Chicago is always giving us a reason to get out. From cultural moments and live entertainment to dining, celebrations, and experiences worth your time, here are 20 standout things happening across the city of Chicago this weekend; Consider this your curated things to do in Chicago guide to spending the weekend well.
These 20 standout events in Chicago should have a spot on your social calendar. Scroll through to see our curated selection and send this to the groupchat! These are the top 20 things to do in Chicago this weekend.
CHICAGO ART FAIR
October 7-11
Merchandise Mart
A new art fair for Chicago. You’re invited to The Chicago Art Fair | Where Leading Galleries Meet the Midwest’s Most Engaged Collectors. Bringing together a select roster of galleries presenting exceptional contemporary, modern, and fine art in one of America’s most influential cultural and collector markets. Stop by the Jean Albano Gallery booth and check out teh work of contemporary artist Bonnie Star.
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JERRY SEINFELD LIVE
October 9 & 10, 2026
The Chicago Theatre
Jerry Seinfeld will perform live for three shows at the Chicago Theatre.
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LOCAVORE SUPPER CLUB 2026
October 9
Locavore Farm | 11588 N. 17500E. Rd. Grant Park, IL 60940
The Hidden Table at Locavore. 24 seats. One hidden place. An unforgettable Friday evening. Only twenty-four guests are welcomed each evening, the experience is deeply personal. After booking, you’ll receive a brief guest profile where you can share favorite foods, meaningful memories, celebrations, dietary preferences, and the small details that make hospitality memorable.
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GORILLAZ WITH LITTLE SIMZ AND DELTRON 3030
October 8
United Center |
Gorillaz is bringing The Mountain Tour to United Center on October 8th! Produced by Live Nation, the tour will see the world’s most successful virtual act once again brought to life on these shores by Gorillaz co-creators Damon Albarn and Jamie Hewlett, with Albarn joined onstage by the Gorillaz live band and some very special guest performers. A truly global phenomenon, Gorillaz have achieved success in entirely groundbreaking and unique ways, touring the world and winning numerous awards including the coveted Jim Henson Creativity Honor. The band is recognized by The Guinness Book Of World Records as the planet’s Most Successful Virtual Act.
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CHICAGO HUMANITIES ANNUAL BENEFIT
October 8
The Geraghty | 2520 S Hoyne Avenue, Chicago
Join us as we kick off our annual Fall Festival!. 2026 Honorees include the Obama Foundation, Robert McCormick Foundation, and Shermann “Dilla” Thomas PLUS a conversation with acclaimed author, artist, performer, and activist Sandra Cisneros, author of The House on Mango Street, and the Poetry Foundation President Michelle Boone.
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SYMPHONY BALL WITH KLAUS MÄKELÄ
October 10
Chicago Symphony Orchestra
Celebrate the 2026/27 Season in grand fashion as Zell Music Director Designate Klaus Mäkelä leads a musical journey to the opulent Babylon of Walton’s Belshazzar’s Feast. The great baritone Thomas Hampson joins the CSO for this dramatic cantata. Following the concert will be the Symphony Gala dinner and festivities at the Four Seasons Hotel Chicago.
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LINCOLN BRUNCH FEST
October 10 | 10am to 2pm
Lincoln Avenue (Wellington to Diversey)
If brunch is your jam—pun fully intended—Lincoln Brunch Fest is the place to be this fall! Returning for its third annual celebration, this can’t-miss event, presented by West Lakeview SSA 27, takes over Lincoln Avenue from Diversey to Wellington this October for a delicious day of food, entertainment and family fun. Top local restaurants will serve FREE samples signature brunch bites and creative new favorites, while live entertainment and kid-friendly activities transform the street into a brunch lover’s paradise.
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SALT SHED OPEN HOUSE: FALL ARBORETUM EDITION
October 10 | 12pm-5pm
The Salt Shed | 1357 N Elston Avenue
Join us for our Fall Open House, an afternoon for you to stop by and experience all there is to offer at the Salt Shed! Bring your family and play games at our eclectic arcade, Elston Electric. Stop by the Three Top Lounge for specialty cocktails and a beautiful rooftop deck and view.
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BED BY 10PM NORTH AMERICA TOUR
October 10 | 4pm – 9pm (Last Entry: 6pm)
Sound Bar | 226 W Ontario Street, Chicago
Bed By 10: The Ultimate 30+ Clubbing Experience! 🎉
Fancy going out for a dance but not keen on sacrificing the next day? We’ve got you covered!
Bed By 10 is a chance for ravers over 30 to relive the peak of the 80s, 90s & early 2000s clubbing scene! Expect crazy visuals and more as our resident DJ spins all the club classics 🚀
Good vibes only! Our event is designed for those who love to dance, socialize, and enjoy great music—all while being home and in bed by 10PM✨
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METAPHOR: REFANTAZIO WITH THE CHICAGO PHILHARMONIC
October 11 | 8pm
The Auditorium Theatre | 4746 N. Racine Avenue
Experience the magnificent orchestral concert featuring music from ATLUS’s award-winning RPG, Metaphor: ReFantazio! After premiering in Japan in 2025 and selling out immediately, this spectacular production, Composed by Shoji Meguro, is now embarking on a world tour. The concert presents a carefully curated selection of music that brings the game’s epic fantasy world to life.
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BECK WITH IOANNA GIKA AND WAYNE FALER
October 9 & 10 | 7:30pm
The Auditorium Theatre |
Eight-time Grammy-winner Beck has traveled light years from his emergence as a reluctant generational spokesperson when “Loser” exploded from a rejected 1992 demo into a ubiquitous 1994 smash. In the decades since, Beck’s singular career has seen him utilize all manners and eras of music, blurring boundaries and blazing a path into the future while simultaneously foraging through the past.
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CHICAGO FIRE FC VS. NEW YORK CITY FC
October 10 | 1:30pm
Soldier Field |
Anime Day. Naruto-Themed jersey giveaway for the first 5k fans.
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SHABOOZEY – OUTLAWS NEVER DIE TOUR
October 9 | 7:30pm
Byline Bank Aragon Ballroom|
Shaboozey is coming to town! The Outlaws Never Die tour supports his album The Outlaw Cherie Lee & Other Western Tales. Featuring rotating guests including Brittney Spencer, Noeline Hofmann, BigXthaPlug, Kashus Culpepper, Noah Cyrus, Carter Faith, and Angel White.$1 from each ticket goes to St. Jude Children’s Research Hospital via PLUS1.
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10TH ANNUAL LINCOLN PARK WINE FEST
October 9-11| 12pm-
1001 W Wrightwood Ave
Get ready to raise a glass 🍷 — the Lincoln Park Wine Fest is proudly celebrating its 10th anniversary 🎉 this year in the heart of Chicago’s Jonquil Park neighborhood. With ten years of bringing together wine lovers, local food vendors 🍽️, and the crisp beauty of autumn 🍁 in the city, this milestone marks a decade of memorable tastings, lively ambiance, and community connection. The festival transforms the park into a vibrant open-air celebration where guests can sip, savor, and socialize in true Chicago style. ✨.
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OLIVIA RODRIGO WITH WOLF ALICE
October 11 & 12 | Gates 5:30pm; Show 7pm
United Center |
Multi-platinum, three-time GRAMMY Award-winning artist Olivia Rodrigo is bringing The Unraveled Tour to United Center on October 11 and 12! The tour supports her third studio album, you seem pretty sad for a girl so in love. The Unraveled Tour follows the success of Olivia Rodrigo’s 2022 debut, The SOUR Tour, and her first headline arena run, the GUTS world tour, which spanned more than 60 cities across 20+ countries throughout 2024 and 2025. The GUTS world tour marked her largest tour to date, with 95 sold-out shows and over 1.4 million fans in attendance..
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LYRIC OPERA PRESENTS DON GIOVANNI
October 10
Lyric Opera House Chicago
The Lyric Opera of Chicago 2026/27 Season kicks off with a thrilling fable of deceit and retribution. Under the baton of Music Director Enrique Mazzola, sharp humor, high drama, and an exquisite score intertwine in the story of a charismatic seducer whose unrepentant lustfulness brings about a most spectacular demise. Bass-baritone and Lyric veteran Christian Van Horn stars as one of opera’s most infamous anti-heroes, crowning a stellar cast. Sung in Italian with projected English titles.
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BEFORE MIDNIGHT: A CINDERELLA TEA EXPERIENCE
October 10 & 11; Saturdays and Sundays through November 14 | 11:00 a.m. – final seating at 3:00 p.m.
The Ritz-Carlton, Chicago
Step into an enchanting experience inspired by the timeless story of Cinderella, with immersive details, whimsical surprises, and memorable moments designed to transport guests into a modern fairytale. Join us for a Cinderella-inspired Afternoon Tea in the Café, set in the heart of The Ritz-Carlton, Chicago. Enjoy a beautifully curated selection of pastries, tea sandwiches, savory bites, and freshly baked scones, complemented by a flute of G.H. Mumm Grand Cordon Rosé Champagne and an exquisite assortment of Ritz-Carlton teas curated by Palais des Thés.
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FGI CHICAGO 11TH RISING STAR AWARDS
October 10 | 11:00 am – 2:00 pm
Public Works Gallery | 2141 W. North Avenue, Chicago
Celebrate the future of Chicagoland’s fashion and beauty industry at the 11th FGI Chicago Rising Star Awards. The FGI Chicago Rising Star Awards recognize outstanding emerging professionals making an impact across Chicagoland’s fashion and beauty industry. This year, 15 finalists across five categories will be celebrated for their creativity, talent and contributions to Chicago’s fashion community. Join FGI Chicago for an inspiring afternoon featuring a grazing brunch, professional networking, finalist displays and the Rising Star Awards ceremony, where the 2026 FGI Chicago Rising Star Award recipients will be revealed.
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2026 BANK OF AMERICA CHICAGO MARATHON
October 11
26.2 Miles Across Chicago
The Bank of America Chicago Marathon is a world class running event returning to the streets of Chicago. Not running? Experience the excitement of the Bank of America Chicago Marathon by watching the sights and sounds of race day check out the course map.
CLICK HERE FOR DETAILS
You can also find more curated events taking place in Chicago this month HERE
*Cover image credit Navy Pier
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