Skip to consent to cookiesSkip navigation
Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Check out what's happening all around Chicago.

Wolff’s Flea Market Opening Day
Oct5
Festivals, Fairs & Special Events

Wolff’s Flea Market Opening Day

Wolff’s Flea Market announces opening day April 20, 2025. Join us for our 34th season outdoors at the Allstate Arena, Rosemont. Sundays 6am-2pm through October…

Sunday, October 5th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Division Street Farmers Market
Oct5
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Sunday, October 5th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Glenwood Sunday Market in Rogers Park
Oct5
Festivals, Fairs & Special Events

Glenwood Sunday Market in Rogers Park

The nonprofit Rogers Park Business Alliance (RPBA) announces 23 local vendors for the 16th anniversary season of the Glenwood Sunday Market, which will operate every…

Sunday, October 5th
9:00 a.m.2:00 p.m.
Glenwood Alfresco
Maxwell Street Market
Oct5
Festivals, Fairs & Special Events

Maxwell Street Market

Visitors to the Maxwell Street Market will experience an eclectic mix of foods and finds—including handmade crafts, resale housewares, clothing, and much more.

Sunday, October 5th
10:00 a.m.3:00 p.m.
Maxwell Street Market
800 S. Desplaines St.
Boo! at the Zoo
Oct5
Festivals, Fairs & Special Events

Boo! at the Zoo

Get ready for a fang-tastic time at BOO! at the Zoo, Brookfield Zoo Chicago’s family-friendly Halloween celebration. This event is packed with not-so-scary thrills, festive decorations,…

Sunday, October 5th
10:00 a.m.5:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
Big Bus Tours’ Hop-On, Hop-Off Tour
Oct5
Tours & Attractions

Big Bus Tours’ Hop-On, Hop-Off Tour

Big Bus Tours’ daily Hop-On, Hop-Off tours offer visitors a convenient way to explore Chicago’s vibrant downtown, including historic landmarks, cultural institutions and hidden gems.…

Sunday, October 5th
10:00 a.m.5:00 p.m.
The World Within: Chicago’s Original & Best Architecture Interiors Tour
Oct5
Tours & Attractions

The World Within: Chicago’s Original & Best Architecture Interiors Tour

“Everything has beauty, but not everyone sees it.”  (Confucius) Everyone does a boat tour when they visit Chicago.  But as fun as that is, it’s…

Sunday, October 5th
11:00 a.m.1:00 p.m.
Chicago Loop & River North
Ninth Annual Lincoln Park Wine Fest
Oct5
Festivals, Fairs & Special Events

Ninth Annual Lincoln Park Wine Fest

Wines from Around the World Featured at 9thAnnual Lincoln Park Wine Fest in Jonquil Park October 3-5 Wine tastings, a food and beverage market, sommeliers on hand…

Sunday, October 5th
11:00 a.m.7:00 p.m.
Jonquil Park
1001 W. Wrightwood Avenue
Simone’s Bar Sweet 16 Anniversary Celebration and 1st Annual Block Party
Oct5
Festivals, Fairs & Special Events

Simone’s Bar Sweet 16 Anniversary Celebration and 1st Annual Block Party

Event Name:Simone’s Sweet 16 Block Party Admission:Free Description (Event Overview):Celebrate 16 years of community, music, and culture at Simone’s Sweet 16 Block Party in Chicago’s…

Sunday, October 5th
11:30 a.m.10:00 p.m.
Simone’s bar Simone’s Bar 960 W 18th Street, Chicago, IL 60608
960 W 18th Street
Rappel In Northwest Chicago
Oct5
Sports & Recreation, Tours & Attractions

Rappel In Northwest Chicago

Conquer your limits at 168 feet up and rappel down the Westin Chicago Northwest in Itasca Illinois. Professional equipment provided and no experience needed. Trained…

Sunday, October 5th
12:00 p.m.3:00 p.m.
Westin Chicago Northwest
400 Park Blvd.
Seadog Architecture Tour on the Chicago River
Oct5
Tours & Attractions

Seadog Architecture Tour on the Chicago River

Soak in unobstructed views of Chicago’s world-famous architecture with an exciting 45-minute ride on our Seadog Chicago River Architecture Tour! Starting right on the Chicago…

Sunday, October 5th
12:30 p.m.1:30 p.m.
City Cruises – River Esplanade
455 N Cityfront Plaza Dr
EXP Presents Horizon of Khufu
Oct5
Tours & Attractions

EXP Presents Horizon of Khufu

Be among the first to experience EXP Rosemont, a brand-new 26,000-square-foot immersive destination blending art, science and technology through rotating world-class experiences. Opening its doors…

Sunday, October 5th
1:00 p.m.8:00 p.m.
EXP
9900 Berwyn Avenue
Crossing Borders // La Caccina // Holocene
Oct5
Festivals, Fairs & Special Events, Music & Comedy

Crossing Borders // La Caccina // Holocene

Ear Taxi Festival presents an ear taxi concert. Celebrate contemporary music with powerful performances from Crossing Borders Music, La Caccina, and Holocene. Crossing Borders’ program…

Sunday, October 5th
2:00 p.m.5:00 p.m.
PianoForte Chicago
1335 South Michigan Avenue
FashionBar The Shows: October 2025 – Modest, Formal, Evening Wear
Oct5
Festivals, Fairs & Special Events, Theatre & Performing Arts

FashionBar The Shows: October 2025 – Modest, Formal, Evening Wear

The closing runway of October 2025, this event presents modest fashion alongside formal and evening wear collections, bringing elegance, refinement, and cultural expression to the…

Sunday, October 5th
2:00 p.m.6:00 p.m.
Water Tower Place
835 N Michigan Ave
Architecture River Tour in Chicago
Oct5
Tours & Attractions

90 Minute Architecture River Tour in Chicago

Experience Chicago’s Best 90-Min Architecture Boat Tour starting May 3, 2025! Led by expert tour guides, this is perfect for all ages. Explore the city’s…

Sunday, October 5th
5:00 p.m.7:00 p.m.
Summer Of George
900 South Wells Street
Big Bus Tours’ Sunset Live Tour
Oct5
Tours & Attractions

Big Bus Tours’ Sunset Live Tour

Big Bus Tours, the global leader in open-top bus sightseeing, invites visitors to experience the enhanced Sunset Live Tour in Chicago. Available May 8 through…

Sunday, October 5th
7:30 p.m.9:15 p.m.
618 N Clark St.
618 N. Clark St
Franz West: Millennium Park
Oct6
Museums, Galleries & Exhibitions, Tours & Attractions

Franz West: Millennium Park

Franz West” Millennium Park features two monumental installations by West: Stonehenge (2011) and Dorit (2002), set against the iconic backdrop of Millennium Park. Stonehenge, with…

Monday, October 6th
Millennium Park
201 E Randolph St
Ear Taxi Festival
Oct6
Festivals, Fairs & Special Events

Ear Taxi Festival

The Ear Taxi Festival 2025, themed “The Composer’s Voice,” is a landmark event showcasing contemporary concert music across Chicagoland from October 3 through November 2,…

Monday, October 6th
Division Street Farmers Market
Oct6
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Monday, October 6th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Homeschool Days at PEPPA PIG World of Play Chicago
Oct6
Tours & Attractions

Homeschool Days at PEPPA PIG World of Play Chicago

Join us for Homeschool Days at Peppa Pig World of Play Chicago, where preschool families can enjoy an OINKTASTIC discount! Experience the magic of Peppa…

Monday, October 6th
10:00 a.m.5:00 p.m.
Peppa Pig World of Play Chicago
5 Woodfield Mall
Boo! at the Zoo
Oct6
Festivals, Fairs & Special Events

Boo! at the Zoo

Get ready for a fang-tastic time at BOO! at the Zoo, Brookfield Zoo Chicago’s family-friendly Halloween celebration. This event is packed with not-so-scary thrills, festive decorations,…

Monday, October 6th
10:00 a.m.5:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
Big Bus Tours’ Hop-On, Hop-Off Tour
Oct6
Tours & Attractions

Big Bus Tours’ Hop-On, Hop-Off Tour

Big Bus Tours’ daily Hop-On, Hop-Off tours offer visitors a convenient way to explore Chicago’s vibrant downtown, including historic landmarks, cultural institutions and hidden gems.…

Monday, October 6th
10:00 a.m.5:00 p.m.
The World Within: Chicago’s Original & Best Architecture Interiors Tour
Oct6
Tours & Attractions

The World Within: Chicago’s Original & Best Architecture Interiors Tour

“Everything has beauty, but not everyone sees it.”  (Confucius) Everyone does a boat tour when they visit Chicago.  But as fun as that is, it’s…

Monday, October 6th
11:00 a.m.1:00 p.m.
Chicago Loop & River North
Seadog Architecture Tour on the Chicago River
Oct6
Tours & Attractions

Seadog Architecture Tour on the Chicago River

Soak in unobstructed views of Chicago’s world-famous architecture with an exciting 45-minute ride on our Seadog Chicago River Architecture Tour! Starting right on the Chicago…

Monday, October 6th
12:30 p.m.1:30 p.m.
City Cruises – River Esplanade
455 N Cityfront Plaza Dr
bean-night

Explore Chicago hotels, flights, deals, and more

Plan your trip

Expedia
Expedia
Expedia
Expedia

CTA Newsletter

Chicago Newsletter

Stay in the know

Sign up

OVG25_enews_cover_for website footer

Chicago Visitors Guide

Start planning today

Get the guide