#1
Sun, Oct 11, 2026 · 7:00pm
Olivia Rodrigo – The Unraveled Tour
Pilsen, West Town & the West Side
Pop star's arena tour opens its two-night Chicago stand, with Wolf Alice as special guest.
One Weekend Only
New York: Columbus Day Weekend 2026
270 picks
The 10 best things to do in Chicago over Columbus Day Weekend (Oct 9–12)
- Olivia Rodrigo – The Unraveled Tour — Sun, Oct 11 7:00pm · Pilsen
- Chicago Blackhawks vs. Carolina Hurricanes — Sat, Oct 10 6:00pm · Pilsen
- Bank of America Chicago Marathon — Sunday, October 11, 7:30 AM start · Downtown
- 74th Annual Chicago Columbus Day Parade — Monday, October 12 · Wacker Drive to Van Buren Street
- Jerry Seinfeld Live! — Fri, Oct 9 7pm; Sat, Oct 10 · 5pm and 8pm · Downtown
- Fall Fest at Lincoln Park Zoo — Sep 25–Oct 18, 2026 · Free · Lincoln Park
- Abbott Health & Fitness Expo — Thursday, October 8 – Saturday, October 10 · Free · Downtown
- Beck – Ride Lonesome Tour — Fri, Oct 9 8:00pm · Downtown
- Chicago Latino Dance Festival at Humboldt — Sunday, October 11, 3:00–5:00 PM · Free · Logan Square
- Mäkelä, Petrushka & Belshazzar’s Feast — Fri, Oct 9 7:30pm · Downtown
What's free this weekend?
- Family Day | Warmups — Saturday, October 10 11 AM–3 PM · Free · Downtown
- Chicago Zine Fest 2026 — Saturday, October 10 11 AM–4 PM · Free · Loop
- teamLab & Allison Martino in Conversation — Sunday, October 11 4–5 PM · Free · Hyde Park
- The Paper Machete — Saturdays at 3pm (doors 1pm) · Free · Uptown
- Indigenous Peoples' Day Celebration at Harrison — Saturday, October 10, 11am–4pm · Free · Pilsen
#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 · 6:00pmPaid ticket required
Chicago Blackhawks vs. Carolina Hurricanes
Pilsen, West Town & the West Side
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
Downtown, the Loop & West Loop
The Chicago Marathon sends runners through the city before a Grant Park finish.
One Day Only
#3Sunday, October 11, 2026, 7:30 AM start · One Day Only
Grant Park, Downtown, the Loop & West LoopRaymondbritt · CC BY-SA 3.0 · Wikimedia CommonsBank of America Chicago Marathon
The Chicago Marathon sends runners through the city before a Grant Park finish.
Add to calendar#4
Dearborn Street, Wacker Drive to Van Buren Street, The 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
Wacker Drive to Van Buren Street, The Loop
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 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.
Add to calendar#5
Fri, Oct 9, 2026 · 7pm; Sat, Oct 10 · 5pm and 8pmTicket required
Jerry Seinfeld Live!
Downtown, the Loop & West Loop
The stand-up legend does a live set at the Chicago Theatre, one night only.
One Weekend Only
#5Fri, 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#6
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleSep 25, 2026–Oct 18, 2026Free
Fall Fest at Lincoln Park Zoo
Lincoln Park, Lakeview & Wrigleyville
Fall Fest at Lincoln Park Zoo is listed for Chicago this weekend.
FreeLimited Run
#6Sep 25, 2026–Oct 18, 2026 · Limited Run
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleFall Fest at Lincoln Park Zoo
Fall Fest at Lincoln Park Zoo is listed for Chicago this weekend.
Add to calendar#7
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
Downtown, the Loop & West Loop
Free and open to anyone: marathon bib pickup and the whole race-weekend trade floor.
FreeOne Weekend Only
#7Thursday, 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#8
Fri, Oct 9, 2026 · 8:00pm
Beck – Ride Lonesome Tour
Downtown, the Loop & West Loop
Beck opens two nights at the Auditorium on a new 25-date North American tour.
One Weekend Only
#8Fri, 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#9
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
Logan Square, Wicker Park & Bucktown
Eight companies dance free and outdoors in Humboldt Park, from Afro-Latin to folkloric styles.
FreeOne Day Only
#9Sunday, 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#10
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
Downtown, the Loop & West Loop
Thomas Hampson joins the CSO, a double chorus and two brass bands for Walton's Babylon cantata.
One Day Only
#10Fri, 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 calendarMore this weekend
#11
Saturday, October 10, 2026, 1:30 PM
Chicago Fire FC vs. New York City FC
Downtown, the Loop & West Loop
The Fire take on New York City FC in an afternoon MLS match at Soldier Field.
One Day Only
#11Saturday, 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#12
Jonquil Park, Lincoln ParkWarren 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
Jonquil Park, Lincoln Park
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
One Weekend Only
#12October 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pm · One Weekend Only
Jonquil Park, Lincoln ParkWarren 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#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
Downtown, the Loop & West Loop
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
Downtown, the Loop & West Loop
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.
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#15
Sun, Oct 11, 2026 · 7:00pm
Interpol – 2026 North American Tour
Logan Square, Wicker Park & Bucktown
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 HouseOct 10, 2026–Oct 18, 2026
Don Giovanni
Lyric Opera House
Don Giovanni is listed for Chicago this weekend.
Limited Run
#16Oct 10, 2026–Oct 18, 2026 · Limited Run
Lyric Opera House#17
Fri, Oct 9, 2026 · 7:00pm
Muna – Gets So Hot Tour
Logan Square, Wicker Park & Bucktown
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, UptownFri, Oct 9, 2026 · 7:30pm
Shaboozey – Outlaws Never Die Tour
Byline Bank Aragon Ballroom, Uptown
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, UptownShaboozey – 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 & WrigleyvilleRuns September 18–October 18, 2026; weekend performances.
Topdog/Underdog
Lincoln Park, Lakeview & Wrigleyville
Topdog/Underdog brings its two-brother drama to Steppenwolf’s Downstairs Theater.
Limited Run
#19Runs September 18–October 18, 2026; weekend performances. · Limited Run
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleTopdog/Underdog
Topdog/Underdog brings its two-brother drama to Steppenwolf’s Downstairs Theater.
Add to calendar#20
Ryan Field, EvanstonGreenstrat at English Wikipedia · Public domain · Wikimedia CommonsSaturday, October 10, 2026, kickoff time to be announcedTickets via Northwestern Athl…
Northwestern vs. Ball State
Ryan Field, Evanston
Northwestern hosts Ball State for a college football matchup at Ryan Field.
Limited Run
#20Saturday, October 10, 2026, kickoff time to be announced · Limited Run
Ryan Field, EvanstonGreenstrat at English Wikipedia · Public domain · Wikimedia CommonsNorthwestern vs. Ball State
Northwestern hosts Ball State for a college football matchup at Ryan Field.
Add to calendar#21
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
Downtown, the Loop & West Loop
The part of marathon Sunday in Grant Park that needs no bib, to 4pm.
One Day Only
#21Sunday, 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#22
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
Hyde Park, Bronzeville & the South Side
The 53rd Pullman House Tour opens private landmark interiors across the historic neighborhood.
One Weekend Only
#22Saturday–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#23
Downtown St. Charles, St. Charles, Far SuburbsAneekr at English Wikipedia · CC BY-SA 3.0 · Wikimedia CommonsFriday, October 9 – Sunday, October 11, 2026
St. Charles Scarecrow Weekend
St. Charles, Far Suburbs
Scarecrow Weekend fills downtown St. Charles with displays and fall activities.
One Weekend Only
#23Friday, October 9 – Sunday, October 11, 2026 · One Weekend Only
Downtown St. Charles, St. Charles, Far SuburbsAneekr at English Wikipedia · CC BY-SA 3.0 · Wikimedia CommonsSt. Charles Scarecrow Weekend
Scarecrow Weekend fills downtown St. Charles with displays and fall activities.
Add to calendar#24
Fri, Oct 9, 2026 · 7:00pm
Pre-Season: Chicago Bulls v Memphis Grizzlies
Pilsen, West Town & the West Side
The Bulls play the Memphis Grizzlies in an NBA preseason game at the United Center.
One Day Only
#24Fri, Oct 9, 2026 · 7:00pm · One Day Only
Pre-Season: Chicago Bulls v Memphis Grizzlies
The Bulls play the Memphis Grizzlies in an NBA preseason game at the United Center.
Add to calendarAbout this list
Stumblday's hand-checked ranking of the best things to do in Chicago over Columbus Day weekend 2026 (Oct 10–12): 270 picks, refreshed weekly. Concerts, festivals, art, markets, and free outdoor events. Monday is the Columbus Day / Indigenous Peoples' Day holiday.