# Cowboy Events | List Of All Upcoming Cowboy Events In Chicago - **Subtitle**: Explore all upcoming cowboy events in Chicago, find information & tickets for upcoming cowboy events happening in Chicago. - **Category**: ## About Explore all upcoming cowboy events in Chicago, find information & tickets for upcoming cowboy events happening in Chicago. ## Events in Chicago - **Event Name**: Wrigleyville Country Fest - Live Music All Day @ Chicago's Top Country Bars - **Description**: Tix include admission, a shot of whiskey, a country brunch buffet, live music & more! This is one party you do not want to miss! Giddy up!About this Event🤠🍻Throw on your cowboy boots, flannels and daisy dukes for the - **Date**: Sat Aug 22 2026 at 11:00 am – Sat Aug 22 2026 at 06:00 pm (-05:00) - **Event URL**: https://allevents.in/chicago/wrigleyville-country-fest-live-music-all-day-chicagos-top-country-bars/100001956944546819 - **Venue**: Wrigleyville's BEST Country Bars TBA - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy81YjhmMmIzODhiZjY3MDBlZjhjMWIwODcyNGZiNzI2MjVjNWEzMzdiNmZkMjAyNDJjNjQ4MjIxNWQ3OTQxMGJlLXJpbWctdzEyMDAtaDYwMC1kYzYxNGE0My1nbWlyLmpwZz92PTE3NjM1MjY4Njc.avif - **Price**: USD 10 to 37 - **Categories**: Music, Festivals, Entertainment, Nonprofit, Contests, Meetups - **Event Name**: Annual Speed & Action Rodeo Horse Show - **Description**: Get ready for thrilling rides and fast-paced fun at the Annual Speed & Action Rodeo Horse Show!About this Event🎉 BROKEN ARROW’S 36TH ANNUAL SPEED & ACTION RODEO HORSE SHOW 🎉 - **Date**: Sun Jun 21 2026 at 02:00 pm – Sun Jun 21 2026 at 09:00 pm (-05:00) - **Event URL**: https://allevents.in/chicago/annual-speed-and-action-rodeo-horse-show/100001987411896482 - **Venue**: South Shore Cultural Center - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvYTgwZWEzY2IyMjZhMzQwNDRiYWM5MzBjYWJkNjQ5N2I5YzlhZTJkNTM0YTA2NzAzZmVjZmZjNTk4MzBmNDc2Yy1yaW1nLXcxMDI0LWg1NDAtZGMyYjI5MzEtZ21pci5qcGc_dj0xNzc2MjAyMzU4.avif - **Price**: USD 15 to 18 - **Categories**: trips-adventures, Contests - **Event Name**: Josh Weathers - **Description**: Information21+ / www.carolspub.comTheres something about Josh Weathersa kind of magic that lives somewhere between the Fort Worth Stockyards and Muscle Shoals. A natural soul that grabs your gut and doesnt let go. A country soul that kn - **Date**: Fri Jul 31 2026 at 09:00 pm (-06:00) - **Event URL**: https://allevents.in/chicago/josh-weathers/210002709795568 - **Venue**: Carol's Pub - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy83ZmFiOTEwMWZmMmE3OGVkYWRhZTY4YTY1ZjkxMWE1ZjBkYzk3NWM0NjAyMWNjMzI0ODdmMDYyMzBlNTJhYWM2LXJpbWctdzEwMjQtaDU3Ni1kYzMwMjgyNi1nbWlyLmpwZz92PTE3NzcwMTM4Mjk.avif - **Price**: USD 17 - **Event Name**: Chicago Hat Walk 2026 - **Description**: Get ready to stroll in style and show off your coolest hats at this fun Chicago hat-themed walk!About this EventWHAT: World Hat Walk Day! Join Chicago hat lovers at the 3rd Annual Chicago Hat Walk as part of World Hat Wal - **Date**: Sun May 10 2026 at 11:00 am – Sun May 10 2026 at 01:00 pm (-05:00) - **Event URL**: https://allevents.in/chicago/chicago-hat-walk-2026/100001988256159696 - **Venue**: Jane M. Byrne Plaza Park - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy9kY2YyMTNmZmUxODRhNDU0YjUxZTVhM2FhMjhlMWMwZjk1MzdmMzMxYmYyMjUwZDhmOWY0MDhiZTJlY2VjNmVmLXJpbWctdzExNzAtaDE0NjgtZGM0ODQ5NDctZ21pci5qcGc_dj0xNzc3MzgwNjYw.avif - **Price**: Free - **Categories**: parties, entertainment - **Event Name**: Four Star Bar Tour: Orange Archer Edition! - **Description**: Good news, travelers! We are back on monthly cadences again. This month, we are off to explore some hidden spots on the city's Southwest Side. Some are a great example of how our city changes through the years. Others? Well I think some spots are preserve - **Date**: Sun May 17 2026 at 03:45 pm – Sun May 17 2026 at 09:30 pm (-05:00) - **Event URL**: https://allevents.in/chicago/four-star-bar-tour-orange-archer-edition/200030042696343 - **Venue**: Exchequer Restaurant & Pub - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9mYzFjMDIzOWU0OTk4ZWUxY2E0ZjMwZDEwOTI3ZTg3OWI5NjZiN2E1MzdkNTM4MmY4ZmZmMzdkNmNmZTdkZDg3LXJpbWctdzEyMDAtaDY4Ni1kYzhjN2U3Ni1nbWlyP3Y9MTc3ODQ1NDI4Mw.avif - **Categories**: Sports, trips-adventures - **Event Name**: Modern Fiction Lilliput Bookclub: Whistler by Ann Patchett - **Description**: Reserve your copy & save 10% (information below).About this EventAs an independent bookstore, we love hosting events like this bookclub and silent bookclub. To keep this group going and support our store, please purch - **Date**: Tue Jul 21 2026 at 06:30 pm – Tue Jul 21 2026 at 07:30 pm (-05:00) - **Event URL**: https://allevents.in/chicago/modern-fiction-lilliput-bookclub-whistler-by-ann-patchett/100001988835999011 - **Venue**: Lilliput Books - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy85OTU1MjVjYjgyZjUyZjM4NzJhNmJjOGY4ZTJiNjA0ZjBkYzk5NDBkMTYxZjRhZGQ4MzI4MWVhYTU2OTFmNmMyLXJpbWctdzM1MC1oNTI5LWRjMDQyZTRhLWdtaXIuanBnP3Y9MTc3ODA3ODI1MA.avif - **Price**: Free - **Categories**: art, literary-art, food-drinks - **Event Name**: Modern Fiction Lilliput Bookclub: Yesteryear by Caro Claire Burke - **Description**: Reserve your copy & save 10% (information below).About this EventAs an independent bookstore, we love hosting events like this bookclub and silent bookclub. To keep this group going and support our store, please purch - **Date**: Tue Jun 23 2026 – Fri Jun 26 2026 (-05:00) - **Event URL**: https://allevents.in/chicago/modern-fiction-lilliput-bookclub-yesteryear-by-caro-claire-burke/100001988000002523 - **Venue**: Lilliput Books - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9hOTVhNWM1OWY4ZDkyNDUxZmZlZjU1MGM2N2E3ODY1MjUzODY4Njc4ZWFhMWMzN2RmMzMyMzE0NTNkMjgwNmRjLXJpbWctdzEwMTQtaDE1MDAtZGNmM2JiNjItZ21pci5qcGc_dj0xNzc3MzgwNjAx.avif - **Price**: Free - **Categories**: art, literary-art, food-drinks ## Trending Events in Chicago - **Event Name**: Rock The Boat Chicago The Biggest All White Yacht Party Juneteenth Weekend - **Description**: The biggest All White daytime yacht party in Chicago. Juneteenth Weekend. Lake Michigan. Early Bird $50.About this Eventhttps://cdn-az.allevents.in/events1/banners/515b4090-f57c-11f0-92d6-d568e2653d8f-rimg-w5 - **Venue**: Anita Dee II Yacht - **Banner**: https://cdn2.allevents.in/thumbs/thumb696f2f5114ff5.jpg - **Event Name**: Rock The Boat Chicago All White Yacht Party Memorial Day Weekend 2026 - **Description**: Chicago biggest Memorial Day weekend yacht party. All white vibes, skyline views, music, and energy all night on the Anita Dee.About this Event 🚢 ROCK THE BOAT CHICAGO - **Venue**: Anita Dee Yacht Charters - **Banner**: https://cdn2.allevents.in/thumbs/thumb69e52d4bbc199.jpg - **Event Name**: African/Caribbean International Festival of Life (IFOL) - 33rd Annual. - **Description**: Celebrate America’s 250th Independence Anniversary @ 33rd AFRICAN/CARIBBEAN INTERNATIONAL FESTIVAL OF LIFE (IFOL) July 4th weekend, Fri., Sat., Sun., 3, 4 & 5th, 2026 @Union Park, 1501 W. Rand - **Venue**: Union Park - **Banner**: https://cdn2.allevents.in/thumbs/thumb69c5af3add268.jpg - **Event Name**: BACK TO THE 90s CHICAGO • Juneteenth Weekend Experience • Music By DJ Self - **Description**: Chicago’s ultimate 90s Juneteenth Weekend experience with throwback hits, DJs, complimentary light bites & nonstop vibes.About this Event https://cdn-az.allevents.in/events10/banners/6860afb0-4abc-11f1-a995-afc12287912d-rimg- - **Venue**: The Hidden Gem - **Banner**: https://cdn-az.allevents.in/events4/banners/2b9d36f4c43dda15fa9b09f32817176af9dc25e2dfcea1d8390d44bcd9ddfdc0-rimg-w1200-h1200-dc030203-gmir.jpg?v=1778230864 - **Event Name**: Eran Hersh Untold Story IV 360 Experience - **Description**: The Monolith Project presents Untold Story IV with Eran Hersh.Join us Saturday, May 16, 2026, at Hideaway in Chicago for Eran Hersh’s Chicago debut — a 360° house music experience built around rhythm, movement, and connection. - **Venue**: Hideaway - **Banner**: https://cdn2.allevents.in/thumbs/thumb69ee64181f34d.jpg - **Event Name**: ERAN HERSH (CHICAGO DEBUT) @ UNTOLD STORY IV - A MONOLITH PROJECT - **Description**: About this eventERAN HERSH — CHICAGO DEBUTUNTOLD STORY IV: THE 360° EXPERIENCEA MONOLITH PROJECTFor the first time, global DJ and producer Eran Hersh comes to Chicago for Untold Story IV — an in - **Venue**: Hideaway - **Banner**: https://cdn-az.allevents.in/events7/banners/b38690929364028051a35d5839575f2fd093d8fd9ebc1c16a72e69cf1b20a9a3-rimg-w735-h616-dcffffff-gmir.jpg?v=1777380684 - **Event Name**: Bollywood cruise party Chicago - **Description**: Step into a world of glitz and glamour at "Bollywood Nights on the Water" hosted by Aarush Entertainment! Get ready to experience a night filled with dazzling performances, pulsating beats, and endless fun under the starlit sky.📅 Da - **Venue**: 896 S Wells St - **Banner**: https://cdn2.allevents.in/thumbs/thumb69fa5b8aa9958.jpg - **Event Name**: 2-Day Chicago Event Planner Certification July 18-19, 2026 - **Description**: Anyone can plan an event with a folding table and a Costco membership.But companies and clients are not just paying for “put together.” They expect you to build and manage real budgets, create detailed timelines, co - **Venue**: Embassy Suites by Hilton Chicago Downtown Magnificent Mile - **Banner**: https://cdn2.allevents.in/thumbs/thumb69e631a3c6a93.jpg - **Event Name**: From Expert Contributor to Authentic Leader: Design Your Leadership Style - **Description**: Stop trying to fit the mold of a 'boss' and start building the leader you actually want to follow.We've all worked for the "accidental manager"; the high performer who was promoted for their technical skill and ability to execute, but left witho - **Venue**: 318 West Adams Street, Chicago, IL, USA - **Banner**: https://cdn2.allevents.in/thumbs/thumb697fec1f52f54.jpg ## FAQs - **Q**: What are the top events in Chicago? - **A:** Wrigleyville Country Fest - Live Music All Day @ Chicago's Top Country Bars (Sat Aug 22 2026 at 11:00 am at Wrigleyville's BEST Country Bars TBA), Annual Speed & Action Rodeo Horse Show (Sun Jun 21 2026 at 02:00 pm at South Shore Cultural Center), Josh Weathers (Fri Jul 31 2026 at 09:00 pm at Carol's Pub), Chicago Hat Walk 2026 (Sun May 10 2026 at 11:00 am at Jane M. Byrne Plaza Park), Four Star Bar Tour: Orange Archer Edition! (Sun May 17 2026 at 03:45 pm at Exchequer Restaurant & Pub). - **Q**: What are the top free events in Chicago? - **A:** Chicago Hat Walk 2026 (Sun May 10 2026 at 11:00 am at Jane M. Byrne Plaza Park), Modern Fiction Lilliput Bookclub: Whistler by Ann Patchett (Tue Jul 21 2026 at 06:30 pm at Lilliput Books), Modern Fiction Lilliput Bookclub: Yesteryear by Caro Claire Burke (Tue Jun 23 2026 at Lilliput Books). - **Q**: What events are happening in Chicago this weekend May 15–17, 2026? - **A:** Four Star Bar Tour: Orange Archer Edition! (Sun May 17 2026 at 03:45 pm at Exchequer Restaurant & Pub). - **Q**: What events are happening in Chicago in May 2026? - **A:** Chicago Hat Walk 2026 (Sun May 10 2026 at 11:00 am at Jane M. Byrne Plaza Park), Four Star Bar Tour: Orange Archer Edition! (Sun May 17 2026 at 03:45 pm at Exchequer Restaurant & Pub). - **Q**: How can I find events in Chicago? - **A:** You can discover upcoming events in Chicago on AllEvents.in. Browse by date, venue, or price to find events that match your interests. - **Q**: How do I buy tickets for events in Chicago? - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets. - **Q**: What are the popular venues for events in Chicago? - **A:** Some popular venues hosting events in Chicago include South Shore Cultural Center, Carol's Pub, Jane M. Byrne Plaza Park. - **Q**: What is the price range for events in Chicago? - **A:** Prices for events in Chicago range from USD 10 to USD 37. Many events also offer free entry. - **Q**: Who are the top organizers for events in Chicago? - **A:** Popular organizers hosting events in Chicago include Wrigleyville Country Fest, Broken Arrow Horseback Riding Club, City Girl Hats. - **Q**: Are there any online events available? - **A:** Yes, many events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere. - **Q**: How can I get notified about new events in Chicago? - **A:** Follow the category on AllEvents.in to get notified when new events are listed in Chicago. ## Explore Events in Nearby Cities - [Events in Cicero](https://allevents.in/cicero) - [Events in Oak Park](https://allevents.in/oak-park) - [Events in Berwyn](https://allevents.in/berwyn) - [Events in Forest Park](https://allevents.in/forest-park-il) - [Events in Elmwood Park](https://allevents.in/elmwood-park-il) - [Events in River Forest](https://allevents.in/river-forest) - [Events in Lincolnwood](https://allevents.in/lincolnwood) - [Events in Riverside](https://allevents.in/riverside-il)