Want to know what’s happening this weekend in Chicago? Look no further. There’s a whole calendar of exciting events, exhibits, and activities taking place all over the city this month in Chicago.
A few of highlights this weekend include:
- The 48th annual Bank of America Chicago Marathon, which runs through 29 neighborhoods
- Chicago Fashion Week, with runway shows and pop-ups around the city
- The 53rd annual Historic Pullman House Tour, offering an inside glimpse of unique residences
- Fun autumnal events like the Lincoln Park Wine Festival and Fall Fest at Lincoln Park Zoo
Plus, Saturday, Oct. 10 has officially been named “Best Big City Day” to celebrate Chicago’s historic win in the Condé Nast Traveler’s Readers’ Choice Awards. Celebrate with a limited-edition “Perfect 10” beer at local Goose Island brewpubs and live house music at City Winery on the Riverwalk starting at 3:30p.m.
Check out just a few of the events and happening in Chicago this weekend, Oct. 9 – 11, 2026.
Bank of America Chicago Marathon
Come cheer on runners during the 48th annual Chicago Marathon, one of the most prestigious marathons in the world.
Watch amateur and elite athletes from around the world race through Chicago’s vibrant neighborhoods, with the race beginning and ending in lakefront Grant Park.
10th Annual Lincoln Park Wine Fest
The tenth annual Lincoln Park Wine Fest transforms tranquil Jonquil Park into a lively celebration of wine October 9–11. Throughout the park, wine and food…
Chicago Fashion Week
This week-long celebration of creativity will shine a spotlight on the city’s groundbreaking design community with more than 50 events and runway shows.
Historic Pullman House Tour
The Annual Historic Pullman House Tour on Oct. 10 and 11 offers exclusive access to the interior of well-preserved private homes throughout the Pullman area, offering visitors a chance to go back in time to the 19th century.
Lincoln Brunch Fest
Celebrate local food, businesses and live music at the third annual Lincoln Brunch Fest on Saturday, Oct. 10, from 10 a.m. to 2 p.m. This…
Handmade Market
Handmade Market Chicago is a unique event to connect the makers of beautiful things to people who appreciate the unique and handmade. There are more…
Indigenous Peoples’ Day Celebration at Harrison
Tierra Colombiana Dance Ensemble presents a free, all-ages Indigenous Peoples’ Day celebration at Harrison (Carter) Park on Saturday, October 10, from 11 a.m. to 4…
Chicago Zine Fest
On Saturday October 10th, Chicago Zine Fest (CZF) will celebrate its 15th year of bringing together independent publishers from the Chicago area, the Midwest, and…
Chicago Art Fair
Taking place October 7 - 10, the inaugural Chicago Art Fair will bring together world-class galleries presenting exceptional contemporary and modern fine art in Chicago’s…
Tenderfest 2026
The world's largest chicken tender festival, is coming to Chicago for the first time ever on Saturday, Oct 10th. The CEO behind Prince Street Pizza,…
Rock and Roll Playhouse – The Music of Grateful Dead for Kids
The Rock and Roll Playhouse: The Music of Grateful Dead for Kids will take place live in Chicago on October 10 and November 22, 2026.…
Beck – Ride Lonesome Tour
Beck is performing at The Auditorium in Chicago on Saturday, October 10, 2026, as part of his "Ride Lonesome Tour".
Mocktoberfest: Chicago’s N/A Oktoberfest
CHICAGO AF PRESENTS MOCKTOBERFEST 2026: GOOD TIMES. ZERO PROOF. Non-alcoholic Oktoberfest comes to Palmhouse on October 10 Tickets now on sale ($35-$50) CHICAGO, Ill., July…
Chicago Latino Dance Festival at Humboldt
The 2026 Chicago Latino Dance Festival brings a free outdoor program to Humboldt Park on Sunday, October 11, from 3 to 5 p.m. The Chicago…
Creepy Cruise
From strange sightings to eerie haunts, mobsters and more, our latest nighttime tour takes you into Chicago's shadowy past. Cruise along the Chicago River as…
Operation Mincemeat: A New Musical
How did a dead body, a fake love letter, and — of all people — Ian Fleming turn the tide of World War II? Olivier…
Fall Fest at Lincoln Park Zoo
Chicago’s favorite free and family-friendly festival is back at Lincoln Park Zoo for another season of harvest-time fun! From September through October, stop by the…
Destinos: Chicago International Latino Theater Festival
The 9th annual Destinos International Latino Theater Festival showcases Latino theatre companies from Chicago and across the country. Choose from a variety of works staged at some of the city’s top independent theatre venues.
The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago Venues
Curious Theatre Branch, with co-producers Chicago Danztheater Ensemble, Chicago Dramatists and Labyrinth Club, are pleased to announce the 37th annual Rhinoceros Theater Festival, September 20…
Jekyll& Hyde
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…
BOO! at the Zoo
Get ready for a boo-tiful day of Halloween fun at BOO! at the Zoo, Brookfield Zoo Chicago's family-friendly fall tradition! Enjoy festive décor, not-so-scary surprises,…
Explore our events calendar for more Chicago events and happenings.
Please note that all events are subject to change.
