{"id":5079,"date":"2026-10-02T05:09:07","date_gmt":"2026-10-02T05:09:07","guid":{"rendered":"https:\/\/onestowatch.com\/live\/best-chicago-october-weekend-activities\/"},"modified":"2026-10-02T05:09:07","modified_gmt":"2026-10-02T05:09:07","slug":"best-chicago-october-weekend-activities","status":"publish","type":"post","link":"https:\/\/onestowatch.com\/live\/best-chicago-october-weekend-activities\/","title":{"rendered":"Best Things To Do In Chicago The Weekend Of October 23"},"content":{"rendered":"<h2 id=\"key-takeaways\">Key Weekend Highlights In Chicago<\/h2> <ul> <li>The weekend of October 23\u201325, 2026 delivers a packed run of concerts, comedy, sports, and Halloween events across Chicago.<\/li> <li>Rebecca Black\u2019s Exhibitionism on Tour at House of Blues Chicago on Friday serves as a focal point for the weekend\u2019s music calendar.<\/li> <li>Saturday pairs major ticketed shows with the 12th annual Arts in the Dark Halloween Parade, the city\u2019s largest Halloween street celebration.<\/li> <li>Every music listing in this guide draws from first-party dates, venues, and ticket links tracked by OnesToWatch Live.<\/li> <li>Locking in Friday and Saturday nights first gives fans the strongest chance to catch the weekend\u2019s most in-demand shows tracked by OnesToWatch Live.<\/li> <\/ul> <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Browse All Chicago Tickets On OnesToWatch Live<\/a><\/p> <h2>Featured Ticket Links For October 23\u201325<\/h2> <p>This section spotlights the weekend\u2019s most notable concerts and comedy shows so readers can secure tickets quickly.<\/p> <ul> <li><strong>Rebecca Black \u2014 Exhibitionism on Tour<\/strong> \u2014 Friday, October 23 \u00b7 House of Blues Chicago <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Frebecca-black-exhibitionism-on-tour-chicago-illinois-10-23-2026%2Fevent%2F040064EFCA86D017&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Rebecca Black<\/a><\/p> <\/li> <li><strong>Tedeschi Trucks Band \u2014 Future Soul 2026 Tour<\/strong> \u2014 Friday, October 23 \u00b7 The Chicago Theatre (7:30 p.m.) <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Ftedeschi-trucks-band-future-soul-2026-chicago-illinois-10-23-2026%2Fevent%2F07006436AB8B6888&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Tedeschi Trucks Band (Night One)<\/a><\/p> <\/li> <li><strong>Yousuke Yukimatsu \u2014 Autumn 2026 Tour<\/strong> \u2014 Friday, October 23 \u00b7 Aragon Ballroom (9:00 p.m.) <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fuuk-uk1matu-autumn-2026-tour-chicago-illinois-10-23-2026%2Fevent%2F040064CCC1FACB72&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Yousuke Yukimatsu<\/a><\/p> <\/li> <li><strong>The Wrecks \u2014 OUTSIDE Tour<\/strong> \u2014 Saturday, October 24 \u00b7 House of Blues Chicago <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fthe-wrecks-finally-outside-tour-chicago-illinois-10-24-2026%2Fevent%2F040064D04DFE4FF5&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For The Wrecks<\/a><\/p> <\/li> <li><strong>Tedeschi Trucks Band \u2014 Future Soul 2026 Tour (Night Two)<\/strong> \u2014 Saturday, October 24 \u00b7 The Chicago Theatre <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Ftedeschi-trucks-band-future-soul-2026-chicago-illinois-10-24-2026%2Fevent%2F07006436AB9068AC&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Tedeschi Trucks Band (Night Two)<\/a><\/p> <\/li> <li><strong>Brett Goldstein<\/strong> \u2014 Sunday, October 25 \u00b7 The Chicago Theatre <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fbrett-goldstein-sex-death-small-talk-chicago-illinois-10-25-2026%2Fevent%2F0700650EA6B35BAA&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Brett Goldstein<\/a><\/p> <\/li> <li><strong>Sleeping With Sirens \u2014 An Ending In Itself Tour<\/strong> \u2014 Sunday, October 25 \u00b7 The Salt Shed Indoors (Shed) <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fsleeping-with-sirens-an-ending-in-chicago-illinois-10-25-2026%2Fevent%2F040064CBC7A3E2C8&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Sleeping With Sirens<\/a><\/p> <\/li> <\/ul> <p>Catch these artists in intimate and mid-size rooms before they graduate to larger arenas and stadiums.<\/p> <figure style=\"text-align: center\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/onestowatch-v2\/2024-12-06_t100132.205_z1733479292-file-1024x683-1741210936.jpeg\" alt=\"2024 12 06 t100132.205 z1733479292 file 1024x683 1741210936\" style=\"max-height: 500px\" loading=\"lazy\"><\/figure><h2>Friday, October 23 \u2014 Full Day Itinerary<\/h2> <p>Friday delivers the densest music lineup of the weekend, with shows covering pop, rock, hip-hop, country, and comedy across every room size.<\/p> <ol> <li> <strong>Rebecca Black \u2014 Exhibitionism on Tour \u00b7 House of Blues Chicago<\/strong>. As featured in the quick links above, Rebecca Black brings the <em>Exhibitionism on Tour<\/em> show to House of Blues Chicago on Friday, October 23. House of Blues offers a mid-capacity layout that keeps the stage close to the floor. This show works well as the anchor for a music-focused Friday night. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Frebecca-black-exhibitionism-on-tour-chicago-illinois-10-23-2026%2Fevent%2F040064EFCA86D017&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Rebecca Black<\/a><\/p> <\/li> <li> <strong>Tedeschi Trucks Band \u2014 Future Soul 2026 Tour \u00b7 The Chicago Theatre<\/strong>. Tedeschi Trucks Band, a Grammy-winning ensemble led by Derek Trucks and Susan Tedeschi, brings its blues-rock sound to The Chicago Theatre. The band\u2019s debut album, <em>Revelator<\/em>, won the 2012 Grammy Award for Best Blues Album. The Future Soul 2026 Tour opens at <a href=\"https:\/\/gigtrip.com\/events\/tedeschi-trucks-band-future-soul-2026-tour-chicago-2026-10-23\" target=\"_blank\" rel=\"noindex nofollow\">7:30 p.m.<\/a> at The Chicago Theatre, 175 N State St. This performance marks night one of a multi-night run at the venue. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Ftedeschi-trucks-band-future-soul-2026-chicago-illinois-10-23-2026%2Fevent%2F07006436AB8B6888&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Tedeschi Trucks Band (Night One)<\/a><\/p> <\/li> <li> <strong>Yousuke Yukimatsu \u2014 Autumn 2026 Tour \u00b7 Aragon Ballroom<\/strong>. <a href=\"https:\/\/mixmag.net\/feature\/impact-yousuke-yukimatsu-japan-experimental-dj-producer-gabber-techno\" target=\"_blank\" rel=\"noindex nofollow\">Yousuke Yukimatsu is an Osaka-born Japanese DJ and producer, now based in Tokyo, known for his experimental, genre-defying DJ sets<\/a>. He brings his Autumn 2026 Tour to the Aragon Ballroom, a venue with a capacity of roughly 5,000, starting at 9:00 p.m. Yukimatsu\u2019s sets often blur the lines between techno, ambient, trance, breakbeat, and pop within a single transition. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fuuk-uk1matu-autumn-2026-tour-chicago-illinois-10-23-2026%2Fevent%2F040064CCC1FACB72&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Yousuke Yukimatsu<\/a><\/p> <\/li> <li> <strong>Sammy Rae &amp; The Friends (With Special Guest Melt) \u00b7 The Salt Shed Indoors (Shed)<\/strong>. This show offers a high-energy ensemble set at one of Chicago\u2019s strongest mid-size indoor venues. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fsammy-rae-the-friends-with-special-chicago-illinois-10-23-2026%2Fevent%2F04006477BA496E98&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Sammy Rae &amp; The Friends<\/a><\/p> <\/li> <li> <strong>Austin Snell \u00b7 Joe\u2019s on Weed Street<\/strong>. Austin Snell headlines a club-level country set in River North at Joe\u2019s on Weed Street. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Faustin-snell-colors-joes-on-weed-street-tickets%2F15020883&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Austin Snell<\/a><\/p> <\/li> <li> <strong>Gilla Band \u00b7 Bottom Lounge<\/strong>. The Dublin post-punk group plays a club-capacity room at Bottom Lounge. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fevent%2FZ7r9jZ1A70zpv&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Gilla Band<\/a><\/p> <\/li> <li> <strong>This Wild Life (With Nate Bergman) \u00b7 Chop Shop<\/strong>. This Wild Life brings acoustic-leaning indie rock to a compact room at Chop Shop. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fevent%2FZ7r9jZ1AAZdab&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For This Wild Life<\/a><\/p> <\/li> <li> <strong>Maggie Rose \u00b7 Garcia\u2019s Chicago<\/strong>. Maggie Rose, a Nashville-rooted singer-songwriter, headlines a West Loop room at Garcia\u2019s Chicago. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fmaggie-rose-chicago-illinois-10-23-2026%2Fevent%2F0400650FEAA2E1A7&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Maggie Rose<\/a><\/p> <\/li> <li> <strong>Grabbitz \u00b7 Outset<\/strong>. Electronic producer and vocalist Grabbitz plays an electronic-focused night at Outset Chicago. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fgrabbitz-chicago-illinois-10-23-2026%2Fevent%2F040064F4E194F696&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Grabbitz<\/a><\/p> <\/li> <li> <strong>PLAYGRND SERIES \u00b7 Thalia Hall<\/strong>. This multi-act showcase takes over Thalia Hall, one of Chicago\u2019s most architecturally distinctive venues in Pilsen. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Fplaygrnd-series-chicago-thalia-hall-tickets%2F15004163&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For PLAYGRND SERIES<\/a><\/p> <\/li> <li> <strong>William Elliott Whitmore \u00b7 Reggies Rock Club<\/strong>. Iowa folk-blues songwriter William Elliott Whitmore performs at South Loop staple Reggies Rock Club. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Fwilliam-elliott-whitmore-meg-reggies-rock-club-tickets%2F14903503%3FREFERRAL_ID%3Dtmfeed&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For William Elliott Whitmore<\/a><\/p> <\/li> <li> <strong>MJT The Band, Desmond Jones, When We Was Kids \u00b7 Reggies Music Joint<\/strong>. A three-act bill fills Reggies\u2019 main room with jam-forward and rock-leaning sets. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Fmjt-the-band-desmond-jones-reggies-music-joint-tickets%2F14998773%3FREFERRAL_ID%3Dtmfeed&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For MJT The Band And More<\/a><\/p> <\/li> <li> <strong>Maryanne Muglia \u00b7 Subterranean<\/strong>. Maryanne Muglia headlines a Wicker Park club show at Subterranean. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fevent%2FZ7r9jZ1A7PS8k&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Maryanne Muglia<\/a><\/p> <\/li> <li> <strong>Adam Ray \u2014 WHO IS ME Tour \u00b7 Athenaeum Theatre<\/strong>. Adam Ray brings his WHO IS ME stand-up tour to the Athenaeum Theatre. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fathenaeumcenter.org%2Fevents%2F2026%2Fadam-ray-who-is-me-tour%2F&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Adam Ray<\/a><\/p> <\/li> <li> <strong>Randy Feltface \u00b7 Vic Theatre<\/strong>. Australian puppet comedian Randy Feltface performs a full stand-up set at the Vic Theatre. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fevent%2FZ7r9jZ1A7xd7g&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Randy Feltface<\/a><\/p> <\/li> <li> <strong>Chicago Blackhawks vs. Montreal Canadiens \u00b7 United Center<\/strong>. The Chicago Blackhawks host the Montreal Canadiens in regular-season NHL play at the United Center. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fchicago-blackhawks-vs-montreal-canadiens-chicago-illinois-10-23-2026%2Fevent%2F040064F0904477E7&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Blackhawks vs. Canadiens<\/a><\/p> <\/li> <\/ol> <p>Beyond concerts and sports, Friday also offers a wide mix of cultural events, tours, and seasonal experiences.<\/p> <p>Additional Friday options include the Chicago Architecture Center River Cruise Aboard First Lady, a 90-minute narrated architecture tour with multiple departures.<\/p> <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fchicago-architecture-center-river-cruise-aboard-chicago-illinois-10-23-2026%2Fevent%2F2100644100D22CD5&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Book River Cruise Tickets<\/a><\/p> <p>Other Friday highlights span comedy, theater, and nightlife across the city.<\/p> <ul> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fhablando-huevadas-us-tour-2026-chicago-illinois-10-23-2026%2Fevent%2F070064F8BDAF68D6&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">Hablando Huevadas at Copernicus Center<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fkokandy-productions-jekyll-hyde-chicago-chicago-illinois-10-23-2026%2Fevent%2F070064CC917A342C&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">Kokandy Productions\u2019 Jekyll &amp; Hyde at Broadway Playhouse at Water Tower Place<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fevent%2FZ7r9jZ1A7POFy&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">Drunk Shakespeare at The Lion Theatre<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fthe-book-of-mormon-chicago-chicago-illinois-10-23-2026%2Fevent%2F070064C57E491EF5&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">The Book of Mormon at Cadillac Palace<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fevent%2FZ7r9jZ1AAZ_aK&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">The Winter\u2019s Tale at The Yard at Chicago Shakespeare<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fvape-the-grease-parody-chicago-illinois-10-23-2026%2Fevent%2F070064EDF9335799&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">Vape! The Grease Parody at Apollo Theater<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fevent%2FZ7r9jZ1A7reQK&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">Second City at its Mainstage<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Fcosmic-country-showcase-empty-bottle-tickets%2F15044563&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">Cosmic Country Showcase at Empty Bottle<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Fhard-country-honky-tonk-with-empty-bottle-tickets%2F14027794&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">Hard Country Honky Tonk (with The Hoyle Brothers) at Empty Bottle<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Fsilvis-everyday-fantastic-om-in-reggies-banannas-shack-tickets%2F14276254%3FREFERRAL_ID%3Dtmfeed&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">Silvis, Everyday Fantastic, Om In Gold at Reggies Banana\u2019s Shack<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Fthe-messengers-carols-pub-tickets%2F15007803&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">The Messengers at Carol\u2019s Pub<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fevent%2FZ7r9jZ1A7-wPf&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">You Can\u2019t Fake the Funk at Black Ensemble Theater<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Fvip-stadium-tour-soldier-field-tickets%2F14324934%3FREFERRAL_ID%3Dtmfeed&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">VIP Stadium Tour at Soldier Field<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fchicago-steel-vs-youngstown-phantoms-chicago-illinois-10-23-2026%2Fevent%2F040064F0AC21B2FE&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">Chicago Steel vs. Youngstown Phantoms at USG Arena<\/a><\/li> <li><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fthe-chicago-theatre-tour-experience-chicago-illinois-10-23-2026%2Fevent%2F07006467A0CC4221&amp;utm_medium=affiliate\" target=\"_blank\" rel=\"noindex nofollow\">Chicago Theatre Tour Experience<\/a><\/li> <\/ul> <p>The Field Museum\u2019s 21+ Secrets and Specimens after-hours event also runs Friday evening. The program features pop-up stories from museum scientists, hands-on mysteries, and a hidden speakeasy inside the museum, with tickets that include light snacks, beer, and wine.<\/p> <p>Zoo Brews: Howls and Growls runs Friday\u2013Saturday, October 23\u201324, 6:30\u201310 p.m. at Lincoln Park Zoo. This 21+ Halloween festival offers beer and cider samples, pumpkin-carving demonstrations, a costume contest, live DJ sets, and unlimited rides on the carousel, giant slide, and Ferris wheel, with tickets priced at $65 in advance or $70 on the event day.<\/p> \n\n<div class=\"wp-block-group aga-native-youtube-container wp-embed-responsive is-layout-flow wp-block-group-is-layout-flow\">\n<figure class=\"wp-block-embed is-type-video is-provider-youtube wp-block-embed-youtube aga-native-youtube wp-embed-aspect-16-9 wp-has-aspect-ratio\"><div class=\"wp-block-embed__wrapper\">\n<iframe title=\"Rebecca Black - Salvation (Official Video)\" width=\"800\" height=\"600\" src=\"https:\/\/www.youtube.com\/embed\/lLBPrAJf52E?feature=oembed\" frameborder=\"0\" allow=\"accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share\" referrerpolicy=\"strict-origin-when-cross-origin\" allowfullscreen><\/iframe>\n<\/div><figcaption class=\"wp-element-caption\"><a href=\"https:\/\/www.youtube.com\/watch?v=lLBPrAJf52E\" target=\"_blank\" rel=\"noopener noreferrer\">Watch on YouTube<\/a><\/figcaption><\/figure>\n<\/div>\n\n<h2>Saturday, October 24 \u2014 Full Day Itinerary<\/h2> <p>Saturday layers a full slate of concerts and late-night parties on top of Chicago\u2019s marquee Halloween street programming.<\/p> <ol start=\"17\"> <li> <strong>The Wrecks \u2014 OUTSIDE Tour \u00b7 House of Blues Chicago<\/strong>. The Wrecks bring their <a href=\"https:\/\/chicago-theater.com\/dates\/range\/2026-10-24\/2026-10-24\/category\/concert\" target=\"_blank\" rel=\"noindex nofollow\">Finally: OUTSIDE Tour<\/a> to House of Blues Chicago on Saturday, October 24, 2026. The band\u2019s hook-heavy catalog fits the mid-capacity, close-quarters layout of the room. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fthe-wrecks-finally-outside-tour-chicago-illinois-10-24-2026%2Fevent%2F040064D04DFE4FF5&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For The Wrecks<\/a><\/p> <\/li> <li> <strong>Tedeschi Trucks Band \u2014 Future Soul 2026 Tour (Night Two) \u00b7 The Chicago Theatre<\/strong>. Night two of the Future Soul 2026 Tour continues the band\u2019s Chicago Theatre run with another blues-rock headlining set. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Ftedeschi-trucks-band-future-soul-2026-chicago-illinois-10-24-2026%2Fevent%2F07006436AB9068AC&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Tedeschi Trucks Band (Night Two)<\/a><\/p> <\/li> <li> <strong>Tank And The Bangas (With Ariel J. And Zeus) \u00b7 Thalia Hall<\/strong>. Tank and the Bangas bring New Orleans-rooted funk and soul to Thalia Hall in Pilsen, with Ariel J. and Zeus in support. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Ftank-and-the-bangas-thalia-hall-tickets%2F14794233&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Tank And The Bangas<\/a><\/p> <\/li> <li> <strong>Fruit Bats (With Matthew Logan Vasquez) \u00b7 The Salt Shed Indoors (Shed)<\/strong>. Fruit Bats headline an indie-folk night at The Salt Shed, with Matthew Logan Vasquez opening. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Ffruit-bats-with-matthew-logan-vasquez-chicago-illinois-10-24-2026%2Fevent%2F04006474B2AB731F&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Fruit Bats<\/a><\/p> <\/li> <li> <strong>Mobb Deep \u00b7 Ramova Theatre<\/strong>. Mobb Deep brings classic Queens hip-hop to the restored Ramova Theatre in Bridgeport. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fevent%2FZ7r9jZ1AAZxv4&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Mobb Deep<\/a><\/p> <\/li> <li> <strong>Shawn James \u00b7 Bottom Lounge<\/strong>. Shawn James delivers a blues-rooted singer-songwriter set at Bottom Lounge. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Fshawn-james-flew-too-bottom-lounge-tickets%2F14206374&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Shawn James<\/a><\/p> <\/li> <li> <strong>Authority Zero (With Counterpunch) \u00b7 Reggies Music Joint<\/strong>. Authority Zero headlines a night of Arizona punk rock with local support from Counterpunch. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketweb.com%2Fevent%2Fauthority-zero-counterpunch-the-run-reggies-music-joint-tickets%2F15002313%3FREFERRAL_ID%3Dtmfeed&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Authority Zero<\/a><\/p> <\/li> <li> <strong>Shane Dawson \u00b7 Vic Theatre<\/strong>. Shane Dawson appears at the Vic Theatre with a live tour that blends storytelling and onstage conversation. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fevent%2FZ7r9jZ1AAv_p_&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Shane Dawson<\/a><\/p> <\/li> <li> <strong>CircuitMOM \u00b7 House of Blues Chicago<\/strong>. CircuitMOM hosts a late-night Halloween party at House of Blues with a club-forward atmosphere. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fcircuitmom-uncle-present-haunted-hollywood-ft-chicago-illinois-10-24-2026%2Fevent%2F04006515AC86F5B9&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For CircuitMOM Halloween Party<\/a><\/p> <\/li> <li> <strong>Nice As F**k \u00b7 Outset<\/strong>. Nice As F**k closes the night with a late show at Outset Chicago. <p><a href=\"https:\/\/ticketmaster.evyy.net\/c\/6581772\/264167\/4272?u=https%3A%2F%2Fwww.ticketmaster.com%2Fnice-as-fk-late-show-chicago-illinois-10-24-2026%2Fevent%2F04006529BABEB55E&amp;utm_medium=affiliate\" class=\"solid-button\" target=\"_blank\" rel=\"noindex nofollow\">Get Tickets For Nice As F**k<\/a><\/p> <\/li> <\/ol><section data-read-next=\"true\"><h2>Read Next<\/h2><ul><li><a href=\"https:\/\/onestowatch.com\/live\/chicago-october-weekend-events\/\" target=\"_blank\">Best Things To Do In Chicago: October 16\u201318, 2026<\/a><\/li><li><a href=\"https:\/\/onestowatch.com\/live\/best-chicago-weekend-activities\/\" target=\"_blank\">Best Things To Do In Chicago This Weekend Oct 16\u201317<\/a><\/li><li><a href=\"https:\/\/onestowatch.com\/live\/chicago-things-to-do-weekend\/\" target=\"_blank\">Best Things To Do in Chicago This Weekend<\/a><\/li><li><a href=\"https:\/\/onestowatch.com\/live\/best-things-to-do-chicago\/\" target=\"_blank\">Best Things To Do in Chicago the Weekend of Sept. 25, 2026<\/a><\/li><li><a href=\"https:\/\/onestowatch.com\/live\/chicago-september-weekend-events\/\" target=\"_blank\">Top Things To Do In Chicago: September 11\u201313, 2026<\/a><\/li><\/ul><\/section>","protected":false},"excerpt":{"rendered":"<p>Plan your Chicago weekend with OnesToWatch Live \u2014 top events, concerts &amp; activities for October 23\u201325, 2026. Get tickets now!<\/p>\n","protected":false},"author":35,"featured_media":5078,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"inline_featured_image":false,"footnotes":""},"categories":[1],"tags":[],"class_list":["post-5079","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-uncategorized"],"_links":{"self":[{"href":"https:\/\/onestowatch.com\/live\/wp-json\/wp\/v2\/posts\/5079","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/onestowatch.com\/live\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/onestowatch.com\/live\/wp-json\/wp\/v2\/types\/post"}],"replies":[{"embeddable":true,"href":"https:\/\/onestowatch.com\/live\/wp-json\/wp\/v2\/comments?post=5079"}],"version-history":[{"count":0,"href":"https:\/\/onestowatch.com\/live\/wp-json\/wp\/v2\/posts\/5079\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/onestowatch.com\/live\/wp-json\/wp\/v2\/media\/5078"}],"wp:attachment":[{"href":"https:\/\/onestowatch.com\/live\/wp-json\/wp\/v2\/media?parent=5079"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/onestowatch.com\/live\/wp-json\/wp\/v2\/categories?post=5079"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/onestowatch.com\/live\/wp-json\/wp\/v2\/tags?post=5079"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}