobatic theater piece set inside an attic.
Goodman Albert Theatre, Downtown, the Loop & West LoopThe Goodman premieres a 7 Fingers acrobatic theater piece set inside an attic.
Water Tower Place, Downtown, the Loop & West LoopChris Rycroft from Cambridge, Massachusetts, United States · CC BY 2.0 · Wikimedia CommonsWater Tower Place closes out its evening wear runway series, tickets $25 to $40.
Water Tower Place, Downtown, the Loop & West LoopChris Rycroft from Cambridge, Massachusetts, United States · CC BY 2.0 · Wikimedia CommonsWater Tower Place closes out its evening wear runway series, tickets $25 to $40.
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopOnFirstWhoIs · CC BY-SA 3.0 · Wikimedia CommonsKurt Elling and Lizz Wright join this show at Orchestra Hall, tickets from $39.
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopOnFirstWhoIs · CC BY-SA 3.0 · Wikimedia CommonsKurt Elling and Lizz Wright join this show at Orchestra Hall, tickets from $39.
Radius - Chicago, 640 West Cermak Rd, Downtown, the Loop & West LoopRuPaul takes the decks at Radius for an Auris house-and-disco night.
Radius - Chicago, 640 West Cermak Rd, Downtown, the Loop & West LoopRuPaul takes the decks at Radius for an Auris house-and-disco night.
Water Tower Place, Downtown, the Loop & West LoopChris Rycroft from Cambridge, Massachusetts, United States · CC BY 2.0 · Wikimedia CommonsA runway show takes over Water Tower Place, with tickets running $25 to $40.
Water Tower Place, Downtown, the Loop & West LoopChris Rycroft from Cambridge, Massachusetts, United States · CC BY 2.0 · Wikimedia CommonsA runway show takes over Water Tower Place, with tickets running $25 to $40.
Jack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West LoopA pumpkin-themed pop-up runs at Jack's Pumpkin Pop-Up downtown.
Jack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West LoopA pumpkin-themed pop-up runs at Jack's Pumpkin Pop-Up downtown.
Museum of Contemporary Photography, South Loop, Downtown, the Loop & West LoopViselippi · CC BY-SA 4.0 · Wikimedia CommonsThis free exhibition at the Museum of Contemporary Photography runs.
Museum of Contemporary Photography, South Loop, Downtown, the Loop & West LoopViselippi · CC BY-SA 4.0 · Wikimedia CommonsThis free exhibition at the Museum of Contemporary Photography runs.
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsCatch this film screening at the Gene Siskel Film Center afternoon.
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsCatch this film screening at the Gene Siskel Film Center afternoon.
Symphony Center-IL, 220 S. Michigan Ave., Downtown, the Loop & West LoopWarren LeMay from Chicago, IL, United States · CC BY-SA 2.0 · Wikimedia CommonsLudovico Einaudi brings a solo-piano evening to Symphony Center on the first Sunday in October.
Symphony Center-IL, 220 S. Michigan Ave., Downtown, the Loop & West LoopWarren LeMay from Chicago, IL, United States · CC BY-SA 2.0 · Wikimedia CommonsLudovico Einaudi brings a solo-piano evening to Symphony Center on the first Sunday in October.
