#1
Sun, Oct 11, 2026 · 7:00pm
Olivia Rodrigo – The Unraveled Tour
Pop star's arena tour opens its two-night Chicago stand, with Wolf Alice as special guest.
One Weekend Only
Chicago: Weekend of Oct 9–12, 2026
Stumblday's hand-checked ranking of the best things to do in Chicago the weekend of Oct 9–12, 2026: 269 picks, refreshed weekly. Concerts, festivals, art, markets, and free outdoor events.
269 picks · checked Sep 21
269 picks
#1Sun, Oct 11, 2026 · 7:00pm · One Weekend Only
Olivia Rodrigo – The Unraveled Tour
Pop star's arena tour opens its two-night Chicago stand, with Wolf Alice as special guest.
Add to calendar#2
Sat, Oct 10, 2026 · 6:00pm
Chicago Blackhawks vs. Carolina Hurricanes
The Blackhawks host the Carolina Hurricanes for a night of NHL hockey at the United Center.
One Day Only
#2Sat, Oct 10, 2026 · 6:00pm · One Day Only
Chicago Blackhawks vs. Carolina Hurricanes
The Blackhawks host the Carolina Hurricanes for a night of NHL hockey at the United Center.
Add to calendar#3
Grant Park, Downtown, the Loop & West LoopRaymondbritt · CC BY-SA 3.0 · Wikimedia CommonsSunday, October 11, 2026, 7:30 AM start
Bank of America Chicago Marathon
A World Marathon Major winds through dozens of neighborhoods and cheering the route needs no bib.
Limited Run
#3Sunday, October 11, 2026, 7:30 AM start · Limited Run
Grant Park, Downtown, the Loop & West LoopRaymondbritt · CC BY-SA 3.0 · Wikimedia CommonsBank of America Chicago Marathon
A World Marathon Major winds through dozens of neighborhoods and cheering the route needs no bib.
Add to calendar#4
Dearborn Street, Wacker Drive to Van Buren Street, The Loop, Downtown, the Loop & West LoopAlphaBeta135 · CC BY 4.0 · Wikimedia CommonsMonday, October 12, 2026; opening ceremony at 12 PM at Dearborn Street and Wacker Drive, then the parade steps off south on Dearborn to Van Buren
74th Annual Chicago Columbus Day Parade
Lou Gramm, Tony Danza and Cristiana Dell'Anna lead the march down Dearborn as grand marshals.
One Day Only
#4Monday, October 12, 2026; opening ceremony at 12 PM at Dearborn Street and Wacker Drive, then the parade steps off south on Dearborn to Van Buren · One Day Only
Dearborn Street, Wacker Drive to Van Buren Street, The Loop, Downtown, the Loop & West LoopAlphaBeta135 · CC BY 4.0 · Wikimedia Commons74th Annual Chicago Columbus Day Parade
Lou Gramm, Tony Danza and Cristiana Dell'Anna lead the march down Dearborn as grand marshals.
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#5
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleJrbarc! · CC BY-SA 4.0 · Wikimedia CommonsSeptember 25–November 1, 2026; pumpkin patch open daily, live pumpkin carving weekends 10am–1pmFree
Fall Fest at Lincoln Park Zoo
Free harvest fun at the zoo: s'mores, pro pumpkin carvers, pick-your-own pumpkins and live music.
FreeLimited Run
#5September 25–November 1, 2026; pumpkin patch open daily, live pumpkin carving weekends 10am–1pm · Limited Run
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleJrbarc! · CC BY-SA 4.0 · Wikimedia CommonsFall Fest at Lincoln Park Zoo
Free harvest fun at the zoo: s'mores, pro pumpkin carvers, pick-your-own pumpkins and live music.
Add to calendar#6
Fri, Oct 9, 2026 · 7pm; Sat, Oct 10 · 5pm and 8pm
Jerry Seinfeld Live!
The stand-up legend does a live set at the Chicago Theatre, one night only.
One Weekend Only
#6Fri, Oct 9, 2026 · 7pm; Sat, Oct 10 · 5pm and 8pm · One Weekend Only
Jerry Seinfeld Live!
The stand-up legend does a live set at the Chicago Theatre, one night only.
Add to calendar#7
United Center, Near West Side, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsMonday, October 12, 2026, 7:00 PMTickets via Ticketmaster
Olivia Rodrigo: The Unraveled Tour – Night Two
The second of two United Center nights, on the holiday, is the other shot at a top pop act.
Limited Run
#7Monday, October 12, 2026, 7:00 PM · Limited Run
United Center, Near West Side, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsOlivia Rodrigo: The Unraveled Tour – Night Two
The second of two United Center nights, on the holiday, is the other shot at a top pop act.
Add to calendar#8
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 CommonsThursday, October 8 – Saturday, October 10, 2026Free and open to the public
Abbott Health & Fitness Expo
Free and open to anyone: marathon bib pickup and the whole race-weekend trade floor.
FreeOne Weekend Only
#8Thursday, October 8 – Saturday, October 10, 2026 · One Weekend Only
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 CommonsAbbott Health & Fitness Expo
Free and open to anyone: marathon bib pickup and the whole race-weekend trade floor.
Add to calendar#9
Fri, Oct 9, 2026 · 8:00pm
Beck – Ride Lonesome Tour
Beck opens two nights at the Auditorium on a new 25-date North American tour.
One Weekend Only
#9Fri, Oct 9, 2026 · 8:00pm · One Weekend Only
Beck – Ride Lonesome Tour
Beck opens two nights at the Auditorium on a new 25-date North American tour.
Add to calendar#10
Humboldt (Alexander Von) Park, Humboldt Park, Logan Square, Wicker Park & BucktownGazeboJake · CC0 · Wikimedia CommonsSunday, October 11, 2026, 3:00–5:00 PMFREE
Chicago Latino Dance Festival at Humboldt
Eight companies dance free and outdoors in Humboldt Park, from Afro-Latin to folkloric styles.
FreeOne Day Only
#10Sunday, October 11, 2026, 3:00–5:00 PM · One Day Only
Humboldt (Alexander Von) Park, Humboldt Park, Logan Square, Wicker Park & BucktownGazeboJake · CC0 · Wikimedia CommonsChicago Latino Dance Festival at Humboldt
Eight companies dance free and outdoors in Humboldt Park, from Afro-Latin to folkloric styles.
Add to calendar#11
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopBeyond My Ken · CC BY-SA 4.0 · Wikimedia CommonsFri, Oct 9, 2026 · 7:30pm
Mäkelä, Petrushka & Belshazzar’s Feast
Thomas Hampson joins the CSO, a double chorus and two brass bands for Walton's Babylon cantata.
One Day Only
#11Fri, Oct 9, 2026 · 7:30pm · One Day Only
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopBeyond My Ken · CC BY-SA 4.0 · Wikimedia CommonsMäkelä, Petrushka & Belshazzar’s Feast
Thomas Hampson joins the CSO, a double chorus and two brass bands for Walton's Babylon cantata.
Add to calendar#12
Saturday, October 10, 2026, 1:30 PM
Chicago Fire FC vs. New York City FC
The Fire take on New York City FC in an afternoon MLS match at Soldier Field.
One Day Only
#12Saturday, October 10, 2026, 1:30 PM · One Day Only
Chicago Fire FC vs. New York City FC
The Fire take on New York City FC in an afternoon MLS match at Soldier Field.
Add to calendar#13
THE MART, River North, Downtown, the Loop & West LoopDavid Wilson from Oak Park, Illinois, USA · CC BY 2.0 · Wikimedia CommonsOctober 7–10, 2026 · Wed 5–8 PM; Thu–Fri 11 AM–8 PM; Sat 11 AM–6 PMTickets via the fair's website
Chicago Art Fair
Galleries at every price point fill THE MART, with guidance for first-time buyers and collectors.
ArtOne Weekend Only
#13October 7–10, 2026 · Wed 5–8 PM; Thu–Fri 11 AM–8 PM; Sat 11 AM–6 PM · One Weekend Only
THE MART, River North, Downtown, the Loop & West LoopDavid Wilson from Oak Park, Illinois, USA · CC BY 2.0 · Wikimedia CommonsChicago Art Fair
Galleries at every price point fill THE MART, with guidance for first-time buyers and collectors.
Add to calendar#14
CIBC Theatre, Downtown, the Loop & West LoopOnasill - Bill Badzo - 144 Million Views from Canada · Public domain · Wikimedia CommonsThrough Oct 11, 2026
Operation Mincemeat: A New Musical
The Olivier-winning musical about a WWII deception plot built around a dead body.
One Weekend Only
#14Through Oct 11, 2026 · One Weekend Only
CIBC Theatre, Downtown, the Loop & West LoopOnasill - Bill Badzo - 144 Million Views from Canada · Public domain · Wikimedia CommonsOperation Mincemeat: A New Musical
The Olivier-winning musical about a WWII deception plot built around a dead body.
Add to calendar#15
Sun, Oct 11, 2026 · 7:00pm
Interpol – 2026 North American Tour
The band's North American tour hits the Salt Shed, with DIIV as special guest.
One Day Only
#15Sun, Oct 11, 2026 · 7:00pm · One Day Only
Interpol – 2026 North American Tour
The band's North American tour hits the Salt Shed, with DIIV as special guest.
Add to calendar#16
Lyric Opera House, Downtown, the Loop & West LoopZesmeralda · CC BY-SA 2.0 · Wikimedia CommonsSat, Oct 10, 2026 · 7:30pm
Don Giovanni
Lyric opens its 2026/27 season with the tale of a charismatic lord's spectacular downfall.
One Day Only
#16Sat, Oct 10, 2026 · 7:30pm · One Day Only
Lyric Opera House, Downtown, the Loop & West LoopZesmeralda · CC BY-SA 2.0 · Wikimedia CommonsDon Giovanni
Lyric opens its 2026/27 season with the tale of a charismatic lord's spectacular downfall.
Add to calendar#17
Fri, Oct 9, 2026 · 7:00pm
Muna – Gets So Hot Tour
MUNA plays an outdoor show at The Salt Shed, with Hemlocke Springs opening the night.
One Day Only
#17Fri, Oct 9, 2026 · 7:00pm · One Day Only
Muna – Gets So Hot Tour
MUNA plays an outdoor show at The Salt Shed, with Hemlocke Springs opening the night.
Add to calendar#18
Byline Bank Aragon Ballroom, Andersonville, Uptown & Lincoln SquareFri, Oct 9, 2026 · 7:30pm
Shaboozey – Outlaws Never Die Tour
The singer behind the smash "A Bar Song (Tipsy)" brings his tour to the Aragon Ballroom.
One Day Only
#18Fri, Oct 9, 2026 · 7:30pm · One Day Only
Byline Bank Aragon Ballroom, Andersonville, Uptown & Lincoln SquareShaboozey – Outlaws Never Die Tour
The singer behind the smash "A Bar Song (Tipsy)" brings his tour to the Aragon Ballroom.
Add to calendar#19
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 7:30pm
Topdog/Underdog
Topdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Limited Run
#19Fri, Oct 9, 2026 · 7:30pm · Limited Run
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleTopdog/Underdog
Topdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Add to calendar#20
Sat, Oct 10, 2026 · 7:30pm
Jpegmafia – The Experimental Rap Tour
JPEGMAFIA takes the Aragon Ballroom stage with special guests redveil and matt proxy.
One Day Only
#20Sat, Oct 10, 2026 · 7:30pm · One Day Only
Jpegmafia – The Experimental Rap Tour
JPEGMAFIA takes the Aragon Ballroom stage with special guests redveil and matt proxy.
Add to calendar#21
Ryan Field, Evanston, Evanston & Oak ParkGreenstrat at English Wikipedia · Public domain · Wikimedia CommonsSaturday, October 10, 2026, kickoff time to be announcedTickets via Northwestern Athl…
Northwestern vs. Ball State
Northwestern plays its Homecoming football game, the only major college home game near Chicago.
Limited Run
#21Saturday, October 10, 2026, kickoff time to be announced · Limited Run
Ryan Field, Evanston, Evanston & Oak ParkGreenstrat at English Wikipedia · Public domain · Wikimedia CommonsNorthwestern vs. Ball State
Northwestern plays its Homecoming football game, the only major college home game near Chicago.
Add to calendar#22
Jonquil Park, Lincoln Park, Lakeview & WrigleyvilleWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsOctober 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pmGeneral admission from $30
Lincoln Park Wine Fest
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
One Weekend Only
#22October 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pm · One Weekend Only
Jonquil Park, Lincoln Park, Lakeview & WrigleyvilleWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsLincoln Park Wine Fest
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
Add to calendar#23
Butler Field, Grant Park, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsSunday, October 11, 2026, 9:30 AM–4:00 PM
27th Mile Post-Race Party
The part of marathon Sunday in Grant Park that needs no bib, to 4pm.
One Day Only
#23Sunday, October 11, 2026, 9:30 AM–4:00 PM · One Day Only
Butler Field, Grant Park, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia Commons27th Mile Post-Race Party
The part of marathon Sunday in Grant Park that needs no bib, to 4pm.
Add to calendar#24
Pullman Exhibit Hall, Pullman, Hyde Park, Bronzeville & the South SideJ. W. Taylor · public domain · Wikimedia CommonsSaturday–Sunday, October 10–11, 2026, 11 a.m.–5 p.m.$21 advance through October 8
53rd Annual Historic Pullman House Tour
The 53rd Pullman House Tour opens private landmark interiors across the historic neighborhood.
One Weekend Only
#24Saturday–Sunday, October 10–11, 2026, 11 a.m.–5 p.m. · One Weekend Only
Pullman Exhibit Hall, Pullman, Hyde Park, Bronzeville & the South SideJ. W. Taylor · public domain · Wikimedia Commons53rd Annual Historic Pullman House Tour
The 53rd Pullman House Tour opens private landmark interiors across the historic neighborhood.
Add to calendar