#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
Things to Do in Chicago on Columbus Day Monday, Oct 12
138 picks
The 10 best things to do in Chicago on Columbus Day Monday, Oct 12
- Olivia Rodrigo – The Unraveled Tour — Sun, Oct 11 7:00pm · Pilsen
- 74th Annual Chicago Columbus Day Parade — Monday, October 12 · Wacker Drive to Van Buren Street
- Fall Fest at Lincoln Park Zoo — Sep 25–Oct 18, 2026 · Free · Lincoln Park
- Don Giovanni — Oct 10–Oct 18, 2026 · Lyric Opera House
- Topdog/Underdog — Runs September 18–October 18 · Lincoln Park
- Olivia Rodrigo: The Unraveled Tour – Night Two — Monday, October 12, 7:00 PM · Pilsen
- Jekyll& Hyde — Oct 2–Oct 18, 2026 · Downtown
- Night of 1,000 Jack-o'-Lanterns — October 7–11, 14–18 and 21–25, 6:30–10:30 PM · Adults from $24 for nonmember… · Glencoe
- F1 Arcade — Open this weekend — recently opened · Downtown
- Chicago Fashion Week — October 8–18; events at venues across the city · Downtown
#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
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
#2Monday, 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#3
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
#3Sep 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#4
Lyric Opera HouseOct 10, 2026–Oct 18, 2026
Don Giovanni
Lyric Opera House
Don Giovanni is listed for Chicago this weekend.
Limited Run
#4Oct 10, 2026–Oct 18, 2026 · Limited Run
Lyric Opera House#5
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
#5Runs 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#6
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
Pilsen, West Town & the West Side
Olivia Rodrigo returns to the United Center for night two of the Unraveled Tour.
One Day Only
#6Monday, October 12, 2026, 7:00 PM · One Day Only
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
Olivia Rodrigo returns to the United Center for night two of the Unraveled Tour.
Add to calendar#7
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West LoopOct 2, 2026–Oct 18, 2026
Jekyll& Hyde
Downtown, the Loop & West Loop
Jekyll& Hyde is listed for Chicago this weekend.
Limited Run
#7Oct 2, 2026–Oct 18, 2026 · Limited Run
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West Loop#8
Chicago Botanic Garden, Glencoe, Far Suburbscultivar413 · CC BY 2.0 · Wikimedia CommonsOctober 7–11, 14–18 and 21–25, 2026, 6:30–10:30 PMAdults from $24 for nonmember…
Night of 1,000 Jack-o'-Lanterns
Glencoe, Far Suburbs
Seventy-five giant pumpkins, live carving and performers light a three-night garden walk.
One Weekend Only
#8October 7–11, 14–18 and 21–25, 2026, 6:30–10:30 PM · One Weekend Only
Chicago Botanic Garden, Glencoe, Far Suburbscultivar413 · CC BY 2.0 · Wikimedia CommonsNight of 1,000 Jack-o'-Lanterns
Seventy-five giant pumpkins, live carving and performers light a three-night garden walk.
Add to calendar#9
F1 Arcade, River North, Downtown, the Loop & West LoopOpen this weekend — recently opened
F1 Arcade
Downtown, the Loop & West Loop
F1 Arcade is listed for Chicago this weekend.
Limited Run
#9Open this weekend — recently opened · Limited Run
F1 Arcade, River North, Downtown, the Loop & West Loop#10
Venues across Chicago, Citywide, Downtown, the Loop & West LoopMatt Reeves / Darkroom Demons · CC0 · Wikimedia CommonsOctober 8–18, 2026; events at venues across the city
Chicago Fashion Week
Downtown, the Loop & West Loop
The citywide fashion calendar spans markets, runway shows and store events.
Limited Run
#10October 8–18, 2026; events at venues across the city · Limited Run
Venues across Chicago, Citywide, Downtown, the Loop & West LoopMatt Reeves / Darkroom Demons · CC0 · Wikimedia CommonsChicago Fashion Week
The citywide fashion calendar spans markets, runway shows and store events.
Add to calendarMore on Columbus Day Monday
#11
Griffin Museum of Science and IndustryOct 10, 2026–Oct 16, 2026$40.00
Escape the Museum at Griffin Museum of Science and Industry
Griffin Museum of Science and Industry
Escape the Museum at Griffin Museum of Science and Industry is listed for Chicago this weekend.
ArtOne Weekend Only
#11Oct 10, 2026–Oct 16, 2026 · One Weekend Only
Griffin Museum of Science and IndustryEscape the Museum at Griffin Museum of Science and Industry
Escape the Museum at Griffin Museum of Science and Industry is listed for Chicago this weekend.
Add to calendar#12
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopSeptember 11–October 18, 2026; selected performances
Play On! — Chicago Shakespeare Theater
Downtown, the Loop & West Loop
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Limited Run
#12September 11–October 18, 2026; selected performances · Limited Run
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopPlay On! — Chicago Shakespeare Theater
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Add to calendar#13
Historic Main Stage at Athenaeum Center, Lincoln Park, Lakeview & WrigleyvilleKeiko Oikawa · Public domain · Wikimedia CommonsMon, Oct 12, 2026 · 7:30pm
Simple TOO Live: An Evening with Yotam Ottolenghi
Lincoln Park, Lakeview & Wrigleyville
Chef Yotam Ottolenghi talks through his new cookbook, the follow-up to Ottolenghi Simple, live.
One Day Only
#13Mon, Oct 12, 2026 · 7:30pm · One Day Only
Historic Main Stage at Athenaeum Center, Lincoln Park, Lakeview & WrigleyvilleKeiko Oikawa · Public domain · Wikimedia CommonsSimple TOO Live: An Evening with Yotam Ottolenghi
Chef Yotam Ottolenghi talks through his new cookbook, the follow-up to Ottolenghi Simple, live.
Add to calendar#14
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsSeptember 15 – October 25, 2026Ticketed via Lookingglass The…
Kowalski
Downtown, the Loop & West Loop
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Limited Run
#14September 15 – October 25, 2026 · Limited Run
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsKowalski
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Add to calendarThe whole weekend, in one email.
Friday at 5pm, one email. Unsubscribe anytime.
#15
Richard H. Driehaus Museum, River North, Downtown, the Loop & West LoopOctober 9, 2026 – April 18, 2027Adults $23
Emma Stebbins: Carving Out History
Downtown, the Loop & West Loop
Emma Stebbins: Carving Out History
ArtLimited Run
#15October 9, 2026 – April 18, 2027 · Limited Run
Richard H. Driehaus Museum, River North, Downtown, the Loop & West Loop#16
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleOct 2, 2026–Oct 18, 2026
Vladimir
Lincoln Park, Lakeview & Wrigleyville
Vladimir is listed for Chicago this weekend.
Limited Run
#16Oct 2, 2026–Oct 18, 2026 · Limited Run
Theater Wit, Lincoln Park, Lakeview & Wrigleyville#17
Music Box Theatre, Southport Corridor, LakeviewSunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM$20 individual programs
Cinema Femme Short Film Festival 2026
Southport Corridor, Lakeview
The festival opens Sunday, then pairs a panel with two shorts programs.
One Weekend Only
#17Sunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM · One Weekend Only
Music Box Theatre, Southport Corridor, LakeviewCinema Femme Short Film Festival 2026
The festival opens Sunday, then pairs a panel with two shorts programs.
Add to calendar#18
Brookfield Zoo ChicagoOct 3, 2026–Oct 18, 2026
BOO! at the Zoo
Brookfield Zoo Chicago
BOO! at the Zoo is listed for Chicago this weekend.
Limited Run
#18Oct 3, 2026–Oct 18, 2026 · Limited Run
Brookfield Zoo Chicago#19
Chicago History Museum, Lincoln ParkGoldnpuppy · CC BY-SA 3.0 · Wikimedia CommonsMonday, October 12, 2026 · 9:30 AM–4:30 PM
Chicago History Museum Illinois Resident Free Day
Chicago History Museum, Lincoln Park
Illinois residents get free Monday access to the museum’s permanent and temporary shows.
FreeOne Day Only
#19Monday, October 12, 2026 · 9:30 AM–4:30 PM · One Day Only
Chicago History Museum, Lincoln ParkGoldnpuppy · CC BY-SA 3.0 · Wikimedia CommonsChicago History Museum Illinois Resident Free Day
Illinois residents get free Monday access to the museum’s permanent and temporary shows.
Add to calendar#20
Green Mill Cocktail Lounge, UptownKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsSaturdays at 3pm (doors 1pm); no end date announcedFREE
The Paper Machete
Green Mill Cocktail Lounge, Uptown
The script is new every week at this free two-hour show in the Green Mill, a bar since 1907.
FreeLimited Run
#20Saturdays at 3pm (doors 1pm); no end date announced · Limited Run
Green Mill Cocktail Lounge, UptownKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsThe Paper Machete
The script is new every week at this free two-hour show in the Green Mill, a bar since 1907.
Add to calendar#21
Abbey Farms, Aurora, Far SuburbsSeptember 19–November 1, 2026; September weekends 10 a.m.–6 p.m.; October Wed–Fri and Sun 10 a.m.–6 p.m., Sat 10 a.m.–10 p.m.$21 online or $23 at the gate…
Pumpkin Daze
Aurora, Far Suburbs
Pumpkin Daze runs September 19–November 1 at Abbey Farms with a corn maze, pumpkins, family rides, games and food.
Limited Run
#21September 19–November 1, 2026; September weekends 10 a.m.–6 p.m.; October Wed–Fri and Sun 10 a.m.–6 p.m., Sat 10 a.m.–10 p.m. · Limited Run
Abbey Farms, Aurora, Far SuburbsPumpkin Daze
Pumpkin Daze runs September 19–November 1 at Abbey Farms with a corn maze, pumpkins, family rides, games and food.
Add to calendar#22
Music Box Theatre, Southport Corridor, LakeviewMonday, October 12, 2026 · 7 PM; post-film director Q&A$15 general admission
Begotten: New Restoration with E. Elias Merhige
Southport Corridor, Lakeview
A new 4K restoration screens with director E. Elias Merhige in person for a Q&A.
Limited Run
#22Monday, October 12, 2026 · 7 PM; post-film director Q&A · Limited Run
Music Box Theatre, Southport Corridor, LakeviewBegotten: New Restoration with E. Elias Merhige
A new 4K restoration screens with director E. Elias Merhige in person for a Q&A.
Add to calendar#23
Inside Chicago Walking Tours, Downtown, the Loop & West LoopSep 18, 2026–Oct 17, 2026
Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Downtown, the Loop & West Loop
Haunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour is listed for Chicago.
Limited Run
#23Sep 18, 2026–Oct 17, 2026 · Limited Run
Inside Chicago Walking Tours, Downtown, the Loop & West LoopHaunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Haunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour is listed for Chicago.
Add to calendar#24
Allstate ArenaOct 10, 2026–Oct 18, 2026$20
Chicago Wolves Hockey
Allstate Arena
Chicago Wolves Hockey is listed for Chicago this weekend.
Limited Run
#24Oct 10, 2026–Oct 18, 2026 · Limited Run
Allstate ArenaAbout this list
Stumblday's hand-checked ranking of the best things to do in Chicago on Columbus Day Monday, Oct 12: 138 picks, refreshed weekly.
