Stumblday's hand-checked ranking of the best things to do in Downtown, the Loop & West Loop the weekend of Oct 9–12, 2026: 97 picks, refreshed weekly.
97 picks · checked Sep 21
Grant Park, Downtown, the Loop & West LoopRaymondbritt · CC BY-SA 3.0 · Wikimedia CommonsA World Marathon Major winds through dozens of neighborhoods and cheering the route needs no bib.
Grant Park, Downtown, the Loop & West LoopRaymondbritt · CC BY-SA 3.0 · Wikimedia CommonsA World Marathon Major winds through dozens of neighborhoods and cheering the route needs no bib.
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Dearborn Street, Wacker Drive to Van Buren Street, The Loop, Downtown, the Loop & West LoopAlphaBeta135 · CC BY 4.0 · Wikimedia CommonsLou Gramm, Tony Danza and Cristiana Dell'Anna lead the march down Dearborn as grand marshals.
Dearborn Street, Wacker Drive to Van Buren Street, The Loop, Downtown, the Loop & West LoopAlphaBeta135 · CC BY 4.0 · Wikimedia CommonsLou Gramm, Tony Danza and Cristiana Dell'Anna lead the march down Dearborn as grand marshals.
Add to calendarThe stand-up legend does a live set at the Chicago Theatre, one night only.
The stand-up legend does a live set at the Chicago Theatre, one night only.
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McCormick Place, North Building, Hall B1, Near South Side, Downtown, the Loop & West LoopWarren LeMay from Chicago, IL, United States · CC BY-SA 2.0 · Wikimedia CommonsFree and open to anyone: marathon bib pickup and the whole race-weekend trade floor.
McCormick Place, North Building, Hall B1, Near South Side, Downtown, the Loop & West LoopWarren LeMay from Chicago, IL, United States · CC BY-SA 2.0 · Wikimedia CommonsFree and open to anyone: marathon bib pickup and the whole race-weekend trade floor.
Add to calendarIt lands the Friday before, plus every Friday until then. Unsubscribe anytime.
Beck opens two nights at the Auditorium on a new 25-date North American tour.
Beck opens two nights at the Auditorium on a new 25-date North American tour.
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Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopBeyond My Ken · CC BY-SA 4.0 · Wikimedia CommonsThomas Hampson joins the CSO, a double chorus and two brass bands for Walton's Babylon cantata.
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopBeyond My Ken · CC BY-SA 4.0 · Wikimedia CommonsThomas Hampson joins the CSO, a double chorus and two brass bands for Walton's Babylon cantata.
Add to calendarThe Fire take on New York City FC in an afternoon MLS match at Soldier Field.
The Fire take on New York City FC in an afternoon MLS match at Soldier Field.
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THE MART, River North, Downtown, the Loop & West LoopDavid Wilson from Oak Park, Illinois, USA · CC BY 2.0 · Wikimedia CommonsGalleries at every price point fill THE MART, with guidance for first-time buyers and collectors.
THE MART, River North, Downtown, the Loop & West LoopDavid Wilson from Oak Park, Illinois, USA · CC BY 2.0 · Wikimedia CommonsGalleries at every price point fill THE MART, with guidance for first-time buyers and collectors.
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CIBC Theatre, Downtown, the Loop & West LoopOnasill - Bill Badzo - 144 Million Views from Canada · Public domain · Wikimedia CommonsThe Olivier-winning musical about a WWII deception plot built around a dead body.
CIBC Theatre, Downtown, the Loop & West LoopOnasill - Bill Badzo - 144 Million Views from Canada · Public domain · Wikimedia CommonsThe Olivier-winning musical about a WWII deception plot built around a dead body.
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Lyric Opera House, Downtown, the Loop & West LoopZesmeralda · CC BY-SA 2.0 · Wikimedia CommonsLyric opens its 2026/27 season with the tale of a charismatic lord's spectacular downfall.
Lyric Opera House, Downtown, the Loop & West LoopZesmeralda · CC BY-SA 2.0 · Wikimedia CommonsLyric opens its 2026/27 season with the tale of a charismatic lord's spectacular downfall.
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Butler Field, Grant Park, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsThe part of marathon Sunday in Grant Park that needs no bib, to 4pm.
Butler Field, Grant Park, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsThe part of marathon Sunday in Grant Park that needs no bib, to 4pm.
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Wintrust Arena, 200 E Cermak Road, Downtown, the Loop & West LoopA WBA lightweight world title is on the line in an in-city arena boxing card.
Wintrust Arena, 200 E Cermak Road, Downtown, the Loop & West LoopA WBA lightweight world title is on the line in an in-city arena boxing card.
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Studebaker Theater, The Loop, Downtown, the Loop & West LoopAlexanderUtz · CC BY-SA 4.0 · Wikimedia CommonsThe Pulitzer winner's follow-up to Trust, in conversation at the 1898 Studebaker.
Studebaker Theater, The Loop, Downtown, the Loop & West LoopAlexanderUtz · CC BY-SA 4.0 · Wikimedia CommonsThe Pulitzer winner's follow-up to Trust, in conversation at the 1898 Studebaker.
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Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West Loopw_lemay · CC BY-SA 2.0 · Wikimedia CommonsThe gothic musical plays five weekend performances at Broadway Playhouse.
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West Loopw_lemay · CC BY-SA 2.0 · Wikimedia CommonsThe gothic musical plays five weekend performances at Broadway Playhouse.
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F1 Arcade, River North, Downtown, the Loop & West LoopA newly opened River North bar with 61 driving simulators, plus brisket tacos and burgers.
F1 Arcade, River North, Downtown, the Loop & West LoopA newly opened River North bar with 61 driving simulators, plus brisket tacos and burgers.
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Venues across Chicago, Citywide, Downtown, the Loop & West LoopMatt Reeves / Darkroom Demons · CC0 · Wikimedia CommonsThe citywide fashion calendar spans markets, runway shows and store events.
Venues across Chicago, Citywide, Downtown, the Loop & West LoopMatt Reeves / Darkroom Demons · CC0 · Wikimedia CommonsThe citywide fashion calendar spans markets, runway shows and store events.
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The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopA new play runs select dates at Chicago Shakespeare's Navy Pier stage.
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopA new play runs select dates at Chicago Shakespeare's Navy Pier stage.
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Grant Park, The Loop, Downtown, the Loop & West LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsThe official 5K sends marathon-weekend runners through a downtown course.
Grant Park, The Loop, Downtown, the Loop & West LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsThe official 5K sends marathon-weekend runners through a downtown course.
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Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsJohnny Galecki stars in this limited engagement about Williams meeting Brando.
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsJohnny Galecki stars in this limited engagement about Williams meeting Brando.
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The Auditorium, The Loop, Downtown, the Loop & West LoopJW Taylor,, photographer. · Public domain · Wikimedia CommonsBeck plays a second Auditorium night, a fallback if the first show sells out or won't fit.
The Auditorium, The Loop, Downtown, the Loop & West LoopJW Taylor,, photographer. · Public domain · Wikimedia CommonsBeck plays a second Auditorium night, a fallback if the first show sells out or won't fit.
Add to calendarA live orchestra plays Shoji Meguro's score for the ATLUS RPG, touring after selling out in Japan.
A live orchestra plays Shoji Meguro's score for the ATLUS RPG, touring after selling out in Japan.
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Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsThe CSO's season gala: Mäkelä conducts Walton's Babylon cantata with baritone Thomas Hampson.
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsThe CSO's season gala: Mäkelä conducts Walton's Babylon cantata with baritone Thomas Hampson.
Add to calendarSwitchfoot brings the Forever Now Tour to House of Blues Chicago with guest Anberlin.
Switchfoot brings the Forever Now Tour to House of Blues Chicago with guest Anberlin.
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Navy Pier, 600 E. Grand Ave., Downtown, the Loop & West LoopTenderFest @ East End Plaza at Navy Pier
Navy Pier, 600 E. Grand Ave., Downtown, the Loop & West Loop