#1
Fri, Oct 9, 2026 · 8:00pm
Zach Top: Cold Beer & Country Music Tour 2026
6920 North Mannheim Road, Evanston & Oak Park
Zach Top headlines Allstate Arena with a full night of his country music.
One Day Only
Things to Do in Oak Park, Chicago Columbus Day Weekend 2026
10 picks
The 10 best things to do in Oak Park, Chicago over Columbus Day Weekend (Oct 9–12)
- Zach Top: Cold Beer & Country Music Tour 2026 — Fri, Oct 9 8:00pm · 6920 North Mannheim Road
- Collect-A-Con Chicago — Saturday, October 10 – Sunday, October 11 · 9301 Bryn Mawr Avenue
- Windycon 52: Sanctuary Among the Stars — Friday–Sunday, October 9–11 Program times TBA · At door: $70 adult weekend · Rosemont
- Music Theater Works Presents: Escape to Margaritaville — Fri, Oct 9 7 PM; Sat, Oct 10 · 7:30 PM; Sun · 9501 Skokie Blvd
- Mocktoberfest: Chicago’s N/A Oktoberfest — Sat, Oct 10 12:00pm · $50 · Evanston & Oak Park
- FitzGerald's Fall Fair 5 — Saturday, October 10, from 11:00 AM · $5 suggested donation · Berwyn
- Third Coast Symphony: Rhapsody in Blue & A World Premiere — Sun, Oct 11 3:00pm · 9501 Skokie Blvd
- Face 2 Face — Sat, Oct 10 7:30pm · 9501 Skokie Blvd
- Picturing the Modern Metropolis: Prints and Photographs — Sep 9–Dec 6, 2026 · Evanston & Oak Park
- The Block Collects 2026 — Sep 9–Dec 6, 2026 · Evanston & Oak Park
#1Fri, Oct 9, 2026 · 8:00pm · One Day Only
Zach Top: Cold Beer & Country Music Tour 2026
Zach Top headlines Allstate Arena with a full night of his country music.
Add to calendar#2
Donald E. Stephens Convention Center, 9301 Bryn Mawr Avenue, Evanston & Oak ParkSaturday, October 10 – Sunday, October 11, 2026; Saturday 10am–6pm, Sunday 10am–5pm
Collect-A-Con Chicago
9301 Bryn Mawr Avenue, Evanston & Oak Park
A two-day trading-card and collectibles convention with vendors from across the hobby.
One Weekend Only
#2Saturday, October 10 – Sunday, October 11, 2026; Saturday 10am–6pm, Sunday 10am–5pm · One Weekend Only
Donald E. Stephens Convention Center, 9301 Bryn Mawr Avenue, Evanston & Oak ParkCollect-A-Con Chicago
A two-day trading-card and collectibles convention with vendors from across the hobby.
Add to calendar#3
Hyatt Regency O'Hare Chicago, Rosemont, Evanston & Oak ParkFriday–Sunday, October 9–11, 2026 · Program times TBAAt door: $70 adult weekend
Windycon 52: Sanctuary Among the Stars
Rosemont, Evanston & Oak Park
Chicago’s long-running sci-fi convention brings literary, gaming, art and fan programs.
One Weekend Only
#3Friday–Sunday, October 9–11, 2026 · Program times TBA · One Weekend Only
Hyatt Regency O'Hare Chicago, Rosemont, Evanston & Oak ParkWindycon 52: Sanctuary Among the Stars
Chicago’s long-running sci-fi convention brings literary, gaming, art and fan programs.
Add to calendar#4
Fri, Oct 9 · 7 PM; Sat, Oct 10 · 7:30 PM; Sun, Oct 11 · 2 PM
Music Theater Works Presents: Escape to Margaritaville
9501 Skokie Blvd, Evanston & Oak Park
Music Theater Works stages Escape to Margaritaville at the North Shore Center.
One Weekend Only
#4Fri, Oct 9 · 7 PM; Sat, Oct 10 · 7:30 PM; Sun, Oct 11 · 2 PM · One Weekend Only
Music Theater Works Presents: Escape to Margaritaville
Music Theater Works stages Escape to Margaritaville at the North Shore Center.
Add to calendar#5
Palmhouse, Evanston & Oak ParkSat, Oct 10, 2026 · 12:00pm$50
Mocktoberfest: Chicago’s N/A Oktoberfest
Palmhouse, Evanston & Oak Park
Mocktoberfest: Chicago’s N/A Oktoberfest has enough weekend energy to earn a spot on the board.
One Day Only
#5Sat, Oct 10, 2026 · 12:00pm · One Day Only
Palmhouse, Evanston & Oak ParkMocktoberfest: Chicago’s N/A Oktoberfest
Mocktoberfest: Chicago’s N/A Oktoberfest has enough weekend energy to earn a spot on the board.
Add to calendar#6
FitzGerald's Patio, Berwyn, Evanston & Oak ParkSaturday, October 10, 2026, from 11:00 AM$5 suggested donation
FitzGerald's Fall Fair 5
Berwyn, Evanston & Oak Park
FitzGerald's Fall Fair 5 has enough weekend energy to earn a spot on the board.
One Day Only
#6Saturday, October 10, 2026, from 11:00 AM · One Day Only
FitzGerald's Patio, Berwyn, Evanston & Oak ParkFitzGerald's Fall Fair 5
FitzGerald's Fall Fair 5 has enough weekend energy to earn a spot on the board.
Add to calendar#7
Sun, Oct 11, 2026 · 3:00pm
Third Coast Symphony: Rhapsody in Blue & A World Premiere
9501 Skokie Blvd, Evanston & Oak Park
Third Coast Symphony: Rhapsody in Blue & A World Premiere has enough weekend energy to earn a spot on the board.
One Day Only
#7Sun, Oct 11, 2026 · 3:00pm · One Day Only
Third Coast Symphony: Rhapsody in Blue & A World Premiere
Third Coast Symphony: Rhapsody in Blue & A World Premiere has enough weekend energy to earn a spot on the board.
Add to calendar#8
Sat, Oct 10, 2026 · 7:30pm
Face 2 Face
9501 Skokie Blvd, Evanston & Oak Park
Face 2 Face performs at the North Shore Center's George Van Dusen Theatre.
One Day Only
#8Sat, Oct 10, 2026 · 7:30pm · One Day Only
Face 2 Face
Face 2 Face performs at the North Shore Center's George Van Dusen Theatre.
Add to calendar#9
Block Museum of Art, Evanston & Oak ParkSep 9, 2026–Dec 6, 2026
Picturing the Modern Metropolis: Prints and Photographs
Block Museum of Art, Evanston & Oak Park
Picturing the Modern Metropolis: Prints and Photographs is listed for Chicago this weekend.
ArtLimited Run
#9Sep 9, 2026–Dec 6, 2026 · Limited Run
Block Museum of Art, Evanston & Oak ParkPicturing the Modern Metropolis: Prints and Photographs
Picturing the Modern Metropolis: Prints and Photographs is listed for Chicago this weekend.
Add to calendar#10
Block Museum of Art, Evanston & Oak ParkSep 9, 2026–Dec 6, 2026
The Block Collects 2026
Block Museum of Art, Evanston & Oak Park
The Block Collects 2026 is listed for Chicago this weekend.
ArtLimited Run
#10Sep 9, 2026–Dec 6, 2026 · Limited Run
Block Museum of Art, Evanston & Oak ParkAbout this list
Stumblday's hand-checked ranking of the best things to do in Oak Park, Chicago, Evanston & Oak Park over Columbus Day weekend 2026 (Oct 10–12): 10 picks.
